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ISSN: 2056-9890

N-(4-Methyl­phen­yl)succinamic acid

aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
*Correspondence e-mail: gowdabt@yahoo.com

(Received 16 December 2010; accepted 19 December 2010; online 24 December 2010)

In the title compound, C11H13NO3, the conformations of the N—H and C=O bonds in the amide segment are anti to each other. Further, the conformations of the amide and carbonyl O atoms of the acid segment are also anti to the adjacent –CH2 groups. The C=O and O—H bonds of the acid group are syn to each other. In the crystal, mol­ecules are packed into infinite chains along the b axis through inter­molecular N—H⋯O and O—H⋯O hydrogen bonds.

Related literature

For background to our study of the effect of ring and side-chain substitution on the solid state geometry of anilides, see: Gowda et al. (2009[Gowda, B. T., Foro, S., Saraswathi, B. S. & Fuess, H. (2009). Acta Cryst. E65, o1827.], 2010a[Gowda, B. T., Foro, S., Saraswathi, B. S. & Fuess, H. (2010a). Acta Cryst. E66, o394.],b[Gowda, B. T., Foro, S., Saraswathi, B. S. & Fuess, H. (2010b). Acta Cryst. E66, o908.]). For modes of inter­linking carb­oxy­lic acids by hydrogen bonds, see: Leiserowitz (1976[Leiserowitz, L. (1976). Acta Cryst. B32, 775-802.]). The packing of mol­ecules involving dimeric hydrogen-bonded association of each carboxyl group with a centrosymmetrically related neighbor has also been observed, see: Jagannathan et al. (1994[Jagannathan, N. R., Rajan, S. S. & Subramanian, E. (1994). J. Chem. Crystallogr. 24, 75-78.]).

[Scheme 1]

Experimental

Crystal data
  • C11H13NO3

  • Mr = 207.22

  • Triclinic, [P \overline 1]

  • a = 4.960 (1) Å

  • b = 8.090 (2) Å

  • c = 13.893 (2) Å

  • α = 83.52 (2)°

  • β = 80.08 (2)°

  • γ = 78.15 (1)°

  • V = 535.70 (19) Å3

  • Z = 2

  • Cu Kα radiation

  • μ = 0.78 mm−1

  • T = 299 K

  • 0.55 × 0.25 × 0.08 mm

Data collection
  • Enraf–Nonius CAD-4 diffractometer

  • Absorption correction: ψ scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.674, Tmax = 0.940

  • 2515 measured reflections

  • 1888 independent reflections

  • 1533 reflections with I > 2σ(I)

  • Rint = 0.024

  • 3 standard reflections every 120 min intensity decay: 1.0%

Refinement
  • R[F2 > 2σ(F2)] = 0.064

  • wR(F2) = 0.194

  • S = 1.06

  • 1888 reflections

  • 143 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.24 e Å−3

  • Δρmin = −0.33 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1N⋯O1i 0.84 (2) 2.15 (2) 2.979 (2) 175 (3)
O3—H3O⋯O2ii 0.84 (2) 1.84 (2) 2.681 (3) 171 (4)
Symmetry codes: (i) x+1, y, z; (ii) -x, -y+1, -z+1.

Data collection: CAD-4-PC (Enraf–Nonius, 1996[Enraf-Nonius (1996). CAD-4-PC. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987[Stoe & Cie (1987). REDU4. Stoe & Cie GmbH, Darmstadt, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

In the present work, as a part of studying the effect of ring and side chain substitutions on the solid state geometry of anilides (Gowda et al., 2009, 2010a, b), the crystal structure of N-(4-methylphenyl)- succinamic acid (I) has been determined. The conformations of N—H and C=O bonds in the amide segment are anti to each other. The conformation of the amide oxygen and the carbonyl oxygen of the acid segment are also anti to each other, similar to that observed in N-(4-Chlorophenyl)succinamic acid (II) (Gowda et al., 2009) and N-(2-methylphenyl)-succinamic acid (III)(Gowda et al., 2010b). but contrary to the syn conformation observed in N-(3-methylphenyl)-succinamic acid (IV) (Gowda et al., 2010a).

Further, the conformation of both the C=O bonds are anti to the H atoms of their adjacent –CH2 groups (Fig. 1) and the C=O and O—H bonds of the acid group are in syn position to each other, similar to that observed in (II), (III) and (IV).

The N—H···O and O—H···O intermolecular hydrogen bonds pack the molecules into infinite chains in the structure (Table 1, Fig.2).

The modes of interlinking carboxylic acids by hydrogen bonds is described elsewhere (Leiserowitz, 1976). The packing of molecules involving dimeric hydrogen bonded association of each carboxyl group with a centrosymmetrically related neighbor has also been observed (Jagannathan et al., 1994).

Related literature top

For background to our study of the effect of ring and side-chain substitution on the solid state geometry of anilides, see: Gowda et al. (2009, 2010a,b). For modes of interlinking carboxylic acids by hydrogen bonds, see: Leiserowitz (1976). The packing of molecules involving dimeric hydrogen-bonded association of each carboxyl group with a centrosymmetrically related neighbor has also been observed, see: Jagannathan et al. (1994);

Experimental top

The solution of succinic anhydride (0.01 mole) in toluene (25 ml) was treated dropwise with the solution of p-toluidine (0.01 mole) also in toluene (20 ml) with constant stirring. The resulting mixture was stirred for about one h and set aside for an additional hour at room temperature for completion of the reaction. The mixture was then treated with dilute hydrochloric acid to remove the unreacted p-toluidine. The resultant solid N-(4-methylphenyl)- succinamic acid was filtered under suction and washed thoroughly with water to remove the unreacted succinic anhydride and succinic acid. It was recrystallized to constant melting point from ethanol. The purity of the compound was checked by elemental analysis and characterized by its infrared and NMR spectra.

The plate like colorless single crystals used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation at room temperature.

Refinement top

The H atoms of the NH group and OH group were located in a difference map and later restrained to the distance N—H = 0.86 (2) Å and O—H = 0.82 (2) Å. The other H atoms were positioned with idealized geometry using a riding model [C—H = 0.93–0.97 Å]. All H atoms were refined with isotropic displacement parameters (set to 1.2 times of the Ueq of the parent atom).

Structure description top

In the present work, as a part of studying the effect of ring and side chain substitutions on the solid state geometry of anilides (Gowda et al., 2009, 2010a, b), the crystal structure of N-(4-methylphenyl)- succinamic acid (I) has been determined. The conformations of N—H and C=O bonds in the amide segment are anti to each other. The conformation of the amide oxygen and the carbonyl oxygen of the acid segment are also anti to each other, similar to that observed in N-(4-Chlorophenyl)succinamic acid (II) (Gowda et al., 2009) and N-(2-methylphenyl)-succinamic acid (III)(Gowda et al., 2010b). but contrary to the syn conformation observed in N-(3-methylphenyl)-succinamic acid (IV) (Gowda et al., 2010a).

Further, the conformation of both the C=O bonds are anti to the H atoms of their adjacent –CH2 groups (Fig. 1) and the C=O and O—H bonds of the acid group are in syn position to each other, similar to that observed in (II), (III) and (IV).

The N—H···O and O—H···O intermolecular hydrogen bonds pack the molecules into infinite chains in the structure (Table 1, Fig.2).

The modes of interlinking carboxylic acids by hydrogen bonds is described elsewhere (Leiserowitz, 1976). The packing of molecules involving dimeric hydrogen bonded association of each carboxyl group with a centrosymmetrically related neighbor has also been observed (Jagannathan et al., 1994).

For background to our study of the effect of ring and side-chain substitution on the solid state geometry of anilides, see: Gowda et al. (2009, 2010a,b). For modes of interlinking carboxylic acids by hydrogen bonds, see: Leiserowitz (1976). The packing of molecules involving dimeric hydrogen-bonded association of each carboxyl group with a centrosymmetrically related neighbor has also been observed, see: Jagannathan et al. (1994);

Computing details top

Data collection: CAD-4-PC (Enraf–Nonius, 1996); cell refinement: CAD-4-PC (Enraf–Nonius, 1996); data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound, showing the atom labelling scheme. The displacement ellipsoids are drawn at the 50% probability level. The H atoms are represented as small spheres of arbitrary radii.
[Figure 2] Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.
3-[(4-methylphenyl)carbamoyl]propanoic acid top
Crystal data top
C11H13NO3Z = 2
Mr = 207.22F(000) = 220
Triclinic, P1Dx = 1.285 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54180 Å
a = 4.960 (1) ÅCell parameters from 25 reflections
b = 8.090 (2) Åθ = 6.3–21.3°
c = 13.893 (2) ŵ = 0.78 mm1
α = 83.52 (2)°T = 299 K
β = 80.08 (2)°Plate, colourless
γ = 78.15 (1)°0.55 × 0.25 × 0.08 mm
V = 535.70 (19) Å3
Data collection top
Enraf–Nonius CAD-4
diffractometer
1533 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.024
Graphite monochromatorθmax = 66.8°, θmin = 3.2°
ω scansh = 15
Absorption correction: ψ scan
(North et al., 1968)
k = 99
Tmin = 0.674, Tmax = 0.940l = 1616
2515 measured reflections3 standard reflections every 120 min
1888 independent reflections intensity decay: 1.0%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.194H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.1156P)2 + 0.1448P]
where P = (Fo2 + 2Fc2)/3
1888 reflections(Δ/σ)max = 0.017
143 parametersΔρmax = 0.24 e Å3
2 restraintsΔρmin = 0.33 e Å3
Crystal data top
C11H13NO3γ = 78.15 (1)°
Mr = 207.22V = 535.70 (19) Å3
Triclinic, P1Z = 2
a = 4.960 (1) ÅCu Kα radiation
b = 8.090 (2) ŵ = 0.78 mm1
c = 13.893 (2) ÅT = 299 K
α = 83.52 (2)°0.55 × 0.25 × 0.08 mm
β = 80.08 (2)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
1533 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.024
Tmin = 0.674, Tmax = 0.9403 standard reflections every 120 min
2515 measured reflections intensity decay: 1.0%
1888 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0642 restraints
wR(F2) = 0.194H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.24 e Å3
1888 reflectionsΔρmin = 0.33 e Å3
143 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.0934 (5)0.7741 (3)0.07532 (16)0.0507 (5)
C20.1340 (6)0.8882 (3)0.10364 (19)0.0650 (6)
H20.27880.93450.05670.078*
C30.1439 (7)0.9328 (4)0.2025 (2)0.0786 (8)
H30.29881.00750.22110.094*
C40.0703 (7)0.8692 (4)0.27428 (19)0.0761 (8)
C50.2991 (7)0.7575 (4)0.2444 (2)0.0802 (8)
H50.44660.71350.29120.096*
C60.3100 (6)0.7110 (3)0.14645 (19)0.0677 (7)
H60.46500.63630.12790.081*
C70.0863 (4)0.6981 (3)0.09714 (16)0.0538 (6)
C80.0133 (5)0.6313 (3)0.19407 (17)0.0603 (6)
H8A0.07070.50910.19520.072*
H8B0.17480.67820.19920.072*
C90.2087 (5)0.6752 (3)0.28162 (17)0.0603 (6)
H9A0.25740.79740.28300.072*
H9B0.37470.63470.27450.072*
C100.1152 (5)0.5994 (3)0.37648 (17)0.0588 (6)
C110.0523 (11)0.9182 (6)0.3816 (2)0.1183 (15)
H11A0.01861.03940.39320.142*
H11B0.09760.87530.39930.142*
H11C0.22450.87090.42060.142*
N10.1202 (4)0.7230 (2)0.02421 (14)0.0533 (5)
H1N0.278 (4)0.719 (3)0.0386 (19)0.064*
O10.3349 (3)0.7206 (3)0.08761 (13)0.0727 (6)
O20.1144 (4)0.5108 (3)0.38248 (14)0.0853 (7)
O30.3025 (4)0.6364 (3)0.45282 (14)0.0935 (8)
H3O0.231 (8)0.598 (5)0.504 (2)0.112*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0523 (12)0.0537 (11)0.0487 (11)0.0180 (9)0.0068 (9)0.0023 (9)
C20.0656 (15)0.0657 (14)0.0593 (14)0.0061 (11)0.0098 (11)0.0021 (11)
C30.088 (2)0.0785 (17)0.0699 (18)0.0168 (14)0.0264 (15)0.0148 (13)
C40.111 (2)0.0768 (17)0.0508 (14)0.0433 (16)0.0182 (14)0.0068 (12)
C50.103 (2)0.0806 (17)0.0537 (15)0.0238 (16)0.0073 (14)0.0088 (13)
C60.0662 (15)0.0722 (15)0.0590 (14)0.0096 (12)0.0006 (11)0.0032 (11)
C70.0464 (12)0.0669 (13)0.0505 (12)0.0183 (10)0.0089 (9)0.0014 (9)
C80.0447 (12)0.0842 (16)0.0522 (13)0.0163 (10)0.0102 (10)0.0061 (11)
C90.0529 (13)0.0755 (15)0.0514 (13)0.0124 (11)0.0098 (10)0.0031 (10)
C100.0568 (13)0.0705 (14)0.0477 (12)0.0142 (11)0.0052 (10)0.0006 (10)
C110.188 (4)0.126 (3)0.0569 (19)0.068 (3)0.030 (2)0.0139 (18)
N10.0414 (9)0.0713 (12)0.0485 (10)0.0151 (8)0.0080 (7)0.0007 (8)
O10.0438 (9)0.1125 (15)0.0629 (11)0.0234 (9)0.0138 (7)0.0128 (9)
O20.0686 (12)0.1219 (17)0.0518 (10)0.0074 (11)0.0100 (8)0.0047 (10)
O30.0740 (13)0.1372 (19)0.0504 (11)0.0077 (12)0.0024 (9)0.0096 (11)
Geometric parameters (Å, º) top
C1—C61.383 (3)C7—C81.518 (3)
C1—C21.386 (3)C8—C91.514 (3)
C1—N11.419 (3)C8—H8A0.9700
C2—C31.387 (4)C8—H8B0.9700
C2—H20.9300C9—C101.497 (3)
C3—C41.383 (5)C9—H9A0.9700
C3—H30.9300C9—H9B0.9700
C4—C51.390 (5)C10—O21.225 (3)
C4—C111.513 (4)C10—O31.302 (3)
C5—C61.378 (4)C11—H11A0.9600
C5—H50.9300C11—H11B0.9600
C6—H60.9300C11—H11C0.9600
C7—O11.237 (3)N1—H1N0.836 (17)
C7—N11.340 (3)O3—H3O0.844 (19)
C6—C1—C2119.1 (2)C7—C8—H8A109.0
C6—C1—N1117.9 (2)C9—C8—H8B109.0
C2—C1—N1123.0 (2)C7—C8—H8B109.0
C1—C2—C3119.5 (2)H8A—C8—H8B107.8
C1—C2—H2120.2C10—C9—C8112.4 (2)
C3—C2—H2120.2C10—C9—H9A109.1
C4—C3—C2121.8 (3)C8—C9—H9A109.1
C4—C3—H3119.1C10—C9—H9B109.1
C2—C3—H3119.1C8—C9—H9B109.1
C3—C4—C5117.8 (2)H9A—C9—H9B107.9
C3—C4—C11120.7 (3)O2—C10—O3122.9 (2)
C5—C4—C11121.4 (3)O2—C10—C9123.8 (2)
C6—C5—C4120.8 (3)O3—C10—C9113.4 (2)
C6—C5—H5119.6C4—C11—H11A109.5
C4—C5—H5119.6C4—C11—H11B109.5
C5—C6—C1120.8 (3)H11A—C11—H11B109.5
C5—C6—H6119.6C4—C11—H11C109.5
C1—C6—H6119.6H11A—C11—H11C109.5
O1—C7—N1124.4 (2)H11B—C11—H11C109.5
O1—C7—C8121.9 (2)C7—N1—C1126.48 (19)
N1—C7—C8113.68 (19)C7—N1—H1N118.0 (19)
C9—C8—C7112.7 (2)C1—N1—H1N115.1 (19)
C9—C8—H8A109.0C10—O3—H3O108 (3)
C6—C1—C2—C31.9 (4)O1—C7—C8—C927.7 (3)
N1—C1—C2—C3179.6 (2)N1—C7—C8—C9154.7 (2)
C1—C2—C3—C41.4 (4)C7—C8—C9—C10176.27 (19)
C2—C3—C4—C50.1 (4)C8—C9—C10—O20.5 (4)
C2—C3—C4—C11179.2 (3)C8—C9—C10—O3179.6 (2)
C3—C4—C5—C60.5 (4)O1—C7—N1—C11.7 (4)
C11—C4—C5—C6178.6 (3)C8—C7—N1—C1175.8 (2)
C4—C5—C6—C10.1 (4)C6—C1—N1—C7146.1 (2)
C2—C1—C6—C51.4 (4)C2—C1—N1—C736.3 (3)
N1—C1—C6—C5179.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.84 (2)2.15 (2)2.979 (2)175 (3)
O3—H3O···O2ii0.84 (2)1.84 (2)2.681 (3)171 (4)
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC11H13NO3
Mr207.22
Crystal system, space groupTriclinic, P1
Temperature (K)299
a, b, c (Å)4.960 (1), 8.090 (2), 13.893 (2)
α, β, γ (°)83.52 (2), 80.08 (2), 78.15 (1)
V3)535.70 (19)
Z2
Radiation typeCu Kα
µ (mm1)0.78
Crystal size (mm)0.55 × 0.25 × 0.08
Data collection
DiffractometerEnraf–Nonius CAD-4
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.674, 0.940
No. of measured, independent and
observed [I > 2σ(I)] reflections
2515, 1888, 1533
Rint0.024
(sin θ/λ)max1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.064, 0.194, 1.06
No. of reflections1888
No. of parameters143
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.24, 0.33

Computer programs: CAD-4-PC (Enraf–Nonius, 1996), REDU4 (Stoe & Cie, 1987), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.836 (17)2.145 (18)2.979 (2)175 (3)
O3—H3O···O2ii0.844 (19)1.84 (2)2.681 (3)171 (4)
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z+1.
 

Acknowledgements

BSS thanks the University Grants Commission, Government of India, New Delhi, for the award of a research fellowship under its faculty improvement program.

References

First citationEnraf–Nonius (1996). CAD-4-PC. Enraf–Nonius, Delft, The Netherlands.  Google Scholar
First citationGowda, B. T., Foro, S., Saraswathi, B. S. & Fuess, H. (2009). Acta Cryst. E65, o1827.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationGowda, B. T., Foro, S., Saraswathi, B. S. & Fuess, H. (2010a). Acta Cryst. E66, o394.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationGowda, B. T., Foro, S., Saraswathi, B. S. & Fuess, H. (2010b). Acta Cryst. E66, o908.  Web of Science CrossRef IUCr Journals Google Scholar
First citationJagannathan, N. R., Rajan, S. S. & Subramanian, E. (1994). J. Chem. Crystallogr. 24, 75–78.  CSD CrossRef CAS Web of Science Google Scholar
First citationLeiserowitz, L. (1976). Acta Cryst. B32, 775–802.  CrossRef CAS IUCr Journals Web of Science Google Scholar
First citationNorth, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.  CrossRef IUCr Journals Web of Science Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationStoe & Cie (1987). REDU4. Stoe & Cie GmbH, Darmstadt, Germany.  Google Scholar

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