4-[(4-Acetyl-phen-yl)amino]-2-methyl-idene-4-oxo-butanoic acid.

In the title compound, C13H13NO4, the N-C(=O) bond length of 1.354 (2) Å is indicative of amide-type resonance. The dihedral angle between the mean planes of the benzene ring and oxo-amine group is 36.4 (3)°, while the mean plane of the 2-methyl-idene group is inclined by 84.2 (01)° from that of the oxo-amine group. In the crystal, classical O-H⋯O hydrogen bonds formed by the carb-oxy-lic acid groups and weak N-H⋯O weak inter-actions formed by the amide groups and supported by weak C-H⋯O inter-actions between the 2-methyl-idene, phenyl and acetyl groups with the carb-oxy-lic acid, oxo-amine and acetyl O atoms, together link the mol-ecules into dimeric chains along [010]. The O-H⋯O hydrogen bonds form R 2 (2)(8) graph-set motifs.

Related literature

For the pharmacological activity of amide derivatives, see: Galanakis et al. (2004 ▶); Kumar & Knaus (1993 ▶); Ban et al. (1998 ▶); Ukrainets et al. (2006 ▶), Lesyk & Zimenkovsky (2004 ▶); Gududuru et al. (2004 ▶). For related structures, see: Nayak et al. (2013a ▶,b ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C13H13NO4

M = 247.24

Triclinic,

a = 5.0164 (5) Å

b = 5.2908 (4) Å

c = 21.8464 (18) Å

α = 92.833 (6)°

β = 90.315 (7)°

γ = 96.222 (7)°

V = 575.67 (8) Å3

Z = 2

Cu Kα radiation

μ = 0.89 mm−1

T = 173 K

0.42 × 0.22 × 0.12 mm

Data collection

Agilent Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T min = 0.756, T max = 1.000

3374 measured reflections

2168 independent reflections

1934 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.134

S = 1.05

2168 reflections

176 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012 ▶); program(s) used to solve structure: SUPERFLIP (Palatinus et al., 2012 ▶); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814012562/zl2589sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814012562/zl2589Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814012562/zl2589Isup3.cml

CCDC reference: 1005968

Additional supporting information: crystallographic information; 3D view; checkCIF report

C13H13NO4	Z = 2
Mr = 247.24	F(000) = 260
Triclinic, P1	Dx = 1.426 Mg m−3
a = 5.0164 (5) Å	Cu Kα radiation, λ = 1.54184 Å
b = 5.2908 (4) Å	Cell parameters from 1583 reflections
c = 21.8464 (18) Å	θ = 6.1–71.3°
α = 92.833 (6)°	µ = 0.89 mm−1
β = 90.315 (7)°	T = 173 K
γ = 96.222 (7)°	Prism, colourless
V = 575.67 (8) Å3	0.42 × 0.22 × 0.12 mm

Agilent Eos Gemini diffractometer	2168 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1934 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm-1	Rint = 0.025
ω scans	θmax = 71.3°, θmin = 4.1°
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	h = −5→6
Tmin = 0.756, Tmax = 1.000	k = −4→6
3374 measured reflections	l = −26→26

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.134	w = 1/[σ2(Fo2) + (0.0796P)2 + 0.1341P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2168 reflections	Δρmax = 0.31 e Å−3
176 parameters	Δρmin = −0.29 e Å−3
0 restraints

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

	x	y	z	Uiso*/Ueq
O1	0.3166 (2)	0.3573 (2)	0.70834 (5)	0.0287 (3)
O2	0.2328 (3)	0.2934 (2)	0.51283 (6)	0.0333 (3)
O3	0.3843 (3)	0.6459 (2)	0.56835 (6)	0.0322 (3)
H3	0.529 (9)	0.681 (8)	0.540 (2)	0.117 (15)*
O4	1.3191 (3)	1.1439 (2)	0.91390 (6)	0.0347 (3)
N1	0.3525 (3)	0.7850 (2)	0.72813 (6)	0.0238 (3)
H1	0.2927	0.9262	0.7169	0.029*
C1	0.2405 (3)	0.5648 (3)	0.70006 (7)	0.0212 (3)
C2	0.0055 (3)	0.5917 (3)	0.65734 (7)	0.0236 (3)
H2A	−0.1643	0.5631	0.6801	0.028*
H2B	0.0205	0.7669	0.6428	0.028*
C3	−0.0012 (3)	0.4045 (3)	0.60311 (7)	0.0230 (3)
C4	0.2171 (3)	0.4458 (3)	0.55784 (7)	0.0235 (3)
C5	−0.1886 (4)	0.2087 (3)	0.59389 (8)	0.0302 (4)
H5A	−0.335 (4)	0.171 (4)	0.6228 (10)	0.030 (5)*
H5B	−0.180 (5)	0.095 (5)	0.5563 (12)	0.051 (7)*
C6	0.5569 (3)	0.8108 (3)	0.77393 (7)	0.0216 (3)
C7	0.7359 (3)	1.0308 (3)	0.77582 (8)	0.0257 (4)
H7	0.7233	1.1541	0.7461	0.031*
C8	0.9319 (3)	1.0702 (3)	0.82088 (8)	0.0254 (4)
H8	1.0534	1.2211	0.8218	0.030*
C9	0.9549 (3)	0.8921 (3)	0.86518 (7)	0.0223 (3)
C10	0.7744 (3)	0.6724 (3)	0.86265 (7)	0.0255 (4)
H10	0.7873	0.5488	0.8923	0.031*
C11	0.5764 (3)	0.6305 (3)	0.81778 (8)	0.0255 (4)
H11	0.4545	0.4799	0.8168	0.031*
C12	1.1696 (3)	0.9468 (3)	0.91332 (7)	0.0253 (4)
C13	1.1922 (4)	0.7541 (3)	0.96093 (8)	0.0343 (4)
H13A	1.2316	0.5927	0.9409	0.051*
H13B	1.0227	0.7275	0.9830	0.051*
H13C	1.3371	0.8164	0.9899	0.051*

	U11	U22	U33	U12	U13	U23
O1	0.0355 (7)	0.0221 (6)	0.0288 (6)	0.0058 (5)	−0.0079 (5)	−0.0017 (4)
O2	0.0372 (7)	0.0338 (7)	0.0269 (6)	−0.0017 (5)	0.0063 (5)	−0.0077 (5)
O3	0.0316 (7)	0.0325 (7)	0.0301 (7)	−0.0053 (5)	0.0045 (5)	−0.0039 (5)
O4	0.0393 (7)	0.0265 (6)	0.0362 (7)	−0.0048 (5)	−0.0101 (5)	0.0006 (5)
N1	0.0264 (7)	0.0206 (6)	0.0253 (7)	0.0068 (5)	−0.0025 (5)	−0.0003 (5)
C1	0.0228 (8)	0.0233 (8)	0.0178 (7)	0.0037 (6)	0.0017 (6)	0.0009 (6)
C2	0.0227 (8)	0.0266 (8)	0.0223 (8)	0.0067 (6)	−0.0002 (6)	−0.0004 (6)
C3	0.0238 (8)	0.0249 (8)	0.0212 (8)	0.0057 (6)	−0.0024 (6)	0.0023 (6)
C4	0.0258 (8)	0.0243 (7)	0.0206 (7)	0.0031 (6)	−0.0027 (6)	0.0009 (6)
C5	0.0304 (9)	0.0330 (9)	0.0262 (8)	−0.0001 (7)	0.0015 (7)	−0.0001 (7)
C6	0.0230 (8)	0.0213 (7)	0.0206 (7)	0.0047 (6)	0.0018 (6)	−0.0025 (6)
C7	0.0302 (9)	0.0217 (8)	0.0257 (8)	0.0038 (6)	0.0007 (6)	0.0038 (6)
C8	0.0264 (8)	0.0210 (7)	0.0281 (8)	−0.0001 (6)	0.0007 (6)	0.0016 (6)
C9	0.0240 (8)	0.0219 (7)	0.0212 (8)	0.0044 (6)	0.0016 (6)	−0.0026 (6)
C10	0.0328 (9)	0.0216 (7)	0.0218 (8)	0.0016 (6)	0.0001 (6)	0.0019 (6)
C11	0.0286 (8)	0.0218 (7)	0.0251 (8)	−0.0014 (6)	0.0000 (6)	0.0003 (6)
C12	0.0288 (8)	0.0224 (8)	0.0245 (8)	0.0038 (6)	−0.0006 (6)	−0.0030 (6)
C13	0.0427 (10)	0.0312 (9)	0.0281 (9)	0.0000 (7)	−0.0097 (7)	0.0027 (7)

O1—C1	1.222 (2)	C6—C7	1.389 (2)
O2—C4	1.249 (2)	C6—C11	1.395 (2)
O3—H3	0.97 (5)	C7—H7	0.9500
O3—C4	1.288 (2)	C7—C8	1.380 (2)
O4—C12	1.216 (2)	C8—H8	0.9500
N1—H1	0.8800	C8—C9	1.397 (2)
N1—C1	1.354 (2)	C9—C10	1.392 (2)
N1—C6	1.420 (2)	C9—C12	1.497 (2)
C1—C2	1.523 (2)	C10—H10	0.9500
C2—H2A	0.9900	C10—C11	1.385 (2)
C2—H2B	0.9900	C11—H11	0.9500
C2—C3	1.504 (2)	C12—C13	1.504 (2)
C3—C4	1.485 (2)	C13—H13A	0.9800
C3—C5	1.328 (2)	C13—H13B	0.9800
C5—H5A	0.98 (2)	C13—H13C	0.9800
C5—H5B	1.00 (3)
C4—O3—H3	118 (2)	C6—C7—H7	120.0
C1—N1—H1	116.8	C8—C7—C6	120.04 (15)
C1—N1—C6	126.47 (13)	C8—C7—H7	120.0
C6—N1—H1	116.8	C7—C8—H8	119.4
O1—C1—N1	123.53 (14)	C7—C8—C9	121.16 (15)
O1—C1—C2	121.41 (14)	C9—C8—H8	119.4
N1—C1—C2	115.05 (13)	C8—C9—C12	118.71 (15)
C1—C2—H2A	109.4	C10—C9—C8	118.15 (15)
C1—C2—H2B	109.4	C10—C9—C12	123.14 (14)
H2A—C2—H2B	108.0	C9—C10—H10	119.3
C3—C2—C1	111.32 (12)	C11—C10—C9	121.32 (15)
C3—C2—H2A	109.4	C11—C10—H10	119.3
C3—C2—H2B	109.4	C6—C11—H11	120.2
C4—C3—C2	116.83 (14)	C10—C11—C6	119.64 (15)
C5—C3—C2	123.91 (15)	C10—C11—H11	120.2
C5—C3—C4	119.26 (15)	O4—C12—C9	120.33 (15)
O2—C4—O3	123.36 (16)	O4—C12—C13	121.36 (16)
O2—C4—C3	120.94 (15)	C9—C12—C13	118.30 (14)
O3—C4—C3	115.70 (14)	C12—C13—H13A	109.5
C3—C5—H5A	122.5 (13)	C12—C13—H13B	109.5
C3—C5—H5B	118.9 (15)	C12—C13—H13C	109.5
H5A—C5—H5B	118.5 (19)	H13A—C13—H13B	109.5
C7—C6—N1	117.63 (14)	H13A—C13—H13C	109.5
C7—C6—C11	119.68 (15)	H13B—C13—H13C	109.5
C11—C6—N1	122.63 (14)
O1—C1—C2—C3	−35.3 (2)	C6—N1—C1—C2	174.03 (14)
N1—C1—C2—C3	145.67 (14)	C6—C7—C8—C9	0.0 (3)
N1—C6—C7—C8	177.47 (14)	C7—C6—C11—C10	−0.1 (2)
N1—C6—C11—C10	−177.45 (14)	C7—C8—C9—C10	0.1 (2)
C1—N1—C6—C7	148.44 (16)	C7—C8—C9—C12	−179.32 (14)
C1—N1—C6—C11	−34.2 (2)	C8—C9—C10—C11	−0.2 (2)
C1—C2—C3—C4	−68.77 (17)	C8—C9—C12—O4	0.6 (2)
C1—C2—C3—C5	111.34 (18)	C8—C9—C12—C13	179.84 (15)
C2—C3—C4—O2	177.03 (14)	C9—C10—C11—C6	0.2 (3)
C2—C3—C4—O3	−3.0 (2)	C10—C9—C12—O4	−178.79 (16)
C5—C3—C4—O2	−3.1 (2)	C10—C9—C12—C13	0.4 (2)
C5—C3—C4—O3	176.90 (15)	C11—C6—C7—C8	0.0 (2)
C6—N1—C1—O1	−5.0 (3)	C12—C9—C10—C11	179.19 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2i	0.97 (5)	1.66 (5)	2.6262 (17)	174 (4)
N1—H1···O1ii	0.88	2.29	3.1039 (17)	154
C5—H5B···O2iii	1.00 (3)	2.48 (3)	3.434 (2)	160 (2)
C7—H7···O1ii	0.95	2.56	3.254 (2)	130
C13—H13A···O4iv	0.98	2.50	3.465 (2)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2i	0.97 (5)	1.66 (5)	2.6262 (17)	174 (4)
N1—H1⋯O1ii	0.88	2.29	3.1039 (17)	154
C5—H5B⋯O2iii	1.00 (3)	2.48 (3)	3.434 (2)	160 (2)
C7—H7⋯O1ii	0.95	2.56	3.254 (2)	130
C13—H13A⋯O4iv	0.98	2.50	3.465 (2)	167

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