1-(5,5-Di-meth-oxy-pent-yl)-3-methyl-imidazolium-2-carboxyl-ate.

The title compound, C12H20N2O4, represents one example of a zwitterionic imidazolium salt with a carboxyl-ate group at the 2-position of the imidazolium ring. The dihedral angle between the heterocyclic ring and the carboxyl-ate group is 31.3 (1)°. The side chain linking the N atom of the ring and the methine C atom has a gauche-anti-anti conformation [torsion angles = -60.3 (2), -175.7 (2) and 178.7 (2)°, respectively]. In the crystal, mol-ecules are linked by short C-H⋯O hydrogen bonds involving the C-H groups in the aromatic ring to generate (001) sheets.

Related literature

For related zwitterionic structures, see: Gurau et al. (2011 ▶); Holbrey et al. (2003 ▶); Smiglak et al. (2007 ▶); Reichert et al. (2010 ▶).

Experimental

Crystal data

C12H20N2O4

M = 256.30

Triclinic,

a = 7.1943 (8) Å

b = 7.3259 (8) Å

c = 13.2263 (15) Å

α = 85.124 (2)°

β = 85.542 (2)°

γ = 72.938 (2)°

V = 662.98 (13) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 200 K

0.3 × 0.15 × 0.15 mm

Data collection

Siemens SMART CCD 1000 diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.940, T max = 1.000

8022 measured reflections

3192 independent reflections

1962 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.178

S = 1.03

3192 reflections

171 parameters

Only H-atom displacement parameters refined

Δρmax = 0.27 e Å−3

Δρmin = −0.32 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SMART; data reduction: SAINT (Bruker, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2013 ▶); molecular graphics: XPMA (Zsolnai, 1996 ▶) and ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813027013/hb7143sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813027013/hb7143Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813027013/hb7143Isup3.mol

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813027013/hb7143Isup4.cml

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

C12H20N2O4	Z = 2
Mr = 256.30	F(000) = 276
Triclinic, P1	Dx = 1.284 Mg m−3
a = 7.1943 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.3259 (8) Å	Cell parameters from 49 reflections
c = 13.2263 (15) Å	θ = 2.8–42.3°
α = 85.124 (2)°	µ = 0.10 mm−1
β = 85.542 (2)°	T = 200 K
γ = 72.938 (2)°	Block, colourless
V = 662.98 (13) Å3	0.3 × 0.15 × 0.15 mm

Siemens SMART CCD 1000 diffractometer	3192 independent reflections
Radiation source: fine-focus sealed tube	1962 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 8 pixels mm-1	θmax = 28.3°, θmin = 1.6°
ω scan	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 1997)	k = −9→9
Tmin = 0.940, Tmax = 1	l = −17→17
8022 measured reflections

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.178	Only H-atom displacement parameters refined
S = 1.03	w = 1/[σ2(Fo2) + (0.1021P)2] where P = (Fo2 + 2Fc2)/3
3192 reflections	(Δ/σ)max < 0.001
171 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

Experimental. Spectroscopic data: 1H NMR (CDCl3): δ = 6.93, s (br), 1H, CH(arom); 6.91 (br), s, 1H, CH(arom); 4.51, t, 3JHH= 7.4 Hz, 2H, NCH2; 4.26, t, 3JHH= 5.5 Hz, 1H, COH; 4.06, s (br), 3H, NCH3; 3.24, s, 6H, OCH3; 1.84, p, 3JHH= 7.4 Hz, 2H, CH2; 1.56, m, 2H, CH2; 1.35, m, CH2.

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. The structure was solved by direct methods and refined to an optimum R1 value with SHELXL. The data of the structure have been deposited at the CCDC with the reference number 962824.

	x	y	z	Uiso*/Ueq
O1	0.1515 (2)	−0.2046 (2)	0.42195 (13)	0.0450 (4)
O2	0.3946 (2)	−0.4369 (2)	0.35645 (13)	0.0472 (4)
O3	0.2709 (3)	0.4306 (3)	−0.04153 (13)	0.0594 (5)
O4	0.2379 (3)	0.1828 (3)	−0.13125 (14)	0.0745 (6)
N1	0.3940 (2)	0.0490 (2)	0.36421 (11)	0.0254 (4)
N2	0.6433 (2)	−0.1977 (2)	0.38760 (11)	0.0252 (4)
C1	0.4498 (3)	−0.1435 (2)	0.37745 (13)	0.0239 (4)
C2	0.3182 (3)	−0.2742 (3)	0.38566 (15)	0.0298 (5)
C3	0.5536 (3)	0.1147 (3)	0.36567 (15)	0.0297 (5)
H3	0.5545	0.2418	0.3572	0.030 (4)*
C4	0.7090 (3)	−0.0391 (3)	0.38158 (14)	0.0303 (5)
H4	0.8366	−0.0377	0.3874	0.030 (4)*
C5	0.7684 (3)	−0.3936 (3)	0.40763 (17)	0.0357 (5)
H5A	0.7251	−0.4468	0.4707	0.050 (4)*
H5B	0.9005	−0.3916	0.4117	0.050 (4)*
H5C	0.7616	−0.4704	0.3535	0.050 (4)*
C6	0.1956 (3)	0.1756 (3)	0.34690 (15)	0.0304 (5)
H6A	0.1940	0.3076	0.3510	0.040 (2)*
H6B	0.1056	0.1465	0.3999	0.040 (2)*
C7	0.1284 (3)	0.1521 (3)	0.24391 (16)	0.0374 (5)
H7A	0.1252	0.0210	0.2416	0.040 (2)*
H7B	−0.0036	0.2345	0.2374	0.040 (2)*
C8	0.2543 (3)	0.1980 (3)	0.15374 (17)	0.0438 (6)
H8A	0.2656	0.3258	0.1580	0.040 (2)*
H8B	0.3838	0.1089	0.1566	0.040 (2)*
C9	0.1725 (4)	0.1868 (4)	0.05333 (18)	0.0491 (6)
H9A	0.0414	0.2734	0.0518	0.040 (2)*
H9B	0.1635	0.0581	0.0491	0.040 (2)*
C10	0.2915 (4)	0.2362 (4)	−0.03937 (18)	0.0577 (7)
H10	0.4288	0.1672	−0.0303	0.042 (6)*
C11	0.4004 (5)	0.4901 (6)	−0.1162 (2)	0.0980 (13)
H11A	0.5322	0.4170	−0.1043	0.122 (6)*
H11B	0.3865	0.6235	−0.1115	0.122 (6)*
H11C	0.3692	0.4695	−0.1828	0.122 (6)*
C12	0.0419 (5)	0.2754 (5)	−0.1545 (2)	0.0674 (8)
H12A	−0.0435	0.2222	−0.1100	0.122 (6)*
H12B	0.0242	0.2570	−0.2237	0.122 (6)*
H12C	0.0125	0.4098	−0.1455	0.122 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0251 (8)	0.0351 (9)	0.0739 (12)	−0.0105 (6)	0.0030 (7)	0.0031 (7)
O2	0.0530 (10)	0.0268 (8)	0.0648 (11)	−0.0175 (7)	0.0080 (8)	−0.0088 (7)
O3	0.0608 (12)	0.0811 (14)	0.0435 (10)	−0.0348 (10)	−0.0001 (8)	0.0047 (9)
O4	0.0951 (16)	0.0718 (14)	0.0456 (11)	−0.0059 (12)	−0.0002 (11)	−0.0108 (9)
N1	0.0264 (8)	0.0199 (8)	0.0290 (8)	−0.0056 (6)	−0.0007 (6)	−0.0009 (6)
N2	0.0236 (8)	0.0233 (8)	0.0276 (8)	−0.0058 (6)	−0.0001 (6)	0.0000 (6)
C1	0.0248 (9)	0.0210 (9)	0.0248 (9)	−0.0053 (7)	−0.0010 (7)	−0.0006 (7)
C2	0.0325 (11)	0.0247 (10)	0.0336 (11)	−0.0114 (8)	−0.0063 (8)	0.0051 (8)
C3	0.0342 (11)	0.0243 (10)	0.0341 (11)	−0.0140 (8)	−0.0013 (8)	−0.0026 (8)
C4	0.0285 (10)	0.0331 (11)	0.0327 (11)	−0.0147 (9)	−0.0006 (8)	−0.0019 (8)
C5	0.0301 (11)	0.0263 (11)	0.0453 (13)	−0.0012 (8)	−0.0043 (9)	0.0042 (9)
C6	0.0272 (10)	0.0211 (9)	0.0390 (11)	−0.0015 (8)	−0.0019 (8)	0.0004 (8)
C7	0.0345 (11)	0.0314 (11)	0.0447 (13)	−0.0078 (9)	−0.0075 (9)	0.0046 (9)
C8	0.0398 (13)	0.0454 (13)	0.0421 (13)	−0.0077 (10)	−0.0037 (10)	0.0043 (10)
C9	0.0574 (15)	0.0446 (14)	0.0436 (14)	−0.0128 (12)	−0.0061 (11)	0.0032 (10)
C10	0.0615 (17)	0.0628 (18)	0.0388 (14)	−0.0021 (14)	−0.0043 (12)	−0.0029 (12)
C11	0.079 (2)	0.180 (4)	0.0543 (19)	−0.076 (3)	−0.0008 (16)	0.022 (2)
C12	0.082 (2)	0.082 (2)	0.0481 (16)	−0.0391 (18)	−0.0070 (15)	−0.0028 (14)

O1—C2	1.234 (2)	C6—C7	1.520 (3)
O2—C2	1.238 (2)	C6—H6A	0.9700
O3—C10	1.386 (3)	C6—H6B	0.9700
O3—C11	1.433 (3)	C7—C8	1.516 (3)
O4—C12	1.419 (3)	C7—H7A	0.9700
O4—C10	1.421 (3)	C7—H7B	0.9700
N1—C1	1.348 (2)	C8—C9	1.512 (3)
N1—C3	1.371 (2)	C8—H8A	0.9700
N1—C6	1.479 (2)	C8—H8B	0.9700
N2—C1	1.345 (2)	C9—C10	1.520 (3)
N2—C4	1.372 (2)	C9—H9A	0.9700
N2—C5	1.468 (2)	C9—H9B	0.9700
C1—C2	1.524 (3)	C10—H10	0.9800
C3—C4	1.349 (3)	C11—H11A	0.9600
C3—H3	0.9300	C11—H11B	0.9600
C4—H4	0.9300	C11—H11C	0.9600
C5—H5A	0.9600	C12—H12A	0.9600
C5—H5B	0.9600	C12—H12B	0.9600
C5—H5C	0.9600	C12—H12C	0.9600
C10—O3—C11	112.8 (2)	C6—C7—H7A	108.6
C12—O4—C10	114.0 (2)	C8—C7—H7B	108.6
C1—N1—C3	109.36 (15)	C6—C7—H7B	108.6
C1—N1—C6	127.21 (16)	H7A—C7—H7B	107.6
C3—N1—C6	123.40 (15)	C9—C8—C7	112.45 (19)
C1—N2—C4	109.59 (15)	C9—C8—H8A	109.1
C1—N2—C5	126.70 (15)	C7—C8—H8A	109.1
C4—N2—C5	123.63 (15)	C9—C8—H8B	109.1
N2—C1—N1	106.65 (15)	C7—C8—H8B	109.1
N2—C1—C2	126.40 (16)	H8A—C8—H8B	107.8
N1—C1—C2	126.86 (16)	C8—C9—C10	114.3 (2)
O1—C2—O2	128.94 (19)	C8—C9—H9A	108.7
O1—C2—C1	115.65 (17)	C10—C9—H9A	108.7
O2—C2—C1	115.39 (17)	C8—C9—H9B	108.7
C4—C3—N1	107.34 (16)	C10—C9—H9B	108.7
C4—C3—H3	126.3	H9A—C9—H9B	107.6
N1—C3—H3	126.3	O3—C10—O4	112.1 (2)
C3—C4—N2	107.05 (16)	O3—C10—C9	107.4 (2)
C3—C4—H4	126.5	O4—C10—C9	112.8 (2)
N2—C4—H4	126.5	O3—C10—H10	108.1
N2—C5—H5A	109.5	O4—C10—H10	108.1
N2—C5—H5B	109.5	C9—C10—H10	108.1
H5A—C5—H5B	109.5	O3—C11—H11A	109.5
N2—C5—H5C	109.5	O3—C11—H11B	109.5
H5A—C5—H5C	109.5	H11A—C11—H11B	109.5
H5B—C5—H5C	109.5	O3—C11—H11C	109.5
N1—C6—C7	111.91 (15)	H11A—C11—H11C	109.5
N1—C6—H6A	109.2	H11B—C11—H11C	109.5
C7—C6—H6A	109.2	O4—C12—H12A	109.5
N1—C6—H6B	109.2	O4—C12—H12B	109.5
C7—C6—H6B	109.2	H12A—C12—H12B	109.5
H6A—C6—H6B	107.9	O4—C12—H12C	109.5
C8—C7—C6	114.69 (18)	H12A—C12—H12C	109.5
C8—C7—H7A	108.6	H12B—C12—H12C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2i	0.93	2.30	3.141 (2)	151
C4—H4···O1ii	0.93	2.30	3.127 (2)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2i	0.93	2.30	3.141 (2)	151
C4—H4⋯O1ii	0.93	2.30	3.127 (2)	148

Symmetry codes: (i) ; (ii) .