N-(4-Methyl-phen-yl)succinamic acid.

In 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. Further, the conformations of the amide and carbonyl O atoms 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, mol-ecules are packed into infinite chains along the b axis through inter-molecular N-H⋯O and O-H⋯O hydrogen bonds.

Related literature

For background to our study of the effect of ring and side-chain substitution on the solid state geometry of anilides, see: Gowda et al. (2009 ▶, 2010a ▶,b ▶). For 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

Crystal data

C11H13NO3

M = 207.22

Triclinic,

a = 4.960 (1) Å

b = 8.090 (2) Å

c = 13.893 (2) Å

α = 83.52 (2)°

β = 80.08 (2)°

γ = 78.15 (1)°

V = 535.70 (19) Å3

Z = 2

Cu Kα radiation

μ = 0.78 mm−1

T = 299 K

0.55 × 0.25 × 0.08 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.674, T max = 0.940

2515 measured reflections

1888 independent reflections

1533 reflections with I > 2σ(I)

R int = 0.024

3 standard reflections every 120 min intensity decay: 1.0%

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.194

S = 1.06

1888 reflections

143 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.33 e Å−3

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ▶); cell refinement: CAD-4-PC; 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810053298/ds2081sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810053298/ds2081Isup2.hkl

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

C11H13NO3	Z = 2
Mr = 207.22	F(000) = 220
Triclinic, P1	Dx = 1.285 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54180 Å
a = 4.960 (1) Å	Cell parameters from 25 reflections
b = 8.090 (2) Å	θ = 6.3–21.3°
c = 13.893 (2) Å	µ = 0.78 mm−1
α = 83.52 (2)°	T = 299 K
β = 80.08 (2)°	Plate, colourless
γ = 78.15 (1)°	0.55 × 0.25 × 0.08 mm
V = 535.70 (19) Å3

Enraf–Nonius CAD-4 diffractometer	1533 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
graphite	θmax = 66.8°, θmin = 3.2°
ω scans	h = −1→5
Absorption correction: ψ scan (North et al., 1968)	k = −9→9
Tmin = 0.674, Tmax = 0.940	l = −16→16
2515 measured reflections	3 standard reflections every 120 min
1888 independent reflections	intensity decay: 1.0%

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.194	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.1156P)2 + 0.1448P] where P = (Fo2 + 2Fc2)/3
1888 reflections	(Δ/σ)max = 0.017
143 parameters	Δρmax = 0.24 e Å−3
2 restraints	Δρmin = −0.33 e Å−3

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
C1	0.0934 (5)	0.7741 (3)	−0.07532 (16)	0.0507 (5)
C2	−0.1340 (6)	0.8882 (3)	−0.10364 (19)	0.0650 (6)
H2	−0.2788	0.9345	−0.0567	0.078*
C3	−0.1439 (7)	0.9328 (4)	−0.2025 (2)	0.0786 (8)
H3	−0.2988	1.0075	−0.2211	0.094*
C4	0.0703 (7)	0.8692 (4)	−0.27428 (19)	0.0761 (8)
C5	0.2991 (7)	0.7575 (4)	−0.2444 (2)	0.0802 (8)
H5	0.4466	0.7135	−0.2912	0.096*
C6	0.3100 (6)	0.7110 (3)	−0.14645 (19)	0.0677 (7)
H6	0.4650	0.6363	−0.1279	0.081*
C7	−0.0863 (4)	0.6981 (3)	0.09714 (16)	0.0538 (6)
C8	0.0133 (5)	0.6313 (3)	0.19407 (17)	0.0603 (6)
H8A	0.0707	0.5091	0.1952	0.072*
H8B	0.1748	0.6782	0.1992	0.072*
C9	−0.2087 (5)	0.6752 (3)	0.28162 (17)	0.0603 (6)
H9A	−0.2574	0.7974	0.2830	0.072*
H9B	−0.3747	0.6347	0.2745	0.072*
C10	−0.1152 (5)	0.5994 (3)	0.37648 (17)	0.0588 (6)
C11	0.0523 (11)	0.9182 (6)	−0.3816 (2)	0.1183 (15)
H11A	0.0186	1.0394	−0.3932	0.142*
H11B	−0.0976	0.8753	−0.3993	0.142*
H11C	0.2245	0.8709	−0.4206	0.142*
N1	0.1202 (4)	0.7230 (2)	0.02421 (14)	0.0533 (5)
H1N	0.278 (4)	0.719 (3)	0.0386 (19)	0.064*
O1	−0.3349 (3)	0.7206 (3)	0.08761 (13)	0.0727 (6)
O2	0.1144 (4)	0.5108 (3)	0.38248 (14)	0.0853 (7)
O3	−0.3025 (4)	0.6364 (3)	0.45282 (14)	0.0935 (8)
H3O	−0.231 (8)	0.598 (5)	0.504 (2)	0.112*

	U11	U22	U33	U12	U13	U23
C1	0.0523 (12)	0.0537 (11)	0.0487 (11)	−0.0180 (9)	−0.0068 (9)	−0.0023 (9)
C2	0.0656 (15)	0.0657 (14)	0.0593 (14)	−0.0061 (11)	−0.0098 (11)	0.0021 (11)
C3	0.088 (2)	0.0785 (17)	0.0699 (18)	−0.0168 (14)	−0.0264 (15)	0.0148 (13)
C4	0.111 (2)	0.0768 (17)	0.0508 (14)	−0.0433 (16)	−0.0182 (14)	0.0068 (12)
C5	0.103 (2)	0.0806 (17)	0.0537 (15)	−0.0238 (16)	0.0073 (14)	−0.0088 (13)
C6	0.0662 (15)	0.0722 (15)	0.0590 (14)	−0.0096 (12)	0.0006 (11)	−0.0032 (11)
C7	0.0464 (12)	0.0669 (13)	0.0505 (12)	−0.0183 (10)	−0.0089 (9)	0.0014 (9)
C8	0.0447 (12)	0.0842 (16)	0.0522 (13)	−0.0163 (10)	−0.0102 (10)	0.0061 (11)
C9	0.0529 (13)	0.0755 (15)	0.0514 (13)	−0.0124 (11)	−0.0098 (10)	0.0031 (10)
C10	0.0568 (13)	0.0705 (14)	0.0477 (12)	−0.0142 (11)	−0.0052 (10)	0.0006 (10)
C11	0.188 (4)	0.126 (3)	0.0569 (19)	−0.068 (3)	−0.030 (2)	0.0139 (18)
N1	0.0414 (9)	0.0713 (12)	0.0485 (10)	−0.0151 (8)	−0.0080 (7)	−0.0007 (8)
O1	0.0438 (9)	0.1125 (15)	0.0629 (11)	−0.0234 (9)	−0.0138 (7)	0.0128 (9)
O2	0.0686 (12)	0.1219 (17)	0.0518 (10)	0.0074 (11)	−0.0100 (8)	0.0047 (10)
O3	0.0740 (13)	0.1372 (19)	0.0504 (11)	0.0077 (12)	−0.0024 (9)	0.0096 (11)

C1—C6	1.383 (3)	C7—C8	1.518 (3)
C1—C2	1.386 (3)	C8—C9	1.514 (3)
C1—N1	1.419 (3)	C8—H8A	0.9700
C2—C3	1.387 (4)	C8—H8B	0.9700
C2—H2	0.9300	C9—C10	1.497 (3)
C3—C4	1.383 (5)	C9—H9A	0.9700
C3—H3	0.9300	C9—H9B	0.9700
C4—C5	1.390 (5)	C10—O2	1.225 (3)
C4—C11	1.513 (4)	C10—O3	1.302 (3)
C5—C6	1.378 (4)	C11—H11A	0.9600
C5—H5	0.9300	C11—H11B	0.9600
C6—H6	0.9300	C11—H11C	0.9600
C7—O1	1.237 (3)	N1—H1N	0.836 (17)
C7—N1	1.340 (3)	O3—H3O	0.844 (19)
C6—C1—C2	119.1 (2)	C7—C8—H8A	109.0
C6—C1—N1	117.9 (2)	C9—C8—H8B	109.0
C2—C1—N1	123.0 (2)	C7—C8—H8B	109.0
C1—C2—C3	119.5 (2)	H8A—C8—H8B	107.8
C1—C2—H2	120.2	C10—C9—C8	112.4 (2)
C3—C2—H2	120.2	C10—C9—H9A	109.1
C4—C3—C2	121.8 (3)	C8—C9—H9A	109.1
C4—C3—H3	119.1	C10—C9—H9B	109.1
C2—C3—H3	119.1	C8—C9—H9B	109.1
C3—C4—C5	117.8 (2)	H9A—C9—H9B	107.9
C3—C4—C11	120.7 (3)	O2—C10—O3	122.9 (2)
C5—C4—C11	121.4 (3)	O2—C10—C9	123.8 (2)
C6—C5—C4	120.8 (3)	O3—C10—C9	113.4 (2)
C6—C5—H5	119.6	C4—C11—H11A	109.5
C4—C5—H5	119.6	C4—C11—H11B	109.5
C5—C6—C1	120.8 (3)	H11A—C11—H11B	109.5
C5—C6—H6	119.6	C4—C11—H11C	109.5
C1—C6—H6	119.6	H11A—C11—H11C	109.5
O1—C7—N1	124.4 (2)	H11B—C11—H11C	109.5
O1—C7—C8	121.9 (2)	C7—N1—C1	126.48 (19)
N1—C7—C8	113.68 (19)	C7—N1—H1N	118.0 (19)
C9—C8—C7	112.7 (2)	C1—N1—H1N	115.1 (19)
C9—C8—H8A	109.0	C10—O3—H3O	108 (3)
C6—C1—C2—C3	1.9 (4)	O1—C7—C8—C9	−27.7 (3)
N1—C1—C2—C3	179.6 (2)	N1—C7—C8—C9	154.7 (2)
C1—C2—C3—C4	−1.4 (4)	C7—C8—C9—C10	176.27 (19)
C2—C3—C4—C5	0.1 (4)	C8—C9—C10—O2	−0.5 (4)
C2—C3—C4—C11	179.2 (3)	C8—C9—C10—O3	179.6 (2)
C3—C4—C5—C6	0.5 (4)	O1—C7—N1—C1	−1.7 (4)
C11—C4—C5—C6	−178.6 (3)	C8—C7—N1—C1	175.8 (2)
C4—C5—C6—C1	0.1 (4)	C6—C1—N1—C7	−146.1 (2)
C2—C1—C6—C5	−1.4 (4)	C2—C1—N1—C7	36.3 (3)
N1—C1—C6—C5	−179.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.84 (2)	2.15 (2)	2.979 (2)	175 (3)
O3—H3O···O2ii	0.84 (2)	1.84 (2)	2.681 (3)	171 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.84 (2)	2.15 (2)	2.979 (2)	175 (3)
O3—H3O⋯O2ii	0.84 (2)	1.84 (2)	2.681 (3)	171 (4)

Symmetry codes: (i) ; (ii) .