3-Methyl-2-propionamido-butanoic acid.

The reaction of propionyl isothio-cyanate with valine was found to give the title compound, C(8)H(15)NO(3), instead of the expected thio-urea product. The whole mol-ecule is non-planar and the carbonyl group is cis to the methyl-butanoic acid group across the C-N bond. Inter-molecular O-H⋯O and N-H⋯O hydrogen bonds build up a two-dimensional network developing parallel to (100).

Related literature

For the crystal structure of N-propionylthio­urea, see: Yamin & Othman (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C8H15NO3

M = 173.21

Monoclinic,

a = 9.477 (3) Å

b = 8.633 (2) Å

c = 12.766 (3) Å

β = 103.123 (6)°

V = 1017.2 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.49 × 0.33 × 0.18 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.959, T max = 0.984

5313 measured reflections

1887 independent reflections

1262 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.167

S = 1.04

1887 reflections

117 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97, PARST (Nardelli, 1995 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809007119/dn2429sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007119/dn2429Isup2.hkl

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

C8H15NO3	F(000) = 376
Mr = 173.21	Dx = 1.131 Mg m−3
Monoclinic, P21/c	Melting point: 475.5 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.477 (3) Å	Cell parameters from 1183 reflections
b = 8.633 (2) Å	θ = 2.2–25.5°
c = 12.766 (3) Å	µ = 0.09 mm−1
β = 103.123 (6)°	T = 298 K
V = 1017.2 (5) Å3	Block, colourless
Z = 4	0.49 × 0.33 × 0.18 mm

Bruker SMART APEX CCD area-detector diffractometer	1887 independent reflections
Radiation source: fine-focus sealed tube	1262 reflections with I > 2σ(I)
graphite	Rint = 0.024
Detector resolution: 83.66 pixels mm-1	θmax = 25.5°, θmin = 2.2°
ω scans	h = −10→11
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −10→10
Tmin = 0.959, Tmax = 0.984	l = −15→8
5313 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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.167	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0815P)2 + 0.2058P] where P = (Fo2 + 2Fc2)/3
1887 reflections	(Δ/σ)max = 0.001
117 parameters	Δρmax = 0.24 e Å−3
2 restraints	Δρmin = −0.15 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
O1	0.58011 (17)	0.1690 (2)	−0.01032 (13)	0.0706 (6)
O2	0.80400 (19)	0.2599 (2)	0.01281 (15)	0.0808 (6)
H2C	0.775 (3)	0.309 (3)	−0.0430 (16)	0.115 (12)*
O3	0.7243 (2)	0.0786 (2)	0.33764 (14)	0.0835 (6)
N1	0.6507 (2)	−0.0073 (2)	0.17012 (15)	0.0523 (5)
H1D	0.5834 (18)	−0.050 (2)	0.1230 (15)	0.058 (7)*
C1	0.3968 (4)	0.0265 (4)	0.3214 (3)	0.1079 (12)
H1A	0.3188	−0.0340	0.3366	0.162*
H1B	0.3602	0.0928	0.2610	0.162*
H1C	0.4390	0.0884	0.3830	0.162*
C2	0.5071 (3)	−0.0769 (3)	0.2963 (2)	0.0776 (8)
H2A	0.4623	−0.1411	0.2354	0.093*
H2B	0.5414	−0.1449	0.3572	0.093*
C3	0.6357 (3)	0.0049 (3)	0.27028 (19)	0.0573 (6)
C4	0.7670 (2)	0.0664 (3)	0.13158 (16)	0.0509 (6)
H4A	0.8199	0.1331	0.1894	0.061*
C5	0.8765 (3)	−0.0509 (3)	0.1042 (2)	0.0684 (7)
H5A	0.9512	0.0083	0.0797	0.082*
C6	0.9513 (3)	−0.1423 (4)	0.2037 (3)	0.1062 (11)
H6A	1.0190	−0.2138	0.1847	0.159*
H6B	0.8802	−0.1983	0.2313	0.159*
H6C	1.0020	−0.0721	0.2576	0.159*
C7	0.8066 (3)	−0.1595 (4)	0.0136 (3)	0.0905 (9)
H7A	0.8782	−0.2296	−0.0012	0.136*
H7B	0.7664	−0.1002	−0.0498	0.136*
H7C	0.7309	−0.2173	0.0345	0.136*
C8	0.7047 (2)	0.1683 (2)	0.03739 (16)	0.0517 (6)

	U11	U22	U33	U12	U13	U23
O1	0.0574 (11)	0.0732 (12)	0.0697 (11)	−0.0047 (8)	−0.0100 (8)	0.0117 (8)
O2	0.0616 (11)	0.1039 (14)	0.0740 (13)	−0.0103 (10)	0.0094 (9)	0.0375 (11)
O3	0.1026 (15)	0.0943 (14)	0.0564 (11)	−0.0129 (11)	0.0237 (10)	−0.0233 (10)
N1	0.0491 (11)	0.0648 (12)	0.0422 (10)	−0.0072 (9)	0.0087 (8)	−0.0021 (9)
C1	0.088 (2)	0.088 (2)	0.162 (4)	−0.0066 (18)	0.057 (2)	0.001 (2)
C2	0.097 (2)	0.0680 (17)	0.0806 (18)	0.0026 (15)	0.0463 (16)	0.0076 (13)
C3	0.0682 (15)	0.0526 (13)	0.0538 (14)	0.0077 (12)	0.0194 (12)	−0.0015 (11)
C4	0.0442 (12)	0.0609 (13)	0.0444 (12)	−0.0073 (10)	0.0035 (9)	0.0038 (10)
C5	0.0495 (13)	0.0817 (17)	0.0755 (17)	0.0093 (12)	0.0172 (12)	0.0186 (14)
C6	0.082 (2)	0.123 (3)	0.110 (2)	0.036 (2)	0.0132 (17)	0.040 (2)
C7	0.091 (2)	0.087 (2)	0.101 (2)	0.0129 (17)	0.0370 (17)	−0.0154 (17)
C8	0.0533 (13)	0.0564 (13)	0.0438 (12)	−0.0049 (11)	0.0077 (10)	−0.0016 (10)

O1—C8	1.200 (2)	C2—H2B	0.9700
O2—C8	1.320 (3)	C4—C8	1.499 (3)
O2—H2C	0.821 (10)	C4—C5	1.546 (3)
O3—C3	1.233 (3)	C4—H4A	0.9800
N1—C3	1.322 (3)	C5—C7	1.519 (4)
N1—C4	1.453 (3)	C5—C6	1.526 (4)
N1—H1D	0.855 (10)	C5—H5A	0.9800
C1—C2	1.464 (4)	C6—H6A	0.9600
C1—H1A	0.9600	C6—H6B	0.9600
C1—H1B	0.9600	C6—H6C	0.9600
C1—H1C	0.9600	C7—H7A	0.9600
C2—C3	1.509 (3)	C7—H7B	0.9600
C2—H2A	0.9700	C7—H7C	0.9600
C8—O2—H2C	114 (2)	C8—C4—H4A	107.5
C3—N1—C4	123.30 (19)	C5—C4—H4A	107.5
C3—N1—H1D	119.2 (16)	C7—C5—C6	110.8 (3)
C4—N1—H1D	117.0 (16)	C7—C5—C4	112.18 (19)
C2—C1—H1A	109.5	C6—C5—C4	111.1 (2)
C2—C1—H1B	109.5	C7—C5—H5A	107.5
H1A—C1—H1B	109.5	C6—C5—H5A	107.5
C2—C1—H1C	109.5	C4—C5—H5A	107.5
H1A—C1—H1C	109.5	C5—C6—H6A	109.5
H1B—C1—H1C	109.5	C5—C6—H6B	109.5
C1—C2—C3	114.5 (2)	H6A—C6—H6B	109.5
C1—C2—H2A	108.6	C5—C6—H6C	109.5
C3—C2—H2A	108.6	H6A—C6—H6C	109.5
C1—C2—H2B	108.6	H6B—C6—H6C	109.5
C3—C2—H2B	108.6	C5—C7—H7A	109.5
H2A—C2—H2B	107.6	C5—C7—H7B	109.5
O3—C3—N1	120.7 (2)	H7A—C7—H7B	109.5
O3—C3—C2	122.9 (2)	C5—C7—H7C	109.5
N1—C3—C2	116.4 (2)	H7A—C7—H7C	109.5
N1—C4—C8	109.76 (17)	H7B—C7—H7C	109.5
N1—C4—C5	112.93 (19)	O1—C8—O2	123.3 (2)
C8—C4—C5	111.44 (18)	O1—C8—C4	125.0 (2)
N1—C4—H4A	107.5	O2—C8—C4	111.72 (19)
C4—N1—C3—O3	−1.7 (3)	C8—C4—C5—C7	−61.5 (3)
C4—N1—C3—C2	179.0 (2)	N1—C4—C5—C6	−62.0 (3)
C1—C2—C3—O3	68.0 (4)	C8—C4—C5—C6	173.9 (2)
C1—C2—C3—N1	−112.7 (3)	N1—C4—C8—O1	−11.6 (3)
C3—N1—C4—C8	−123.5 (2)	C5—C4—C8—O1	114.2 (3)
C3—N1—C4—C5	111.5 (2)	N1—C4—C8—O2	167.87 (19)
N1—C4—C5—C7	62.6 (3)	C5—C4—C8—O2	−66.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1D···O1i	0.86 (2)	2.13 (2)	2.978 (3)	177 (2)
O2—H2C···O3ii	0.82 (2)	1.78 (2)	2.598 (3)	176 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1D⋯O1i	0.855 (18)	2.125 (18)	2.978 (3)	176.6 (16)
O2—H2C⋯O3ii	0.82 (2)	1.78 (2)	2.598 (3)	176 (2)

Symmetry codes: (i) ; (ii) .