1-Benzyl-3-methyl-imidazolium chloride 0.25-hydrate.

The asymmetric unit of the title compound, C(11)H(13)N(2) (+)·Cl(-), contains two independent ion pairs and and half a solvent water mol-ecule (m site symmetry for the O atom). The imidazole ring is oriented at dihedral angles of 66.61 (3) and 89.17 (3)° with respect to the aromatic ring in the two cations. In the crystal, O-H⋯(O,Cl) hydrogen bonds and π-π stacking inter-actions between the imidazole ring of one mol-ecule and the aromatic ring of another [perpendicular distance = 3.4 (4) Å] link the mol-ecules.

Related literature

For general background to ionic liquids, see: Fukaya et al. (2006 ▶); Ranu et al. (2005 ▶); Chen et al. (2005 ▶); Blanchard et al. (2001 ▶); Zhang et al. (2006 ▶); Katayanagi et al. (2004 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C11H13N2 +·Cl−·0.25H2O

M = 213.19

Orthorhombic,

a = 11.452 (2) Å

b = 11.410 (2) Å

c = 34.867 (7) Å

V = 4555.8 (16) Å3

Z = 16

Mo Kα radiation

μ = 0.30 mm−1

T = 113 K

0.22 × 0.20 × 0.16 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2000 ▶) T min = 0.937, T max = 0.953

30046 measured reflections

4022 independent reflections

3619 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.119

S = 1.08

4022 reflections

268 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CrystalClear (Rigaku, 2000 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809053306/bq2176sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809053306/bq2176Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C11H13N2+·Cl−·0.25(H2O)	Dx = 1.243 Mg m−3
Mr = 213.19	Melting point: 251 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 6089 reflections
a = 11.452 (2) Å	θ = 2.1–27.9°
b = 11.410 (2) Å	µ = 0.30 mm−1
c = 34.867 (7) Å	T = 113 K
V = 4555.8 (16) Å3	Block, colorless
Z = 16	0.22 × 0.20 × 0.16 mm
F(000) = 1800

Rigaku Saturn diffractometer	4022 independent reflections
Radiation source: rotating anode	3619 reflections with I > 2σ(I)
confocal	Rint = 0.041
ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2000)	h = −13→13
Tmin = 0.937, Tmax = 0.953	k = −13→11
30046 measured reflections	l = −41→39

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0667P)2 + 2.0145P] where P = (Fo2 + 2Fc2)/3
4022 reflections	(Δ/σ)max = 0.001
268 parameters	Δρmax = 0.30 e Å−3
3 restraints	Δρmin = −0.28 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.47805 (4)	1.03154 (4)	0.348689 (12)	0.02641 (15)
Cl2	0.55772 (5)	0.75655 (5)	0.519211 (14)	0.03879 (17)
N1	0.76243 (14)	0.70800 (14)	0.42512 (4)	0.0275 (4)
N2	0.77675 (14)	0.78892 (14)	0.36959 (4)	0.0279 (4)
N3	0.30575 (13)	0.63833 (13)	0.43738 (4)	0.0242 (3)
N4	0.27524 (13)	0.73929 (13)	0.38612 (4)	0.0230 (3)
C1	0.7808 (2)	0.6275 (2)	0.45759 (6)	0.0454 (6)
H1A	0.7798	0.5481	0.4485	0.068*
H1B	0.7196	0.6382	0.4761	0.068*
H1C	0.8549	0.6437	0.4693	0.068*
C2	0.81984 (17)	0.70586 (17)	0.39202 (5)	0.0290 (4)
H2	0.8801	0.6547	0.3857	0.035*
C3	0.68949 (18)	0.84657 (18)	0.38902 (6)	0.0315 (5)
H3	0.6446	0.9085	0.3799	0.038*
C4	0.68136 (17)	0.79632 (18)	0.42386 (6)	0.0312 (5)
H4	0.6303	0.8175	0.4434	0.037*
C5	0.8163 (2)	0.8133 (2)	0.33005 (6)	0.0432 (6)
H5A	0.8946	0.7825	0.3267	0.052*
H5B	0.8197	0.8975	0.3263	0.052*
C6	0.73773 (18)	0.76060 (18)	0.30011 (5)	0.0284 (4)
C7	0.76298 (19)	0.6509 (2)	0.28553 (6)	0.0393 (5)
H7	0.8274	0.6097	0.2946	0.047*
C8	0.6929 (2)	0.6021 (2)	0.25757 (7)	0.0520 (7)
H8	0.7101	0.5280	0.2480	0.062*
C9	0.5978 (2)	0.6625 (2)	0.24371 (6)	0.0494 (7)
H9	0.5519	0.6302	0.2244	0.059*
C10	0.5710 (2)	0.7711 (2)	0.25864 (7)	0.0474 (6)
H10	0.5061	0.8116	0.2496	0.057*
C11	0.6401 (2)	0.82016 (19)	0.28689 (6)	0.0374 (5)
H11	0.6211	0.8931	0.2970	0.045*
C12	0.2976 (2)	0.54811 (19)	0.46704 (6)	0.0358 (5)
H12A	0.2647	0.5814	0.4899	0.054*
H12B	0.3742	0.5182	0.4726	0.054*
H12C	0.2487	0.4854	0.4582	0.054*
C13	0.24416 (16)	0.64328 (16)	0.40510 (5)	0.0239 (4)
H13	0.1888	0.5888	0.3972	0.029*
C14	0.35863 (16)	0.79782 (16)	0.40711 (5)	0.0271 (4)
H14	0.3952	0.8677	0.4004	0.032*
C15	0.37723 (16)	0.73477 (17)	0.43921 (5)	0.0272 (4)
H15	0.4288	0.7531	0.4589	0.033*
C16	0.22392 (18)	0.77900 (18)	0.34989 (5)	0.0291 (4)
H16A	0.1832	0.7141	0.3379	0.035*
H16B	0.2859	0.8036	0.3327	0.035*
C17	0.13971 (17)	0.87942 (16)	0.35559 (5)	0.0251 (4)
C18	0.12909 (19)	0.96458 (18)	0.32750 (6)	0.0350 (5)
H18	0.1755	0.9605	0.3057	0.042*
C19	0.0500 (2)	1.05586 (19)	0.33155 (7)	0.0457 (6)
H19	0.0432	1.1120	0.3123	0.055*
C20	−0.0183 (2)	1.0634 (2)	0.36397 (8)	0.0463 (6)
H20	−0.0710	1.1249	0.3668	0.056*
C21	−0.00839 (19)	0.9798 (2)	0.39217 (7)	0.0389 (5)
H21	−0.0541	0.9852	0.4141	0.047*
C22	0.06960 (17)	0.88692 (17)	0.38806 (5)	0.0282 (4)
H22	0.0748	0.8299	0.4070	0.034*
O1	0.4899 (3)	0.9725 (3)	0.46644 (11)	0.0506 (9)	0.50
H1D	0.504 (5)	0.998 (4)	0.4438 (6)	0.061*	0.50
H1E	0.474 (5)	1.026 (3)	0.4830 (9)	0.061*	0.50

	U11	U22	U33	U12	U13	U23
Cl1	0.0257 (3)	0.0269 (3)	0.0266 (2)	0.00190 (18)	0.00007 (17)	0.00296 (17)
Cl2	0.0373 (3)	0.0435 (3)	0.0356 (3)	0.0013 (2)	−0.0102 (2)	0.0026 (2)
N1	0.0301 (9)	0.0269 (9)	0.0255 (8)	−0.0025 (7)	−0.0035 (6)	0.0001 (6)
N2	0.0274 (9)	0.0304 (9)	0.0259 (8)	−0.0078 (7)	−0.0030 (6)	−0.0001 (7)
N3	0.0244 (8)	0.0234 (8)	0.0249 (8)	0.0034 (6)	0.0008 (6)	0.0020 (6)
N4	0.0228 (8)	0.0213 (8)	0.0249 (8)	0.0025 (6)	−0.0010 (6)	−0.0013 (6)
C1	0.0541 (15)	0.0445 (14)	0.0377 (11)	−0.0041 (11)	−0.0141 (10)	0.0141 (10)
C2	0.0242 (10)	0.0304 (11)	0.0325 (10)	0.0018 (8)	−0.0028 (8)	−0.0064 (8)
C3	0.0285 (10)	0.0271 (10)	0.0387 (11)	0.0012 (8)	−0.0084 (8)	−0.0028 (8)
C4	0.0241 (10)	0.0355 (11)	0.0339 (10)	0.0015 (8)	0.0009 (8)	−0.0080 (9)
C5	0.0435 (13)	0.0593 (15)	0.0270 (10)	−0.0251 (12)	0.0001 (9)	0.0043 (10)
C6	0.0309 (11)	0.0318 (10)	0.0225 (9)	−0.0094 (8)	0.0019 (8)	0.0029 (8)
C7	0.0292 (11)	0.0429 (13)	0.0457 (12)	0.0009 (10)	0.0079 (9)	−0.0036 (10)
C8	0.0530 (15)	0.0537 (15)	0.0493 (14)	−0.0125 (13)	0.0188 (12)	−0.0275 (12)
C9	0.0505 (15)	0.0755 (18)	0.0221 (10)	−0.0270 (14)	0.0028 (10)	−0.0111 (11)
C10	0.0398 (13)	0.0664 (17)	0.0360 (12)	−0.0086 (12)	−0.0101 (10)	0.0171 (12)
C11	0.0461 (13)	0.0303 (11)	0.0359 (11)	−0.0011 (10)	0.0002 (10)	0.0042 (9)
C12	0.0386 (12)	0.0356 (12)	0.0330 (10)	0.0047 (9)	0.0031 (9)	0.0123 (9)
C13	0.0224 (9)	0.0213 (9)	0.0279 (9)	−0.0004 (7)	0.0001 (7)	−0.0006 (7)
C14	0.0227 (9)	0.0226 (9)	0.0359 (10)	−0.0027 (8)	−0.0021 (8)	−0.0016 (8)
C15	0.0231 (10)	0.0285 (10)	0.0301 (10)	−0.0001 (8)	−0.0035 (8)	−0.0041 (8)
C16	0.0346 (11)	0.0323 (11)	0.0204 (9)	0.0038 (9)	0.0000 (8)	0.0003 (8)
C17	0.0264 (10)	0.0223 (9)	0.0267 (9)	−0.0013 (8)	−0.0067 (7)	0.0000 (7)
C18	0.0414 (12)	0.0306 (11)	0.0329 (10)	−0.0063 (9)	−0.0096 (9)	0.0080 (8)
C19	0.0552 (15)	0.0241 (11)	0.0580 (15)	−0.0024 (10)	−0.0319 (12)	0.0087 (10)
C20	0.0380 (13)	0.0302 (12)	0.0708 (17)	0.0085 (10)	−0.0283 (12)	−0.0149 (12)
C21	0.0266 (11)	0.0421 (13)	0.0479 (13)	0.0042 (9)	−0.0087 (9)	−0.0178 (11)
C22	0.0274 (10)	0.0285 (10)	0.0287 (9)	−0.0012 (8)	−0.0045 (8)	−0.0019 (8)
O1	0.055 (2)	0.041 (2)	0.056 (2)	−0.0050 (17)	0.0031 (18)	−0.0113 (16)

N1—C2	1.328 (2)	C9—C10	1.379 (4)
N1—C4	1.371 (3)	C9—H9	0.9300
N1—C1	1.473 (2)	C10—C11	1.382 (3)
N2—C2	1.324 (3)	C10—H10	0.9300
N2—C3	1.375 (3)	C11—H11	0.9300
N2—C5	1.478 (2)	C12—H12A	0.9600
N3—C13	1.329 (2)	C12—H12B	0.9600
N3—C15	1.373 (2)	C12—H12C	0.9600
N3—C12	1.462 (2)	C13—H13	0.9300
N4—C13	1.328 (2)	C14—C15	1.348 (3)
N4—C14	1.376 (2)	C14—H14	0.9300
N4—C16	1.465 (2)	C15—H15	0.9300
C1—H1A	0.9600	C16—C17	1.511 (3)
C1—H1B	0.9600	C16—H16A	0.9700
C1—H1C	0.9600	C16—H16B	0.9700
C2—H2	0.9300	C17—C18	1.385 (3)
C3—C4	1.347 (3)	C17—C22	1.391 (3)
C3—H3	0.9300	C18—C19	1.387 (3)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.504 (3)	C19—C20	1.378 (4)
C5—H5A	0.9700	C19—H19	0.9300
C5—H5B	0.9700	C20—C21	1.375 (4)
C6—C7	1.382 (3)	C20—H20	0.9300
C6—C11	1.387 (3)	C21—C22	1.393 (3)
C7—C8	1.380 (3)	C21—H21	0.9300
C7—H7	0.9300	C22—H22	0.9300
C8—C9	1.376 (4)	O1—H1D	0.860 (10)
C8—H8	0.9300	O1—H1E	0.857 (10)
C2—N1—C4	108.72 (16)	C9—C10—H10	119.8
C2—N1—C1	125.85 (18)	C11—C10—H10	119.8
C4—N1—C1	125.42 (18)	C10—C11—C6	120.0 (2)
C2—N2—C3	108.79 (16)	C10—C11—H11	120.0
C2—N2—C5	124.87 (19)	C6—C11—H11	120.0
C3—N2—C5	126.34 (18)	N3—C12—H12A	109.5
C13—N3—C15	108.77 (15)	N3—C12—H12B	109.5
C13—N3—C12	126.51 (17)	H12A—C12—H12B	109.5
C15—N3—C12	124.70 (16)	N3—C12—H12C	109.5
C13—N4—C14	108.73 (15)	H12A—C12—H12C	109.5
C13—N4—C16	125.25 (16)	H12B—C12—H12C	109.5
C14—N4—C16	125.93 (16)	N4—C13—N3	108.34 (16)
N1—C1—H1A	109.5	N4—C13—H13	125.8
N1—C1—H1B	109.5	N3—C13—H13	125.8
H1A—C1—H1B	109.5	C15—C14—N4	107.00 (17)
N1—C1—H1C	109.5	C15—C14—H14	126.5
H1A—C1—H1C	109.5	N4—C14—H14	126.5
H1B—C1—H1C	109.5	C14—C15—N3	107.15 (16)
N2—C2—N1	108.40 (17)	C14—C15—H15	126.4
N2—C2—H2	125.8	N3—C15—H15	126.4
N1—C2—H2	125.8	N4—C16—C17	112.14 (15)
C4—C3—N2	106.93 (18)	N4—C16—H16A	109.2
C4—C3—H3	126.5	C17—C16—H16A	109.2
N2—C3—H3	126.5	N4—C16—H16B	109.2
C3—C4—N1	107.16 (17)	C17—C16—H16B	109.2
C3—C4—H4	126.4	H16A—C16—H16B	107.9
N1—C4—H4	126.4	C18—C17—C22	118.81 (19)
N2—C5—C6	112.86 (17)	C18—C17—C16	119.67 (18)
N2—C5—H5A	109.0	C22—C17—C16	121.50 (17)
C6—C5—H5A	109.0	C17—C18—C19	120.8 (2)
N2—C5—H5B	109.0	C17—C18—H18	119.6
C6—C5—H5B	109.0	C19—C18—H18	119.6
H5A—C5—H5B	107.8	C20—C19—C18	120.1 (2)
C7—C6—C11	119.36 (19)	C20—C19—H19	120.0
C7—C6—C5	119.5 (2)	C18—C19—H19	120.0
C11—C6—C5	121.1 (2)	C21—C20—C19	119.8 (2)
C8—C7—C6	120.2 (2)	C21—C20—H20	120.1
C8—C7—H7	119.9	C19—C20—H20	120.1
C6—C7—H7	119.9	C20—C21—C22	120.5 (2)
C9—C8—C7	120.5 (2)	C20—C21—H21	119.8
C9—C8—H8	119.8	C22—C21—H21	119.8
C7—C8—H8	119.8	C17—C22—C21	120.04 (19)
C8—C9—C10	119.5 (2)	C17—C22—H22	120.0
C8—C9—H9	120.2	C21—C22—H22	120.0
C10—C9—H9	120.2	H1D—O1—H1E	114.7 (19)
C9—C10—C11	120.4 (2)
C3—N2—C2—N1	0.4 (2)	C14—N4—C13—N3	−0.5 (2)
C5—N2—C2—N1	−178.98 (17)	C16—N4—C13—N3	−177.32 (16)
C4—N1—C2—N2	−0.8 (2)	C15—N3—C13—N4	0.7 (2)
C1—N1—C2—N2	177.98 (18)	C12—N3—C13—N4	178.88 (17)
C2—N2—C3—C4	0.2 (2)	C13—N4—C14—C15	0.1 (2)
C5—N2—C3—C4	179.59 (18)	C16—N4—C14—C15	176.88 (16)
N2—C3—C4—N1	−0.7 (2)	N4—C14—C15—N3	0.4 (2)
C2—N1—C4—C3	1.0 (2)	C13—N3—C15—C14	−0.7 (2)
C1—N1—C4—C3	−177.85 (18)	C12—N3—C15—C14	−178.89 (17)
C2—N2—C5—C6	99.5 (2)	C13—N4—C16—C17	103.1 (2)
C3—N2—C5—C6	−79.8 (3)	C14—N4—C16—C17	−73.2 (2)
N2—C5—C6—C7	−93.2 (2)	N4—C16—C17—C18	147.06 (18)
N2—C5—C6—C11	86.7 (3)	N4—C16—C17—C22	−34.8 (3)
C11—C6—C7—C8	1.2 (3)	C22—C17—C18—C19	0.0 (3)
C5—C6—C7—C8	−178.9 (2)	C16—C17—C18—C19	178.16 (19)
C6—C7—C8—C9	0.5 (3)	C17—C18—C19—C20	0.7 (3)
C7—C8—C9—C10	−1.6 (4)	C18—C19—C20—C21	−0.4 (3)
C8—C9—C10—C11	1.1 (3)	C19—C20—C21—C22	−0.5 (3)
C9—C10—C11—C6	0.7 (3)	C18—C17—C22—C21	−0.9 (3)
C7—C6—C11—C10	−1.8 (3)	C16—C17—C22—C21	−179.04 (18)
C5—C6—C11—C10	178.28 (19)	C20—C21—C22—C17	1.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1E···O1i	0.86 (1)	1.81 (4)	2.434 (7)	128 (4)
O1—H1E···Cl2i	0.86 (1)	2.51 (3)	3.179 (3)	135 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1E⋯O1i	0.86 (1)	1.81 (4)	2.434 (7)	128 (4)
O1—H1E⋯Cl2i	0.86 (1)	2.51 (3)	3.179 (3)	135 (4)

Symmetry code: (i) .