The zwitterion 1-butyl­imidazolium-3-(n-butane­sulfonate)

The mol­ecule of the title compound, C₁₁H₂₀N₂O₃S, contains a positively charged imidazolium head group and a negatively charged sulfonate tethered together by a four-carbon chain. There is weak intermolecular hydrogen bonding within the structure between the sulfonate O atoms and the H atoms of the imidazolium ring. The sulfonate group causes a twisting of the butyl chain and a decrease in the dihedral angle between the second and third carbon chain compared to the unsubstituted butyl group.

Key indicators

• Single-crystal X-ray study
• T = 123 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.053
• wR factor = 0.145
• Data-to-parameter ratio = 20.8

checkCIF/PLATON results

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Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: X-SEED (please provide reference); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED and POV-RAY (please provide reference).

1-butylimidazolium-3-(n-butanesulfonate)

Crystal data

C11H20N2O3S	Dx = 1.326 Mg m^−3
Mr = 260.35	Melting point: 152 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
a = 12.6914 (2) Å	Cell parameters from 29344 reflections
b = 11.7483 (2) Å	θ = 3.7–28.3°
c = 17.4988 (2) Å	µ = 0.25 mm^−1
V = 2609.11 (7) Å^3	T = 123 K
Z = 8	Prismatic, colorless
F(000) = 1120	0.30 × 0.30 × 0.25 mm

Data collection

Nonius KappaCCD diffractometer	2334 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.063
Graphite monochromator	θmax = 28.3°, θmin = 3.7°
1° frames in φ and ω scans	h = −16→16
29344 measured reflections	k = −15→15
3219 independent reflections	l = −23→23

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.145	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0634P)^2 + 2.971P] where P = (Fo^2 + 2Fc^2)/3
3219 reflections	(Δ/σ)max < 0.001
155 parameters	Δρmax = 0.89 e Å^−3
0 restraints	Δρmin = −0.53 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.02453 (5)	0.25632 (5)	0.42055 (3)	0.02276 (17)
O1	0.07181 (14)	0.31725 (14)	0.35618 (9)	0.0298 (4)
N1	0.45586 (14)	−0.10332 (15)	0.67671 (10)	0.0185 (4)
O2	−0.02227 (15)	0.33272 (15)	0.47598 (10)	0.0374 (5)
N2	0.31918 (14)	−0.06981 (14)	0.60666 (10)	0.0188 (4)
C2	0.42081 (17)	−0.04640 (18)	0.61588 (12)	0.0204 (5)
H2	0.4616	0.0026	0.5844	0.025*
O3	−0.04361 (14)	0.16492 (16)	0.39571 (11)	0.0376 (5)
C4	0.28788 (18)	−0.14392 (18)	0.66354 (12)	0.0208 (5)
H4	0.2191	−0.1741	0.6706	0.025*
C5	0.37313 (17)	−0.16533 (18)	0.70714 (12)	0.0204 (4)
H5	0.3759	−0.2138	0.7506	0.024*
C11	0.56611 (17)	−0.1030 (2)	0.70334 (13)	0.0246 (5)
H11A	0.5675	−0.1109	0.7597	0.029*
H11B	0.5992	−0.0293	0.6901	0.029*
C12	0.62906 (17)	−0.1994 (2)	0.66744 (12)	0.0245 (5)
H12A	0.7050	−0.1842	0.6752	0.029*
H12B	0.6157	−0.1998	0.6117	0.029*
C13	0.60336 (19)	−0.3174 (2)	0.69949 (13)	0.0268 (5)
H13A	0.6211	−0.3193	0.7546	0.032*
H13B	0.5268	−0.3316	0.6944	0.032*
C14	0.6636 (2)	−0.4114 (2)	0.65845 (17)	0.0421 (7)
H14A	0.6453	−0.4108	0.6041	0.063*
H14B	0.6448	−0.4853	0.6806	0.063*
H14C	0.7395	−0.3986	0.6643	0.063*
C31	0.24745 (19)	−0.01585 (19)	0.55127 (12)	0.0249 (5)
H31A	0.1950	−0.0722	0.5333	0.030*
H31B	0.2881	0.0112	0.5065	0.030*
C32	0.1912 (2)	0.0839 (2)	0.58853 (14)	0.0311 (6)
H32A	0.2431	0.1453	0.5978	0.037*
H32B	0.1638	0.0591	0.6388	0.037*
C33	0.0999 (2)	0.1327 (2)	0.54175 (14)	0.0297 (5)
H33A	0.0503	0.0702	0.5293	0.036*
H33B	0.0615	0.1887	0.5735	0.036*
C34	0.13359 (18)	0.1897 (2)	0.46833 (13)	0.0252 (5)
H34A	0.1655	0.1323	0.4340	0.030*
H34B	0.1878	0.2478	0.4798	0.030*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0296 (3)	0.0208 (3)	0.0178 (3)	0.0050 (2)	−0.0044 (2)	0.0011 (2)
O1	0.0354 (10)	0.0297 (9)	0.0244 (8)	0.0026 (7)	0.0005 (7)	0.0046 (7)
N1	0.0194 (9)	0.0184 (9)	0.0176 (8)	0.0007 (7)	−0.0010 (7)	0.0004 (7)
O2	0.0520 (12)	0.0353 (10)	0.0250 (9)	0.0219 (9)	0.0051 (8)	0.0037 (7)
N2	0.0208 (9)	0.0164 (8)	0.0192 (9)	0.0021 (7)	−0.0011 (7)	0.0026 (7)
C2	0.0264 (11)	0.0166 (10)	0.0184 (10)	−0.0012 (8)	0.0012 (9)	0.0018 (8)
O3	0.0335 (10)	0.0364 (10)	0.0429 (11)	−0.0066 (8)	−0.0144 (9)	0.0080 (8)
C4	0.0207 (10)	0.0190 (10)	0.0228 (11)	0.0013 (8)	0.0032 (9)	0.0022 (8)
C5	0.0220 (11)	0.0203 (10)	0.0188 (10)	0.0020 (8)	0.0024 (9)	0.0027 (8)
C11	0.0201 (11)	0.0282 (12)	0.0254 (11)	−0.0025 (9)	−0.0068 (10)	0.0000 (9)
C12	0.0166 (10)	0.0357 (13)	0.0214 (11)	−0.0002 (9)	−0.0017 (9)	0.0012 (10)
C13	0.0257 (12)	0.0320 (12)	0.0229 (11)	0.0048 (10)	0.0015 (9)	−0.0002 (10)
C14	0.0396 (15)	0.0386 (15)	0.0481 (16)	0.0093 (13)	0.0102 (13)	−0.0004 (13)
C31	0.0304 (12)	0.0236 (11)	0.0207 (10)	0.0032 (9)	−0.0077 (10)	0.0025 (9)
C32	0.0345 (13)	0.0291 (12)	0.0298 (12)	0.0122 (10)	−0.0087 (11)	0.0004 (10)
C33	0.0332 (13)	0.0303 (12)	0.0256 (12)	0.0109 (10)	−0.0010 (10)	0.0029 (10)
C34	0.0249 (11)	0.0250 (11)	0.0256 (11)	0.0029 (9)	−0.0022 (10)	−0.0014 (9)

Geometric parameters (Å, º)

S1—O3	1.4456 (19)	C12—H12B	0.9900
S1—O2	1.4489 (18)	C13—C14	1.523 (3)
S1—O1	1.4633 (17)	C13—H13A	0.9900
S1—C34	1.797 (2)	C13—H13B	0.9900
N1—C2	1.333 (3)	C14—H14A	0.9800
N1—C5	1.385 (3)	C14—H14B	0.9800
N1—C11	1.475 (3)	C14—H14C	0.9800
N2—C2	1.329 (3)	C31—C32	1.520 (3)
N2—C4	1.381 (3)	C31—H31A	0.9900
N2—C31	1.473 (3)	C31—H31B	0.9900
C2—H2	0.9500	C32—C33	1.530 (3)
C4—C5	1.348 (3)	C32—H32A	0.9900
C4—H4	0.9500	C32—H32B	0.9900
C5—H5	0.9500	C33—C34	1.511 (3)
C11—C12	1.522 (3)	C33—H33A	0.9900
C11—H11A	0.9900	C33—H33B	0.9900
C11—H11B	0.9900	C34—H34A	0.9900
C12—C13	1.531 (3)	C34—H34B	0.9900
C12—H12A	0.9900
O3—S1—O2	114.60 (12)	C12—C13—H13A	109.2
O3—S1—O1	112.17 (11)	C14—C13—H13B	109.2
O2—S1—O1	112.36 (11)	C12—C13—H13B	109.2
O3—S1—C34	106.09 (11)	H13A—C13—H13B	107.9
O2—S1—C34	105.91 (11)	C13—C14—H14A	109.5
O1—S1—C34	104.80 (11)	C13—C14—H14B	109.5
C2—N1—C5	108.54 (18)	H14A—C14—H14B	109.5
C2—N1—C11	124.57 (18)	C13—C14—H14C	109.5
C5—N1—C11	126.83 (18)	H14A—C14—H14C	109.5
C2—N2—C4	108.80 (18)	H14B—C14—H14C	109.5
C2—N2—C31	126.21 (18)	N2—C31—C32	109.88 (17)
C4—N2—C31	124.59 (18)	N2—C31—H31A	109.7
N2—C2—N1	108.48 (18)	C32—C31—H31A	109.7
N2—C2—H2	125.8	N2—C31—H31B	109.7
N1—C2—H2	125.8	C32—C31—H31B	109.7
C5—C4—N2	107.14 (19)	H31A—C31—H31B	108.2
C5—C4—H4	126.4	C31—C32—C33	114.5 (2)
N2—C4—H4	126.4	C31—C32—H32A	108.6
C4—C5—N1	107.03 (18)	C33—C32—H32A	108.6
C4—C5—H5	126.5	C31—C32—H32B	108.6
N1—C5—H5	126.5	C33—C32—H32B	108.6
N1—C11—C12	111.43 (18)	H32A—C32—H32B	107.6
N1—C11—H11A	109.3	C34—C33—C32	114.0 (2)
C12—C11—H11A	109.3	C34—C33—H33A	108.8
N1—C11—H11B	109.3	C32—C33—H33A	108.8
C12—C11—H11B	109.3	C34—C33—H33B	108.8
H11A—C11—H11B	108.0	C32—C33—H33B	108.8
C11—C12—C13	114.29 (18)	H33A—C33—H33B	107.7
C11—C12—H12A	108.7	C33—C34—S1	111.76 (16)
C13—C12—H12A	108.7	C33—C34—H34A	109.3
C11—C12—H12B	108.7	S1—C34—H34A	109.3
C13—C12—H12B	108.7	C33—C34—H34B	109.3
H12A—C12—H12B	107.6	S1—C34—H34B	109.3
C14—C13—C12	112.1 (2)	H34A—C34—H34B	107.9
C14—C13—H13A	109.2
C11—C12—C13—C14	176.6 (2)	C31—C32—C33—C34	−67.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2^i	0.95	2.21	3.067 (3)	149
C4—H4···O3^ii	0.95	2.51	3.278 (3)	138
C5—H5···O1^iii	0.95	2.31	3.236 (3)	165
C11—H11A···O3^iii	0.99	2.48	3.456 (3)	168
C11—H11B···O1^i	0.99	2.64	3.515 (3)	147
C14—H14C···O1^iv	0.98	2.60	3.545 (4)	161
C31—H31A···O3^ii	0.99	2.53	3.259 (3)	130

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