N-(2-Methyl­phen­yl)succinamic acid

Gowda, B.T.; Foro, S.; Saraswathi, B.S.; Fuess, H.

doi:10.1107/S1600536810010329

organic compounds

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Volume 66| Part 4| April 2010| Page o908

doi:10.1107/S1600536810010329

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N-(2-Methylphenyl)succinamic acid

B. Thimme Gowda,^a ^* Sabine Foro,^b B. S. Saraswathi ^a and Hartmut Fuess ^b

^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 20 February 2010; accepted 19 March 2010; online 24 March 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 syn to the ortho-methyl group in the benzene ring. In the crystal, O—H⋯O interactions lead to carboxylic acid inversion dimers and intermolecular N—H⋯O hydrogen bonds link the molecules into infinite chains. In addition, the crystal structure exhibits intermolecular C—H⋯π interactions between one of the methyl H atoms and the benzene ring of neighbouring molecules.

Related literature

For our study of the effect of ring and side-chain substitutions on the crystal structures of anilides and for related structures, see: Gowda et al. (2007 ; 2009 ; 2010 ); Jagannathan et al. (1994 ). For the modes of interlinking carboxylic acids by hydrogen bonds, see: Leiserowitz (1976 ).

Experimental

Crystal data

C₁₁H₁₃NO₃
M_r = 207.22
Triclinic, $[P \overline 1]$
a = 4.7756 (9) Å
b = 6.1854 (9) Å
c = 18.275 (3) Å
α = 86.20 (2)°
β = 83.02 (1)°
γ = 88.45 (2)°
V = 534.55 (15) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 299 K
0.40 × 0.12 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.963, T_max = 0.994
2928 measured reflections
1873 independent reflections
1426 reflections with I > 2σ(I)
R_int = 0.010

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.149
S = 1.10
1873 reflections
143 parameters
13 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.81 (4)	2.13 (4)	2.922 (3)	164 (3)
O3—H3O⋯O2ⁱⁱ	0.85 (2)	1.82 (2)	2.664 (3)	173 (5)
C11—H11A⋯Cgⁱⁱⁱ	0.96	2.81	3.596 (4)	139
Symmetry codes: (i) x-1, y, z; (ii) -x, -y+2, -z+1; (iii) x, 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 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810010329/lx2138sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810010329/lx2138Isup2.hkl

checkCIF report

Comment top

As a part of studying the effect of ring and side chain substitutions on the crystal structures of anilides (Gowda et al., 2007; 2009; 2010), the crystal structure of N-(2-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-(2-chlorophenyl)succinamic acid (II) (Gowda et al., 2009), but contrary to the syn conformation observed in N-(3-methylphenyl)succinamic acid (III) (Gowda et al., 2010). 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 syn to the ortho- methyl group in the benzene ring, similar to that observed between the amide hydrogen and the ortho-Cl 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). Additionally, the crystal packing (Fig. 2) is further stabilized by intermolecular C—H···π interactions between the methyl H atom and the benzene ring of neighbouring molecules, with a C11—H11A···Cgⁱⁱⁱ (Table 1; Cg is the centroid of the C1–C6 benzene ring). 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 study of the effect of ring and side-chain substitutions on the

crystal structures of anilides and for related structures, see: Gowda et al. (2007; 2009; 2010); Jagannathan et al. (1994). For the modes of interlinking carboxylic acids by hydrogen bonds, see: Leiserowitz (1976).

Experimental top

The solution of succinic anhydride (0.01 mole) in toluene (25 ml) was treated dropwise with the solution of o-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 o-toluidine. The resultant solid N-(2-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 needle like colorless single crystals used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation at room temperature.

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) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	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.
	Fig. 2. O—H···O, N—H···O and C—H···π interactions (dotted lines) in the crystal structure of the title compound. Cg denotes the ring centroid. [Symmetry codes : (i) x - 1, y, z; (ii) - x, - y + 2, - z + 1; (iii) x, y + 1, z; (iv) x + 1, y, z; (v) x, y - 1, z.]

N-(2-Methylphenyl)succinamic acid top

Crystal data top

C₁₁H₁₃NO₃	Z = 2
M_r = 207.22	F(000) = 220
Triclinic, P1	D_x = 1.287 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.7756 (9) Å	Cell parameters from 1326 reflections
b = 6.1854 (9) Å	θ = 3.3–27.7°
c = 18.275 (3) Å	µ = 0.09 mm⁻¹
α = 86.20 (2)°	T = 299 K
β = 83.02 (1)°	Needle, colourless
γ = 88.45 (2)°	0.40 × 0.12 × 0.06 mm
V = 534.55 (15) Å³

Data collection top

Oxford Diffraction Xcalibur diffractometer	1873 independent reflections
Radiation source: fine-focus sealed tube	1426 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.010
Detector resolution: 10.0 pixels mm^-1	θ_max = 25.0°, θ_min = 3.3°
ϕ and ω scans	h = −5→4
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −7→7
T_min = 0.963, T_max = 0.994	l = −21→21
2928 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.060	Hydrogen site location: difference Fourier map
wR(F²) = 0.149	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.0463P)² + 0.4371P] where P = (F_o² + 2F_c²)/3
1873 reflections	(Δ/σ)_max < 0.001
143 parameters	Δρ_max = 0.33 e Å⁻³
13 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₁H₁₃NO₃	γ = 88.45 (2)°
M_r = 207.22	V = 534.55 (15) Å³
Triclinic, P1	Z = 2
a = 4.7756 (9) Å	Mo Kα radiation
b = 6.1854 (9) Å	µ = 0.09 mm⁻¹
c = 18.275 (3) Å	T = 299 K
α = 86.20 (2)°	0.40 × 0.12 × 0.06 mm
β = 83.02 (1)°

Data collection top

Oxford Diffraction Xcalibur diffractometer	1873 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	1426 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.994	R_int = 0.010
2928 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	13 restraints
wR(F²) = 0.149	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.33 e Å⁻³
1873 reflections	Δρ_min = −0.31 e Å⁻³
143 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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

	x	y	z	U_iso*/U_eq
C1	0.0519 (5)	−0.0093 (4)	0.80080 (16)	0.0415 (7)
C2	−0.0898 (6)	−0.0197 (5)	0.87207 (16)	0.0445 (7)
C3	−0.0147 (7)	−0.1877 (5)	0.92098 (19)	0.0577 (9)
H3	−0.1085	−0.1994	0.9687	0.069*
C4	0.1940 (8)	−0.3363 (5)	0.9006 (2)	0.0685 (10)
H4	0.2402	−0.4465	0.9344	0.082*
C5	0.3342 (8)	−0.3227 (5)	0.8307 (2)	0.0648 (10)
H5	0.4767	−0.4227	0.8170	0.078*
C6	0.2631 (7)	−0.1594 (5)	0.78027 (19)	0.0538 (8)
H6	0.3572	−0.1504	0.7326	0.065*
C7	0.1616 (5)	0.2852 (5)	0.70612 (15)	0.0424 (7)
C8	0.0310 (5)	0.4576 (5)	0.65761 (16)	0.0476 (8)
H8A	−0.1193	0.3942	0.6354	0.057*
H8B	−0.0521	0.5710	0.6880	0.057*
C9	0.2412 (6)	0.5563 (5)	0.59738 (17)	0.0504 (8)
H9A	0.4044	0.6001	0.6192	0.060*
H9B	0.3040	0.4467	0.5632	0.060*
C10	0.1294 (6)	0.7472 (5)	0.55537 (16)	0.0474 (8)
C11	−0.3113 (7)	0.1471 (6)	0.89617 (19)	0.0583 (9)
H11A	−0.2352	0.2894	0.8858	0.087*
H11B	−0.3683	0.1241	0.9483	0.087*
H11C	−0.4716	0.1340	0.8699	0.087*
N1	−0.0225 (5)	0.1572 (4)	0.74871 (14)	0.0440 (6)
H1N	−0.189 (7)	0.181 (6)	0.7458 (19)	0.066*
O1	0.4164 (4)	0.2708 (4)	0.70798 (13)	0.0665 (8)
O2	−0.0821 (6)	0.8479 (5)	0.57850 (15)	0.0915 (10)
O3	0.2743 (7)	0.8021 (5)	0.49406 (15)	0.0937 (10)
H3O	0.201 (10)	0.914 (6)	0.474 (3)	0.141*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0352 (14)	0.0405 (15)	0.0501 (17)	−0.0014 (12)	−0.0162 (12)	0.0080 (13)
C2	0.0374 (15)	0.0466 (17)	0.0493 (17)	−0.0046 (12)	−0.0111 (13)	0.0108 (14)
C3	0.0569 (19)	0.056 (2)	0.058 (2)	−0.0059 (16)	−0.0119 (15)	0.0210 (16)
C4	0.078 (2)	0.0465 (19)	0.081 (3)	0.0029 (18)	−0.028 (2)	0.0240 (18)
C5	0.068 (2)	0.0458 (19)	0.082 (3)	0.0179 (16)	−0.0214 (19)	0.0020 (18)
C6	0.0546 (18)	0.0494 (18)	0.059 (2)	0.0056 (15)	−0.0137 (15)	−0.0010 (15)
C7	0.0285 (13)	0.0535 (17)	0.0441 (16)	0.0032 (12)	−0.0069 (11)	0.0090 (13)
C8	0.0322 (14)	0.0579 (19)	0.0505 (18)	0.0028 (13)	−0.0069 (12)	0.0156 (15)
C9	0.0401 (15)	0.0571 (19)	0.0502 (18)	0.0089 (14)	−0.0007 (13)	0.0130 (15)
C10	0.0388 (15)	0.0537 (18)	0.0463 (17)	0.0047 (14)	−0.0009 (13)	0.0122 (14)
C11	0.0491 (18)	0.066 (2)	0.056 (2)	0.0067 (16)	−0.0015 (15)	0.0094 (16)
N1	0.0280 (11)	0.0517 (15)	0.0509 (14)	0.0021 (11)	−0.0099 (10)	0.0143 (11)
O1	0.0273 (10)	0.0858 (17)	0.0817 (17)	0.0013 (10)	−0.0105 (10)	0.0374 (13)
O2	0.0759 (17)	0.0922 (19)	0.0891 (19)	0.0379 (15)	0.0237 (14)	0.0444 (15)
O3	0.102 (2)	0.0900 (19)	0.0713 (17)	0.0412 (16)	0.0292 (15)	0.0383 (14)

Geometric parameters (Å, º) top

C1—C6	1.387 (4)	C7—C8	1.512 (4)
C1—C2	1.391 (4)	C8—C9	1.506 (4)
C1—N1	1.423 (3)	C8—H8A	0.9700
C2—C3	1.393 (4)	C8—H8B	0.9700
C2—C11	1.505 (4)	C9—C10	1.488 (4)
C3—C4	1.372 (5)	C9—H9A	0.9700
C3—H3	0.9300	C9—H9B	0.9700
C4—C5	1.367 (5)	C10—O2	1.218 (4)
C4—H4	0.9300	C10—O3	1.274 (4)
C5—C6	1.385 (5)	C11—H11A	0.9600
C5—H5	0.9300	C11—H11B	0.9600
C6—H6	0.9300	C11—H11C	0.9600
C7—O1	1.222 (3)	N1—H1N	0.81 (4)
C7—N1	1.340 (4)	O3—H3O	0.85 (2)

C6—C1—C2	120.7 (3)	C7—C8—H8A	109.0
C6—C1—N1	120.0 (3)	C9—C8—H8B	109.0
C2—C1—N1	119.3 (3)	C7—C8—H8B	109.0
C1—C2—C3	117.5 (3)	H8A—C8—H8B	107.8
C1—C2—C11	121.4 (2)	C10—C9—C8	114.1 (2)
C3—C2—C11	121.1 (3)	C10—C9—H9A	108.7
C4—C3—C2	121.7 (3)	C8—C9—H9A	108.7
C4—C3—H3	119.1	C10—C9—H9B	108.7
C2—C3—H3	119.1	C8—C9—H9B	108.7
C5—C4—C3	120.2 (3)	H9A—C9—H9B	107.6
C5—C4—H4	119.9	O2—C10—O3	122.0 (3)
C3—C4—H4	119.9	O2—C10—C9	122.6 (3)
C4—C5—C6	119.7 (3)	O3—C10—C9	115.4 (3)
C4—C5—H5	120.1	C2—C11—H11A	109.5
C6—C5—H5	120.1	C2—C11—H11B	109.5
C5—C6—C1	120.1 (3)	H11A—C11—H11B	109.5
C5—C6—H6	119.9	C2—C11—H11C	109.5
C1—C6—H6	119.9	H11A—C11—H11C	109.5
O1—C7—N1	123.0 (2)	H11B—C11—H11C	109.5
O1—C7—C8	121.8 (2)	C7—N1—C1	124.8 (2)
N1—C7—C8	115.1 (2)	C7—N1—H1N	117 (3)
C9—C8—C7	112.8 (2)	C1—N1—H1N	118 (3)
C9—C8—H8A	109.0	C10—O3—H3O	110 (4)

C6—C1—C2—C3	−1.1 (4)	N1—C1—C6—C5	−179.4 (3)
N1—C1—C2—C3	178.7 (3)	O1—C7—C8—C9	17.9 (5)
C6—C1—C2—C11	177.5 (3)	N1—C7—C8—C9	−164.8 (3)
N1—C1—C2—C11	−2.7 (4)	C7—C8—C9—C10	−171.8 (3)
C1—C2—C3—C4	1.0 (5)	C8—C9—C10—O2	17.7 (5)
C11—C2—C3—C4	−177.6 (3)	C8—C9—C10—O3	−164.0 (3)
C2—C3—C4—C5	−0.2 (5)	O1—C7—N1—C1	0.0 (5)
C3—C4—C5—C6	−0.6 (6)	C8—C7—N1—C1	−177.2 (3)
C4—C5—C6—C1	0.5 (5)	C6—C1—N1—C7	−48.9 (4)
C2—C1—C6—C5	0.4 (5)	C2—C1—N1—C7	131.2 (3)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.81 (4)	2.13 (4)	2.922 (3)	164 (3)
O3—H3O···O2ⁱⁱ	0.85 (2)	1.82 (2)	2.664 (3)	173 (5)
C11—H11A···Cgⁱⁱⁱ	0.96	2.81	3.596 (4)	139

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

Experimental details

Crystal data
Chemical formula	C₁₁H₁₃NO₃
M_r	207.22
Crystal system, space group	Triclinic, P1
Temperature (K)	299
a, b, c (Å)	4.7756 (9), 6.1854 (9), 18.275 (3)
α, β, γ (°)	86.20 (2), 83.02 (1), 88.45 (2)
V (Å³)	534.55 (15)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.40 × 0.12 × 0.06

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.963, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	2928, 1873, 1426
R_int	0.010
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.149, 1.10
No. of reflections	1873
No. of parameters	143
No. of restraints	13
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.31

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.81 (4)	2.13 (4)	2.922 (3)	164 (3)
O3—H3O···O2ⁱⁱ	0.85 (2)	1.82 (2)	2.664 (3)	173 (5)
C11—H11A···Cgⁱⁱⁱ	0.96	2.81	3.596 (4)	139.2

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

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COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o908

doi:10.1107/S1600536810010329

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access