N-(β-Carb-oxy-eth-yl)-α-isoleucine.

The title compound, {2-[(2-carbamoyleth-yl)amino]-3-methyl-penta-noic acid}, C(9)H(18)N(2)O(3), is of inter-est with respect to its biological activity. It was formed during an addition reaction between acryl-amide and the amino acid isoleucine. The crystal structure is a three-dimensional network built up by inter-molecular N-H⋯O and O-H⋯N hydrogen bonds.

Related literature

For toxicological investigations on acryl­amide, see: Besaratinia & Pfeifer (2007 ▶); Parzefall (2008 ▶); Bowyer et al. (2009 ▶); Wang et al. (2010 ▶); Mei et al. (2010 ▶); Koyama et al. (2011 ▶); Lee et al. (2012 ▶); Nixon et al. (2012 ▶); Rice (2005 ▶). For directives on monitoring acryl­amide in drinking water, see: EU (2000 ▶). For the determination of acryl­amide in different media, see: Zangrando et al. (2012 ▶); Marin et al. (2006 ▶); Lucentini et al. (2009 ▶); Keramat et al. (2011 ▶); Tareke et al. (2002 ▶); Pittet et al. (2004 ▶); Castle & Eriksson (2005 ▶); Mizukami et al. (2006 ▶); Dias Soares et al. (2009 ▶); Alpmann & Morlock (2008 ▶); Preston et al. (2009 ▶); Perez & Osterman-Golkar (2003 ▶).

Experimental

Crystal data

C9H18N2O3

M = 202.25

Orthorhombic,

a = 5.2989 (17) Å

b = 9.024 (3) Å

c = 23.268 (7) Å

V = 1112.6 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.64 × 0.06 × 0.06 mm

Data collection

Bruker APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ▶) T min = 0.944, T max = 0.994

7386 measured reflections

1516 independent reflections

1124 reflections with I > 2σ(I)

R int = 0.074

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.114

S = 0.95

1516 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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 ▶) and ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681205146X/bg2493sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681205146X/bg2493Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681205146X/bg2493Isup3.mol

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681205146X/bg2493Isup4.cml

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

C9H18N2O3	F(000) = 440
Mr = 202.25	Dx = 1.207 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1516 reflections
a = 5.2989 (17) Å	θ = 1.8–27.5°
b = 9.024 (3) Å	µ = 0.09 mm−1
c = 23.268 (7) Å	T = 298 K
V = 1112.6 (6) Å3	Needle, colourless
Z = 4	0.64 × 0.06 × 0.06 mm

Bruker APEX CCD area-detector diffractometer	1516 independent reflections
Radiation source: fine-focus sealed tube	1124 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.074
ω/2θ scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SHELXTL [SADABS?]; Sheldrick, 2008)	h = −6→6
Tmin = 0.944, Tmax = 0.994	k = −10→11
7386 measured reflections	l = −30→25

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H-atom parameters constrained
S = 0.95	w = 1/[σ2(Fo2) + (0.0694P)2] where P = (Fo2 + 2Fc2)/3
1516 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.27 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
C10	0.7698 (9)	0.2828 (6)	0.55528 (14)	0.1012 (15)
H102	0.6633	0.2437	0.5256	0.152*
H101	0.9239	0.2271	0.5568	0.152*
H103	0.8073	0.3848	0.5472	0.152*
C9	0.6365 (7)	0.2719 (4)	0.61206 (12)	0.0594 (8)
H9A	0.6549	0.1718	0.6267	0.071*
H9B	0.4579	0.2899	0.6062	0.071*
C11	0.6607 (8)	0.5381 (3)	0.64355 (12)	0.0669 (10)
H11A	0.7246	0.6032	0.6728	0.100*
H11B	0.4800	0.5454	0.6422	0.100*
H11C	0.7297	0.5661	0.6070	0.100*
C8	0.7355 (5)	0.3811 (3)	0.65718 (9)	0.0416 (6)
H8	0.9202	0.3770	0.6555	0.050*
C6	0.6585 (4)	0.3299 (3)	0.71788 (9)	0.0303 (5)
H61	0.7165	0.2210	0.7210	0.036*
C7	0.3729 (4)	0.3374 (3)	0.72786 (10)	0.0325 (5)
O3	0.2475 (3)	0.22453 (18)	0.71760 (8)	0.0472 (5)
O2	0.2878 (3)	0.45814 (17)	0.74539 (7)	0.0461 (5)
H21	0.1361	0.4499	0.7516	0.069*
N5	0.7864 (3)	0.42102 (19)	0.76255 (7)	0.0287 (4)
H51	0.7098	0.5195	0.7647	0.034*
C4	0.7693 (5)	0.3514 (3)	0.82032 (9)	0.0387 (6)
H41	0.8359	0.2514	0.8184	0.046*
H42	0.5935	0.3452	0.8317	0.046*
C3	0.9138 (5)	0.4382 (3)	0.86474 (10)	0.0437 (6)
H31	0.8541	0.5398	0.8653	0.052*
H32	1.0916	0.4392	0.8549	0.052*
C2	0.8789 (5)	0.3691 (3)	0.92360 (11)	0.0441 (6)
O1	0.6669 (4)	0.3386 (3)	0.94118 (8)	0.0640 (7)
N1	1.0852 (5)	0.3443 (3)	0.95370 (10)	0.0571 (7)
H1A	1.0748	0.3050	0.9873	0.069*
H1B	1.2303	0.3674	0.9398	0.069*

	U11	U22	U33	U12	U13	U23
C10	0.107 (4)	0.145 (4)	0.051 (2)	0.017 (4)	0.002 (2)	−0.022 (2)
C9	0.0570 (19)	0.073 (2)	0.0485 (16)	0.0103 (17)	−0.0078 (16)	−0.0115 (14)
C11	0.087 (3)	0.0601 (19)	0.0532 (16)	−0.0004 (19)	0.0045 (18)	0.0146 (14)
C8	0.0266 (12)	0.0569 (16)	0.0414 (13)	0.0032 (12)	0.0010 (11)	0.0006 (11)
C6	0.0201 (10)	0.0329 (11)	0.0379 (12)	0.0000 (9)	−0.0006 (9)	−0.0035 (9)
C7	0.0210 (10)	0.0351 (13)	0.0414 (12)	0.0018 (10)	−0.0020 (10)	0.0028 (10)
O3	0.0258 (9)	0.0366 (9)	0.0792 (13)	−0.0046 (8)	−0.0105 (9)	0.0016 (8)
O2	0.0176 (7)	0.0442 (10)	0.0765 (12)	0.0006 (7)	0.0048 (8)	−0.0150 (8)
N5	0.0205 (8)	0.0306 (9)	0.0351 (9)	0.0005 (8)	0.0001 (7)	0.0010 (7)
C4	0.0326 (12)	0.0442 (14)	0.0391 (13)	−0.0061 (12)	−0.0010 (11)	0.0080 (10)
C3	0.0359 (14)	0.0528 (16)	0.0423 (14)	−0.0086 (12)	−0.0040 (11)	0.0059 (12)
C2	0.0343 (13)	0.0568 (17)	0.0412 (13)	−0.0005 (12)	−0.0004 (12)	0.0029 (12)
O1	0.0384 (11)	0.1044 (19)	0.0493 (11)	−0.0072 (12)	0.0022 (9)	0.0191 (11)
N1	0.0412 (13)	0.087 (2)	0.0436 (12)	0.0016 (13)	−0.0024 (11)	0.0155 (12)

C10—C9	1.501 (5)	C7—O3	1.239 (3)
C10—H102	0.9600	C7—O2	1.248 (3)
C10—H101	0.9600	O2—H21	0.8200
C10—H103	0.9600	N5—C4	1.487 (3)
C9—C8	1.532 (4)	N5—H51	0.9781
C9—H9A	0.9700	C4—C3	1.506 (3)
C9—H9B	0.9700	C4—H41	0.9700
C11—C8	1.506 (4)	C4—H42	0.9700
C11—H11A	0.9600	C3—C2	1.516 (3)
C11—H11B	0.9600	C3—H31	0.9700
C11—H11C	0.9600	C3—H32	0.9700
C8—C6	1.541 (3)	C2—O1	1.226 (3)
C8—H8	0.9800	C2—N1	1.318 (3)
C6—N5	1.489 (3)	N1—H1A	0.8600
C6—C7	1.532 (3)	N1—H1B	0.8600
C6—H61	1.0319
C9—C10—H102	109.5	C7—C6—H61	109.0
C9—C10—H101	109.5	C8—C6—H61	105.7
H102—C10—H101	109.5	O3—C7—O2	125.9 (2)
C9—C10—H103	109.5	O3—C7—C6	117.7 (2)
H102—C10—H103	109.5	O2—C7—C6	116.4 (2)
H101—C10—H103	109.5	C7—O2—H21	109.5
C10—C9—C8	113.5 (3)	C4—N5—C6	111.72 (17)
C10—C9—H9A	108.9	C4—N5—H51	108.1
C8—C9—H9A	108.9	C6—N5—H51	110.5
C10—C9—H9B	108.9	N5—C4—C3	111.69 (19)
C8—C9—H9B	108.9	N5—C4—H41	109.3
H9A—C9—H9B	107.7	C3—C4—H41	109.3
C8—C11—H11A	109.5	N5—C4—H42	109.3
C8—C11—H11B	109.5	C3—C4—H42	109.3
H11A—C11—H11B	109.5	H41—C4—H42	107.9
C8—C11—H11C	109.5	C4—C3—C2	110.1 (2)
H11A—C11—H11C	109.5	C4—C3—H31	109.6
H11B—C11—H11C	109.5	C2—C3—H31	109.6
C11—C8—C9	111.8 (2)	C4—C3—H32	109.6
C11—C8—C6	113.9 (2)	C2—C3—H32	109.6
C9—C8—C6	110.2 (2)	H31—C3—H32	108.2
C11—C8—H8	106.9	O1—C2—N1	123.0 (2)
C9—C8—H8	106.9	O1—C2—C3	120.3 (2)
C6—C8—H8	106.9	N1—C2—C3	116.7 (2)
N5—C6—C7	108.63 (18)	C2—N1—H1A	120.0
N5—C6—C8	110.73 (18)	C2—N1—H1B	120.0
C7—C6—C8	112.77 (19)	H1A—N1—H1B	120.0
N5—C6—H61	110.0
C10—C9—C8—C11	71.4 (4)	N5—C6—C7—O2	35.8 (3)
C10—C9—C8—C6	−160.9 (3)	C8—C6—C7—O2	−87.3 (3)
C11—C8—C6—N5	−62.4 (3)	C7—C6—N5—C4	70.3 (2)
C9—C8—C6—N5	171.1 (2)	C8—C6—N5—C4	−165.35 (18)
C11—C8—C6—C7	59.6 (3)	C6—N5—C4—C3	176.1 (2)
C9—C8—C6—C7	−66.9 (3)	N5—C4—C3—C2	176.6 (2)
N5—C6—C7—O3	−144.6 (2)	C4—C3—C2—O1	−49.4 (4)
C8—C6—C7—O3	92.2 (3)	C4—C3—C2—N1	130.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.86	2.17	2.982 (3)	159
N1—H1B···O1ii	0.86	2.33	3.097 (4)	149
O2—H21···N5iii	0.82	1.89	2.708 (2)	176
N5—H51···O3iv	0.98	1.91	2.783 (3)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.86	2.17	2.982 (3)	159
N1—H1B⋯O1ii	0.86	2.33	3.097 (4)	149
O2—H21⋯N5iii	0.82	1.89	2.708 (2)	176
N5—H51⋯O3iv	0.98	1.91	2.783 (3)	147

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