1-Benzyl-3-phenyl­imidazolium hexa­fluoro­phosphate

Jiang, P.

doi:10.1107/S1600536809031584

organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2177

doi:10.1107/S1600536809031584

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1-Benzyl-3-phenylimidazolium hexafluorophosphate

Ping Jiang ^a ^*

^aSchool of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China
^*Correspondence e-mail: jphdp868@126.com

(Received 29 July 2009; accepted 11 August 2009; online 19 August 2009)

in the title compound, C₁₆H₁₅N₂⁺·PF₆⁻, a precursor of N-heterocyclic carbene, the phenyl and benzyl rings are twisted away from the central imidazolium ring system, making dihedral angles of 70.30 (8) and 32.03 (10)°, respectively. The crystal structure is stabilized by C—H⋯F hydrogen bonds. Furthermore, P—F⋯π interactions involving imidazolium rings are observed [F⋯π = 2.9857 (16), P⋯π = 4.1630 (16) Å, P—F⋯π = 127.92 (6)°].

Related literature

The first stable N-heterocyclic carbene was isolated by Arduengo et al. (1991 ). For the synthesis, see: Liu et al. (2003 ). For related structures, see: Wan et al. (2008 ). For related structures, see: Newman et al. (2007 ); Herrmann (2002 ); Yang et al. (2009 ).

Experimental

Crystal data

C₁₆H₁₅N₂⁺·PF₆⁻
M_r = 380.27
Triclinic, $[P \overline 1]$
a = 9.221 (2) Å
b = 10.046 (3) Å
c = 10.108 (2) Å
α = 110.733 (2)°
β = 91.969 (2)°
γ = 110.315 (2)°
V = 807.9 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 93 K
0.43 × 0.40 × 0.37 mm

Data collection

Rigaku SPIDER diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.905, T_max = 0.919
4739 measured reflections
2902 independent reflections
2361 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.084
S = 1.00
2902 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯F1ⁱ	0.95	2.50	3.099 (2)	121
C8—H8⋯F6ⁱ	0.95	2.50	3.392 (2)	156
C9—H9⋯F5ⁱⁱ	0.95	2.34	3.247 (2)	159
C10—H10A⋯F4ⁱⁱ	0.99	2.49	3.444 (2)	161
C10—H10B⋯F3ⁱⁱⁱ	0.99	2.49	3.455 (3)	164
Symmetry codes: (i) x-1, y-1, z; (ii) x-1, y-1, z-1; (iii) -x+1, -y+1, -z+1.

Data collection: RAPID-AUTO (Rigaku/MSC, 2004 ); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809031584/at2854sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809031584/at2854Isup2.hkl

checkCIF report

Comment top

Initiated by the isolation of the first stable N-heterocyclic carbene (NHC) by Arduengo et al. (1991), numerous stable NHC ligands has been prepared. 1,3-Disubstitutedimidazolium salts are considerable good precursor for synthesis of transition metal NHCs. In addition, the study of biological activities of imidazolium salts have been reported during these years. We report herein the synthesis and crystal structure of the title compound (I).

In (I), bond lengths and angles in title molecule (Fig. 1) are normal. The phenyl ring make dihedral angles with the benzyl ring and the imidazolium ring of 70.30 (8)° and 32.03 (10)°, respectively.

The crystal structure is stabilized by C—H···F hydrogen bonds (Table 1). Furthermore, P—F···π interactions involving imidazolium rings [F1···Cg1^iv = 2.9857 (16) Å, P1···Cg1^iv = 4.1630 (16) Å, P1—F1··· Cg1^iv = 127.92 (6)°, where Cg1 is a centroid of the N1/N2/C7–C9 ring; symmetry code: (iv) -x+2, -y+1, -z+1] are observed.

Related literature top

The first stable N-heterocyclic carbene was isolated by

Arduengo et al. (1991). For the synthesis, see: Liu et al. (2003). For related structures, see: Wan et al. (2008). For related literature [on what subject?], see: Newman et al. (2007); Herrmann (2002); Yang et al. (2009).

Experimental top

The title compound was prepared according to the reported procedure of Liu et al. (2003). Colourless single crystals suitable for X-ray diffraction were obtained by recrystallization from dichloromethane and pPetroleum ether.

Computing details top

Data collection: RAPID-AUTO (Rigaku/MSC, 2004); cell refinement: RAPID-AUTO (Rigaku/MSC, 2004); data reduction: RAPID-AUTO (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atomic numbering.

1-Benzyl-3-phenylimidazolium hexafluorophosphate top

Crystal data top

C₁₆H₁₅N₂⁺·PF₆⁻	Z = 2
M_r = 380.27	F(000) = 388
Triclinic, P1	D_x = 1.563 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.221 (2) Å	Cell parameters from 2516 reflections
b = 10.046 (3) Å	θ = 3.1–27.5°
c = 10.108 (2) Å	µ = 0.24 mm⁻¹
α = 110.733 (2)°	T = 93 K
β = 91.969 (2)°	Block, colourless
γ = 110.315 (2)°	0.43 × 0.40 × 0.37 mm
V = 807.9 (3) Å³

Data collection top

Rigaku SPIDER diffractometer	2902 independent reflections
Radiation source: Rotating Anode	2361 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
ω scans	θ_max = 25.5°, θ_min = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −11→7
T_min = 0.905, T_max = 0.919	k = −11→12
4739 measured reflections	l = −12→11

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.084	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.043P)² + 0.066P] where P = (F_o² + 2F_c²)/3
2902 reflections	(Δ/σ)_max < 0.001
226 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₆H₁₅N₂⁺·PF₆⁻	γ = 110.315 (2)°
M_r = 380.27	V = 807.9 (3) Å³
Triclinic, P1	Z = 2
a = 9.221 (2) Å	Mo Kα radiation
b = 10.046 (3) Å	µ = 0.24 mm⁻¹
c = 10.108 (2) Å	T = 93 K
α = 110.733 (2)°	0.43 × 0.40 × 0.37 mm
β = 91.969 (2)°

Data collection top

Rigaku SPIDER diffractometer	2902 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2361 reflections with I > 2σ(I)
T_min = 0.905, T_max = 0.919	R_int = 0.017
4739 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.084	H-atom parameters constrained
S = 1.00	Δρ_max = 0.22 e Å⁻³
2902 reflections	Δρ_min = −0.28 e Å⁻³
226 parameters

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
P1	1.23197 (5)	1.00569 (5)	0.79232 (5)	0.02127 (14)
F1	1.38948 (11)	1.06413 (12)	0.73171 (11)	0.0297 (3)
F2	1.07593 (13)	0.94747 (15)	0.85307 (13)	0.0444 (3)
F3	1.16399 (13)	1.10464 (14)	0.73467 (12)	0.0380 (3)
F4	1.30246 (13)	0.90834 (14)	0.85235 (12)	0.0381 (3)
F5	1.30920 (14)	1.15038 (13)	0.94289 (11)	0.0427 (3)
F6	1.15883 (14)	0.86186 (13)	0.64242 (12)	0.0433 (3)
N1	0.47043 (15)	0.20046 (16)	0.35708 (14)	0.0188 (3)
N2	0.28468 (15)	−0.02584 (16)	0.25378 (14)	0.0192 (3)
C1	0.5504 (2)	0.4242 (2)	0.29382 (18)	0.0235 (4)
H1	0.4593	0.3740	0.2211	0.028*
C2	0.6550 (2)	0.5713 (2)	0.31694 (19)	0.0255 (4)
H2	0.6367	0.6216	0.2581	0.031*
C3	0.7858 (2)	0.6454 (2)	0.42503 (18)	0.0241 (4)
H3	0.8553	0.7475	0.4422	0.029*
C4	0.8153 (2)	0.5709 (2)	0.50786 (19)	0.0270 (4)
H4	0.9061	0.6213	0.5810	0.032*
C5	0.7131 (2)	0.4229 (2)	0.48495 (19)	0.0243 (4)
H5	0.7337	0.3714	0.5416	0.029*
C6	0.58132 (19)	0.3514 (2)	0.37897 (18)	0.0191 (4)
C7	0.4319 (2)	0.1417 (2)	0.46130 (18)	0.0218 (4)
H7	0.4787	0.1912	0.5602	0.026*
C8	0.3160 (2)	0.0014 (2)	0.39716 (18)	0.0223 (4)
H8	0.2652	−0.0662	0.4423	0.027*
C9	0.37939 (19)	0.0950 (2)	0.23205 (18)	0.0194 (4)
H9	0.3822	0.1051	0.1421	0.023*
C10	0.1627 (2)	−0.1631 (2)	0.14214 (19)	0.0233 (4)
H10A	0.1772	−0.1595	0.0467	0.028*
H10B	0.0580	−0.1612	0.1581	0.028*
C11	0.16757 (19)	−0.3114 (2)	0.14213 (17)	0.0197 (4)
C12	0.28553 (19)	−0.3616 (2)	0.08983 (18)	0.0224 (4)
H12	0.3691	−0.2983	0.0598	0.027*
C13	0.2811 (2)	−0.5030 (2)	0.08160 (18)	0.0254 (4)
H13	0.3614	−0.5368	0.0453	0.030*
C14	0.1600 (2)	−0.5965 (2)	0.12598 (18)	0.0255 (4)
H14	0.1569	−0.6941	0.1195	0.031*
C15	0.0439 (2)	−0.5460 (2)	0.17967 (18)	0.0248 (4)
H15	−0.0385	−0.6087	0.2113	0.030*
C16	0.04776 (19)	−0.4049 (2)	0.18733 (17)	0.0219 (4)
H16	−0.0325	−0.3713	0.2240	0.026*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0232 (3)	0.0215 (3)	0.0217 (3)	0.0089 (2)	0.0073 (2)	0.0108 (2)
F1	0.0233 (5)	0.0358 (7)	0.0297 (6)	0.0075 (5)	0.0084 (5)	0.0159 (5)
F2	0.0366 (7)	0.0571 (9)	0.0629 (8)	0.0237 (6)	0.0301 (6)	0.0422 (7)
F3	0.0390 (7)	0.0481 (8)	0.0470 (7)	0.0250 (6)	0.0148 (6)	0.0323 (7)
F4	0.0498 (7)	0.0469 (8)	0.0437 (7)	0.0330 (6)	0.0230 (6)	0.0315 (6)
F5	0.0644 (8)	0.0339 (7)	0.0229 (6)	0.0196 (6)	0.0073 (6)	0.0029 (6)
F6	0.0445 (7)	0.0274 (7)	0.0348 (7)	−0.0020 (6)	−0.0008 (5)	0.0025 (6)
N1	0.0206 (7)	0.0181 (8)	0.0174 (8)	0.0075 (6)	0.0029 (6)	0.0066 (7)
N2	0.0197 (7)	0.0187 (8)	0.0184 (8)	0.0076 (6)	0.0021 (6)	0.0063 (7)
C1	0.0236 (9)	0.0251 (10)	0.0214 (10)	0.0088 (8)	0.0026 (8)	0.0094 (8)
C2	0.0305 (10)	0.0247 (10)	0.0259 (10)	0.0122 (8)	0.0077 (8)	0.0134 (9)
C3	0.0251 (9)	0.0209 (10)	0.0239 (10)	0.0065 (8)	0.0083 (8)	0.0081 (8)
C4	0.0244 (9)	0.0275 (11)	0.0228 (10)	0.0061 (8)	−0.0002 (8)	0.0070 (9)
C5	0.0264 (9)	0.0238 (10)	0.0227 (10)	0.0086 (8)	0.0015 (8)	0.0103 (9)
C6	0.0211 (9)	0.0178 (9)	0.0177 (9)	0.0081 (7)	0.0058 (7)	0.0053 (8)
C7	0.0308 (10)	0.0232 (10)	0.0148 (9)	0.0128 (8)	0.0059 (7)	0.0086 (8)
C8	0.0292 (10)	0.0234 (10)	0.0174 (9)	0.0121 (8)	0.0070 (8)	0.0093 (8)
C9	0.0203 (8)	0.0216 (10)	0.0164 (9)	0.0088 (7)	0.0023 (7)	0.0068 (8)
C10	0.0210 (9)	0.0238 (10)	0.0216 (10)	0.0059 (8)	−0.0007 (7)	0.0078 (8)
C11	0.0202 (8)	0.0204 (10)	0.0146 (9)	0.0059 (7)	−0.0017 (7)	0.0049 (8)
C12	0.0187 (9)	0.0248 (10)	0.0218 (10)	0.0060 (8)	0.0038 (7)	0.0092 (8)
C13	0.0233 (9)	0.0292 (11)	0.0229 (10)	0.0120 (8)	−0.0007 (8)	0.0079 (9)
C14	0.0293 (10)	0.0209 (10)	0.0218 (10)	0.0065 (8)	−0.0052 (8)	0.0073 (8)
C15	0.0225 (9)	0.0265 (11)	0.0205 (10)	0.0019 (8)	−0.0006 (8)	0.0116 (9)
C16	0.0200 (9)	0.0264 (10)	0.0147 (9)	0.0063 (8)	0.0007 (7)	0.0057 (8)

Geometric parameters (Å, º) top

P1—F2	1.5875 (11)	C5—C6	1.378 (2)
P1—F3	1.5933 (11)	C5—H5	0.9500
P1—F6	1.5942 (12)	C7—C8	1.345 (2)
P1—F1	1.5978 (11)	C7—H7	0.9500
P1—F5	1.6052 (12)	C8—H8	0.9500
P1—F4	1.6066 (11)	C9—H9	0.9500
N1—C9	1.336 (2)	C10—C11	1.505 (2)
N1—C7	1.380 (2)	C10—H10A	0.9900
N1—C6	1.437 (2)	C10—H10B	0.9900
N2—C9	1.323 (2)	C11—C16	1.389 (2)
N2—C8	1.376 (2)	C11—C12	1.396 (2)
N2—C10	1.474 (2)	C12—C13	1.379 (2)
C1—C2	1.385 (2)	C12—H12	0.9500
C1—C6	1.389 (2)	C13—C14	1.391 (2)
C1—H1	0.9500	C13—H13	0.9500
C2—C3	1.383 (2)	C14—C15	1.386 (2)
C2—H2	0.9500	C14—H14	0.9500
C3—C4	1.380 (2)	C15—C16	1.380 (2)
C3—H3	0.9500	C15—H15	0.9500
C4—C5	1.386 (2)	C16—H16	0.9500
C4—H4	0.9500

F2—P1—F3	90.46 (6)	C5—C6—C1	121.20 (17)
F2—P1—F6	90.77 (7)	C5—C6—N1	120.21 (15)
F3—P1—F6	90.53 (7)	C1—C6—N1	118.58 (15)
F2—P1—F1	179.73 (6)	C8—C7—N1	107.46 (15)
F3—P1—F1	89.79 (6)	C8—C7—H7	126.3
F6—P1—F1	89.34 (6)	N1—C7—H7	126.3
F2—P1—F5	90.23 (7)	C7—C8—N2	107.13 (15)
F3—P1—F5	90.14 (7)	C7—C8—H8	126.4
F6—P1—F5	178.80 (7)	N2—C8—H8	126.4
F1—P1—F5	89.66 (6)	N2—C9—N1	108.96 (14)
F2—P1—F4	89.83 (6)	N2—C9—H9	125.5
F3—P1—F4	179.11 (7)	N1—C9—H9	125.5
F6—P1—F4	90.31 (7)	N2—C10—C11	112.54 (14)
F1—P1—F4	89.92 (6)	N2—C10—H10A	109.1
F5—P1—F4	89.02 (7)	C11—C10—H10A	109.1
C9—N1—C7	107.81 (14)	N2—C10—H10B	109.1
C9—N1—C6	125.48 (14)	C11—C10—H10B	109.1
C7—N1—C6	126.60 (15)	H10A—C10—H10B	107.8
C9—N2—C8	108.63 (14)	C16—C11—C12	118.95 (16)
C9—N2—C10	124.79 (14)	C16—C11—C10	119.61 (15)
C8—N2—C10	126.53 (14)	C12—C11—C10	121.34 (15)
C2—C1—C6	118.79 (17)	C13—C12—C11	120.18 (16)
C2—C1—H1	120.6	C13—C12—H12	119.9
C6—C1—H1	120.6	C11—C12—H12	119.9
C3—C2—C1	120.50 (17)	C12—C13—C14	120.50 (17)
C3—C2—H2	119.8	C12—C13—H13	119.8
C1—C2—H2	119.8	C14—C13—H13	119.8
C4—C3—C2	119.89 (17)	C15—C14—C13	119.44 (17)
C4—C3—H3	120.1	C15—C14—H14	120.3
C2—C3—H3	120.1	C13—C14—H14	120.3
C3—C4—C5	120.38 (17)	C16—C15—C14	120.11 (16)
C3—C4—H4	119.8	C16—C15—H15	119.9
C5—C4—H4	119.8	C14—C15—H15	119.9
C6—C5—C4	119.21 (17)	C15—C16—C11	120.81 (16)
C6—C5—H5	120.4	C15—C16—H16	119.6
C4—C5—H5	120.4	C11—C16—H16	119.6

C6—C1—C2—C3	−1.4 (3)	C8—N2—C9—N1	−0.49 (18)
C1—C2—C3—C4	1.9 (3)	C10—N2—C9—N1	177.44 (14)
C2—C3—C4—C5	−1.0 (3)	C7—N1—C9—N2	0.77 (18)
C3—C4—C5—C6	−0.3 (3)	C6—N1—C9—N2	−175.77 (14)
C4—C5—C6—C1	0.8 (3)	C9—N2—C10—C11	132.27 (16)
C4—C5—C6—N1	−177.50 (15)	C8—N2—C10—C11	−50.2 (2)
C2—C1—C6—C5	0.0 (3)	N2—C10—C11—C16	109.96 (17)
C2—C1—C6—N1	178.40 (15)	N2—C10—C11—C12	−73.7 (2)
C9—N1—C6—C5	−151.02 (16)	C16—C11—C12—C13	0.9 (2)
C7—N1—C6—C5	33.1 (2)	C10—C11—C12—C13	−175.41 (16)
C9—N1—C6—C1	30.6 (2)	C11—C12—C13—C14	−0.4 (3)
C7—N1—C6—C1	−145.30 (16)	C12—C13—C14—C15	−0.4 (3)
C9—N1—C7—C8	−0.76 (18)	C13—C14—C15—C16	0.7 (2)
C6—N1—C7—C8	175.73 (15)	C14—C15—C16—C11	−0.2 (2)
N1—C7—C8—N2	0.46 (18)	C12—C11—C16—C15	−0.6 (2)
C9—N2—C8—C7	0.01 (18)	C10—C11—C16—C15	175.78 (15)
C10—N2—C8—C7	−177.88 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···F1ⁱ	0.95	2.50	3.099 (2)	121
C8—H8···F6ⁱ	0.95	2.50	3.392 (2)	156
C9—H9···F5ⁱⁱ	0.95	2.34	3.247 (2)	159
C10—H10A···F4ⁱⁱ	0.99	2.49	3.444 (2)	161
C10—H10B···F3ⁱⁱⁱ	0.99	2.49	3.455 (3)	164

Symmetry codes: (i) x−1, y−1, z; (ii) x−1, y−1, z−1; (iii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₅N₂⁺·PF₆⁻
M_r	380.27
Crystal system, space group	Triclinic, P1
Temperature (K)	93
a, b, c (Å)	9.221 (2), 10.046 (3), 10.108 (2)
α, β, γ (°)	110.733 (2), 91.969 (2), 110.315 (2)
V (Å³)	807.9 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.43 × 0.40 × 0.37

Data collection
Diffractometer	Rigaku SPIDER diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.905, 0.919
No. of measured, independent and observed [I > 2σ(I)] reflections	4739, 2902, 2361
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.084, 1.00
No. of reflections	2902
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.28

Computer programs: RAPID-AUTO (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···F1ⁱ	0.95	2.50	3.099 (2)	121
C8—H8···F6ⁱ	0.95	2.50	3.392 (2)	156
C9—H9···F5ⁱⁱ	0.95	2.34	3.247 (2)	159
C10—H10A···F4ⁱⁱ	0.99	2.49	3.444 (2)	161
C10—H10B···F3ⁱⁱⁱ	0.99	2.49	3.455 (3)	164

Symmetry codes: (i) x−1, y−1, z; (ii) x−1, y−1, z−1; (iii) −x+1, −y+1, −z+1.

Acknowledgements

The authors thank the Fund Projects of Sichuan Educational department (grant No. 2005 A104).

References

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