N-(3,4-Dimethyl-phen-yl)succinamic acid.

Abstract

The asymmetric unit of the title compound, C(12)H(15)NO(3), contains two independent mol-ecules. In both mol-ecules, the conformations of the amide oxygen and the carbonyl O atom of the acid segment are anti to the adjacent CH(2) groups. In the crystal, both molecules form inversion dimers linked by pairs of O-H⋯O hydrogen bonds and N-H⋯O interactions link the dimers into [100] chains.

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N-(3,4-Dimethylphenyl)succinamic acid
B. Thimme Gowda,a* Sabine Foro,bB. S. Saraswathiaand
Hartmut Fuessb
aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199,
Mangalore, India, andbInstitute of Materials Science, Darmstadt University of
Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
Correspondence e-mail: gowdabt@yahoo.com
Received 8 January 2010; accepted 16 January 2010
Key indicators: single-crystal X-ray study; T = 299 K; mean ?(C–C) = 0.002 A ˚;
R factor = 0.042; wR factor = 0.118; data-to-parameter ratio = 14.9.
The asymmetric unit of the title compound, C12H15NO3,
contains two independent molecules. In both molecules, the
conformations of the amide oxygen and the carbonyl O atom
of the acid segment are anti to the adjacent CH2groups. In the
crystal, both molecules form inversion dimers linked by pairs
of O—H???O hydrogen bonds and N—H???O interactions link
the dimers into [100] chains.
Related literature
For the crystal structures of related anilides, see: Gowda et al.
(2007); Gowda, Foro, Saraswathi & Fuess (2009); Gowda,
Foro, Saraswathi et al. (2009). For the modes of interlinking
carboxylic acids by hydrogen bonds, see: Leiserowitz (1976);
Jagannathan et al. (1994).
Experimental
Crystal data
C12H15NO3
Mr= 221.25
Triclinic, P1
a = 9.736 (1) A˚
b = 9.919 (1) A˚
c = 12.601 (2) A˚
? = 106.42 (1)?
? = 100.98 (1)?
? = 99.81 (1)?
V = 1112.9 (2) A˚3
Z = 4
Mo K? radiation
? = 0.10 mm?1
T = 299 K
0.44 ? 0.40 ? 0.16 mm
Data collection
Oxford Diffraction Xcalibur
diffractometer with a Sapphire
CCD detector
Absorption correction: multi-scan
(CrysAlis RED; Oxford
Diffraction, 2009)
Tmin= 0.959, Tmax= 0.985
7776 measured reflections
4538 independent reflections
3173 reflections with I > 2?(I)
Rint= 0.013
Refinement
R[F2> 2?(F2)] = 0.042
wR(F2) = 0.118
S = 1.03
4538 reflections
305 parameters
2 restraints
H atoms treated by a mixture of
independent and constrained
refinement
??max= 0.17 e A˚?3
??min= ?0.17 e A˚?3
Table 1
Hydrogen-bond geometry (A˚,?).
D—H???A
O3—H3O???O5i
N1—H1N???O4ii
O6—H6O???O2i
N2—H2N???O1
Symmetry codes: (i) ?x þ 1;?y;?z; (ii) x ? 1;y;z.
D—HH???AD???AD—H???A
0.85 (2)
0.894 (18)
0.88 (2)
0.87 (2)
1.82 (2)
2.127 (18)
1.78 (2)
2.26 (2)
2.6681 (18)
2.9909 (18)
2.6555 (18)
3.0676 (19)
174 (2)
162.5 (15)
175 (2)
154.7 (17)
Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell
refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduc-
tion: CrysAlis RED; program(s) used to solve structure: SHELXS97
(Sheldrick, 2008); program(s) used to refine structure: SHELXL97
(Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); soft-
ware used to prepare material for publication: SHELXL97.
BSS thanks the University Grants Commission, Govern-
ment of India, New Delhi, for the award of a research
fellowship under its faculty improvement program.
Supplementary data and figures for this paper are available from the
IUCr electronic archives (Reference: RZ2408).
References
Gowda, B. T., Foro, S., Saraswathi, B. S. & Fuess, H. (2009). Acta Cryst. E65,
o1722.
Gowda, B. T., Foro, S., Saraswathi, B. S., Terao, H. & Fuess, H. (2009). Acta
Cryst. E65, o466.
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.
Spek, A. L. (2009). Acta Cryst. D65, 148–155.
organic compounds
o436
Gowda et al.
doi:10.1107/S1600536810002084
Acta Cryst. (2010). E66, o436
Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368

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Acta Cryst. (2010). E66, o436 [ doi:10.1107/S1600536810002084 ]
N-(3,4-Dimethylphenyl)succinamic acid
B. T. Gowda, S. Foro, B. S. Saraswathi and H. Fuess
Comment
As a part of studying the effect of the ring and side chain substitutions on the crystal structures of anilides (Gowda et al.,
2007; Gowda, Foro, Saraswathi & Fuess, 2009; Gowda, Foro, Saraswathi et al., 2009), we report herein the crystal structure
of N-(3,4-dimethylphenyl)succinamic acid (I). The asymmetric unit of (I) contains two independent molecules (Fig. 1).
The conformations of the N—H and C═O bonds in the amide segments are anti to each other. Further, the conformation
of the amide oxygen and the carbonyl oxygen of the acid segment are anti to the H atoms of their adjacent CH2 groups,
while the conformation of the C=O and O—H bonds of the acid group are in syn position to each other, similar to that ob-
served in N-(3,4-dichlorophenyl)succinamic acid monohydrate (II) (Gowda, Foro, Saraswathi & Fuess, 2009) and N-(2,6-
dimethylphenyl)succinamic acid (III) (Gowda, Foro, Saraswathi et al., 2009).
The conformation of the amide hydrogen in (I) is syn to the meta-methyl group in the benzene ring, contrary to the
anti conformation observed between the amide hydrogen and the meta-Cl in (II). Further, 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
(II). N—H···O and O—H···O intermolecular hydrogen bonds pack the molecules into chains running parallel to the a axis
(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
A solution of succinic anhydride (0.02 mol) in toluene (25 ml) was treated dropwise with a solution of 3,4-dimethylaniline
(0.02 mol) in toluene (20 ml) with constant stirring. The resulting mixture was stirred for about one hour and set aside for an
additional hour at room temperature for the completion of reaction. The mixture was then treated with dilute hydrochloric
acid to remove the unreacted 3,4-dimethylaniline. The resultant solid N-(3,4-dimethylphenyl)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 colourless single crystals used in X-ray diffraction studies were grown by slow evaporation at room temperature
of an ethanolic solution.
Refinement
The H atoms of the NH groups were located in a difference Fourier map and their positions refined with N—H =
0.87 (2)–0.89 (2) %A. The H atoms of the OH groups were located in a difference Fourier map and the O—H distance

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restrained to 0.82 (2) Å. All other H atoms were positioned with idealized geometry using a riding model with C—H =
0.93–0.97 Å and refined with isotropic displacement parameters set to 1.2 times of the Ueq of the parent atom.
Figures
Fig. 1. The molecular structure of the title compound, showing the atom labelling scheme.
Displacement ellipsoids are drawn at the 50% probability level. The H atoms are represented
as small spheres of arbitrary radii.
Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed
lines.
N-(3,4-Dimethylphenyl)succinamic acid
Crystal data
C12H15NO3
Mr = 221.25
Z = 4
F(000) = 472
Dx = 1.320 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 2369 reflections
θ = 3.1–27.7°
µ = 0.10 mm−1
T = 299 K
Rod, colourless
0.44 × 0.40 × 0.16 mm
Triclinic, P1
Hall symbol: -P 1
a = 9.736 (1) Å
b = 9.919 (1) Å
c = 12.601 (2) Å
α = 106.42 (1)°
β = 100.98 (1)°
γ = 99.81 (1)°
V = 1112.9 (2) Å3
Data collection
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
Radiation source: fine-focus sealed tube
graphite
Rotation method data acquisition using ω and φ
scans.
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
Tmin = 0.959, Tmax = 0.985
4538 independent reflections
3173 reflections with I > 2σ(I)
Rint = 0.013
θmax = 26.4°, θmin = 3.1°
h = −11→12
k = −12→10

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7776 measured reflections
l = −14→15
Refinement
Refinement on F2
Primary atom site location: structure-invariant direct
methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring
sites
H atoms treated by a mixture of independent and
constrained refinement
w = 1/[σ2(Fo2) + (0.0517P)2 + 0.2735P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.17 e Å−3
Δρmin = −0.17 e Å−3
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.042
wR(F2) = 0.118
S = 1.03
4538 reflections
305 parameters
2 restraints
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 mat-
rix. 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, convention-
al 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)
x
0.25568 (12)
0.15120 (14)
0.20038 (15)
0.243 (2)
0.08150 (14)
−0.013 (2)
0.16800 (16)
0.11108 (17)
0.0170
0.19110 (18)
0.33168 (18)
0.38529 (18)
0.4780
0.30594 (17)
y
0.46649 (13)
0.11617 (14)
0.09014 (14)
0.030 (2)
0.53340 (15)
0.5115 (19)
0.63065 (16)
0.64457 (17)
0.5949
0.73073 (17)
0.80814 (18)
0.79638 (18)
0.8489
0.70921 (17)
z
0.13575 (10)
0.05553 (10)
−0.11316 (10)
−0.0934 (17)
0.22197 (11)
0.2162 (14)
0.32941 (13)
0.42386 (14)
0.4138
0.53296 (14)
0.54764 (14)
0.45219 (15)
0.4613
0.34342 (14)
Uiso*/Ueq
0.0454 (3)
0.0529 (3)
0.0530 (3)
0.064*
0.0380 (3)
0.046*
0.0344 (4)
0.0382 (4)
0.046*
0.0395 (4)
0.0409 (4)
0.0436 (4)
0.052*
0.0409 (4)
O1
O2
O3
H3O
N1
H1N
C1
C2
H2
C3
C4
C5
H5
C6