3-(Ethyl­dimethyl­ammonio)­propanesulfonate

In the title sulfobetaine (NDSB-195), C₇H₁₇NO₃S, the three-methyl­ene spacer between the ammonium and sulfonate groups is in a fully extended conformation. Inter­actions between the charged ammonium and sulfonate groups are the most important for the crystal packing.

Key indicators

• Single-crystal X-ray study
• T = 106 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.034
• wR factor = 0.092
• Data-to-parameter ratio = 16.7

checkCIF/PLATON results

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Computing details

Data collection: HKL-2000 (Otwinowski & Minor, 1997); cell refinement: HKL-2000; data reduction: HKL-2000; program(s) used to solve structure: HKL-3000SM (Minor et al., 2006) and SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: HKL-3000SM and SHELXL97 (Sheldrick, 1997); molecular graphics: HKL-3000SM, ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: HKL-3000SM.

ethyldimethylammoniopropane sulfonate

Crystal data

C7H17NO3S	F(000) = 848
Mr = 195.28	Dx = 1.365 Mg m^−3
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54179 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1839 reflections
a = 12.369 (1) Å	θ = 6.2–72.3°
b = 11.964 (1) Å	µ = 2.82 mm^−1
c = 12.844 (1) Å	T = 106 K
V = 1900.7 (3) Å^3	Block, colorless
Z = 8	0.23 × 0.16 × 0.08 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	1839 independent reflections
Radiation source: fine-focus sealed tube	1695 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
Detector resolution: 10 pixels mm^-1	θmax = 72.3°, θmin = 6.2°
ω scan with χ offset	h = −15→15
Absorption correction: multi-scan (Otwinowski et al., 2003)	k = −14→13
Tmin = 0.61, Tmax = 0.80	l = −15→15
3381 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.034	H-atom parameters constrained
wR(F^2) = 0.092	w = 1/[σ^2(Fo^2) + (0.0463P)^2 + 1.4076P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
1839 reflections	Δρmax = 0.29 e Å^−3
110 parameters	Δρmin = −0.36 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00085 (14)

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	0.08225 (3)	−0.00207 (3)	0.27742 (3)	0.02018 (16)
O2	0.04113 (9)	−0.10449 (9)	0.32375 (9)	0.0269 (3)
O1	0.16302 (9)	0.05369 (10)	0.34126 (9)	0.0298 (3)
O3	0.11746 (11)	−0.01688 (10)	0.16996 (9)	0.0315 (3)
C6	−0.31850 (13)	0.31409 (14)	0.42197 (12)	0.0253 (4)
H6A	−0.3686	0.2735	0.3791	0.038*
H6B	−0.2884	0.3749	0.3828	0.038*
H6C	−0.3555	0.3429	0.4819	0.038*
C1	−0.02895 (13)	0.09220 (14)	0.27026 (11)	0.0225 (4)
H1A	−0.0042	0.1623	0.2407	0.027*
H1B	−0.0831	0.0614	0.2238	0.027*
N1	−0.22956 (10)	0.23744 (11)	0.45639 (10)	0.0193 (3)
C3	−0.17376 (12)	0.19619 (13)	0.35859 (11)	0.0209 (3)
H3A	−0.1465	0.2605	0.3208	0.025*
H3B	−0.2272	0.1600	0.3148	0.025*
C2	−0.08100 (12)	0.11531 (13)	0.37575 (12)	0.0213 (3)
H2A	−0.1076	0.0463	0.4060	0.026*
H2B	−0.0284	0.1476	0.4230	0.026*
C7	−0.15231 (13)	0.30257 (14)	0.52325 (12)	0.0239 (3)
H7A	−0.0948	0.2545	0.5459	0.036*
H7B	−0.1900	0.3314	0.5829	0.036*
H7C	−0.1228	0.3635	0.4838	0.036*
C4	−0.27470 (14)	0.13824 (14)	0.51561 (12)	0.0258 (4)
H4A	−0.3198	0.0950	0.4688	0.031*
H4B	−0.2150	0.0909	0.5369	0.031*
C5	−0.34045 (14)	0.16784 (15)	0.61085 (13)	0.0307 (4)
H5A	−0.3658	0.1006	0.6435	0.046*
H5B	−0.4012	0.2129	0.5906	0.046*
H5C	−0.2962	0.2089	0.6589	0.046*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0231 (2)	0.0171 (3)	0.0203 (2)	0.00097 (13)	0.00163 (13)	−0.00102 (13)
O2	0.0272 (6)	0.0207 (6)	0.0329 (6)	0.0003 (5)	0.0030 (5)	0.0047 (5)
O1	0.0252 (6)	0.0256 (7)	0.0387 (7)	0.0001 (5)	−0.0049 (5)	−0.0071 (5)
O3	0.0410 (7)	0.0293 (7)	0.0244 (6)	0.0075 (5)	0.0098 (5)	−0.0015 (5)
C6	0.0235 (8)	0.0272 (9)	0.0251 (8)	0.0075 (7)	−0.0002 (6)	0.0028 (7)
C1	0.0269 (8)	0.0198 (9)	0.0209 (8)	0.0021 (6)	−0.0001 (6)	−0.0006 (6)
N1	0.0216 (6)	0.0167 (7)	0.0196 (6)	0.0006 (5)	−0.0007 (5)	0.0005 (5)
C3	0.0248 (7)	0.0203 (8)	0.0176 (7)	0.0022 (6)	0.0000 (6)	0.0004 (6)
C2	0.0241 (8)	0.0191 (8)	0.0207 (7)	0.0014 (6)	0.0003 (6)	0.0000 (6)
C7	0.0251 (8)	0.0224 (8)	0.0243 (8)	−0.0021 (6)	−0.0020 (6)	−0.0051 (6)
C4	0.0329 (9)	0.0184 (9)	0.0260 (8)	−0.0032 (6)	0.0037 (7)	0.0016 (6)
C5	0.0348 (9)	0.0259 (10)	0.0315 (9)	−0.0004 (7)	0.0091 (7)	0.0041 (7)

Geometric parameters (Å, º)

S1—O2	1.4541 (12)	C3—C2	1.517 (2)
S1—O1	1.4546 (12)	C3—H3A	0.9700
S1—O3	1.4581 (12)	C3—H3B	0.9700
S1—C1	1.7811 (16)	C2—H2A	0.9700
C6—N1	1.4988 (19)	C2—H2B	0.9700
C6—H6A	0.9600	C7—H7A	0.9600
C6—H6B	0.9600	C7—H7B	0.9600
C6—H6C	0.9600	C7—H7C	0.9600
C1—C2	1.525 (2)	C4—C5	1.511 (2)
C1—H1A	0.9700	C4—H4A	0.9700
C1—H1B	0.9700	C4—H4B	0.9700
N1—C7	1.5025 (19)	C5—H5A	0.9600
N1—C3	1.5159 (19)	C5—H5B	0.9600
N1—C4	1.516 (2)	C5—H5C	0.9600
O2—S1—O1	113.33 (7)	N1—C3—H3B	108.4
O2—S1—O3	112.92 (7)	C2—C3—H3B	108.4
O1—S1—O3	112.60 (8)	H3A—C3—H3B	107.4
O2—S1—C1	106.54 (7)	C3—C2—C1	107.80 (12)
O1—S1—C1	105.61 (7)	C3—C2—H2A	110.1
O3—S1—C1	105.00 (7)	C1—C2—H2A	110.1
N1—C6—H6A	109.5	C3—C2—H2B	110.1
N1—C6—H6B	109.5	C1—C2—H2B	110.1
H6A—C6—H6B	109.5	H2A—C2—H2B	108.5
N1—C6—H6C	109.5	N1—C7—H7A	109.5
H6A—C6—H6C	109.5	N1—C7—H7B	109.5
H6B—C6—H6C	109.5	H7A—C7—H7B	109.5
C2—C1—S1	113.26 (11)	N1—C7—H7C	109.5
C2—C1—H1A	108.9	H7A—C7—H7C	109.5
S1—C1—H1A	108.9	H7B—C7—H7C	109.5
C2—C1—H1B	108.9	C5—C4—N1	114.89 (13)
S1—C1—H1B	108.9	C5—C4—H4A	108.5
H1A—C1—H1B	107.7	N1—C4—H4A	108.5
C6—N1—C7	108.55 (12)	C5—C4—H4B	108.5
C6—N1—C3	106.79 (11)	N1—C4—H4B	108.5
C7—N1—C3	110.66 (11)	H4A—C4—H4B	107.5
C6—N1—C4	110.89 (12)	C4—C5—H5A	109.5
C7—N1—C4	110.70 (12)	C4—C5—H5B	109.5
C3—N1—C4	109.18 (12)	H5A—C5—H5B	109.5
N1—C3—C2	115.57 (12)	C4—C5—H5C	109.5
N1—C3—H3A	108.4	H5A—C5—H5C	109.5
C2—C3—H3A	108.4	H5B—C5—H5C	109.5
O2—S1—C1—C2	57.69 (13)	N1—C3—C2—C1	−174.78 (13)
O1—S1—C1—C2	−63.11 (13)	S1—C1—C2—C3	179.97 (11)
O3—S1—C1—C2	177.69 (12)	C6—N1—C4—C5	−57.95 (17)
C6—N1—C3—C2	−179.22 (13)	C7—N1—C4—C5	62.59 (18)
C7—N1—C3—C2	62.82 (17)	C3—N1—C4—C5	−175.35 (13)
C4—N1—C3—C2	−59.26 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O3^i	0.97	2.36	3.302 (2)	164
C4—H4B···O1^ii	0.97	2.42	3.250 (2)	143
C7—H7C···O3^iii	0.96	2.44	3.318 (2)	152
C7—H7B···O1^iv	0.96	2.48	3.347 (2)	150

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