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N-(3-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 8 January 2010; accepted 12 January 2010; online 16 January 2010)

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[Gowda, B. T., Kozisek, J., Svoboda, I. & Fuess, H. (2007). Z. Naturforsch. Teil A, 62, 91-100.]; 2009a[Gowda, B. T., Foro, S., Saraswathi, B. S. & Fuess, H. (2009a). Acta Cryst. E65, o1827.],b[Gowda, B. T., Foro, S., Saraswathi, B. S., Terao, H. & Fuess, H. (2009b). Acta Cryst. E65, o399.]). For the modes of inter­linking carboxylic acids by hydrogen bonds, see: Leiserowitz (1976[Leiserowitz, L. (1976). Acta Cryst. B32, 775-802.]). For the packing of mol­ecules involving dimeric hydrogen-bonded association of each carboxyl group with a centrosymmetrically related neighbor, 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

  • Orthorhombic, P c c n

  • 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[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.961, Tmax = 0.980

  • 9274 measured reflections

  • 2228 independent reflections

  • 1772 reflections with I > 2σ(I)

  • Rint = 0.019

Refinement
  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1N⋯O1i 0.863 (19) 2.02 (2) 2.8597 (17) 163.5 (16)
O3—H3O⋯O2ii 0.83 (1) 1.82 (1) 2.6542 (18) 177 (2)
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) -x+1, -y+1, -z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); data reduction: CrysAlis RED; 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

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).

Related literature top

For our studies on the effect of ring and side-chain substitutions on the

solid-state geometry of anilides, see: Gowda et al. (2007; 2009a,b). For the modes of interlinking carboxylic acids by hydrogen bonds, see: Leiserowitz (1976). For the packing of molecules involving dimeric hydrogen-bonded association of each carboxyl group with a centrosymmetrically related neighbor, 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 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 top

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).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); 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.
[Figure 2] Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.
N-(3-Methylphenyl)succinamic acid top
Crystal data top
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 top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
2228 independent reflections
Radiation source: fine-focus sealed tube1772 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
Rotation method data acquisition using ω and ϕ scans.θmax = 26.4°, θmin = 3.0°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
h = 1513
Tmin = 0.961, Tmax = 0.980k = 2525
9274 measured reflectionsl = 911
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 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
Crystal data top
C11H13NO3V = 2181.1 (2) Å3
Mr = 207.22Z = 8
Orthorhombic, PccnMo Kα radiation
a = 12.0661 (8) ŵ = 0.09 mm1
b = 20.220 (1) ÅT = 299 K
c = 8.9398 (5) Å0.44 × 0.34 × 0.22 mm
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
2228 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
1772 reflections with I > 2σ(I)
Tmin = 0.961, Tmax = 0.980Rint = 0.019
9274 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0451 restraint
wR(F2) = 0.121H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.18 e Å3
2228 reflectionsΔρmin = 0.21 e Å3
167 parameters
Special details top

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) top
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) top
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, º) top
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—C51.6 (2)
C7—N1—C1—C6140.25 (16)N1—C1—C6—C5179.93 (15)
C6—C1—C2—C32.4 (2)C1—N1—C7—O10.1 (3)
N1—C1—C2—C3179.29 (14)C1—N1—C7—C8179.98 (14)
C1—C2—C3—C41.4 (3)O1—C7—C8—C95.6 (2)
C1—C2—C3—C11177.74 (18)N1—C7—C8—C9174.51 (14)
C2—C3—C4—C50.5 (3)C7—C8—C9—C1064.8 (2)
C11—C3—C4—C5179.61 (19)C8—C9—C10—O221.9 (2)
C3—C4—C5—C61.3 (3)C8—C9—C10—O3160.00 (15)
C4—C5—C6—C10.3 (3)
Hydrogen-bond geometry (Å, º) top
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, z1/2; (ii) x+1, y+1, z.

Experimental details

Crystal data
Chemical formulaC11H13NO3
Mr207.22
Crystal system, space groupOrthorhombic, Pccn
Temperature (K)299
a, b, c (Å)12.0661 (8), 20.220 (1), 8.9398 (5)
V3)2181.1 (2)
Z8
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.44 × 0.34 × 0.22
Data collection
DiffractometerOxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2009)
Tmin, Tmax0.961, 0.980
No. of measured, independent and
observed [I > 2σ(I)] reflections
9274, 2228, 1772
Rint0.019
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.121, 1.05
No. of reflections2228
No. of parameters167
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.18, 0.21

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), 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···O1i0.863 (19)2.02 (2)2.8597 (17)163.5 (16)
O3—H3O···O2ii0.832 (10)1.823 (10)2.6542 (18)177 (2)
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x+1, y+1, z.
 

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 citationGowda, B. T., Foro, S., Saraswathi, B. S. & Fuess, H. (2009a). Acta Cryst. E65, o1827.  Web of Science CSD CrossRef IUCr Journals
First citationGowda, B. T., Foro, S., Saraswathi, B. S., Terao, H. & Fuess, H. (2009b). Acta Cryst. E65, o399.  Web of Science CSD CrossRef IUCr Journals
First citationGowda, B. T., Kozisek, J., Svoboda, I. & Fuess, H. (2007). Z. Naturforsch. Teil A, 62, 91–100.  CAS
First citationJagannathan, N. R., Rajan, S. S. & Subramanian, E. (1994). J. Chem. Crystallogr. 24, 75–78.  CSD CrossRef CAS Web of Science
First citationLeiserowitz, L. (1976). Acta Cryst. B32, 775–802.  CrossRef CAS IUCr Journals Web of Science
First citationOxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals

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