4-[(4-Acetyl­phen­yl)amino]-2-methyl­idene-4-oxo­butanoic acid

Narayana, B.; Nayak, P.S.; Sarojini, B.K.; Jasinski, J.P.

doi:10.1107/S1600536814012562

organic compounds

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ISSN: 2056-9890

Volume 70| Part 7| July 2014| Pages o752-o753

https://doi.org/10.1107/S1600536814012562

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4-[(4-Acetylphenyl)amino]-2-methylidene-4-oxobutanoic acid

B. Narayana,^a Prakash S. Nayak,^b Balladka K. Sarojini ^c and Jerry P. Jasinski ^d ^*

^aDepartment of Studies in Chemistry, Mangalore University, Mangaloagangotri 574 199, India, ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, ^cDepartment of Studies in Chemistry, Industrial Chemistry Section, Mangalore University, Mangalagangotri 574 199, India, and ^dDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
^*Correspondence e-mail: jjasinski@keene.edu

(Received 19 May 2014; accepted 30 May 2014; online 7 June 2014)

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 oxoamine group is 36.4 (3)°, while the mean plane of the 2-methylidene group is inclined by 84.2 (01)° from that of the oxoamine group. In the crystal, classical O—H⋯O hydrogen bonds formed by the carboxylic acid groups and weak N—H⋯O weak interactions formed by the amide groups and supported by weak C—H⋯O interactions between the 2-methylidene, phenyl and acetyl groups with the carboxylic acid, oxoamine and acetyl O atoms, together link the molecules into dimeric chains along [010]. The O—H⋯O hydrogen bonds form R₂²(8) graph-set motifs.

CCDC reference: 1005968

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_r = 247.24
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.048
wR(F²) = 0.134
S = 1.05
2168 reflections
176 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.29 e Å⁻³

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⋯O4^iv	0.98	2.50	3.465 (2)	167
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x, y+1, z; (iii) -x, -y, -z+1; (iv) x, y-1, z.

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.

Supporting information

CCDC reference: 1005968

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S1600536814012562/zl2589sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536814012562/zl2589Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536814012562/zl2589Isup3.cml

checkCIF report

Comment top

Amide bonds play a major role in the elaboration and composition of biological systems, which are the main chemical bonds that link amino acid building blocks together to give proteins. Amide bonds are not limited to biological systems and are indeed present in a huge array of molecules, including major marketed drugs. Amide derivatives possessing anti-inflammatory (Galanakis et al., 2004; Kumar et al., 1993; Ban et al., 1998), antimicrobial (Ukrainets et al., 2006), anti-tubercular (Lesyk et al., 2004) and antiproliferative (Gududuru et al., 2004) activities are reported in the literature. Crystal structures of some amide derivatives related to the title compound include, viz., 4-(4-iodoanilino)-2-methylene-4-oxobutanoic acid and 4-(3-fluoro-4-methylanilino)-2-methylidene-4-oxobutanoic acid (Nayak et al., 2013a,b). Hence in view of its potential pharmacological importance, the title compound 4-[(4-acetylphenyl)amino]-2-methylidene-4-oxobutanoic acid, C₁₃H₁₃NO₄, was synthesized from 3-methylidenedihydrofuran-2,5-dione with good yields and its crystal structure is reported here.

In the title compound, The C=C bond is present as its anti-Saytzeff tautomer. The N–C(=O) bond length of 1.354 (2)A (A) is indicative of amide-type resonance (Fig. 1). All other bond lengths are in normal ranges (Allen et al., 1987). In the crystal, classical O—H···O hydrogen bonds formed by the carboxylic groups and N—H···O weak intermolecular interactions formed by the amide groups and supported additionally by weak C—H···O intermolecular interactions between the 2-methylidene, phenyl and acetyl groups with the carboxylic, oxoamine and acetyl oxygen atoms (Table 1), together link the molecules into dimeric chains along [0 1 0] (Fig. 2). The O—H···O hydrogen bonds form R₂²(8) graph-set motifs. The dihedral angle between the mean planes of the phenyl ring (C6–C10) and oxoamine group (C1/C2/O1/N1) is 36.4 (3)°, while the mean plane of the 2-methylidene group (C2–C5) is further inclined by 84.2 (1)° from that of the oxoamine group.

Related literature top

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 top

3-Methylidenedihydrofuran-2,5-dione (0.112 g, 1 mmol) was dissolved in a 30 ml acetone and stirred at ambient temperature. 4-Aminoacetophenone (0.135 g, 1 mmol) in 20 mL acetone was added over 30 mins (Fig. 3). After sirring for 1.5 h the slurry was filtered. The solid was washed with acetone and dried to give the title compound, C₁₃H₁₃NO₄. Single crystals were grown from methanol and toluene (1:1) mixture by the slow evaporation method (yield. 0.248 g, 87.32%, m.p.: 461–463 K).

Structure description top

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).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); 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 (Dolomanov et al., 2009).

Figures top

	Fig. 1. ORTEP drawing of C₁₃H₁₃NO₄, showing the labeling scheme with 30% probability displacement ellipsoids.
	Fig. 2. Molecular packing for C₁₃H₁₃NO₄, viewed along the a axis. Dashed lines indicate O—H···O hydrogen bonds in an R₂²[8] motif format and weak N—H···O, C—H···O intermolecular interactions together linking the molecules into dimeric chains along [0 1 0]. H atoms not involved in hydrogen bonding have been removed for clarity.
	Fig. 3. Synthesis of C₁₃H₁₃NO₄.

4-[(4-Acetylphenyl)amino]-2-methylidene-4-oxobutanoic acid top

Crystal data top

C₁₃H₁₃NO₄	Z = 2
M_r = 247.24	F(000) = 260
Triclinic, P1	D_x = 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

Data collection top

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	R_int = 0.025
ω scans	θ_max = 71.3°, θ_min = 4.1°
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	h = −5→6
T_min = 0.756, T_max = 1.000	k = −4→6
3374 measured reflections	l = −26→26

Refinement top

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(F_o²) + (0.0796P)² + 0.1341P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2168 reflections	Δρ_max = 0.31 e Å⁻³
176 parameters	Δρ_min = −0.29 e Å⁻³
0 restraints

Crystal data top

C₁₃H₁₃NO₄	γ = 96.222 (7)°
M_r = 247.24	V = 575.67 (8) Å³
Triclinic, P1	Z = 2
a = 5.0164 (5) Å	Cu Kα radiation
b = 5.2908 (4) Å	µ = 0.89 mm⁻¹
c = 21.8464 (18) Å	T = 173 K
α = 92.833 (6)°	0.42 × 0.22 × 0.12 mm
β = 90.315 (7)°

Data collection top

Agilent Eos Gemini diffractometer	2168 independent reflections
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	1934 reflections with I > 2σ(I)
T_min = 0.756, T_max = 1.000	R_int = 0.025
3374 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.31 e Å⁻³
2168 reflections	Δρ_min = −0.29 e Å⁻³
176 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O4^iv	0.98	2.50	3.465 (2)	167

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

Hydrogen-bond geometry (Å, º) top

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)	154.2
C5—H5B···O2ⁱⁱⁱ	1.00 (3)	2.48 (3)	3.434 (2)	160 (2)
C7—H7···O1ⁱⁱ	0.95	2.56	3.254 (2)	130.3
C13—H13A···O4^iv	0.98	2.50	3.465 (2)	166.9

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

Acknowledgements

BN thanks the UGC for financial assistance through a BSR one-time grant for the purchase of chemicals. PSN thanks Mangalore University for research facilities and DST–PURSE financial assistance. JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

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