N-(2-Methyl-phen-yl)succinamic acid.

In the crystal structure of the title compound, C(11)H(13)NO(3), 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 inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into infinite chains. In addition, the crystal structure exhibits inter-molecular C-H⋯π inter-actions between one of the methyl H atoms and the benzene ring of neighbouring mol-ecules.

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 = 207.22

Triclinic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.149

S = 1.10

1873 reflections

143 parameters

13 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.31 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); 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.

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

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

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

C11H13NO3	Z = 2
Mr = 207.22	F(000) = 220
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0463P)2 + 0.4371P] where P = (Fo2 + 2Fc2)/3
1873 reflections	(Δ/σ)max < 0.001
143 parameters	Δρmax = 0.33 e Å−3
13 restraints	Δρmin = −0.31 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) ; (iii) .