Crystal structure of 1-benzyl-3-methyl-1H-imidazolium hexa-fluorido-phosphate.

In the title salt, C11H13N2 (+)·PF6 (-), the dihedral angle between the planes of the imidazole and benzene rings is 84.72 (4)°. In the crystal, C-H⋯F inter-actions connect the cation and anion pairs into a three-dimensional network. Weak π-π inter-actions are observed between the imidazolium ring and the aromatic benzene ring of an adjacent mol-ecule with C⋯C and C⋯N distances ranging from 3.3714 (16) to 3.4389 (15) Å.

Related literature

For related structures containing imidazolium rings bearing N-benzyl groups, see: Haque et al. (2012 ▶); Jiang (2009 ▶); Lu et al. (2010 ▶); Pi et al. (2009 ▶). For an overview of applications for ionic liquids, see: Plechkova & Seddon (2008 ▶). For applications of benzyl-containing ionic liquids, see: Mahurin et al. (2011 ▶). For the synthesis of the title compound, see: Shkrob et al. (2013 ▶). For use of imidazolium compounds as carbene precursors, see: Scholl et al. (1999 ▶).

Experimental

Crystal data

C11H13N2 +·F6P−

M = 318.20

Monoclinic,

a = 10.4989 (3) Å

b = 11.2755 (3) Å

c = 11.9769 (3) Å

β = 109.926 (1)°

V = 1332.95 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 100 K

0.45 × 0.27 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2014 ▶) T min = 0.906, T max = 0.991

42589 measured reflections

3188 independent reflections

2746 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.083

S = 1.07

3188 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.42 e Å−3

Data collection: APEX2 (Bruker, 2014 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814024301/zl2605sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814024301/zl2605Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814024301/zl2605Isup3.mol

Click here for additional data file.

. DOI: 10.1107/S1600536814024301/zl2605fig1.tif

The mol­ecular structure of the title compound with 50% probability ellipsoids. Nitro­gen atoms shown in blue, carbon in grey, fluorine in pink, and phospho­rous in green.

Click here for additional data file.

. DOI: 10.1107/S1600536814024301/zl2605fig2.tif

Diagram of the hydrogen bonding observed in the title compound shown as pink dotted lines.

CCDC reference: 1032692

Additional supporting information: crystallographic information; 3D view; checkCIF report

C11H13N2+·F6P−	F(000) = 648
Mr = 318.20	Dx = 1.586 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.4989 (3) Å	Cell parameters from 9735 reflections
b = 11.2755 (3) Å	θ = 2.6–27.9°
c = 11.9769 (3) Å	µ = 0.27 mm−1
β = 109.926 (1)°	T = 100 K
V = 1332.95 (6) Å3	Plates, colourless
Z = 4	0.45 × 0.27 × 0.12 mm

Bruker APEXII CCD diffractometer	2746 reflections with I > 2σ(I)
Detector resolution: 8.33 pixels mm-1	Rint = 0.055
combination of ω and φ–scans	θmax = 27.9°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −13→13
Tmin = 0.906, Tmax = 0.991	k = −14→14
42589 measured reflections	l = −15→15
3188 independent reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031	H-atom parameters constrained
wR(F2) = 0.083	w = 1/[σ2(Fo2) + (0.0416P)2 + 0.409P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
3188 reflections	Δρmax = 0.27 e Å−3
182 parameters	Δρmin = −0.42 e Å−3
0 restraints

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.

	x	y	z	Uiso*/Ueq
N1	0.71519 (10)	0.47646 (9)	0.73967 (9)	0.0195 (2)
N2	0.51532 (10)	0.53231 (9)	0.72989 (9)	0.0177 (2)
C1	0.64714 (12)	0.54719 (10)	0.78756 (10)	0.0188 (2)
H1	0.6860	0.5997	0.8523	0.023*
C2	0.62396 (13)	0.41476 (11)	0.64770 (11)	0.0219 (3)
H2	0.6453	0.3583	0.5979	0.026*
C3	0.49888 (13)	0.44926 (10)	0.64138 (11)	0.0210 (2)
H3	0.4154	0.4217	0.5866	0.025*
C4	0.86303 (13)	0.46510 (13)	0.77897 (13)	0.0296 (3)
H4A	0.8957	0.4942	0.7165	0.044*
H4B	0.8883	0.3816	0.7954	0.044*
H4C	0.9039	0.5119	0.8513	0.044*
C5	0.40534 (13)	0.59543 (11)	0.75594 (11)	0.0226 (3)
H5A	0.4451	0.6509	0.8229	0.027*
H5B	0.3491	0.5373	0.7803	0.027*
C6	0.31700 (12)	0.66383 (11)	0.64927 (11)	0.0190 (2)
C7	0.36887 (12)	0.76192 (10)	0.60829 (10)	0.0196 (2)
H7	0.4604	0.7850	0.6469	0.023*
C8	0.28734 (14)	0.82614 (11)	0.51126 (11)	0.0244 (3)
H8	0.3230	0.8933	0.4841	0.029*
C9	0.15414 (15)	0.79246 (13)	0.45415 (12)	0.0303 (3)
H9	0.0986	0.8364	0.3877	0.036*
C10	0.10175 (14)	0.69493 (14)	0.49367 (14)	0.0334 (3)
H10	0.0105	0.6716	0.4540	0.040*
C11	0.18284 (13)	0.63074 (12)	0.59182 (13)	0.0276 (3)
H11	0.1464	0.5644	0.6194	0.033*
P1	0.76866 (3)	0.81119 (3)	0.62758 (3)	0.01967 (10)
F1	0.71267 (8)	0.80793 (7)	0.73665 (7)	0.0306 (2)
F2	0.90222 (8)	0.74247 (7)	0.70492 (7)	0.0333 (2)
F3	0.82307 (9)	0.81640 (8)	0.51809 (7)	0.0363 (2)
F4	0.63354 (7)	0.88092 (7)	0.54915 (7)	0.02663 (18)
F5	0.69426 (10)	0.68792 (7)	0.58054 (8)	0.0392 (2)
F6	0.84023 (8)	0.93566 (7)	0.67485 (8)	0.0310 (2)

	U11	U22	U33	U12	U13	U23
N1	0.0232 (5)	0.0161 (5)	0.0195 (5)	0.0017 (4)	0.0076 (4)	0.0036 (4)
N2	0.0232 (5)	0.0154 (4)	0.0148 (5)	0.0016 (4)	0.0069 (4)	0.0008 (4)
C1	0.0253 (6)	0.0146 (5)	0.0157 (5)	−0.0003 (4)	0.0061 (5)	0.0018 (4)
C2	0.0336 (7)	0.0163 (5)	0.0161 (6)	0.0028 (5)	0.0089 (5)	0.0001 (4)
C3	0.0293 (6)	0.0163 (5)	0.0155 (6)	−0.0010 (5)	0.0051 (5)	−0.0014 (4)
C4	0.0227 (6)	0.0292 (7)	0.0372 (8)	0.0041 (5)	0.0106 (6)	0.0070 (6)
C5	0.0271 (6)	0.0219 (6)	0.0224 (6)	0.0049 (5)	0.0132 (5)	0.0034 (5)
C6	0.0215 (6)	0.0171 (5)	0.0203 (6)	0.0023 (4)	0.0095 (5)	−0.0015 (4)
C7	0.0239 (6)	0.0183 (5)	0.0178 (6)	−0.0010 (5)	0.0088 (5)	−0.0033 (5)
C8	0.0387 (7)	0.0165 (6)	0.0200 (6)	0.0050 (5)	0.0127 (6)	−0.0005 (5)
C9	0.0345 (7)	0.0288 (7)	0.0235 (7)	0.0145 (6)	0.0043 (6)	−0.0007 (5)
C10	0.0206 (6)	0.0375 (8)	0.0368 (8)	0.0035 (5)	0.0030 (6)	−0.0075 (6)
C11	0.0236 (6)	0.0239 (6)	0.0364 (8)	−0.0024 (5)	0.0115 (6)	−0.0017 (6)
P1	0.02424 (17)	0.01596 (16)	0.01680 (17)	−0.00009 (11)	0.00438 (13)	0.00205 (11)
F1	0.0351 (4)	0.0369 (5)	0.0204 (4)	−0.0067 (3)	0.0103 (3)	0.0022 (3)
F2	0.0365 (5)	0.0288 (4)	0.0271 (4)	0.0110 (3)	0.0013 (3)	0.0054 (3)
F3	0.0406 (5)	0.0465 (5)	0.0264 (4)	0.0185 (4)	0.0175 (4)	0.0112 (4)
F4	0.0224 (4)	0.0296 (4)	0.0265 (4)	0.0025 (3)	0.0065 (3)	0.0077 (3)
F5	0.0572 (6)	0.0205 (4)	0.0282 (5)	−0.0093 (4)	−0.0007 (4)	−0.0038 (3)
F6	0.0262 (4)	0.0201 (4)	0.0450 (5)	−0.0052 (3)	0.0099 (4)	−0.0014 (3)

N1—C1	1.3247 (16)	C6—C11	1.3914 (18)
N1—C2	1.3768 (16)	C7—H7	0.9500
N1—C4	1.4660 (16)	C7—C8	1.3891 (17)
N2—C1	1.3301 (16)	C8—H8	0.9500
N2—C3	1.3805 (15)	C8—C9	1.384 (2)
N2—C5	1.4774 (15)	C9—H9	0.9500
C1—H1	0.9500	C9—C10	1.383 (2)
C2—H2	0.9500	C10—H10	0.9500
C2—C3	1.3468 (18)	C10—C11	1.396 (2)
C3—H3	0.9500	C11—H11	0.9500
C4—H4A	0.9800	P1—F1	1.6053 (8)
C4—H4B	0.9800	P1—F2	1.5935 (8)
C4—H4C	0.9800	P1—F3	1.6000 (8)
C5—H5A	0.9900	P1—F4	1.6139 (8)
C5—H5B	0.9900	P1—F5	1.5999 (8)
C5—C6	1.5098 (17)	P1—F6	1.6016 (8)
C6—C7	1.3939 (17)
C1—N1—C2	108.65 (10)	C6—C7—H7	119.8
C1—N1—C4	125.58 (11)	C8—C7—C6	120.33 (12)
C2—N1—C4	125.77 (11)	C8—C7—H7	119.8
C1—N2—C3	108.67 (10)	C7—C8—H8	120.0
C1—N2—C5	125.40 (10)	C9—C8—C7	120.08 (12)
C3—N2—C5	125.93 (11)	C9—C8—H8	120.0
N1—C1—N2	108.57 (10)	C8—C9—H9	119.9
N1—C1—H1	125.7	C10—C9—C8	120.11 (13)
N2—C1—H1	125.7	C10—C9—H9	119.9
N1—C2—H2	126.3	C9—C10—H10	120.0
C3—C2—N1	107.35 (11)	C9—C10—C11	120.05 (13)
C3—C2—H2	126.3	C11—C10—H10	120.0
N2—C3—H3	126.6	C6—C11—C10	120.10 (13)
C2—C3—N2	106.76 (11)	C6—C11—H11	119.9
C2—C3—H3	126.6	C10—C11—H11	119.9
N1—C4—H4A	109.5	F1—P1—F4	89.53 (4)
N1—C4—H4B	109.5	F2—P1—F1	90.55 (5)
N1—C4—H4C	109.5	F2—P1—F3	90.29 (5)
H4A—C4—H4B	109.5	F2—P1—F4	179.90 (5)
H4A—C4—H4C	109.5	F2—P1—F5	90.55 (5)
H4B—C4—H4C	109.5	F2—P1—F6	90.39 (4)
N2—C5—H5A	109.3	F3—P1—F1	179.05 (5)
N2—C5—H5B	109.3	F3—P1—F4	89.63 (4)
N2—C5—C6	111.49 (10)	F3—P1—F6	90.11 (5)
H5A—C5—H5B	108.0	F5—P1—F1	89.80 (5)
C6—C5—H5A	109.3	F5—P1—F3	90.64 (5)
C6—C5—H5B	109.3	F5—P1—F4	89.51 (5)
C7—C6—C5	120.15 (11)	F5—P1—F6	178.80 (5)
C11—C6—C5	120.52 (11)	F6—P1—F1	89.44 (4)
C11—C6—C7	119.32 (12)	F6—P1—F4	89.56 (4)
N1—C2—C3—N2	0.15 (13)	C5—N2—C1—N1	−179.75 (10)
N2—C5—C6—C7	−67.85 (14)	C5—N2—C3—C2	179.52 (11)
N2—C5—C6—C11	112.96 (13)	C5—C6—C7—C8	−179.04 (11)
C1—N1—C2—C3	−0.35 (13)	C5—C6—C11—C10	179.65 (12)
C1—N2—C3—C2	0.11 (13)	C6—C7—C8—C9	−0.45 (18)
C1—N2—C5—C6	121.23 (12)	C7—C6—C11—C10	0.45 (19)
C2—N1—C1—N2	0.42 (13)	C7—C8—C9—C10	0.14 (19)
C3—N2—C1—N1	−0.33 (13)	C8—C9—C10—C11	0.5 (2)
C3—N2—C5—C6	−58.10 (15)	C9—C10—C11—C6	−0.8 (2)
C4—N1—C1—N2	−179.05 (11)	C11—C6—C7—C8	0.16 (18)
C4—N1—C2—C3	179.12 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···F3i	0.95	2.23	3.1503 (14)	164
C1—H1···F4i	0.95	2.61	3.2860 (14)	129
C3—H3···F5ii	0.95	2.30	3.1456 (15)	148
C9—H9···F2iii	0.95	2.60	3.2680 (16)	128

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C1H1F3i	0.95	2.23	3.1503(14)	164
C1H1F4i	0.95	2.61	3.2860(14)	129
C3H3F5ii	0.95	2.30	3.1456(15)	148
C9H9F2iii	0.95	2.60	3.2680(16)	128

Symmetry codes: (i) ; (ii) ; (iii) .