1-Benzyl-3-[3-(naphthalen-2-yl­oxy)prop­yl]imidazolium hexa­fluoro­phosphate

Huang, K.; Du, B.-X.; Liu, C.-L.

doi:10.1107/S1600536811026663

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2062

doi:10.1107/S1600536811026663

Open

access

1-Benzyl-3-[3-(naphthalen-2-yloxy)propyl]imidazolium hexafluorophosphate

Kun Huang,^a ^* Bin-Xin Du ^b and Chang-Lu Liu ^a

^aDepartment of Chemistry and Chemical Engineering, Sichuan University of Arts and Science, Dazhou 635000, People's Republic of China, and ^bSichuan University of Arts and Science, Dazhou 635000, People's Republic of China
^*Correspondence e-mail: greatwall520@163.com

(Received 14 June 2011; accepted 4 July 2011; online 16 July 2011)

In the title salt, C₂₃H₂₃N₂O⁺·PF₆⁻, the PF₆⁻ anion is highly disordered (occupancy ratios of 0.35:0.35:0.3, 0.7:0.15:0.15, 0.7:0.3 and 0.35:0.35:0.15:0.15) with the four F atoms in the equatorial plane rotating about the axial F—P—F bond. The mean plane of the imidazole ring makes dihedral angles of 82.44 (17) and 14.39 (16)°, respectively, with the mean planes of the benzene ring and the naphthalene ring system. The crystal structure is stabilized by C—H⋯F hydrogen bonds. In addition, π–π [centroid–centroid distances = 3.7271 (19)–3.8895 (17) Å] and C—H⋯π interactions are observed.

Related literature

For the first free carbenes isolated, see: Arduengo et al. (1991 ). For applications of N-heterocyclic carbene ligands in transmetalation, see: Lin et al. (2009 ); Wang, Song et al. (2005 ); Wang, Xu et al. (2005 ). For the synthesis of the title compound, see: Corma et al. (2004 ). For related structures, see: Wang, Song et al. (2005). For standard bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₃H₂₃N₂O⁺·PF₆⁻
M_r = 488.40
Monoclinic, C 2/c
a = 28.3309 (5) Å
b = 10.2447 (2) Å
c = 20.0969 (4) Å
β = 130.296 (1)°
V = 4448.87 (15) Å³
Z = 8
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 296 K
0.20 × 0.20 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.963, T_max = 0.972
19608 measured reflections
5095 independent reflections
3915 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.145
S = 1.04
5095 reflections
371 parameters
210 restraints
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C4/C9/C10 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯F2ⁱ	0.93	2.41	3.304 (3)	160
C19—H19⋯F2ⁱⁱ	0.93	2.49	3.393 (3)	162
C14—H14⋯F4A	0.93	2.48	3.406 (6)	171
C4—H4⋯F5Aⁱⁱⁱ	0.93	2.55	3.315 (11)	140
C13—H13B⋯Cg2^iv	0.97	2.65	3.560 (3)	157
Symmetry codes: (i) x, y+1, z; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) -x, -y+1, -z; (iv) -x, -y+2, -z.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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/S1600536811026663/lr2017sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811026663/lr2017Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811026663/lr2017Isup3.cml

checkCIF report

Comment top

The discovery of the first free N-heterocyclic carbene (NHC) was disclosed by Arduengo and coworks (Arduengo et al., 1991). 1,3-disubstituted imidazolium salts are widely used as precursors for the synthesize of transition metal NHC's (Lin et al., 2009; Wang, Song et al., 2005; Wang, Xu et al., 2005). Herein we report on the crystal structure of the title compound, a new NHC precursor.

The molecular structure of the title compound is shown in Fig. 1. Bond lengths (Allen et al., 1987) and angles in the cation are normal. The mean plane of the imidazole ring makes dihedral angles with the mean planes of the benzene and naphthalene rings of 82.44 (17)° and 14.39 (16)°, respectively. The PF₆^- is disordered with as many as three sites found for some of the four F atoms (F3—F6) in the equatorial plane.

In the crystal there are weak π–π interactions involving the imidazole and naphthalene rings with centroid-centroid distances, Cg1···Cg3ⁱ, Cg2···Cg3ⁱⁱ and Cg2···Cg2ⁱⁱ of 3.731 (2), 3.7271 (19) and 3.8895 (17) Å, respectively [symmetry codes: (i) -x, 2 - y, -z; (ii) -x, y, -1/2 -z. Cg1 centroid of the imidazole ring (N1,N2,C14—C16); Cg2 centroid of ring (C1—C4,C9,C10); Cg3 centroid of ring (C5—C10)]. In addition, C—H···F hydrogen bonds and C—H···π interactions are observed (Table 1 and Fig. 2).

Related literature top

For the first free carbenes isolated, see: Arduengo et al. (1991). For applications of N-heterocyclic carbene ligands in transmetalation, see: Lin et al. (2009); Wang, Song et al. (2005); Wang, Xu et al. (2005). For the synthesis of the title compound, see: Corma et al. (2004). For related structures, see: Wang, Song et al. (2005). For standard bond lengths, see: Allen et al. (1987).

Experimental top

The title compound was prepared according to the reported procedures (Corma et al., 2004). Colourless single crystals suitable for X-ray diffraction were obtained by recrystallization from acetonitrile and ethyl ether (v:v = 1:1).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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. A view of the molecular structure of the title compound with atom numbering. The displacement ellipsoids are drawn at the 30% probability level. Only part of the disordered PF₆^- atoms are shown.
	Fig. 2. Part of crystal packing of the title compound, showing the cations and anions linked via C—H···F interactions (dashed lines). H atoms not involved in these interactions have been omitted for clarity.

1-Benzyl-3-[3-(naphthalen-2-yloxy)propyl]imidazolium hexafluorophosphate top

Crystal data top

C₂₃H₂₃N₂O⁺·PF₆⁻	F(000) = 2016
M_r = 488.40	D_x = 1.458 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5985 reflections
a = 28.3309 (5) Å	θ = 2.7–27.2°
b = 10.2447 (2) Å	µ = 0.19 mm⁻¹
c = 20.0969 (4) Å	T = 296 K
β = 130.296 (1)°	Block, colourless
V = 4448.87 (15) Å³	0.20 × 0.20 × 0.15 mm
Z = 8

Data collection top

Bruker SMART CCD area-detector diffractometer	5095 independent reflections
Radiation source: fine-focus sealed tube	3915 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ϕ and ω scans	θ_max = 27.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −36→36
T_min = 0.963, T_max = 0.972	k = −13→13
19608 measured reflections	l = −26→26

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.057	H-atom parameters constrained
wR(F²) = 0.145	w = 1/[σ²(F_o²) + (0.0515P)² + 4.9635P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.003
5095 reflections	Δρ_max = 0.35 e Å⁻³
371 parameters	Δρ_min = −0.39 e Å⁻³
210 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00093 (14)

Crystal data top

C₂₃H₂₃N₂O⁺·PF₆⁻	V = 4448.87 (15) Å³
M_r = 488.40	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 28.3309 (5) Å	µ = 0.19 mm⁻¹
b = 10.2447 (2) Å	T = 296 K
c = 20.0969 (4) Å	0.20 × 0.20 × 0.15 mm
β = 130.296 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	5095 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3915 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.972	R_int = 0.031
19608 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	210 restraints
wR(F²) = 0.145	H-atom parameters constrained
S = 1.04	Δρ_max = 0.35 e Å⁻³
5095 reflections	Δρ_min = −0.39 e Å⁻³
371 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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)
O1	0.06916 (7)	0.87976 (16)	−0.00405 (10)	0.0616 (5)
N1	0.20226 (8)	1.10961 (17)	0.27117 (11)	0.0448 (5)
N2	0.27187 (8)	1.03723 (18)	0.40219 (11)	0.0488 (6)
C1	−0.00745 (9)	0.9740 (2)	−0.14818 (13)	0.0479 (6)
C2	0.02224 (10)	0.8706 (2)	−0.09241 (13)	0.0475 (6)
C3	0.00510 (10)	0.7413 (2)	−0.12412 (15)	0.0521 (7)
C4	−0.04215 (10)	0.7189 (2)	−0.21032 (15)	0.0535 (7)
C5	−0.12511 (11)	0.8038 (3)	−0.35933 (15)	0.0605 (8)
C6	−0.15535 (11)	0.9062 (3)	−0.41528 (15)	0.0659 (9)
C7	−0.13672 (11)	1.0334 (3)	−0.38480 (15)	0.0611 (8)
C8	−0.08860 (10)	1.0564 (2)	−0.29828 (15)	0.0547 (7)
C9	−0.05671 (9)	0.9525 (2)	−0.23861 (13)	0.0447 (6)
C10	−0.07497 (9)	0.8233 (2)	−0.27019 (13)	0.0473 (7)
C11	0.08538 (10)	1.0064 (2)	0.03396 (14)	0.0536 (7)
C12	0.13234 (10)	0.9878 (2)	0.13195 (14)	0.0539 (7)
C13	0.14909 (9)	1.1174 (2)	0.17730 (13)	0.0490 (7)
C14	0.22160 (9)	1.0060 (2)	0.32192 (13)	0.0459 (6)
C15	0.28478 (12)	1.1662 (2)	0.40219 (16)	0.0619 (8)
C16	0.24136 (11)	1.2109 (2)	0.32116 (16)	0.0600 (8)
C17	0.30690 (10)	0.9486 (3)	0.47728 (14)	0.0582 (8)
C18	0.37109 (10)	0.9213 (2)	0.50999 (14)	0.0505 (7)
C19	0.38433 (11)	0.9188 (3)	0.45503 (16)	0.0627 (9)
C20	0.44286 (13)	0.8888 (3)	0.4866 (2)	0.0774 (11)
C21	0.48900 (14)	0.8610 (3)	0.5734 (2)	0.0828 (10)
C22	0.47645 (13)	0.8651 (3)	0.6284 (2)	0.0845 (10)
C23	0.41781 (12)	0.8944 (3)	0.59729 (16)	0.0688 (9)
H1	0.00460	1.05870	−0.12690	0.0580*
H3	0.02620	0.67140	−0.08600	0.0620*
H4	−0.05320	0.63340	−0.23040	0.0640*
H5	−0.13790	0.71910	−0.38050	0.0730*
H6	−0.18850	0.89110	−0.47400	0.0790*
H7	−0.15700	1.10310	−0.42340	0.0730*
H8	−0.07680	1.14190	−0.27850	0.0660*
H11A	0.04910	1.05140	0.01760	0.0640*
H11B	0.10310	1.05770	0.01420	0.0640*
H12A	0.11520	0.93120	0.15040	0.0650*
H12B	0.16920	0.94650	0.14780	0.0650*
H13A	0.15860	1.17850	0.15050	0.0590*
H13B	0.11370	1.15110	0.16920	0.0590*
H14	0.20300	0.92410	0.30420	0.0550*
H15	0.31760	1.21370	0.44970	0.0740*
H16	0.23820	1.29570	0.30210	0.0720*
H17A	0.28460	0.86680	0.46090	0.0700*
H17B	0.30990	0.98660	0.52410	0.0700*
H19	0.35340	0.93770	0.39610	0.0750*
H20	0.45130	0.88720	0.44890	0.0930*
H21	0.52850	0.83950	0.59450	0.1000*
H22	0.50780	0.84800	0.68750	0.1010*
H23	0.40970	0.89610	0.63530	0.0830*
P1	0.19683 (3)	0.60238 (6)	0.31472 (4)	0.0536 (2)
F1	0.19758 (14)	0.6908 (2)	0.37951 (18)	0.1311 (13)
F2	0.20206 (13)	0.5170 (2)	0.25553 (14)	0.1257 (12)
F3A1	0.2634 (5)	0.6501 (17)	0.3723 (11)	0.131 (5)	0.350
F3A2	0.2482 (4)	0.6998 (10)	0.3320 (8)	0.071 (3)	0.350
F3B	0.2173 (9)	0.7164 (9)	0.2875 (11)	0.102 (5)	0.300
F4A	0.1558 (4)	0.7068 (5)	0.2407 (3)	0.148 (2)	0.700
F4B1	0.1325 (7)	0.617 (2)	0.2333 (15)	0.138 (6)	0.150
F4B2	0.1395 (9)	0.665 (3)	0.2819 (19)	0.137 (9)	0.150
F5A	0.1349 (3)	0.5355 (9)	0.2739 (7)	0.221 (4)	0.700
F5B	0.1705 (8)	0.4928 (12)	0.3317 (10)	0.100 (5)	0.300
F6A1	0.2462 (7)	0.5115 (12)	0.3909 (7)	0.097 (4)	0.350
F6A2	0.2118 (8)	0.4825 (11)	0.3762 (7)	0.094 (4)	0.350
F6B1	0.2609 (7)	0.540 (3)	0.3665 (14)	0.104 (7)	0.150
F6B2	0.2639 (11)	0.566 (4)	0.3971 (15)	0.115 (8)	0.150

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0601 (9)	0.0549 (10)	0.0432 (8)	0.0002 (8)	0.0215 (7)	−0.0003 (7)
N1	0.0444 (9)	0.0445 (9)	0.0433 (9)	0.0008 (7)	0.0274 (8)	−0.0019 (7)
N2	0.0472 (9)	0.0547 (11)	0.0414 (9)	−0.0020 (8)	0.0272 (8)	−0.0037 (8)
C1	0.0472 (11)	0.0462 (11)	0.0476 (11)	−0.0061 (9)	0.0294 (10)	−0.0051 (9)
C2	0.0438 (10)	0.0530 (12)	0.0417 (10)	−0.0021 (9)	0.0258 (9)	0.0000 (9)
C3	0.0559 (12)	0.0466 (12)	0.0528 (12)	0.0024 (10)	0.0347 (11)	0.0040 (10)
C4	0.0610 (13)	0.0441 (12)	0.0572 (13)	−0.0051 (10)	0.0390 (12)	−0.0068 (10)
C5	0.0597 (14)	0.0635 (15)	0.0489 (13)	−0.0043 (11)	0.0309 (11)	−0.0132 (11)
C6	0.0550 (13)	0.0847 (19)	0.0429 (12)	0.0063 (13)	0.0249 (11)	−0.0081 (12)
C7	0.0583 (14)	0.0700 (16)	0.0488 (13)	0.0154 (12)	0.0319 (11)	0.0087 (11)
C8	0.0554 (13)	0.0520 (13)	0.0528 (12)	0.0031 (10)	0.0333 (11)	0.0019 (10)
C9	0.0415 (10)	0.0514 (12)	0.0439 (10)	−0.0017 (9)	0.0288 (9)	−0.0017 (9)
C10	0.0460 (11)	0.0530 (12)	0.0453 (11)	−0.0017 (9)	0.0306 (10)	−0.0055 (9)
C11	0.0480 (11)	0.0564 (13)	0.0439 (11)	−0.0020 (10)	0.0241 (10)	−0.0017 (10)
C12	0.0473 (11)	0.0575 (13)	0.0450 (11)	0.0009 (10)	0.0245 (10)	0.0001 (10)
C13	0.0439 (11)	0.0556 (13)	0.0419 (11)	0.0048 (9)	0.0252 (9)	0.0032 (9)
C14	0.0445 (10)	0.0468 (11)	0.0431 (10)	−0.0056 (9)	0.0268 (9)	−0.0046 (9)
C15	0.0651 (15)	0.0518 (13)	0.0556 (14)	−0.0115 (11)	0.0331 (12)	−0.0165 (11)
C16	0.0647 (14)	0.0434 (12)	0.0578 (14)	−0.0062 (11)	0.0333 (12)	−0.0090 (10)
C17	0.0536 (13)	0.0743 (16)	0.0404 (11)	−0.0015 (11)	0.0276 (10)	0.0047 (11)
C18	0.0511 (12)	0.0472 (12)	0.0426 (11)	−0.0058 (9)	0.0255 (10)	−0.0031 (9)
C19	0.0578 (14)	0.0751 (17)	0.0500 (13)	−0.0036 (12)	0.0325 (11)	−0.0086 (12)
C20	0.0726 (17)	0.081 (2)	0.089 (2)	−0.0050 (15)	0.0570 (17)	−0.0115 (16)
C21	0.0587 (16)	0.0665 (18)	0.105 (2)	0.0072 (13)	0.0448 (18)	0.0044 (17)
C22	0.0608 (16)	0.083 (2)	0.0673 (18)	0.0112 (15)	0.0223 (14)	0.0197 (16)
C23	0.0647 (15)	0.0763 (17)	0.0480 (13)	0.0036 (13)	0.0286 (12)	0.0109 (12)
P1	0.0594 (4)	0.0487 (3)	0.0567 (4)	0.0039 (3)	0.0394 (3)	0.0031 (3)
F1	0.214 (3)	0.0915 (15)	0.175 (2)	−0.0149 (16)	0.165 (2)	−0.0274 (15)
F2	0.220 (3)	0.0890 (14)	0.1101 (16)	−0.0037 (15)	0.1257 (18)	−0.0170 (12)
F4A	0.173 (5)	0.086 (3)	0.107 (3)	0.039 (3)	0.055 (3)	0.045 (2)
F5A	0.114 (4)	0.182 (7)	0.290 (9)	−0.075 (4)	0.096 (5)	−0.006 (7)
F3A1	0.084 (5)	0.156 (12)	0.125 (10)	−0.036 (7)	0.055 (6)	−0.045 (8)
F3A2	0.066 (5)	0.075 (6)	0.092 (7)	−0.014 (4)	0.060 (5)	−0.005 (5)
F4B1	0.035 (6)	0.090 (12)	0.118 (14)	0.010 (8)	−0.027 (7)	0.013 (11)
F3B	0.184 (13)	0.053 (4)	0.127 (9)	0.022 (8)	0.127 (9)	0.030 (6)
F4B2	0.069 (10)	0.108 (15)	0.183 (19)	0.034 (10)	0.059 (12)	−0.026 (16)
F6A1	0.113 (9)	0.075 (7)	0.062 (4)	0.030 (7)	0.038 (6)	0.024 (4)
F5B	0.144 (10)	0.087 (7)	0.128 (9)	−0.066 (7)	0.115 (8)	−0.047 (7)
F6A2	0.140 (10)	0.074 (6)	0.075 (6)	0.034 (8)	0.073 (7)	0.030 (5)
F6B1	0.062 (7)	0.120 (14)	0.160 (14)	0.027 (8)	0.085 (9)	0.016 (12)
F6B2	0.106 (13)	0.114 (17)	0.046 (8)	0.003 (12)	0.014 (7)	0.042 (11)

Geometric parameters (Å, º) top

P1—F6A2	1.593 (12)	C7—C8	1.368 (3)
P1—F6B1	1.53 (3)	C8—C9	1.409 (3)
P1—F6B2	1.56 (3)	C9—C10	1.413 (3)
P1—F3A1	1.521 (19)	C11—C12	1.515 (3)
P1—F3A2	1.607 (14)	C12—C13	1.503 (3)
P1—F4B1	1.47 (2)	C15—C16	1.336 (3)
P1—F1	1.575 (3)	C17—C18	1.507 (5)
P1—F2	1.559 (3)	C18—C23	1.379 (3)
P1—F4A	1.572 (5)	C18—C19	1.377 (4)
P1—F5A	1.536 (12)	C19—C20	1.373 (6)
P1—F3B	1.55 (2)	C20—C21	1.372 (4)
P1—F4B2	1.45 (3)	C21—C22	1.363 (6)
P1—F6A1	1.548 (12)	C22—C23	1.378 (6)
P1—F5B	1.504 (19)	C1—H1	0.9300
F1—F4B2	1.57 (3)	C3—H3	0.9300
F3A1—F3A2	0.81 (2)	C4—H4	0.9300
F3A1—F6A1	1.62 (2)	C5—H5	0.9300
F4B1—F4B2	0.99 (4)	C6—H6	0.9300
F6A1—F6A2	0.87 (3)	C7—H7	0.9300
F6B1—F6B2	0.62 (4)	C8—H8	0.9300
O1—C2	1.370 (3)	C11—H11A	0.9700
O1—C11	1.423 (3)	C11—H11B	0.9700
N1—C13	1.469 (3)	C12—H12B	0.9700
N1—C14	1.321 (3)	C12—H12A	0.9700
N1—C16	1.369 (3)	C13—H13A	0.9700
N2—C17	1.466 (3)	C13—H13B	0.9700
N2—C15	1.371 (3)	C14—H14	0.9300
N2—C14	1.327 (3)	C15—H15	0.9300
C1—C2	1.366 (3)	C16—H16	0.9300
C1—C9	1.421 (3)	C17—H17B	0.9700
C2—C3	1.413 (3)	C17—H17A	0.9700
C3—C4	1.359 (3)	C19—H19	0.9300
C4—C10	1.417 (3)	C20—H20	0.9300
C5—C6	1.361 (4)	C21—H21	0.9300
C5—C10	1.406 (3)	C22—H22	0.9300
C6—C7	1.391 (4)	C23—H23	0.9300

F6B1—P1—F6B2	23.3 (15)	C1—C9—C10	119.41 (18)
F1—P1—F4B2	62.2 (12)	C8—C9—C10	118.57 (19)
F1—P1—F6A1	90.5 (6)	C1—C9—C8	122.02 (19)
F1—P1—F5B	89.2 (7)	C4—C10—C5	122.8 (2)
F1—P1—F6A2	87.0 (6)	C4—C10—C9	118.48 (19)
F1—P1—F6B1	107.6 (9)	C5—C10—C9	118.7 (2)
F1—P1—F6B2	84.5 (13)	O1—C11—C12	106.88 (16)
F2—P1—F4A	92.1 (3)	C11—C12—C13	110.15 (17)
F2—P1—F5A	89.0 (4)	N1—C13—C12	112.96 (17)
F3A1—P1—F2	94.5 (7)	N1—C14—N2	109.15 (19)
F2—P1—F3A2	89.6 (5)	N2—C15—C16	107.2 (2)
F2—P1—F4B1	82.5 (10)	N1—C16—C15	107.76 (19)
F2—P1—F3B	84.9 (7)	N2—C17—C18	112.7 (2)
F2—P1—F4B2	122.2 (12)	C19—C18—C23	118.8 (3)
F2—P1—F6A1	86.9 (6)	C17—C18—C23	119.1 (3)
F2—P1—F5B	93.5 (7)	C17—C18—C19	122.1 (2)
F2—P1—F6A2	92.9 (6)	C18—C19—C20	120.5 (3)
F2—P1—F6B1	68.2 (9)	C19—C20—C21	120.4 (4)
F2—P1—F6B2	91.4 (13)	C20—C21—C22	119.4 (4)
F4A—P1—F5A	84.7 (5)	C21—C22—C23	120.6 (3)
F3A1—P1—F3A2	29.7 (8)	C18—C23—C22	120.3 (3)
F3A1—P1—F6A1	63.8 (9)	C9—C1—H1	120.00
F3A1—P1—F6A2	94.6 (10)	C2—C1—H1	120.00
F3A2—P1—F6A1	92.7 (8)	C4—C3—H3	120.00
F3A2—P1—F6A2	124.2 (8)	C2—C3—H3	120.00
F1—P1—F2	175.2 (2)	C3—C4—H4	119.00
F1—P1—F4A	89.9 (3)	C10—C4—H4	119.00
F1—P1—F5A	95.6 (4)	C10—C5—H5	119.00
F1—P1—F3A1	80.7 (7)	C6—C5—H5	119.00
F1—P1—F3A2	86.5 (5)	C5—C6—H6	120.00
F1—P1—F4B1	101.9 (10)	C7—C6—H6	120.00
F1—P1—F3B	92.9 (7)	C6—C7—H7	120.00
F6A1—P1—F6A2	32.0 (11)	C8—C7—H7	120.00
F4B1—P1—F6B2	171.8 (17)	C7—C8—H8	120.00
F4B1—P1—F4B2	39.7 (15)	C9—C8—H8	119.00
F4B1—P1—F6B1	150.5 (13)	O1—C11—H11A	110.00
F4B2—P1—F6B2	145.9 (17)	O1—C11—H11B	110.00
F3B—P1—F5B	174.0 (9)	C12—C11—H11A	110.00
F4B2—P1—F6B1	169.0 (15)	C12—C11—H11B	110.00
P1—F1—F4B2	55.0 (12)	H11A—C11—H11B	109.00
P1—F3A1—F6A1	58.9 (9)	H12A—C12—H12B	108.00
F3A2—F3A1—F6A1	138 (2)	C11—C12—H12B	110.00
P1—F3A1—F3A2	81.1 (17)	C11—C12—H12A	110.00
P1—F3A2—F3A1	69.2 (16)	C13—C12—H12A	110.00
P1—F4B1—F4B2	69 (2)	C13—C12—H12B	110.00
P1—F4B2—F1	62.9 (13)	N1—C13—H13B	109.00
F1—F4B2—F4B1	134 (3)	N1—C13—H13A	109.00
P1—F4B2—F4B1	71 (2)	H13A—C13—H13B	108.00
P1—F6A1—F3A1	57.3 (8)	C12—C13—H13A	109.00
P1—F6A1—F6A2	76.8 (12)	C12—C13—H13B	109.00
F3A1—F6A1—F6A2	131.3 (17)	N1—C14—H14	125.00
P1—F6A2—F6A1	71.2 (12)	N2—C14—H14	125.00
P1—F6B1—F6B2	81 (4)	C16—C15—H15	126.00
P1—F6B2—F6B1	76 (3)	N2—C15—H15	126.00
C2—O1—C11	117.66 (17)	C15—C16—H16	126.00
C13—N1—C14	127.16 (18)	N1—C16—H16	126.00
C13—N1—C16	124.91 (18)	N2—C17—H17A	109.00
C14—N1—C16	107.93 (18)	H17A—C17—H17B	108.00
C14—N2—C17	125.6 (2)	C18—C17—H17B	109.00
C15—N2—C17	126.4 (2)	N2—C17—H17B	109.00
C14—N2—C15	107.99 (18)	C18—C17—H17A	109.00
C2—C1—C9	120.23 (19)	C18—C19—H19	120.00
O1—C2—C1	125.23 (19)	C20—C19—H19	120.00
O1—C2—C3	114.29 (18)	C21—C20—H20	120.00
C1—C2—C3	120.48 (19)	C19—C20—H20	120.00
C2—C3—C4	120.1 (2)	C22—C21—H21	120.00
C3—C4—C10	121.29 (19)	C20—C21—H21	120.00
C6—C5—C10	121.4 (3)	C21—C22—H22	120.00
C5—C6—C7	120.1 (2)	C23—C22—H22	120.00
C6—C7—C8	120.2 (2)	C18—C23—H23	120.00
C7—C8—C9	121.0 (2)	C22—C23—H23	120.00

C11—O1—C2—C1	5.0 (5)	C10—C5—C6—C7	0.3 (6)
C11—O1—C2—C3	−174.6 (3)	C6—C5—C10—C4	−179.5 (3)
C2—O1—C11—C12	173.4 (3)	C6—C5—C10—C9	1.1 (5)
C14—N1—C13—C12	−24.7 (4)	C5—C6—C7—C8	−1.1 (6)
C16—N1—C13—C12	154.2 (3)	C6—C7—C8—C9	0.5 (5)
C13—N1—C14—N2	178.5 (3)	C7—C8—C9—C1	−178.7 (3)
C16—N1—C14—N2	−0.5 (4)	C7—C8—C9—C10	0.8 (5)
C13—N1—C16—C15	−178.3 (3)	C1—C9—C10—C4	−1.6 (4)
C14—N1—C16—C15	0.8 (4)	C1—C9—C10—C5	177.9 (3)
C15—N2—C14—N1	0.1 (4)	C8—C9—C10—C4	178.9 (3)
C17—N2—C14—N1	179.9 (3)	C8—C9—C10—C5	−1.5 (5)
C14—N2—C15—C16	0.4 (4)	O1—C11—C12—C13	−176.6 (3)
C17—N2—C15—C16	−179.4 (3)	C11—C12—C13—N1	−169.8 (3)
C14—N2—C17—C18	113.9 (3)	N2—C15—C16—N1	−0.7 (4)
C15—N2—C17—C18	−66.4 (4)	N2—C17—C18—C19	−31.7 (3)
C9—C1—C2—O1	−178.4 (3)	N2—C17—C18—C23	150.2 (2)
C9—C1—C2—C3	1.1 (5)	C17—C18—C19—C20	−177.6 (3)
C2—C1—C9—C8	179.9 (3)	C23—C18—C19—C20	0.6 (4)
C2—C1—C9—C10	0.4 (5)	C17—C18—C23—C22	178.0 (3)
O1—C2—C3—C4	178.0 (3)	C19—C18—C23—C22	−0.3 (4)
C1—C2—C3—C4	−1.5 (5)	C18—C19—C20—C21	−0.1 (5)
C2—C3—C4—C10	0.3 (5)	C19—C20—C21—C22	−0.9 (5)
C3—C4—C10—C5	−178.3 (3)	C20—C21—C22—C23	1.2 (5)
C3—C4—C10—C9	1.2 (5)	C21—C22—C23—C18	−0.7 (5)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C1–C4/C9/C10 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···F2ⁱ	0.93	2.41	3.304 (3)	160
C19—H19···F2ⁱⁱ	0.93	2.49	3.393 (3)	162
C14—H14···F4A	0.93	2.48	3.406 (6)	171
C4—H4···F5Aⁱⁱⁱ	0.93	2.55	3.315 (11)	140
C13—H13B···Cg2^iv	0.97	2.65	3.560 (3)	157

Symmetry codes: (i) x, y+1, z; (ii) −x+1/2, y+1/2, −z+1/2; (iii) −x, −y+1, −z; (iv) −x, −y+2, −z.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₃N₂O⁺·PF₆⁻
M_r	488.40
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	28.3309 (5), 10.2447 (2), 20.0969 (4)
β (°)	130.296 (1)
V (Å³)	4448.87 (15)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.20 × 0.20 × 0.15

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.963, 0.972
No. of measured, independent and observed [I > 2σ(I)] reflections	19608, 5095, 3915
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.145, 1.04
No. of reflections	5095
No. of parameters	371
No. of restraints	210
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.39

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C1–C4/C9/C10 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···F2ⁱ	0.93	2.41	3.304 (3)	160
C19—H19···F2ⁱⁱ	0.93	2.49	3.393 (3)	162
C14—H14···F4A	0.93	2.48	3.406 (6)	171
C4—H4···F5Aⁱⁱⁱ	0.93	2.55	3.315 (11)	140
C13—H13B···Cg2^iv	0.97	2.65	3.560 (3)	157

Symmetry codes: (i) x, y+1, z; (ii) −x+1/2, y+1/2, −z+1/2; (iii) −x, −y+1, −z; (iv) −x, −y+2, −z.

Acknowledgements

The authors thank Professor Helen Stoeckli-Evans (Neuchâtel) for valuable discussions.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Arduengo, A. J., Harlow, R. L. & Kline, M. (1991). J. Am. Chem. Soc. 113, 361–363. CSD CrossRef CAS Web of Science Google Scholar
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Corma, A., García, H. & Leyva, A. (2004). Tetrahedron, 60, 8553–8560. Web of Science CrossRef CAS Google Scholar
Lin, J. C. Y., Huang, R. T. W., Lee, C. S., Bhattacharyya, A., Hwang, W. S. & Lin, I. J. B. (2009). Chem. Rev. 109, 3561–3598. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, J. W., Song, H. B., Li, Q. S., Xu, F. B. & Zhang, Z. Z. (2005). Inorg. Chim. Acta, 358, 3653–3658. Web of Science CSD CrossRef CAS Google Scholar
Wang, J. W., Xu, F. B., Li, Q. S., Song, H. B. & Zhang, Z. Z. (2005). Inorg. Chem. Commun. 8, 1053–1055. 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 67| Part 8| August 2011| Page o2062

doi:10.1107/S1600536811026663

Open

access