3-(1-Methyl-3-imidazolio)propane-sulfonate: a precursor to a Brønsted acid ionic liquid.

The title compound, C(7)H(12)N(2)O(3)S, is a zwitterion precursor to a Brønsted acid ionic liquid with potential as an acid catalyst. The C-N-C-C torsion angle of 100.05 (8)° allows the positively charged imidazolium head group and the negatively charged sulfonate group to inter-act with neighboring zwitterions, forming a C-H⋯O hydrogen-bonding network; the shortest among these inter-actions is 2.9512 (9) Å. The C-H⋯O inter-actions can be described by graph-set notation as two R(2) (2)(16) and one R(2) (2)(5) hydrogen-bonded rings.

Related literature

For the use of functionalized ionic liquids (ILs) as Brønsted acid catalysts for organic reactions, see: Cole et al. (2002 ▶); Yoshizawa et al. (2001 ▶). The local structure of ILs is often conserved on transition from the solid state to the liquid state, see: Henderson et al. (2007 ▶); Reichert et al. (2007 ▶); Triolo et al. (2006 ▶). For a related structure, see: Pringle et al. (2003 ▶). For polymorphs of ionic liquids, see: Holbrey et al. (2003 ▶) and for the applications of ionic liquids, see: Plechkova & Seddon (2008 ▶).

Experimental

Crystal data

C7H12N2O3S

M = 204.25

Monoclinic,

a = 9.8164 (4) Å

b = 11.7421 (5) Å

c = 7.9769 (3) Å

β = 94.878 (2)°

V = 916.13 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.33 mm−1

T = 296 K

0.29 × 0.28 × 0.13 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: for a sphere (SADABS; Bruker, 2007 ▶) T min = 0.910, T max = 0.958

21327 measured reflections

8299 independent reflections

5726 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.120

S = 1.03

8299 reflections

166 parameters

All H-atom parameters refined

Δρmax = 0.55 e Å−3

Δρmin = −0.47 e Å−3

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.

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536810004344/kp2241sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810004344/kp2241Isup2.hkl

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

C7H12N2O3S	F(000) = 432
Mr = 204.25	Dx = 1.481 Mg m−3
Monoclinic, P21/c	Melting point: 482 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.8164 (4) Å	Cell parameters from 4851 reflections
b = 11.7421 (5) Å	θ = 3.1–41.1°
c = 7.9769 (3) Å	µ = 0.33 mm−1
β = 94.878 (2)°	T = 296 K
V = 916.13 (6) Å3	Plate, colourless
Z = 4	0.29 × 0.28 × 0.13 mm

Bruker SMART CCD area-detector diffractometer	8299 independent reflections
Radiation source: fine-focus sealed tube	5726 reflections with I > 2σ(I)
graphite	Rint = 0.033
phi and ω scans	θmax = 47.1°, θmin = 3.1°
Absorption correction: for a sphere (SADABS; Bruker, 2007)	h = −20→13
Tmin = 0.910, Tmax = 0.958	k = −19→24
21327 measured reflections	l = −16→16

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	All H-atom parameters refined
S = 1.03	w = 1/[σ2(Fo2) + (0.0574P)2 + 0.0483P] where P = (Fo2 + 2Fc2)/3
8299 reflections	(Δ/σ)max = 0.002
166 parameters	Δρmax = 0.55 e Å−3
0 restraints	Δρmin = −0.47 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
S1	0.288447 (16)	0.459431 (14)	0.711035 (19)	0.01929 (4)
O1	0.18103 (7)	0.54452 (5)	0.71911 (8)	0.02993 (12)
O2	0.42331 (6)	0.50523 (8)	0.76230 (9)	0.03616 (15)
O3	0.25705 (8)	0.35528 (5)	0.79823 (8)	0.03407 (14)
N3	0.17238 (6)	0.51000 (5)	0.16133 (7)	0.01989 (9)
N1	0.28516 (6)	0.65793 (5)	0.08981 (8)	0.02208 (9)
C2	0.29151 (7)	0.54584 (6)	0.11322 (8)	0.02096 (10)
H2A	0.3704 (14)	0.5037 (13)	0.1080 (19)	0.037 (3)*
C4	0.08588 (8)	0.60254 (6)	0.16753 (10)	0.02580 (12)
H4A	−0.0036 (14)	0.5991 (11)	0.2077 (16)	0.034 (3)*
C5	0.15675 (8)	0.69513 (7)	0.12222 (11)	0.02724 (13)
H5A	0.1323 (14)	0.7688 (12)	0.1137 (17)	0.037 (3)*
C6	0.39573 (9)	0.72763 (8)	0.03336 (12)	0.03149 (15)
H6A	0.3932 (15)	0.8024 (14)	0.0813 (19)	0.044 (4)*
H6B	0.4809 (19)	0.6923 (15)	0.063 (2)	0.061 (5)*
H6C	0.3820 (17)	0.7417 (17)	−0.081 (2)	0.067 (5)*
C7	0.14604 (8)	0.39419 (6)	0.21968 (8)	0.02303 (11)
H7A	0.0552 (13)	0.3717 (11)	0.1696 (15)	0.027 (3)*
H7B	0.2156 (12)	0.3490 (11)	0.1741 (15)	0.026 (3)*
C8	0.15267 (7)	0.38976 (6)	0.41105 (8)	0.02112 (10)
H8A	0.0853 (14)	0.4389 (12)	0.4510 (18)	0.033 (3)*
H8B	0.1301 (13)	0.3105 (12)	0.4405 (17)	0.036 (3)*
C9	0.29159 (7)	0.42456 (8)	0.49418 (9)	0.02574 (12)
H9A	0.3243 (16)	0.4859 (13)	0.444 (2)	0.043 (4)*
H9B	0.3600 (16)	0.3658 (13)	0.4885 (18)	0.043 (4)*

	U11	U22	U33	U12	U13	U23
S1	0.01791 (6)	0.02075 (7)	0.01894 (6)	−0.00086 (5)	0.00002 (4)	0.00099 (4)
O1	0.0309 (3)	0.0258 (2)	0.0325 (3)	0.0079 (2)	−0.0007 (2)	−0.00600 (19)
O2	0.0218 (2)	0.0569 (4)	0.0287 (3)	−0.0109 (3)	−0.0044 (2)	−0.0016 (3)
O3	0.0510 (4)	0.0231 (2)	0.0281 (2)	−0.0029 (2)	0.0032 (2)	0.00664 (19)
N3	0.0201 (2)	0.01929 (19)	0.02006 (19)	0.00022 (16)	0.00055 (16)	−0.00017 (15)
N1	0.0208 (2)	0.0222 (2)	0.0233 (2)	−0.00089 (18)	0.00185 (17)	0.00077 (17)
C2	0.0201 (2)	0.0225 (2)	0.0204 (2)	0.00164 (19)	0.00209 (18)	0.00037 (18)
C4	0.0200 (3)	0.0237 (3)	0.0339 (3)	0.0023 (2)	0.0034 (2)	0.0011 (2)
C5	0.0245 (3)	0.0214 (3)	0.0361 (3)	0.0030 (2)	0.0042 (2)	0.0014 (2)
C6	0.0295 (4)	0.0310 (3)	0.0347 (4)	−0.0069 (3)	0.0068 (3)	0.0048 (3)
C7	0.0289 (3)	0.0190 (2)	0.0207 (2)	−0.0029 (2)	−0.0008 (2)	−0.00147 (18)
C8	0.0208 (2)	0.0220 (2)	0.0204 (2)	−0.00162 (19)	0.00092 (18)	−0.00033 (18)
C9	0.0180 (2)	0.0392 (4)	0.0200 (2)	0.0002 (2)	0.00188 (18)	−0.0015 (2)

S1—O3	1.4529 (6)	C5—H5A	0.899 (14)
S1—O2	1.4550 (6)	C6—H6A	0.959 (16)
S1—O1	1.4580 (6)	C6—H6B	0.945 (19)
S1—C9	1.7805 (7)	C6—H6C	0.924 (19)
N3—C2	1.3298 (9)	C7—C8	1.5233 (9)
N3—C4	1.3825 (9)	C7—H7A	0.982 (13)
N3—C7	1.4673 (9)	C7—H7B	0.961 (12)
N1—C2	1.3301 (9)	C8—C9	1.5207 (10)
N1—C5	1.3791 (10)	C8—H8A	0.952 (14)
N1—C6	1.4607 (10)	C8—H8B	0.990 (14)
C2—H2A	0.923 (14)	C9—H9A	0.898 (16)
C4—C5	1.3562 (11)	C9—H9B	0.967 (16)
C4—H4A	0.961 (14)
O3—S1—O2	113.68 (5)	H6A—C6—H6B	110.8 (14)
O3—S1—O1	111.84 (4)	N1—C6—H6C	110.7 (11)
O2—S1—O1	112.24 (5)	H6A—C6—H6C	102.9 (15)
O3—S1—C9	107.06 (4)	H6B—C6—H6C	112.0 (15)
O2—S1—C9	105.52 (4)	N3—C7—C8	110.85 (5)
O1—S1—C9	105.84 (4)	N3—C7—H7A	107.3 (7)
C2—N3—C4	108.62 (6)	C8—C7—H7A	111.0 (7)
C2—N3—C7	124.60 (6)	N3—C7—H7B	104.0 (7)
C4—N3—C7	126.28 (6)	C8—C7—H7B	112.9 (7)
C2—N1—C5	108.65 (6)	H7A—C7—H7B	110.4 (10)
C2—N1—C6	124.78 (7)	C9—C8—C7	112.84 (6)
C5—N1—C6	126.54 (7)	C9—C8—H8A	108.3 (8)
N3—C2—N1	108.77 (6)	C7—C8—H8A	110.0 (8)
N3—C2—H2A	127.3 (9)	C9—C8—H8B	111.1 (8)
N1—C2—H2A	123.6 (9)	C7—C8—H8B	106.2 (8)
C5—C4—N3	106.86 (7)	H8A—C8—H8B	108.4 (11)
C5—C4—H4A	128.8 (8)	C8—C9—S1	113.36 (5)
N3—C4—H4A	124.1 (8)	C8—C9—H9A	111.2 (10)
C4—C5—N1	107.09 (7)	S1—C9—H9A	106.8 (10)
C4—C5—H5A	130.7 (9)	C8—C9—H9B	112.9 (9)
N1—C5—H5A	122.2 (9)	S1—C9—H9B	106.2 (9)
N1—C6—H6A	110.2 (9)	H9A—C9—H9B	105.9 (13)
N1—C6—H6B	110.1 (11)
C2—N3—C7—C8	100.05 (8)	C4—N3—C7—C8	−70.97 (8)
N3—C7—C8—C9	−60.48 (8)	N3—C7—C8—C9	−60.48 (8)
C7—C8—C9—S1	163.00 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O2i	0.923 (14)	2.197 (14)	2.9512 (9)	138.4 (12)
C5—H5A···O1ii	0.899 (14)	2.381 (15)	3.1573 (10)	144.6 (12)
C4—H4A···O1iii	0.961 (14)	2.528 (14)	3.3268 (11)	140.5 (11)
C4—H4A···O3iii	0.961 (14)	2.541 (14)	3.4364 (11)	155.0 (11)
C7—H7B···O3iv	0.961 (12)	2.613 (12)	3.1693 (10)	117.2 (9)
C8—H8B···O3iv	0.990 (14)	2.621 (13)	3.2086 (9)	118.1 (9)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O2i	0.923 (14)	2.197 (14)	2.9512 (9)	138.4 (12)
C5—H5A⋯O1ii	0.899 (14)	2.381 (15)	3.1573 (10)	144.6 (12)
C4—H4A⋯O1iii	0.961 (14)	2.528 (14)	3.3268 (11)	140.5 (11)
C4—H4A⋯O3iii	0.961 (14)	2.541 (14)	3.4364 (11)	155.0 (11)
C7—H7B⋯O3iv	0.961 (12)	2.613 (12)	3.1693 (10)	117.2 (9)
C8—H8B⋯O3iv	0.990 (14)	2.621 (13)	3.2086 (9)	118.1 (9)

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