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Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): o394.
Published online 2010 January 16. doi:  10.1107/S1600536810001480
PMCID: PMC2979942

N-(3-Methyl­phen­yl)succinamic acid

Abstract

In the crystal structure of the title compound, C11H13NO3, the conformations of the N—H and C=O bonds in the amide segment are anti to each other, and that of the amide H atom is anti to the meta-methyl group in the benzene ring. Furthermore, the conformations of the amide oxygen and the carbonyl O atom 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, the mol­ecules are packed into infinite chains through inter­molecular N—H(...)O and O—H(...)O hydrogen bonds.

Related literature

For our studies on the effect of ring and side-chain substitutions on the solid-state geometry of anilides, see: Gowda et al. (2007 [triangle]; 2009a [triangle],b [triangle]). For the modes of inter­linking carboxylic acids by hydrogen bonds, see: Leiserowitz (1976 [triangle]). For the packing of mol­ecules involving dimeric hydrogen-bonded association of each carboxyl group with a centrosymmetrically related neighbor, see: Jagannathan et al. (1994 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o394-scheme1.jpg

Experimental

Crystal data

  • C11H13NO3
  • M r = 207.22
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o394-efi1.jpg
  • a = 12.0661 (8) Å
  • b = 20.220 (1) Å
  • c = 8.9398 (5) Å
  • V = 2181.1 (2) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 299 K
  • 0.44 × 0.34 × 0.22 mm

Data collection

  • Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 [triangle]) T min = 0.961, T max = 0.980
  • 9274 measured reflections
  • 2228 independent reflections
  • 1772 reflections with I > 2σ(I)
  • R int = 0.019

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 0.121
  • S = 1.05
  • 2228 reflections
  • 167 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.21 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 [triangle]); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 [triangle]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810001480/bq2189sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810001480/bq2189Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

As a part of studying the effect of ring and side chain substitutions on the solid state geometry of anilides (Gowda et al., 2007; 2009a,b), we report herein the crystal structure of N-(3-methylphenyl)succinamic acid (I). The conformations of N—H and C=O bonds in the amide segment are anti to each other. But the conformation of the amide oxygen and the carbonyl oxygen of the acid segment are syn to each other, contrary to the anti conformation observed in N-(4-Chlorophenyl)succinamic acid (II) (Gowda et al., 2009a) and N-(2-chlorophenyl)- succinamic acid (III)(Gowda et al., 2009b). 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) and (III).

The conformation of the amide hydrogen is anti to the meta- methyl group in the benzene ring, contrary to the syn conformation observed between the amide hydrogen and the ortho-Cl in (III).

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).

Experimental

The solution of succinic anhydride (0.01 mole) in toluene (25 ml) was treated dropwise with the solution of m-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 m-toluidine. The resultant solid N-(3-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 rod like colorless single crystals used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation at room temperature.

Refinement

The H atoms of the CH3 group were positioned with idealized geometry using a riding model with C—H = 0.96 Å. The other H atoms were located in a difference map and their positions refined [N—H = 0.86 (2) %A, C—H = 0.93 (2)–1.01 (2) Å.], while the H atom of the OH group was later restrained to the distance O—H = 0.82 (1) Å. All H atoms were refined with isotropic displacement parameters (set to 1.2 times of the Ueq of the parent atom).

Figures

Fig. 1.
Molecular structure of the title compound, showing the atom labelling scheme. The displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
Molecular packing of the title compound with hydrogen bonding shown as dashed lines.

Crystal data

C11H13NO3F(000) = 880
Mr = 207.22Dx = 1.262 Mg m3
Orthorhombic, PccnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2acCell parameters from 4700 reflections
a = 12.0661 (8) Åθ = 2.5–27.8°
b = 20.220 (1) ŵ = 0.09 mm1
c = 8.9398 (5) ÅT = 299 K
V = 2181.1 (2) Å3Rod, colourless
Z = 80.44 × 0.34 × 0.22 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector2228 independent reflections
Radiation source: fine-focus sealed tube1772 reflections with I > 2σ(I)
graphiteRint = 0.019
Rotation method data acquisition using ω and [var phi] scans.θmax = 26.4°, θmin = 3.0°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)h = −15→13
Tmin = 0.961, Tmax = 0.980k = −25→25
9274 measured reflectionsl = −9→11

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121H atoms treated by a mixture of independent and constrained refinement
S = 1.05w = 1/[σ2(Fo2) + (0.0567P)2 + 0.6529P] where P = (Fo2 + 2Fc2)/3
2228 reflections(Δ/σ)max = 0.029
167 parametersΔρmax = 0.18 e Å3
1 restraintΔρmin = −0.21 e Å3

Special details

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
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)

xyzUiso*/Ueq
O10.60319 (12)0.30046 (6)0.00527 (12)0.0586 (4)
O20.51371 (10)0.44029 (6)−0.12328 (15)0.0604 (4)
O30.64575 (11)0.48088 (7)0.02306 (17)0.0681 (4)
H3O0.5948 (14)0.5046 (10)0.056 (3)0.082*
N10.55127 (12)0.24064 (6)−0.19678 (14)0.0449 (3)
H1N0.5651 (14)0.2366 (9)−0.291 (2)0.054*
C10.49463 (12)0.18766 (7)−0.12564 (16)0.0398 (4)
C20.42443 (13)0.19787 (8)−0.00544 (18)0.0456 (4)
H20.4131 (14)0.2440 (10)0.0343 (19)0.055*
C30.37093 (14)0.14509 (9)0.0632 (2)0.0541 (4)
C40.38770 (17)0.08225 (9)0.0064 (2)0.0617 (5)
H40.3523 (18)0.0467 (10)0.052 (2)0.074*
C50.45474 (17)0.07211 (9)−0.1154 (2)0.0627 (5)
H50.4654 (17)0.0287 (11)−0.156 (2)0.075*
C60.50913 (15)0.12444 (8)−0.1827 (2)0.0505 (4)
H60.5552 (15)0.1191 (9)−0.270 (2)0.061*
C70.60056 (13)0.29228 (7)−0.13003 (16)0.0401 (4)
C80.65448 (16)0.34114 (8)−0.23546 (18)0.0470 (4)
H8A0.5993 (15)0.3536 (8)−0.311 (2)0.056*
H8B0.7113 (15)0.3183 (8)−0.285 (2)0.056*
C90.69866 (15)0.40119 (9)−0.1542 (2)0.0514 (4)
H9A0.7504 (17)0.3894 (9)−0.078 (2)0.062*
H9B0.7338 (16)0.4291 (9)−0.223 (2)0.062*
C100.61046 (13)0.44199 (7)−0.08284 (18)0.0449 (4)
C110.2978 (2)0.15574 (12)0.1975 (3)0.0901 (8)
H11A0.22190.15820.16600.108*
H11B0.31830.19620.24620.108*
H11C0.30670.11950.26580.108*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0916 (10)0.0551 (7)0.0292 (6)−0.0188 (6)0.0069 (6)−0.0009 (5)
O20.0537 (7)0.0579 (7)0.0698 (8)0.0037 (6)−0.0091 (6)−0.0140 (6)
O30.0554 (8)0.0659 (8)0.0831 (10)0.0010 (6)−0.0092 (7)−0.0255 (7)
N10.0613 (8)0.0467 (7)0.0267 (6)−0.0016 (6)0.0071 (6)−0.0018 (5)
C10.0431 (8)0.0422 (8)0.0342 (7)0.0017 (6)−0.0055 (6)0.0014 (6)
C20.0459 (9)0.0474 (8)0.0436 (9)0.0020 (7)0.0020 (7)0.0015 (7)
C30.0424 (9)0.0623 (10)0.0577 (10)−0.0037 (7)0.0012 (8)0.0128 (8)
C40.0574 (11)0.0524 (10)0.0752 (13)−0.0111 (8)−0.0087 (10)0.0160 (9)
C50.0740 (13)0.0417 (9)0.0724 (13)−0.0008 (8)−0.0147 (11)−0.0031 (8)
C60.0569 (10)0.0483 (9)0.0463 (9)0.0059 (7)−0.0047 (8)−0.0042 (7)
C70.0499 (9)0.0410 (7)0.0294 (7)0.0048 (6)0.0062 (6)0.0010 (6)
C80.0560 (10)0.0482 (9)0.0367 (8)0.0014 (7)0.0130 (8)0.0038 (7)
C90.0490 (9)0.0527 (9)0.0525 (10)−0.0063 (8)0.0105 (8)0.0061 (8)
C100.0493 (9)0.0380 (7)0.0473 (9)−0.0073 (6)−0.0001 (7)0.0057 (6)
C110.0777 (14)0.0925 (16)0.0999 (18)−0.0039 (12)0.0402 (13)0.0214 (14)

Geometric parameters (Å, °)

O1—C71.2212 (17)C4—H40.93 (2)
O2—C101.2226 (19)C5—C61.383 (3)
O3—C101.302 (2)C5—H50.96 (2)
O3—H3O0.832 (10)C6—H60.96 (2)
N1—C71.3416 (19)C7—C81.513 (2)
N1—C11.4210 (19)C8—C91.512 (2)
N1—H1N0.863 (19)C8—H8A0.983 (19)
C1—C21.384 (2)C8—H8B0.940 (19)
C1—C61.387 (2)C9—C101.490 (2)
C2—C31.390 (2)C9—H9A0.95 (2)
C2—H21.008 (19)C9—H9B0.94 (2)
C3—C41.383 (3)C11—H11A0.9600
C3—C111.505 (3)C11—H11B0.9600
C4—C51.372 (3)C11—H11C0.9600
C10—O3—H3O111.1 (16)O1—C7—C8121.17 (14)
C7—N1—C1126.93 (12)N1—C7—C8114.95 (13)
C7—N1—H1N115.0 (12)C9—C8—C7112.13 (13)
C1—N1—H1N117.2 (12)C9—C8—H8A111.4 (10)
C2—C1—C6120.02 (15)C7—C8—H8A107.8 (10)
C2—C1—N1121.97 (13)C9—C8—H8B111.4 (11)
C6—C1—N1117.99 (14)C7—C8—H8B106.8 (11)
C1—C2—C3120.83 (15)H8A—C8—H8B107.1 (15)
C1—C2—H2119.6 (10)C10—C9—C8113.49 (15)
C3—C2—H2119.5 (10)C10—C9—H9A107.6 (12)
C4—C3—C2118.37 (17)C8—C9—H9A111.9 (11)
C4—C3—C11120.66 (17)C10—C9—H9B105.8 (11)
C2—C3—C11120.96 (18)C8—C9—H9B109.0 (11)
C5—C4—C3121.00 (17)H9A—C9—H9B108.8 (16)
C5—C4—H4120.2 (13)O2—C10—O3122.97 (15)
C3—C4—H4118.8 (13)O2—C10—C9122.68 (15)
C4—C5—C6120.73 (17)O3—C10—C9114.33 (15)
C4—C5—H5120.9 (13)C3—C11—H11A109.5
C6—C5—H5118.4 (13)C3—C11—H11B109.5
C5—C6—C1119.01 (17)H11A—C11—H11B109.5
C5—C6—H6122.7 (11)C3—C11—H11C109.5
C1—C6—H6118.2 (11)H11A—C11—H11C109.5
O1—C7—N1123.88 (14)H11B—C11—H11C109.5
C7—N1—C1—C241.4 (2)C2—C1—C6—C5−1.6 (2)
C7—N1—C1—C6−140.25 (16)N1—C1—C6—C5−179.93 (15)
C6—C1—C2—C32.4 (2)C1—N1—C7—O10.1 (3)
N1—C1—C2—C3−179.29 (14)C1—N1—C7—C8−179.98 (14)
C1—C2—C3—C4−1.4 (3)O1—C7—C8—C9−5.6 (2)
C1—C2—C3—C11177.74 (18)N1—C7—C8—C9174.51 (14)
C2—C3—C4—C5−0.5 (3)C7—C8—C9—C10−64.8 (2)
C11—C3—C4—C5−179.61 (19)C8—C9—C10—O2−21.9 (2)
C3—C4—C5—C61.3 (3)C8—C9—C10—O3160.00 (15)
C4—C5—C6—C1−0.3 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.863 (19)2.02 (2)2.8597 (17)163.5 (16)
O3—H3O···O2ii0.83 (1)1.82 (1)2.6542 (18)177 (2)

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+1, −y+1, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2189).

References

  • Gowda, B. T., Foro, S., Saraswathi, B. S. & Fuess, H. (2009a). Acta Cryst. E65, o1827. [PMC free article] [PubMed]
  • Gowda, B. T., Foro, S., Saraswathi, B. S., Terao, H. & Fuess, H. (2009b). Acta Cryst. E65, o399. [PMC free article] [PubMed]
  • Gowda, B. T., Kozisek, J., Svoboda, I. & Fuess, H. (2007). Z. Naturforsch. Teil A, 62, 91–100.
  • Jagannathan, N. R., Rajan, S. S. & Subramanian, E. (1994). J. Chem. Crystallogr.24, 75–78.
  • Leiserowitz, L. (1976). Acta Cryst. B32, 775–802.
  • Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED Oxford Diffraction Ltd, Yarnton, England.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

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