1-[Bicyclo[4.2.0]octa-1(6),2,4-trien-3-yl]-3-[bicyclo[4.2.0]octa-1(6),2,4-trien-3-yl­methyl]imidazolium hexa­fluoro­phos­phate

Zhu, F.-H.; Yang, J.-X.; Mao, Z.-H.; Xie, R.-G.

doi:10.1107/S1600536807067086

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o434

doi:10.1107/S1600536807067086

Open

access

1-[Bicyclo[4.2.0]octa-1(6),2,4-trien-3-yl]-3-[bicyclo[4.2.0]octa-1(6),2,4-trien-3-ylmethyl]imidazolium hexafluorophosphate

Fang-Hua Zhu,^a Jun-Xiao Yang,^b Zhi-Hua Mao ^c and Ru-Gang Xie ^a ^*

^aCollege of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China, ^bSchool of Materials Science and Engineering, Southwest University of Science and Technology, Mianyang 621010, People's Republic of China, and ^cAnalytical and Testing Center, Sichuan University, Chengdu 610064, People's Republic of China
^*Correspondence e-mail: orgxie@scu.edu.cn

(Received 29 November 2007; accepted 15 December 2007; online 11 January 2008)

In the title compound, C₂₀H₁₉N₂⁺·PF₆⁻, the two benzocyclobutene units are essentially planar and they form dihedral angles of 38.0 (2) and 72.7 (2)°, with the central imidazolium ring. In the crystal structure, weak C—H⋯π and π-–π stacking interactions [centroid–centroid distance = 3.742 (2) Å] contribute to the stability of the crystal structure. The PF₆⁻ ion is disordered over two positions with site occupancies of 0.869 (9) and 0.131 (9).

Related literature

For related literature, see: Farona (1996 ); Kirchhoff & Bruza (1993 ); Michellys et al. (2001 ); Nemeto & Fukumoto (1998 ); Zhang et al. (2006 ).

Experimental

Crystal data

C₂₀H₁₉N₂⁺·F₆P⁻
M_r = 432.34
Triclinic, $[P \overline 1]$
a = 9.311 (3) Å
b = 10.138 (3) Å
c = 10.562 (3) Å
α = 86.82 (2)°
β = 86.44 (2)°
γ = 73.61 (2)°
V = 953.9 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 296 (2) K
0.28 × 0.25 × 0.18 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
3558 measured reflections
3522 independent reflections
2238 reflections with I > 2σ(I)
R_int = 0.006
3 standard reflections every 300 reflections intensity decay: 4.6%

Refinement

R[F² > 2σ(F²)] = 0.075
wR(F²) = 0.223
S = 1.15
3522 reflections
299 parameters
81 restraints
H-atom parameters constrained
Δρ_max = 0.64 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C3–C8 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2B⋯Cg1ⁱ	0.97	3.00	3.813 (5)	143
Symmetry code: (i) -x+1, -y-1, -z+1.

Data collection: DIFRAC (Gabe & White, 1993 ); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807067086/ci2536sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536807067086/ci2536Isup2.hkl

checkCIF report

Comment top

Benzocyclobutenes (BCBs) are important building blocks for new polymers and advanced materials (Nemeto & Fukumoto, 1998; Michellys et al., 2001). Most of the reported benzocyclobutene monomers in the literature are bis-BCB-functionalized compounds owing to their highly crosslinked structure and their excellent properties such as the insolubility, low solvent pickup and good thermal stability (Farona, 1996; Zhang et al., 2006; Kirchhoff & Bruza, 1993). We report here the crystal structure of the title compound, a novel bisbenzocyclobutene-terminated imidazolium which was obtained by an anion metathesis between 1-(4-benzocyclobutenyl)-3-(4-benzocyclobutenylmethyl) imidazolium choloride and hexafluorophosphate ammonium.

The two benzocyclobutene units are essentially planar. The plane of the C1—C8 and C13—C20 benzocyclobutene units form dihedral angles of 38.0 (2) and 72.7 (2)°, respectively, with the central imidazolium ring.

A combination of intermolecular π-π and C—H···π interactions provide packing forces in the crystal structure of the title compound. A π-π interaction between C13—C15/C18—C20 benzene ring and its symmetry- related counterpart at (-x, 1 - y, -z), with their centroids separated by 3.742 (2) Å, plays an important part in the connection of two adjacent molecules. In addition, a weak C—H···π interaction between C2—H2B group and C3—C8 benzene ring at (1 - x, -1 - y, 1 - z) contributes to the crystal packing (Table 1).

Related literature top

For related literature, see: Farona (1996); Kirchhoff & Bruza (1993); Michellys et al. (2001); Nemeto & Fukumoto (1998); Zhang et al. (2006).

Experimental top

4-(N-imidazolyl)benzocyclobutene (5 mmol, 850 mg) and 4-cholomethylbenzocyclobutene (5 mmol, 760 mg) were placed in a two-necked round-bottomed flask under a nitrogen atmosphere, and the mixture was heated at 353 K for 3 h. After the reaction was completed, the resulting 1-(4-benzocyclobutenyl)-3-(4-benzocyclobutenylmethyl)imidazolium chloride, [BBMI][Cl^-], was obtained in 85% yield (1.381 g). [BBMI][Cl^-] was dissolved in deioned water, and NH₄PF₆ was added to replace Cl^- ions by PF₆^- ions, to obtain the title compound as a white solid (yield 1.331 g). Colourless crystals of the title compound were obtained by recrystallization of the solid from acetone and ethanol (1:1 v/v). ¹ H NMR (400 MHz, CDCl₃,): δ 8.84 (s, 1H), 7.41 (t, 1H), 7.31 (m, 2H), 7.27 (2 d, 1H), 7.22 (d, 1H), 7.18 (d, J = 8.0 Hz, 1H), 7.15 (s, 1H), 7.09 (d, J = 7.6 Hz, 1H), 5.37 (s, 2H), 3.21 (s, 4H), 3.17 (s, 4H); ¹³C NMR (100 MHz, CDCl₃,): δ 148.58, 148.04, 7.65, 147.21, 133.71, 133.42, 130.78, 128.20, 124.45, 123.53, 122.77, 121.88, 121.46, 117.09, 54.52, 29.47, 29.32 p.p.m.

Computing details top

Data collection: DIFRAC (Gabe & White, 1993); cell refinement: DIFRAC (Gabe & White, 1993); data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 2003).

Figures top

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

1-[Bicyclo[4.2.0]octa-1(6),2,4-trien-3-yl]-3-[bicyclo[4.2.0]octa- 1(6),2,4-trien-3-ylmethyl]imidazolium hexafluorophosphate top

Crystal data top

C₂₀H₁₉N₂⁺·F₆P⁻	Z = 2
M_r = 432.34	F(000) = 444
Triclinic, P1	D_x = 1.505 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.311 (3) Å	Cell parameters from 20 reflections
b = 10.138 (3) Å	θ = 4.9–9.1°
c = 10.562 (3) Å	µ = 0.21 mm⁻¹
α = 86.82 (2)°	T = 296 K
β = 86.44 (2)°	Block, colourless
γ = 73.61 (2)°	0.28 × 0.25 × 0.18 mm
V = 953.9 (5) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.006
Radiation source: fine-focus sealed tube	θ_max = 25.5°, θ_min = 1.9°
Graphite monochromator	h = −10→11
ω/2θ scans	k = −2→12
3558 measured reflections	l = −12→12
3522 independent reflections	3 standard reflections every 300 reflections
2238 reflections with I > 2σ(I)	intensity decay: 4.6%

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)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.223	H-atom parameters constrained
S = 1.15	w = 1/[σ²(F_o²) + (0.1349P)²] where P = (F_o² + 2F_c²)/3
3522 reflections	(Δ/σ)_max = 0.001
299 parameters	Δρ_max = 0.64 e Å⁻³
81 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₂₀H₁₉N₂⁺·F₆P⁻	γ = 73.61 (2)°
M_r = 432.34	V = 953.9 (5) Å³
Triclinic, P1	Z = 2
a = 9.311 (3) Å	Mo Kα radiation
b = 10.138 (3) Å	µ = 0.21 mm⁻¹
c = 10.562 (3) Å	T = 296 K
α = 86.82 (2)°	0.28 × 0.25 × 0.18 mm
β = 86.44 (2)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.006
3558 measured reflections	3 standard reflections every 300 reflections
3522 independent reflections	intensity decay: 4.6%
2238 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.075	81 restraints
wR(F²) = 0.223	H-atom parameters constrained
S = 1.15	Δρ_max = 0.64 e Å⁻³
3522 reflections	Δρ_min = −0.41 e Å⁻³
299 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	Occ. (<1)
N1	0.3258 (3)	−0.0608 (3)	0.3056 (3)	0.0388 (7)
N2	0.1779 (3)	0.1062 (3)	0.1997 (3)	0.0412 (7)
C1	0.7078 (6)	−0.4108 (5)	0.5742 (4)	0.0654 (13)
H1A	0.6556	−0.4310	0.6520	0.078*
H1B	0.7911	−0.3758	0.5917	0.078*
C2	0.7481 (5)	−0.5286 (5)	0.4784 (4)	0.0658 (13)
H2A	0.8522	−0.5547	0.4476	0.079*
H2B	0.7152	−0.6086	0.5066	0.079*
C3	0.6426 (4)	−0.4283 (4)	0.3899 (4)	0.0486 (10)
C4	0.5802 (5)	−0.4138 (4)	0.2742 (4)	0.0534 (11)
H4	0.6062	−0.4838	0.2166	0.064*
C5	0.4756 (4)	−0.2881 (4)	0.2472 (3)	0.0477 (10)
H5	0.4297	−0.2731	0.1700	0.057*
C6	0.4397 (4)	−0.1854 (4)	0.3348 (3)	0.0385 (8)
C7	0.5044 (4)	−0.2001 (4)	0.4520 (3)	0.0452 (9)
H7	0.4809	−0.1304	0.5099	0.054*
C8	0.6057 (5)	−0.3256 (4)	0.4753 (3)	0.0474 (9)
C9	0.2990 (4)	0.0017 (3)	0.1915 (3)	0.0381 (8)
H9	0.3572	−0.0247	0.1175	0.046*
C10	0.1233 (5)	0.1122 (4)	0.3233 (4)	0.0583 (12)
H10	0.0378	0.1759	0.3552	0.070*
C11	0.2151 (5)	0.0095 (4)	0.3902 (4)	0.0525 (10)
H11	0.2059	−0.0104	0.4768	0.063*
C12	0.1133 (4)	0.2028 (4)	0.0937 (3)	0.0457 (9)
H12A	0.0101	0.2026	0.0854	0.055*
H12B	0.1688	0.1715	0.0150	0.055*
C13	0.1181 (4)	0.3462 (4)	0.1145 (3)	0.0394 (8)
C14	−0.0027 (4)	0.4358 (4)	0.1797 (3)	0.0414 (9)
H14	−0.0882	0.4103	0.2072	0.050*
C15	0.0126 (4)	0.5639 (4)	0.2006 (3)	0.0446 (9)
C16	−0.0632 (5)	0.7005 (4)	0.2603 (5)	0.0611 (12)
H16A	−0.0769	0.6945	0.3520	0.073*
H16B	−0.1550	0.7522	0.2215	0.073*
C17	0.0771 (5)	0.7460 (4)	0.2122 (4)	0.0613 (12)
H17A	0.0569	0.8218	0.1496	0.074*
H17B	0.1360	0.7622	0.2793	0.074*
C18	0.1361 (4)	0.6058 (4)	0.1564 (3)	0.0448 (9)
C19	0.2544 (4)	0.5185 (4)	0.0891 (4)	0.0494 (10)
H19	0.3375	0.5464	0.0583	0.059*
C20	0.2429 (4)	0.3886 (4)	0.0702 (3)	0.0465 (10)
H20	0.3209	0.3271	0.0264	0.056*
P1	0.67915 (11)	0.11989 (10)	0.17994 (9)	0.0466 (4)
F1	0.5204 (3)	0.1791 (4)	0.2485 (3)	0.0890 (10)
F2	0.8367 (3)	0.0567 (3)	0.1101 (3)	0.0964 (11)
F3	0.6267 (4)	0.0006 (4)	0.1205 (3)	0.0908 (17)	0.869 (9)
F4	0.7321 (5)	0.0220 (4)	0.2990 (3)	0.109 (2)	0.869 (9)
F5	0.7340 (4)	0.2334 (4)	0.2388 (5)	0.112 (2)	0.869 (9)
F6	0.6275 (5)	0.2124 (5)	0.0586 (4)	0.120 (2)	0.869 (9)
F3A	0.6793 (7)	−0.018 (2)	0.2185 (12)	0.127 (14)	0.131 (9)
F4A	0.7527 (10)	0.1314 (12)	0.3022 (15)	0.090 (10)	0.131 (9)
F5A	0.6805 (7)	0.260 (2)	0.1369 (12)	0.103 (11)	0.131 (9)
F6A	0.6104 (10)	0.1040 (12)	0.0613 (16)	0.093 (10)	0.131 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0443 (17)	0.0364 (15)	0.0320 (15)	−0.0048 (13)	−0.0036 (12)	−0.0025 (12)
N2	0.0480 (18)	0.0395 (16)	0.0332 (15)	−0.0068 (14)	−0.0038 (13)	−0.0028 (12)
C1	0.075 (3)	0.066 (3)	0.047 (2)	−0.005 (2)	−0.023 (2)	0.011 (2)
C2	0.064 (3)	0.065 (3)	0.056 (3)	0.002 (2)	−0.013 (2)	0.012 (2)
C3	0.046 (2)	0.051 (2)	0.042 (2)	−0.0017 (18)	−0.0069 (16)	0.0010 (17)
C4	0.050 (2)	0.055 (2)	0.046 (2)	0.0046 (18)	−0.0117 (17)	−0.0145 (18)
C5	0.049 (2)	0.055 (2)	0.0348 (19)	−0.0043 (18)	−0.0110 (16)	−0.0087 (17)
C6	0.0361 (18)	0.0414 (19)	0.0340 (17)	−0.0041 (15)	−0.0050 (14)	0.0004 (14)
C7	0.057 (2)	0.048 (2)	0.0287 (17)	−0.0099 (18)	−0.0066 (16)	−0.0024 (15)
C8	0.055 (2)	0.050 (2)	0.0331 (18)	−0.0094 (18)	−0.0107 (16)	0.0070 (16)
C9	0.044 (2)	0.0407 (19)	0.0286 (16)	−0.0088 (16)	−0.0053 (14)	−0.0017 (14)
C10	0.068 (3)	0.049 (2)	0.042 (2)	0.008 (2)	0.0080 (19)	−0.0024 (18)
C11	0.061 (3)	0.050 (2)	0.0356 (19)	0.0015 (19)	0.0081 (18)	−0.0034 (16)
C12	0.052 (2)	0.046 (2)	0.0351 (18)	−0.0040 (17)	−0.0135 (16)	−0.0021 (16)
C13	0.0406 (19)	0.0434 (19)	0.0305 (17)	−0.0041 (15)	−0.0117 (14)	0.0019 (14)
C14	0.0363 (19)	0.043 (2)	0.0417 (19)	−0.0050 (15)	−0.0094 (15)	0.0040 (15)
C15	0.041 (2)	0.043 (2)	0.044 (2)	−0.0004 (16)	−0.0123 (16)	0.0019 (16)
C16	0.058 (3)	0.043 (2)	0.075 (3)	−0.0011 (19)	−0.008 (2)	−0.008 (2)
C17	0.063 (3)	0.050 (2)	0.071 (3)	−0.015 (2)	−0.014 (2)	−0.002 (2)
C18	0.045 (2)	0.047 (2)	0.0414 (19)	−0.0100 (17)	−0.0131 (16)	0.0077 (16)
C19	0.042 (2)	0.064 (3)	0.044 (2)	−0.0179 (19)	−0.0051 (17)	0.0037 (18)
C20	0.040 (2)	0.056 (2)	0.0373 (19)	−0.0024 (17)	−0.0069 (16)	−0.0042 (17)
P1	0.0469 (6)	0.0481 (6)	0.0409 (6)	−0.0061 (5)	−0.0024 (4)	−0.0045 (4)
F1	0.0595 (17)	0.125 (2)	0.0650 (17)	0.0038 (16)	0.0102 (13)	−0.0246 (17)
F2	0.0592 (18)	0.098 (2)	0.127 (3)	−0.0126 (16)	0.0273 (18)	−0.042 (2)
F3	0.093 (3)	0.122 (4)	0.078 (3)	−0.060 (3)	0.027 (2)	−0.048 (3)
F4	0.165 (4)	0.074 (3)	0.054 (2)	0.023 (3)	−0.021 (2)	0.0058 (18)
F5	0.105 (3)	0.082 (3)	0.158 (5)	−0.031 (2)	0.003 (3)	−0.061 (3)
F6	0.151 (4)	0.106 (4)	0.060 (2)	0.024 (3)	0.002 (2)	0.034 (2)
F3A	0.122 (19)	0.094 (16)	0.18 (2)	−0.059 (14)	−0.017 (16)	0.033 (16)
F4A	0.077 (13)	0.105 (19)	0.079 (13)	−0.006 (12)	−0.049 (11)	0.013 (12)
F5A	0.140 (19)	0.086 (15)	0.091 (17)	−0.050 (13)	0.001 (14)	0.004 (13)
F6A	0.145 (18)	0.095 (17)	0.052 (12)	−0.048 (14)	−0.024 (11)	−0.012 (12)

Geometric parameters (Å, º) top

N1—C9	1.334 (4)	C12—H12B	0.97
N1—C11	1.382 (4)	C13—C20	1.395 (5)
N1—C6	1.435 (4)	C13—C14	1.400 (5)
N2—C9	1.313 (4)	C14—C15	1.378 (5)
N2—C10	1.370 (5)	C14—H14	0.93
N2—C12	1.484 (4)	C15—C18	1.381 (6)
C1—C8	1.517 (5)	C15—C16	1.518 (5)
C1—C2	1.558 (6)	C16—C17	1.552 (7)
C1—H1A	0.97	C16—H16A	0.97
C1—H1B	0.97	C16—H16B	0.97
C2—C3	1.522 (5)	C17—C18	1.510 (5)
C2—H2A	0.97	C17—H17A	0.97
C2—H2B	0.97	C17—H17B	0.97
C3—C4	1.368 (5)	C18—C19	1.387 (5)
C3—C8	1.371 (5)	C19—C20	1.378 (5)
C4—C5	1.395 (5)	C19—H19	0.93
C4—H4	0.93	C20—H20	0.93
C5—C6	1.386 (5)	P1—F3A	1.43 (3)
C5—H5	0.93	P1—F5A	1.47 (2)
C6—C7	1.393 (5)	P1—F6A	1.48 (2)
C7—C8	1.373 (5)	P1—F4A	1.524 (18)
C7—H7	0.93	P1—F5	1.556 (4)
C9—H9	0.93	P1—F6	1.563 (4)
C10—C11	1.343 (5)	P1—F4	1.572 (4)
C10—H10	0.93	P1—F1	1.576 (3)
C11—H11	0.93	P1—F2	1.579 (3)
C12—C13	1.497 (5)	P1—F3	1.597 (4)
C12—H12A	0.97

C9—N1—C11	107.5 (3)	C15—C14—H14	122.0
C9—N1—C6	126.8 (3)	C13—C14—H14	122.0
C11—N1—C6	125.4 (3)	C14—C15—C18	123.0 (3)
C9—N2—C10	108.2 (3)	C14—C15—C16	144.1 (4)
C9—N2—C12	125.8 (3)	C18—C15—C16	93.0 (3)
C10—N2—C12	125.9 (3)	C15—C16—C17	86.7 (3)
C8—C1—C2	86.7 (3)	C15—C16—H16A	114.2
C8—C1—H1A	114.2	C17—C16—H16A	114.2
C2—C1—H1A	114.2	C15—C16—H16B	114.2
C8—C1—H1B	114.2	C17—C16—H16B	114.2
C2—C1—H1B	114.2	H16A—C16—H16B	111.4
H1A—C1—H1B	111.4	C18—C17—C16	86.8 (3)
C3—C2—C1	86.3 (3)	C18—C17—H17A	114.2
C3—C2—H2A	114.3	C16—C17—H17A	114.2
C1—C2—H2A	114.3	C18—C17—H17B	114.2
C3—C2—H2B	114.3	C16—C17—H17B	114.2
C1—C2—H2B	114.3	H17A—C17—H17B	111.3
H2A—C2—H2B	111.4	C15—C18—C19	121.1 (4)
C4—C3—C8	122.4 (3)	C15—C18—C17	93.5 (3)
C4—C3—C2	144.0 (4)	C19—C18—C17	145.3 (4)
C8—C3—C2	93.5 (3)	C20—C19—C18	116.7 (4)
C3—C4—C5	116.3 (3)	C20—C19—H19	121.6
C3—C4—H4	121.8	C18—C19—H19	121.6
C5—C4—H4	121.8	C19—C20—C13	122.2 (3)
C6—C5—C4	120.5 (3)	C19—C20—H20	118.9
C6—C5—H5	119.8	C13—C20—H20	118.9
C4—C5—H5	119.8	F3A—P1—F5A	178.4 (5)
C5—C6—C7	123.0 (3)	F3A—P1—F6A	88.8 (6)
C5—C6—N1	118.5 (3)	F5A—P1—F6A	90.0 (6)
C7—C6—N1	118.5 (3)	F3A—P1—F4A	89.6 (6)
C8—C7—C6	114.7 (3)	F5A—P1—F4A	91.5 (6)
C8—C7—H7	122.7	F6A—P1—F4A	178.2 (6)
C6—C7—H7	122.7	F5—P1—F6	92.2 (3)
C3—C8—C7	123.1 (3)	F5—P1—F4	89.7 (3)
C3—C8—C1	93.5 (3)	F6—P1—F4	177.9 (2)
C7—C8—C1	143.4 (3)	F3A—P1—F1	91.1 (2)
N2—C9—N1	109.6 (3)	F5A—P1—F1	90.1 (2)
N2—C9—H9	125.2	F6A—P1—F1	91.5 (2)
N1—C9—H9	125.2	F4A—P1—F1	89.5 (2)
C11—C10—N2	107.8 (3)	F5—P1—F1	89.43 (19)
C11—C10—H10	126.1	F6—P1—F1	90.82 (19)
N2—C10—H10	126.1	F4—P1—F1	90.17 (19)
C10—C11—N1	106.8 (3)	F3A—P1—F2	87.5 (2)
C10—C11—H11	126.6	F5A—P1—F2	91.3 (2)
N1—C11—H11	126.6	F6A—P1—F2	87.4 (2)
N2—C12—C13	111.8 (3)	F4A—P1—F2	91.5 (2)
N2—C12—H12A	109.3	F5—P1—F2	92.30 (19)
C13—C12—H12A	109.3	F6—P1—F2	89.4 (2)
N2—C12—H12B	109.3	F4—P1—F2	89.5 (2)
C13—C12—H12B	109.3	F1—P1—F2	178.25 (18)
H12A—C12—H12B	107.9	F5—P1—F3	178.5 (2)
C20—C13—C14	120.9 (3)	F6—P1—F3	88.8 (3)
C20—C13—C12	119.8 (3)	F4—P1—F3	89.3 (2)
C14—C13—C12	119.3 (3)	F1—P1—F3	91.61 (18)
C15—C14—C13	116.0 (4)	F2—P1—F3	86.66 (17)

C8—C1—C2—C3	0.8 (3)	C12—N2—C10—C11	−178.3 (4)
C1—C2—C3—C4	−177.7 (7)	N2—C10—C11—N1	−0.8 (5)
C1—C2—C3—C8	−0.9 (4)	C9—N1—C11—C10	0.7 (5)
C8—C3—C4—C5	−0.3 (7)	C6—N1—C11—C10	−174.1 (4)
C2—C3—C4—C5	176.0 (6)	C9—N2—C12—C13	−115.5 (4)
C3—C4—C5—C6	0.3 (7)	C10—N2—C12—C13	63.2 (5)
C4—C5—C6—C7	0.4 (7)	N2—C12—C13—C20	89.8 (4)
C4—C5—C6—N1	−176.8 (4)	N2—C12—C13—C14	−89.5 (4)
C9—N1—C6—C5	−35.6 (6)	C20—C13—C14—C15	−2.4 (5)
C11—N1—C6—C5	138.2 (4)	C12—C13—C14—C15	177.0 (3)
C9—N1—C6—C7	147.2 (4)	C13—C14—C15—C18	2.5 (5)
C11—N1—C6—C7	−39.0 (5)	C13—C14—C15—C16	−178.8 (5)
C5—C6—C7—C8	−0.9 (6)	C14—C15—C16—C17	−179.7 (5)
N1—C6—C7—C8	176.2 (3)	C18—C15—C16—C17	−0.8 (3)
C4—C3—C8—C7	−0.3 (7)	C15—C16—C17—C18	0.8 (3)
C2—C3—C8—C7	−178.1 (4)	C14—C15—C18—C19	−1.0 (6)
C4—C3—C8—C1	178.7 (4)	C16—C15—C18—C19	179.7 (3)
C2—C3—C8—C1	0.9 (4)	C14—C15—C18—C17	−179.9 (3)
C6—C7—C8—C3	0.9 (6)	C16—C15—C18—C17	0.9 (3)
C6—C7—C8—C1	−177.5 (6)	C16—C17—C18—C15	−0.9 (3)
C2—C1—C8—C3	−0.9 (4)	C16—C17—C18—C19	−179.2 (6)
C2—C1—C8—C7	177.7 (6)	C15—C18—C19—C20	−0.7 (5)
C10—N2—C9—N1	−0.2 (4)	C17—C18—C19—C20	177.3 (5)
C12—N2—C9—N1	178.7 (3)	C18—C19—C20—C13	0.8 (5)
C11—N1—C9—N2	−0.3 (4)	C14—C13—C20—C19	0.8 (5)
C6—N1—C9—N2	174.4 (3)	C12—C13—C20—C19	−178.6 (3)
C9—N2—C10—C11	0.6 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···Cg1ⁱ	0.97	3.00	3.813 (5)	143

Symmetry code: (i) −x+1, −y−1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₉N₂⁺·F₆P⁻
M_r	432.34
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	9.311 (3), 10.138 (3), 10.562 (3)
α, β, γ (°)	86.82 (2), 86.44 (2), 73.61 (2)
V (Å³)	953.9 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.28 × 0.25 × 0.18

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3558, 3522, 2238
R_int	0.006
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.075, 0.223, 1.15
No. of reflections	3522
No. of parameters	299
No. of restraints	81
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.64, −0.41

Computer programs: DIFRAC (Gabe & White, 1993), NRCVAX (Gabe et al., 1989), SHELXS97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996), SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···Cg1ⁱ	0.97	3.00	3.813 (5)	143

Symmetry code: (i) −x+1, −y−1, −z+1.

Acknowledgements

The authors are grateful to the National Natural Science Foundation of China (grant No. 20574046) for financial support.

References

Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Farona, M. F. (1996). Prog. Polym. Sci. 21, 505–555. CrossRef CAS Web of Science Google Scholar
Gabe, E. J., Le Page, Y., Charland, J.-P., Lee, F. L. & White, P. S. (1989). J. Appl. Cryst. 22, 384–387. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gabe, E. J. & White, P. S. (1993). DIFRAC. American Crystallographic Association, Pittsburgh Meeting. Abstract PA104. Google Scholar
Kirchhoff, R. A. & Bruza, K. J. (1993). Prog. Polym. Sci. 18, 85–185. CrossRef CAS Web of Science Google Scholar
Michellys, P., Maurin, P., Toupet, L., Pellissier, H. & Santelli, M. (2001). J. Org. Chem. 66, 115–122. Web of Science CSD CrossRef PubMed CAS Google Scholar
Nemeto, H. & Fukumoto, K. (1998). Tetrahedron, 54, 5425–5464. Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, Y., Gao, J., Shen, X. & Huang, F. (2006). J. Appl. Polym. Sci. 99, 1705–1719. Web of Science CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o434

doi:10.1107/S1600536807067086

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1-[Bi­cyclo[4.2.0]octa-1(6),2,4-trien-3-yl]-3-[bi­cyclo[4.2.0]octa-1(6),2,4-trien-3-yl­methyl]imidazolium hexa­fluoro­phos­phate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1-[Bicyclo[4.2.0]octa-1(6),2,4-trien-3-yl]-3-[bicyclo[4.2.0]octa-1(6),2,4-trien-3-ylmethyl]imidazolium hexafluorophosphate