N-(3-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 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 -CH(2) groups. The C=O and O-H bonds of the acid group are syn to each other. In the crystal, the mol-ecules are packed into infinite chains through inter-molecular 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 ▶; 2009 ▶). 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

Crystal data

C11H13NO3

M = 207.22

Orthorhombic,

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 ▶) T min = 0.961, T max = 0.980

9274 measured reflections

2228 independent reflections

1772 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 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

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 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810001480/bq2189sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810001480/bq2189Isup2.hkl

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

C11H13NO3	F(000) = 880
Mr = 207.22	Dx = 1.262 Mg m−3
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 4700 reflections
a = 12.0661 (8) Å	θ = 2.5–27.8°
b = 20.220 (1) Å	µ = 0.09 mm−1
c = 8.9398 (5) Å	T = 299 K
V = 2181.1 (2) Å3	Rod, colourless
Z = 8	0.44 × 0.34 × 0.22 mm

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2228 independent reflections
Radiation source: fine-focus sealed tube	1772 reflections with I > 2σ(I)
graphite	Rint = 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 = −15→13
Tmin = 0.961, Tmax = 0.980	k = −25→25
9274 measured reflections	l = −9→11

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H 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 parameters	Δρmax = 0.18 e Å−3
1 restraint	Δρmin = −0.21 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	0.60319 (12)	0.30046 (6)	0.00527 (12)	0.0586 (4)
O2	0.51371 (10)	0.44029 (6)	−0.12328 (15)	0.0604 (4)
O3	0.64575 (11)	0.48088 (7)	0.02306 (17)	0.0681 (4)
H3O	0.5948 (14)	0.5046 (10)	0.056 (3)	0.082*
N1	0.55127 (12)	0.24064 (6)	−0.19678 (14)	0.0449 (3)
H1N	0.5651 (14)	0.2366 (9)	−0.291 (2)	0.054*
C1	0.49463 (12)	0.18766 (7)	−0.12564 (16)	0.0398 (4)
C2	0.42443 (13)	0.19787 (8)	−0.00544 (18)	0.0456 (4)
H2	0.4131 (14)	0.2440 (10)	0.0343 (19)	0.055*
C3	0.37093 (14)	0.14509 (9)	0.0632 (2)	0.0541 (4)
C4	0.38770 (17)	0.08225 (9)	0.0064 (2)	0.0617 (5)
H4	0.3523 (18)	0.0467 (10)	0.052 (2)	0.074*
C5	0.45474 (17)	0.07211 (9)	−0.1154 (2)	0.0627 (5)
H5	0.4654 (17)	0.0287 (11)	−0.156 (2)	0.075*
C6	0.50913 (15)	0.12444 (8)	−0.1827 (2)	0.0505 (4)
H6	0.5552 (15)	0.1191 (9)	−0.270 (2)	0.061*
C7	0.60056 (13)	0.29228 (7)	−0.13003 (16)	0.0401 (4)
C8	0.65448 (16)	0.34114 (8)	−0.23546 (18)	0.0470 (4)
H8A	0.5993 (15)	0.3536 (8)	−0.311 (2)	0.056*
H8B	0.7113 (15)	0.3183 (8)	−0.285 (2)	0.056*
C9	0.69866 (15)	0.40119 (9)	−0.1542 (2)	0.0514 (4)
H9A	0.7504 (17)	0.3894 (9)	−0.078 (2)	0.062*
H9B	0.7338 (16)	0.4291 (9)	−0.223 (2)	0.062*
C10	0.61046 (13)	0.44199 (7)	−0.08284 (18)	0.0449 (4)
C11	0.2978 (2)	0.15574 (12)	0.1975 (3)	0.0901 (8)
H11A	0.2219	0.1582	0.1660	0.108*
H11B	0.3183	0.1962	0.2462	0.108*
H11C	0.3067	0.1195	0.2658	0.108*

	U11	U22	U33	U12	U13	U23
O1	0.0916 (10)	0.0551 (7)	0.0292 (6)	−0.0188 (6)	0.0069 (6)	−0.0009 (5)
O2	0.0537 (7)	0.0579 (7)	0.0698 (8)	0.0037 (6)	−0.0091 (6)	−0.0140 (6)
O3	0.0554 (8)	0.0659 (8)	0.0831 (10)	0.0010 (6)	−0.0092 (7)	−0.0255 (7)
N1	0.0613 (8)	0.0467 (7)	0.0267 (6)	−0.0016 (6)	0.0071 (6)	−0.0018 (5)
C1	0.0431 (8)	0.0422 (8)	0.0342 (7)	0.0017 (6)	−0.0055 (6)	0.0014 (6)
C2	0.0459 (9)	0.0474 (8)	0.0436 (9)	0.0020 (7)	0.0020 (7)	0.0015 (7)
C3	0.0424 (9)	0.0623 (10)	0.0577 (10)	−0.0037 (7)	0.0012 (8)	0.0128 (8)
C4	0.0574 (11)	0.0524 (10)	0.0752 (13)	−0.0111 (8)	−0.0087 (10)	0.0160 (9)
C5	0.0740 (13)	0.0417 (9)	0.0724 (13)	−0.0008 (8)	−0.0147 (11)	−0.0031 (8)
C6	0.0569 (10)	0.0483 (9)	0.0463 (9)	0.0059 (7)	−0.0047 (8)	−0.0042 (7)
C7	0.0499 (9)	0.0410 (7)	0.0294 (7)	0.0048 (6)	0.0062 (6)	0.0010 (6)
C8	0.0560 (10)	0.0482 (9)	0.0367 (8)	0.0014 (7)	0.0130 (8)	0.0038 (7)
C9	0.0490 (9)	0.0527 (9)	0.0525 (10)	−0.0063 (8)	0.0105 (8)	0.0061 (8)
C10	0.0493 (9)	0.0380 (7)	0.0473 (9)	−0.0073 (6)	−0.0001 (7)	0.0057 (6)
C11	0.0777 (14)	0.0925 (16)	0.0999 (18)	−0.0039 (12)	0.0402 (13)	0.0214 (14)

O1—C7	1.2212 (17)	C4—H4	0.93 (2)
O2—C10	1.2226 (19)	C5—C6	1.383 (3)
O3—C10	1.302 (2)	C5—H5	0.96 (2)
O3—H3O	0.832 (10)	C6—H6	0.96 (2)
N1—C7	1.3416 (19)	C7—C8	1.513 (2)
N1—C1	1.4210 (19)	C8—C9	1.512 (2)
N1—H1N	0.863 (19)	C8—H8A	0.983 (19)
C1—C2	1.384 (2)	C8—H8B	0.940 (19)
C1—C6	1.387 (2)	C9—C10	1.490 (2)
C2—C3	1.390 (2)	C9—H9A	0.95 (2)
C2—H2	1.008 (19)	C9—H9B	0.94 (2)
C3—C4	1.383 (3)	C11—H11A	0.9600
C3—C11	1.505 (3)	C11—H11B	0.9600
C4—C5	1.372 (3)	C11—H11C	0.9600
C10—O3—H3O	111.1 (16)	O1—C7—C8	121.17 (14)
C7—N1—C1	126.93 (12)	N1—C7—C8	114.95 (13)
C7—N1—H1N	115.0 (12)	C9—C8—C7	112.13 (13)
C1—N1—H1N	117.2 (12)	C9—C8—H8A	111.4 (10)
C2—C1—C6	120.02 (15)	C7—C8—H8A	107.8 (10)
C2—C1—N1	121.97 (13)	C9—C8—H8B	111.4 (11)
C6—C1—N1	117.99 (14)	C7—C8—H8B	106.8 (11)
C1—C2—C3	120.83 (15)	H8A—C8—H8B	107.1 (15)
C1—C2—H2	119.6 (10)	C10—C9—C8	113.49 (15)
C3—C2—H2	119.5 (10)	C10—C9—H9A	107.6 (12)
C4—C3—C2	118.37 (17)	C8—C9—H9A	111.9 (11)
C4—C3—C11	120.66 (17)	C10—C9—H9B	105.8 (11)
C2—C3—C11	120.96 (18)	C8—C9—H9B	109.0 (11)
C5—C4—C3	121.00 (17)	H9A—C9—H9B	108.8 (16)
C5—C4—H4	120.2 (13)	O2—C10—O3	122.97 (15)
C3—C4—H4	118.8 (13)	O2—C10—C9	122.68 (15)
C4—C5—C6	120.73 (17)	O3—C10—C9	114.33 (15)
C4—C5—H5	120.9 (13)	C3—C11—H11A	109.5
C6—C5—H5	118.4 (13)	C3—C11—H11B	109.5
C5—C6—C1	119.01 (17)	H11A—C11—H11B	109.5
C5—C6—H6	122.7 (11)	C3—C11—H11C	109.5
C1—C6—H6	118.2 (11)	H11A—C11—H11C	109.5
O1—C7—N1	123.88 (14)	H11B—C11—H11C	109.5
C7—N1—C1—C2	41.4 (2)	C2—C1—C6—C5	−1.6 (2)
C7—N1—C1—C6	−140.25 (16)	N1—C1—C6—C5	−179.93 (15)
C6—C1—C2—C3	2.4 (2)	C1—N1—C7—O1	0.1 (3)
N1—C1—C2—C3	−179.29 (14)	C1—N1—C7—C8	−179.98 (14)
C1—C2—C3—C4	−1.4 (3)	O1—C7—C8—C9	−5.6 (2)
C1—C2—C3—C11	177.74 (18)	N1—C7—C8—C9	174.51 (14)
C2—C3—C4—C5	−0.5 (3)	C7—C8—C9—C10	−64.8 (2)
C11—C3—C4—C5	−179.61 (19)	C8—C9—C10—O2	−21.9 (2)
C3—C4—C5—C6	1.3 (3)	C8—C9—C10—O3	160.00 (15)
C4—C5—C6—C1	−0.3 (3)

D—H···A	D—H	H···A	D···A	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)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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) ; (ii) .