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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 1| January 2011| Page o236
https://doi.org/10.1107/S160053681005292X

N-(2,3-Di­methyl­phen­yl)succinamic acid

B. S. Saraswathi,a Sabine Foro,b B. Thimme Gowdaa* and Hartmut Fuessb

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 13 December 2010; accepted 16 December 2010; online 24 December 2010)

In the title compound, C12H15NO3, the conformations of N—H and C=O bonds in the amide segment are anti to each other and that of the amide H atom is syn to the ortho- and meta-methyl groups in the benzene ring. In the crystal, the mol­ecules are linked into infinite chains through inter­molecular O—H⋯O and N—H⋯O hydrogen bonds.

Related literature

For background to our study of the effect of ring and side-chain substitutions on the crystal structures of anilides, see: Gowda et al. (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, o436.],c[Gowda, B. T., Foro, S., Saraswathi, B. S. & Fuess, H. (2010c). Acta Cryst. E66, o908.]). For the 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

  • C12H15NO3

  • Mr = 221.25

  • Triclinic, [P \overline 1]

  • a = 4.8379 (4) Å

  • b = 10.0424 (6) Å

  • c = 11.9876 (8) Å

  • α = 90.222 (6)°

  • β = 99.614 (7)°

  • γ = 98.506 (6)°

  • V = 567.67 (7) Å3

  • Z = 2

  • Cu Kα radiation

  • μ = 0.77 mm−1

  • T = 299 K

  • 0.40 × 0.25 × 0.10 mm
Data collection

  • Enraf–Nonius CAD-4 diffractometer

  • 3962 measured reflections

  • 2017 independent reflections

  • 1751 reflections with I > 2σ(I)

  • Rint = 0.035

  • 3 standard reflections every 120 min intensity decay: 0.5%
Refinement

  • R[F2 > 2σ(F2)] = 0.064

  • wR(F2) = 0.183

  • S = 1.11

  • 2017 reflections

  • 154 parameters

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

  • Δρmax = 0.42 e Å−3

  • Δρmin = −0.31 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1N⋯O1i 0.87 (3) 2.04 (3) 2.909 (2) 174 (2)
O2—H2O⋯O3ii 0.85 (3) 1.90 (4) 2.679 (2) 152 (3)
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y+1, -z+3.

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

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681005292X/bq2264sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681005292X/bq2264Isup2.hkl

checkCIF report


Comment top

In the present work, as a part of studying the effect of ring and side chain substitutions on the crystal structures of anilides (Gowda et al., 2010a,b,c), the crystal structure of N-(2,3-dimethylphenyl)-succinamic acid (I) has been determined. The conformations of N—H and C═O bonds in the amide segment are anti to each other (Fig. 1). The conformation of the amide oxygen and the carbonyl oxygen of the acid segment are almost midway between the syn and anti conformations, in contrast to the anti conformation observed in N-(2-methylphenyl)succinamic acid (II) (Gowda et al., 2010c) and the syn conformation observed in N-(3-methylphenyl)succinamic acid (III) (Gowda et al., 2010a). Further, the conformation of the amide C═O bond is anti to the H atoms of its adjacent –CH2 groups (Fig. 1) and that of the carbonyl oxygen of the acid segment is almost midway between the syn and anti conformations. 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 syn to the ortho- and meta-methyl groups in the benzene ring, similar to that observed between the amide hydrogen and the ortho-methyl group in (II), but contrary to the anti conformation observed between the amide hydrogen and the meta-methyl group in the benzene ring of (III).

The intermolecular O—H···O and N—H···O 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 substitutions on the crystal structures of anilides, see: Gowda et al. (2010a,b,c). For the 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 2,3-dimethylaniline (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 2,3-dimethylaniline. The resultant solid N-(2,3-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 prism 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 OH group and of the NH group were located in a difference map and their positions refined [O—H = 0.85 (3) Å, N—H = 0.87 (3) 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 crystal structures of anilides (Gowda et al., 2010a,b,c), the crystal structure of N-(2,3-dimethylphenyl)-succinamic acid (I) has been determined. The conformations of N—H and C═O bonds in the amide segment are anti to each other (Fig. 1). The conformation of the amide oxygen and the carbonyl oxygen of the acid segment are almost midway between the syn and anti conformations, in contrast to the anti conformation observed in N-(2-methylphenyl)succinamic acid (II) (Gowda et al., 2010c) and the syn conformation observed in N-(3-methylphenyl)succinamic acid (III) (Gowda et al., 2010a). Further, the conformation of the amide C═O bond is anti to the H atoms of its adjacent –CH2 groups (Fig. 1) and that of the carbonyl oxygen of the acid segment is almost midway between the syn and anti conformations. 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 syn to the ortho- and meta-methyl groups in the benzene ring, similar to that observed between the amide hydrogen and the ortho-methyl group in (II), but contrary to the anti conformation observed between the amide hydrogen and the meta-methyl group in the benzene ring of (III).

The intermolecular O—H···O and N—H···O 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 substitutions on the crystal structures of anilides, see: Gowda et al. (2010a,b,c). For the 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 labeling 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-(2,3-Dimethylphenyl)succinamic acid top
Crystal data top
C12H15NO3Z = 2
Mr = 221.25F(000) = 236
Triclinic, P1Dx = 1.294 Mg m−3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54180 Å
a = 4.8379 (4) ÅCell parameters from 25 reflections
b = 10.0424 (6) Åθ = 5.9–22.4°
c = 11.9876 (8) ŵ = 0.77 mm−1
α = 90.222 (6)°T = 299 K
β = 99.614 (7)°Prism, colorless
γ = 98.506 (6)°0.40 × 0.25 × 0.10 mm
V = 567.67 (7) Å3
Data collection top
Enraf–Nonius CAD-4
diffractometer		Rint = 0.035
Radiation source: fine-focus sealed tubeθmax = 66.9°, θmin = 3.7°
Graphite monochromatorh = −5→5
ω/2θ scansk = −11→11
3962 measured reflectionsl = −14→14
2017 independent reflections3 standard reflections every 120 min
1751 reflections with I > 2σ(I) intensity decay: 0.5%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.064H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.183 w = 1/[σ2(Fo2) + (0.1035P)2 + 0.1611P]
where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max = 0.003
2017 reflectionsΔρmax = 0.42 e Å−3
154 parametersΔρmin = −0.31 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.025 (4)
Crystal data top
C12H15NO3γ = 98.506 (6)°
Mr = 221.25V = 567.67 (7) Å3
Triclinic, P1Z = 2
a = 4.8379 (4) ÅCu Kα radiation
b = 10.0424 (6) ŵ = 0.77 mm−1
c = 11.9876 (8) ÅT = 299 K
α = 90.222 (6)°0.40 × 0.25 × 0.10 mm
β = 99.614 (7)°
Data collection top
Enraf–Nonius CAD-4
diffractometer		Rint = 0.035
3962 measured reflections3 standard reflections every 120 min
2017 independent reflections intensity decay: 0.5%
1751 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0640 restraints
wR(F2) = 0.183H atoms treated by a mixture of independent and constrained refinement
S = 1.11Δρmax = 0.42 e Å−3
2017 reflectionsΔρmin = −0.31 e Å−3
154 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
C1−0.0305 (4)0.17546 (19)0.88221 (15)0.0389 (5)
C20.0537 (4)0.21089 (18)0.77926 (15)0.0396 (5)
C3−0.0852 (4)0.1370 (2)0.68124 (17)0.0481 (5)
C4−0.3018 (5)0.0324 (2)0.6889 (2)0.0597 (6)
H4−0.3937−0.01630.62360.072*
C5−0.3839 (5)−0.0011 (2)0.7909 (2)0.0655 (7)
H5−0.5314−0.07100.79420.079*
C6−0.2461 (4)0.0697 (2)0.88872 (19)0.0534 (6)
H6−0.29760.04640.95820.064*
C7−0.0169 (4)0.3000 (2)1.05958 (16)0.0502 (6)
C80.1749 (4)0.3738 (3)1.15994 (17)0.0560 (6)
H8A0.36760.35701.16080.067*
H8B0.17340.46991.15290.067*
C90.0814 (5)0.3293 (2)1.26929 (17)0.0545 (6)
H9A−0.11280.34421.26770.065*
H9B0.08720.23361.27720.065*
C100.2680 (4)0.4050 (2)1.36885 (16)0.0481 (5)
C110.2885 (4)0.3245 (2)0.77306 (18)0.0518 (5)
H11A0.45810.28880.76550.062*
H11B0.32180.37970.84090.062*
H11C0.23610.37780.70880.062*
C12−0.0018 (6)0.1712 (3)0.56799 (19)0.0684 (7)
H12A0.19520.16440.57090.082*
H12B−0.03290.26150.55000.082*
H12C−0.11440.10960.51090.082*
N10.1111 (3)0.24747 (17)0.98335 (13)0.0432 (5)
H1N0.295 (6)0.262 (2)0.998 (2)0.052*
O1−0.2754 (3)0.2922 (2)1.05008 (14)0.0823 (7)
O20.4948 (4)0.3603 (2)1.40631 (16)0.0769 (6)
H2O0.538 (7)0.397 (3)1.472 (3)0.092*
O30.2004 (4)0.50537 (19)1.40937 (15)0.0762 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0239 (9)0.0495 (10)0.0406 (9)0.0034 (7)−0.0001 (7)−0.0042 (7)
C20.0310 (10)0.0455 (10)0.0418 (10)0.0092 (7)0.0022 (7)−0.0021 (7)
C30.0462 (12)0.0536 (11)0.0440 (11)0.0177 (9)−0.0027 (8)−0.0079 (8)
C40.0548 (14)0.0571 (12)0.0587 (13)0.0069 (10)−0.0133 (10)−0.0185 (10)
C50.0453 (13)0.0560 (12)0.0837 (16)−0.0122 (10)−0.0043 (11)−0.0092 (11)
C60.0394 (11)0.0598 (12)0.0556 (12)−0.0062 (9)0.0045 (9)0.0024 (9)
C70.0230 (9)0.0834 (14)0.0413 (10)0.0000 (8)0.0041 (7)−0.0105 (9)
C80.0285 (10)0.0906 (16)0.0439 (11)−0.0054 (9)0.0051 (8)−0.0160 (10)
C90.0400 (11)0.0723 (14)0.0469 (11)−0.0019 (9)0.0045 (8)−0.0115 (9)
C100.0388 (11)0.0676 (13)0.0375 (10)0.0039 (9)0.0089 (8)−0.0060 (9)
C110.0449 (12)0.0574 (12)0.0525 (11)0.0008 (9)0.0124 (9)0.0030 (9)
C120.0806 (18)0.0824 (16)0.0441 (12)0.0265 (13)0.0034 (11)−0.0066 (10)
N10.0196 (8)0.0677 (11)0.0391 (8)−0.0010 (7)0.0026 (6)−0.0072 (7)
O10.0220 (8)0.1555 (19)0.0645 (10)0.0054 (9)0.0015 (7)−0.0449 (11)
O20.0544 (11)0.1007 (14)0.0710 (11)0.0252 (9)−0.0140 (8)−0.0343 (10)
O30.0715 (12)0.0869 (12)0.0660 (11)0.0300 (10)−0.0155 (9)−0.0277 (9)
Geometric parameters (Å, º) top
C1—C61.387 (3)C8—H8A0.9700
C1—C21.394 (3)C8—H8B0.9700
C1—N11.425 (2)C9—C101.499 (3)
C2—C31.402 (3)C9—H9A0.9700
C2—C111.498 (3)C9—H9B0.9700
C3—C41.385 (3)C10—O31.227 (3)
C3—C121.507 (3)C10—O21.261 (3)
C4—C51.376 (4)C11—H11A0.9600
C4—H40.9300C11—H11B0.9600
C5—C61.384 (3)C11—H11C0.9600
C5—H50.9300C12—H12A0.9600
C6—H60.9300C12—H12B0.9600
C7—O11.227 (2)C12—H12C0.9600
C7—N11.334 (3)N1—H1N0.87 (3)
C7—C81.508 (3)O2—H2O0.85 (3)
C8—C91.505 (3)
C6—C1—C2121.34 (18)H8A—C8—H8B108.0
C6—C1—N1119.13 (17)C10—C9—C8111.26 (17)
C2—C1—N1119.52 (16)C10—C9—H9A109.4
C1—C2—C3118.49 (18)C8—C9—H9A109.4
C1—C2—C11121.03 (16)C10—C9—H9B109.4
C3—C2—C11120.48 (17)C8—C9—H9B109.4
C4—C3—C2119.54 (19)H9A—C9—H9B108.0
C4—C3—C12119.9 (2)O3—C10—O2123.04 (19)
C2—C3—C12120.5 (2)O3—C10—C9120.7 (2)
C5—C4—C3121.38 (19)O2—C10—C9116.29 (19)
C5—C4—H4119.3C2—C11—H11A109.5
C3—C4—H4119.3C2—C11—H11B109.5
C4—C5—C6119.8 (2)H11A—C11—H11B109.5
C4—C5—H5120.1C2—C11—H11C109.5
C6—C5—H5120.1H11A—C11—H11C109.5
C5—C6—C1119.5 (2)H11B—C11—H11C109.5
C5—C6—H6120.3C3—C12—H12A109.5
C1—C6—H6120.3C3—C12—H12B109.5
O1—C7—N1123.30 (18)H12A—C12—H12B109.5
O1—C7—C8120.46 (18)C3—C12—H12C109.5
N1—C7—C8116.23 (16)H12A—C12—H12C109.5
C9—C8—C7111.27 (17)H12B—C12—H12C109.5
C9—C8—H8A109.4C7—N1—C1125.13 (16)
C7—C8—H8A109.4C7—N1—H1N115.0 (16)
C9—C8—H8B109.4C1—N1—H1N119.8 (16)
C7—C8—H8B109.4C10—O2—H2O101 (2)
C6—C1—C2—C30.1 (3)C2—C1—C6—C5−1.0 (3)
N1—C1—C2—C3178.85 (16)N1—C1—C6—C5−179.77 (19)
C6—C1—C2—C11−179.43 (19)O1—C7—C8—C949.2 (3)
N1—C1—C2—C11−0.7 (3)N1—C7—C8—C9−131.8 (2)
C1—C2—C3—C40.4 (3)C7—C8—C9—C10−178.67 (19)
C11—C2—C3—C4180.00 (19)C8—C9—C10—O395.5 (3)
C1—C2—C3—C12−179.90 (18)C8—C9—C10—O2−83.7 (3)
C11—C2—C3—C12−0.4 (3)O1—C7—N1—C1−0.3 (4)
C2—C3—C4—C5−0.1 (3)C8—C7—N1—C1−179.29 (19)
C12—C3—C4—C5−179.7 (2)C6—C1—N1—C7−51.1 (3)
C3—C4—C5—C6−0.8 (4)C2—C1—N1—C7130.1 (2)
C4—C5—C6—C11.4 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.87 (3)2.04 (3)2.909 (2)174 (2)
O2—H2O···O3ii0.85 (3)1.90 (4)2.679 (2)152 (3)
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z+3.

Experimental details

Crystal data
Chemical formulaC12H15NO3
Mr221.25
Crystal system, space groupTriclinic, P1
Temperature (K)299
a, b, c (Å)4.8379 (4), 10.0424 (6), 11.9876 (8)
α, β, γ (°)90.222 (6), 99.614 (7), 98.506 (6)
V (Å3)567.67 (7)
Z2
Radiation typeCu Kα
µ (mm−1)0.77
Crystal size (mm)0.40 × 0.25 × 0.10
Data collection
DiffractometerEnraf–Nonius CAD-4
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		3962, 2017, 1751
Rint0.035
(sin θ/λ)max (Å−1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.064, 0.183, 1.11
No. of reflections2017
No. of parameters154
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.42, −0.31

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···O1i0.87 (3)2.04 (3)2.909 (2)174 (2)
O2—H2O···O3ii0.85 (3)1.90 (4)2.679 (2)152 (3)
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z+3.
 

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

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ISSN: 2056-9890
Volume 67| Part 1| January 2011| Page o236
https://doi.org/10.1107/S160053681005292X
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