3-(2-Acetyl-anilino)propanoic acid.

The title mol-ecule, C(11)H(13)NO(3), has its propanoic acid group in an extended conformation, such that the mol-ecule is nearly planar, with a mean deviation of 0.036 Å [the maxima being 0.106 (1) and 0.110 (1) Å for the two methyl-ene C atoms]. The NH group forms an intra-molecular hydrogen bond with the acetyl group; in the crystal COOH group forms a centrosymmetric hydrogen-bonded dimer.

Related literature

For general background, see: Crosby et al. (1961 ▶, 1962 ▶); Foley et al. (2003 ▶); Walker Jr et al. (2004 ▶); Yoshihara et al. (2001 ▶). For related structures, see: Slater et al. (2006 ▶). For hydrogen-bonding patterns, see: Etter (1990 ▶).

Experimental

Crystal data

C11H13NO3

M = 207.22

Triclinic,

a = 5.1935 (10) Å

b = 9.8342 (16) Å

c = 9.920 (2) Å

α = 77.084 (12)°

β = 85.174 (11)°

γ = 83.019 (12)°

V = 489.32 (16) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 90.0 (5) K

0.30 × 0.20 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer with an Oxford Cryosystems Cryostream cooler

Absorption correction: none

11014 measured reflections

3012 independent reflections

2467 reflections with I > 2s(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.113

S = 1.04

3012 reflections

143 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.29 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808035277/pv2116sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808035277/pv2116Isup2.hkl

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

C11H13NO3	Z = 2
Mr = 207.22	F000 = 220
Triclinic, P1	Dx = 1.406 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 5.1935 (10) Å	Cell parameters from 2652 reflections
b = 9.8342 (16) Å	θ = 2.5–30.8º
c = 9.920 (2) Å	µ = 0.10 mm−1
α = 77.084 (12)º	T = 90.0 (5) K
β = 85.174 (11)º	Fragment, colorless
γ = 83.019 (12)º	0.30 × 0.20 × 0.10 mm
V = 489.32 (16) Å3

Nonius KappaCCD diffractometer with an Oxford Cryosystems Cryostream cooler	2467 reflections with I > 2s(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
Monochromator: graphite	θmax = 30.8º
T = 90.0(5) K	θmin = 2.6º
ω scans with κ offsets	h = −7→7
Absorption correction: none	k = −13→13
11014 measured reflections	l = −14→14
3012 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.113	w = 1/[σ2(Fo2) + (0.0573P)2 + 0.1339P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
3012 reflections	Δρmax = 0.39 e Å−3
143 parameters	Δρmin = −0.29 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. 1H (CDCl3): δ(p.p.m.) 9.02 (s, 1H), 7.78 (d, J = 8.0 Hz, 1H), 7.38 (t, J = 8.0 Hz, 1H), 6.74 (d, J = 8.0 Hz, 1H), 6.62 (t, J = 8.0 Hz, 1H), 3.58 (t, J = 7.0 Hz, 2H), 2.73 (t, J = 7.0 Hz, 2H), and 2.60 (s, 3H). 13C (CDCl3): δ (p.p.m.) 201.1, 176.7, 150.5, 135.2, 132.9, 117.9, 114.5, 111.3, 37.9, 33.8, and 27.9. IR (thin film, KBr plates, cm-1): 3297 (m), 2925 (w, br), 2881 (sh, w), 2635 (w), 2373 (w), 1698 (s), 1634 (s), 1569 (m), 1517 (m), 1430 (m), 1366 (sh), 1326(m), 1240 (s), 1156 (w), 1092(w), 1031(w), 943 (m), 825(w), 742 (m), 675(w), and 624 (w). Crystals were grown by evaporation from CDCl3.

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	0.96261 (15)	0.13504 (8)	0.35274 (7)	0.01656 (17)
O2	0.30686 (15)	−0.07587 (8)	0.93327 (7)	0.01593 (17)
H2O	0.183 (3)	−0.0849 (15)	1.0039 (16)	0.024*
O3	0.04143 (14)	0.11745 (8)	0.85415 (7)	0.01599 (17)
N1	0.53905 (17)	0.21868 (9)	0.49711 (8)	0.01437 (18)
H1N	0.673 (3)	0.1541 (14)	0.4924 (13)	0.017*
C1	0.70722 (18)	0.35189 (10)	0.27655 (10)	0.01194 (19)
C2	0.51897 (19)	0.33391 (10)	0.39115 (10)	0.01242 (19)
C3	0.3083 (2)	0.43948 (11)	0.39170 (10)	0.0161 (2)
H3	0.1787	0.4282	0.4657	0.019*
C4	0.2866 (2)	0.55873 (11)	0.28701 (11)	0.0168 (2)
H4	0.1438	0.6283	0.2906	0.020*
C5	0.4725 (2)	0.57819 (11)	0.17590 (11)	0.0165 (2)
H5	0.4581	0.6605	0.1043	0.020*
C6	0.6778 (2)	0.47510 (10)	0.17238 (10)	0.0145 (2)
H6	0.8038	0.4879	0.0967	0.017*
C7	0.92650 (19)	0.24478 (10)	0.26361 (10)	0.01281 (19)
C8	1.1133 (2)	0.26868 (11)	0.13707 (10)	0.0157 (2)
H8A	1.2116	0.3472	0.1386	0.024*
H8B	1.0155	0.2905	0.0532	0.024*
H8C	1.2337	0.1838	0.1374	0.024*
C9	0.34277 (19)	0.19459 (11)	0.61054 (10)	0.0142 (2)
H9A	0.1798	0.1767	0.5757	0.017*
H9B	0.3060	0.2789	0.6508	0.017*
C10	0.43852 (19)	0.06928 (10)	0.72115 (10)	0.01378 (19)
H10A	0.4756	−0.0145	0.6801	0.017*
H10B	0.6025	0.0875	0.7548	0.017*
C11	0.24229 (19)	0.04048 (10)	0.84099 (10)	0.01244 (19)

	U11	U22	U33	U12	U13	U23
O1	0.0166 (4)	0.0146 (3)	0.0149 (3)	0.0019 (3)	0.0026 (3)	0.0012 (3)
O2	0.0148 (4)	0.0162 (4)	0.0127 (3)	0.0014 (3)	0.0038 (3)	0.0020 (3)
O3	0.0152 (4)	0.0162 (4)	0.0132 (3)	0.0019 (3)	0.0041 (3)	0.0003 (3)
N1	0.0136 (4)	0.0144 (4)	0.0111 (4)	0.0025 (3)	0.0048 (3)	0.0014 (3)
C1	0.0110 (4)	0.0123 (4)	0.0114 (4)	−0.0009 (3)	0.0016 (3)	−0.0012 (3)
C2	0.0127 (4)	0.0134 (4)	0.0104 (4)	−0.0015 (3)	0.0016 (3)	−0.0018 (3)
C3	0.0145 (5)	0.0179 (5)	0.0141 (4)	0.0014 (4)	0.0030 (3)	−0.0027 (4)
C4	0.0160 (5)	0.0150 (5)	0.0177 (5)	0.0030 (4)	0.0004 (4)	−0.0030 (4)
C5	0.0174 (5)	0.0135 (4)	0.0162 (5)	0.0002 (4)	0.0000 (4)	0.0005 (3)
C6	0.0152 (4)	0.0145 (4)	0.0125 (4)	−0.0021 (4)	0.0021 (3)	−0.0006 (3)
C7	0.0115 (4)	0.0146 (4)	0.0118 (4)	−0.0016 (3)	0.0015 (3)	−0.0024 (3)
C8	0.0146 (4)	0.0162 (5)	0.0136 (4)	0.0001 (4)	0.0045 (3)	−0.0005 (3)
C9	0.0126 (4)	0.0169 (5)	0.0109 (4)	−0.0001 (3)	0.0033 (3)	−0.0008 (3)
C10	0.0126 (4)	0.0155 (4)	0.0113 (4)	−0.0007 (3)	0.0028 (3)	−0.0005 (3)
C11	0.0132 (4)	0.0130 (4)	0.0107 (4)	−0.0022 (3)	0.0015 (3)	−0.0020 (3)

O1—C7	1.2384 (12)	C4—H4	0.9500
O2—C11	1.3228 (12)	C5—C6	1.3829 (14)
O2—H2O	0.909 (16)	C5—H5	0.9500
O3—C11	1.2278 (12)	C6—H6	0.9500
N1—C2	1.3628 (12)	C7—C8	1.5135 (13)
N1—C9	1.4519 (12)	C8—H8A	0.9800
N1—H1N	0.887 (14)	C8—H8B	0.9800
C1—C6	1.4075 (13)	C8—H8C	0.9800
C1—C2	1.4299 (13)	C9—C10	1.5193 (14)
C1—C7	1.4722 (14)	C9—H9A	0.9900
C2—C3	1.4145 (14)	C9—H9B	0.9900
C3—C4	1.3819 (14)	C10—C11	1.4993 (13)
C3—H3	0.9500	C10—H10A	0.9900
C4—C5	1.3983 (15)	C10—H10B	0.9900
C11—O2—H2O	108.7 (9)	O1—C7—C8	118.76 (9)
C2—N1—C9	122.44 (8)	C1—C7—C8	119.13 (8)
C2—N1—H1N	117.8 (9)	C7—C8—H8A	109.5
C9—N1—H1N	119.7 (9)	C7—C8—H8B	109.5
C6—C1—C2	118.53 (9)	H8A—C8—H8B	109.5
C6—C1—C7	119.47 (9)	C7—C8—H8C	109.5
C2—C1—C7	122.00 (8)	H8A—C8—H8C	109.5
N1—C2—C3	120.39 (9)	H8B—C8—H8C	109.5
N1—C2—C1	121.56 (9)	N1—C9—C10	109.68 (8)
C3—C2—C1	118.05 (9)	N1—C9—H9A	109.7
C4—C3—C2	121.48 (9)	C10—C9—H9A	109.7
C4—C3—H3	119.3	N1—C9—H9B	109.7
C2—C3—H3	119.3	C10—C9—H9B	109.7
C3—C4—C5	120.76 (9)	H9A—C9—H9B	108.2
C3—C4—H4	119.6	C11—C10—C9	111.66 (8)
C5—C4—H4	119.6	C11—C10—H10A	109.3
C6—C5—C4	118.62 (9)	C9—C10—H10A	109.3
C6—C5—H5	120.7	C11—C10—H10B	109.3
C4—C5—H5	120.7	C9—C10—H10B	109.3
C5—C6—C1	122.54 (9)	H10A—C10—H10B	107.9
C5—C6—H6	118.7	O3—C11—O2	122.63 (9)
C1—C6—H6	118.7	O3—C11—C10	123.78 (9)
O1—C7—C1	122.11 (9)	O2—C11—C10	113.59 (8)
C9—N1—C2—C3	3.20 (15)	C2—C1—C6—C5	−0.84 (15)
C9—N1—C2—C1	−176.52 (9)	C7—C1—C6—C5	178.13 (10)
C6—C1—C2—N1	−178.48 (9)	C6—C1—C7—O1	179.42 (9)
C7—C1—C2—N1	2.57 (15)	C2—C1—C7—O1	−1.64 (15)
C6—C1—C2—C3	1.80 (14)	C6—C1—C7—C8	−0.98 (14)
C7—C1—C2—C3	−177.15 (9)	C2—C1—C7—C8	177.96 (9)
N1—C2—C3—C4	178.57 (10)	C2—N1—C9—C10	−172.10 (9)
C1—C2—C3—C4	−1.71 (15)	N1—C9—C10—C11	179.81 (8)
C2—C3—C4—C5	0.58 (16)	C9—C10—C11—O3	−6.99 (14)
C3—C4—C5—C6	0.45 (16)	C9—C10—C11—O2	173.73 (8)
C4—C5—C6—C1	−0.30 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O3i	0.909 (16)	1.747 (16)	2.6531 (11)	174.7 (14)
N1—H1N···O1	0.887 (14)	1.980 (14)	2.6690 (12)	133.4 (11)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯O3i	0.909 (16)	1.747 (16)	2.6531 (11)	174.7 (14)
N1—H1N⋯O1	0.887 (14)	1.980 (14)	2.6690 (12)	133.4 (11)

Symmetry code: (i) .