N-(2,4,6-Trimethyl-phen-yl)succinamic acid.

The amide bond in the title compound {systematic name: 3-[(2,4,6-trimethyl-phen-yl)amino-carbon-yl]propionic acid}, C(13)H(17)NO(3), has a trans conformation. In the crystal, two mol-ecules form a centrosymmetric dimer connected by pairs of O-H⋯O hydrogen bonds. Inter-molecular N-H⋯O hydrogen bonds link the dimers into a three dimensional network.

Related literature

For related structures, see: Gowda et al. (2009 ▶); Jagannathan et al. (1994 ▶). For the modes of inter­linking carboxylic acids by hydrogen bonds, see: Leiserowitz (1976 ▶).

Experimental

Crystal data

C13H17NO3

M = 235.28

Triclinic,

a = 4.7646 (4) Å

b = 10.859 (1) Å

c = 13.111 (2) Å

α = 70.217 (8)°

β = 86.158 (8)°

γ = 79.351 (8)°

V = 627.31 (12) Å3

Z = 2

Cu Kα radiation

μ = 0.72 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 = 0.692, T max = 0.945

3109 measured reflections

2234 independent reflections

1918 reflections with I > 2σ(I)

R int = 0.014

3 standard reflections frequency: 120 min intensity decay: 1.0%

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.145

S = 1.05

2234 reflections

182 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.30 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/S1600536809029791/bt5016sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809029791/bt5016Isup2.hkl

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

C13H17NO3	Z = 2
Mr = 235.28	F(000) = 252
Triclinic, P1	Dx = 1.246 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54180 Å
a = 4.7646 (4) Å	Cell parameters from 25 reflections
b = 10.859 (1) Å	θ = 4.4–22.9°
c = 13.111 (2) Å	µ = 0.72 mm−1
α = 70.217 (8)°	T = 299 K
β = 86.158 (8)°	Plate, colourless
γ = 79.351 (8)°	0.55 × 0.25 × 0.08 mm
V = 627.31 (12) Å3

Enraf–Nonius CAD-4 diffractometer	1918 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.014
graphite	θmax = 67.0°, θmin = 3.6°
ω/2θ scans	h = −5→2
Absorption correction: ψ scan (North et al., 1968)	k = −12→12
Tmin = 0.692, Tmax = 0.945	l = −15→15
3109 measured reflections	3 standard reflections every 120 min
2234 independent reflections	intensity decay: 1.0%

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.145	w = 1/[σ2(Fo2) + (0.0856P)2 + 0.1672P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.004
2234 reflections	Δρmax = 0.30 e Å−3
182 parameters	Δρmin = −0.30 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.016 (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	0.3669 (3)	0.77823 (17)	0.30593 (13)	0.0376 (4)
C2	0.5805 (4)	0.67491 (18)	0.36121 (15)	0.0452 (4)
C3	0.6582 (5)	0.6700 (2)	0.46280 (16)	0.0549 (5)
H3	0.804 (5)	0.598 (2)	0.5015 (19)	0.066*
C4	0.5306 (4)	0.7610 (2)	0.51124 (15)	0.0512 (5)
C5	0.3135 (4)	0.8597 (2)	0.45520 (15)	0.0469 (5)
H5	0.225 (5)	0.923 (2)	0.4870 (18)	0.056*
C6	0.2278 (3)	0.87030 (18)	0.35308 (14)	0.0400 (4)
C7	0.4594 (3)	0.81334 (16)	0.11383 (13)	0.0368 (4)
C8	0.3304 (4)	0.8203 (2)	0.00956 (15)	0.0494 (5)
H8A	0.214 (5)	0.912 (2)	−0.0210 (18)	0.059*
H8B	0.205 (5)	0.749 (2)	0.0314 (18)	0.059*
C9	0.5540 (4)	0.8015 (2)	−0.07431 (16)	0.0543 (5)
H9A	0.683 (5)	0.867 (2)	−0.0887 (19)	0.065*
H9B	0.474 (5)	0.815 (2)	−0.142 (2)	0.065*
C10	0.7408 (4)	0.6682 (2)	−0.04148 (15)	0.0479 (5)
C11	0.7206 (5)	0.5687 (2)	0.31581 (18)	0.0607 (6)
H11A	0.8884	0.5946	0.2757	0.073*
H11B	0.5898	0.5570	0.2686	0.073*
H11C	0.7730	0.4868	0.3741	0.073*
C12	0.6208 (6)	0.7531 (3)	0.62154 (18)	0.0727 (7)
H12A	0.8203	0.7163	0.6316	0.087*
H12B	0.5120	0.6975	0.6763	0.087*
H12C	0.5875	0.8406	0.6270	0.087*
C13	−0.0127 (4)	0.9782 (2)	0.29629 (16)	0.0508 (5)
H13A	−0.1896	0.9451	0.3122	0.061*
H13B	0.0210	1.0057	0.2195	0.061*
H13C	−0.0227	1.0527	0.3210	0.061*
N1	0.2852 (3)	0.78867 (15)	0.20030 (11)	0.0396 (4)
H1N	0.108 (5)	0.790 (2)	0.1887 (16)	0.047*
O1	0.7050 (2)	0.83144 (14)	0.11738 (10)	0.0497 (4)
O2	0.9467 (3)	0.65764 (18)	−0.11116 (13)	0.0680 (5)
H2O	1.049 (6)	0.577 (3)	−0.091 (2)	0.082*
O3	0.7089 (3)	0.57886 (15)	0.04196 (13)	0.0631 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0274 (8)	0.0490 (9)	0.0385 (9)	−0.0093 (7)	0.0005 (6)	−0.0158 (7)
C2	0.0415 (9)	0.0474 (9)	0.0448 (9)	−0.0008 (8)	−0.0037 (7)	−0.0159 (8)
C3	0.0538 (12)	0.0562 (11)	0.0483 (11)	0.0068 (9)	−0.0139 (9)	−0.0151 (9)
C4	0.0503 (11)	0.0610 (11)	0.0425 (10)	−0.0052 (9)	−0.0069 (8)	−0.0188 (8)
C5	0.0424 (10)	0.0570 (11)	0.0450 (10)	−0.0039 (8)	0.0014 (8)	−0.0244 (9)
C6	0.0280 (8)	0.0502 (10)	0.0417 (9)	−0.0060 (7)	0.0020 (6)	−0.0159 (7)
C7	0.0226 (8)	0.0466 (9)	0.0426 (9)	−0.0003 (6)	−0.0025 (6)	−0.0190 (7)
C8	0.0281 (9)	0.0769 (13)	0.0448 (10)	0.0025 (9)	−0.0051 (7)	−0.0273 (9)
C9	0.0417 (10)	0.0776 (14)	0.0417 (10)	0.0032 (9)	−0.0022 (8)	−0.0241 (9)
C10	0.0373 (9)	0.0713 (12)	0.0450 (10)	−0.0081 (8)	0.0019 (7)	−0.0332 (10)
C11	0.0688 (14)	0.0530 (11)	0.0553 (12)	0.0092 (10)	−0.0086 (10)	−0.0202 (9)
C12	0.0836 (17)	0.0828 (16)	0.0519 (12)	0.0025 (13)	−0.0207 (11)	−0.0276 (11)
C13	0.0356 (10)	0.0627 (12)	0.0517 (10)	0.0049 (8)	−0.0025 (8)	−0.0226 (9)
N1	0.0213 (7)	0.0588 (9)	0.0420 (8)	−0.0074 (6)	−0.0022 (6)	−0.0206 (7)
O1	0.0221 (6)	0.0789 (9)	0.0516 (7)	−0.0109 (6)	−0.0004 (5)	−0.0249 (7)
O2	0.0600 (10)	0.0758 (10)	0.0631 (9)	0.0032 (8)	0.0198 (7)	−0.0280 (8)
O3	0.0569 (9)	0.0678 (9)	0.0624 (9)	−0.0033 (7)	0.0161 (7)	−0.0256 (8)

C1—C6	1.393 (2)	C8—H8B	1.02 (2)
C1—C2	1.395 (2)	C9—C10	1.491 (3)
C1—N1	1.426 (2)	C9—H9A	0.99 (3)
C2—C3	1.387 (3)	C9—H9B	0.94 (3)
C2—C11	1.502 (3)	C10—O3	1.215 (2)
C3—C4	1.378 (3)	C10—O2	1.311 (2)
C3—H3	0.96 (2)	C11—H11A	0.9600
C4—C5	1.385 (3)	C11—H11B	0.9600
C4—C12	1.507 (3)	C11—H11C	0.9600
C5—C6	1.387 (2)	C12—H12A	0.9600
C5—H5	0.94 (2)	C12—H12B	0.9600
C6—C13	1.506 (2)	C12—H12C	0.9600
C7—O1	1.228 (2)	C13—H13A	0.9600
C7—N1	1.341 (2)	C13—H13B	0.9600
C7—C8	1.509 (2)	C13—H13C	0.9600
C8—C9	1.517 (3)	N1—H1N	0.86 (2)
C8—H8A	1.01 (2)	O2—H2O	0.88 (3)
C6—C1—C2	121.06 (15)	C8—C9—H9A	110.4 (14)
C6—C1—N1	119.24 (15)	C10—C9—H9B	107.1 (14)
C2—C1—N1	119.69 (15)	C8—C9—H9B	112.8 (15)
C3—C2—C1	117.88 (17)	H9A—C9—H9B	106 (2)
C3—C2—C11	119.76 (17)	O3—C10—O2	123.15 (19)
C1—C2—C11	122.34 (17)	O3—C10—C9	123.67 (17)
C4—C3—C2	122.86 (18)	O2—C10—C9	113.17 (18)
C4—C3—H3	119.0 (14)	C2—C11—H11A	109.5
C2—C3—H3	118.1 (14)	C2—C11—H11B	109.5
C3—C4—C5	117.53 (17)	H11A—C11—H11B	109.5
C3—C4—C12	121.54 (19)	C2—C11—H11C	109.5
C5—C4—C12	120.93 (19)	H11A—C11—H11C	109.5
C4—C5—C6	122.27 (17)	H11B—C11—H11C	109.5
C4—C5—H5	118.5 (14)	C4—C12—H12A	109.5
C6—C5—H5	119.2 (14)	C4—C12—H12B	109.5
C5—C6—C1	118.35 (16)	H12A—C12—H12B	109.5
C5—C6—C13	120.18 (16)	C4—C12—H12C	109.5
C1—C6—C13	121.46 (15)	H12A—C12—H12C	109.5
O1—C7—N1	123.22 (15)	H12B—C12—H12C	109.5
O1—C7—C8	121.66 (15)	C6—C13—H13A	109.5
N1—C7—C8	115.11 (14)	C6—C13—H13B	109.5
C7—C8—C9	112.74 (15)	H13A—C13—H13B	109.5
C7—C8—H8A	106.9 (13)	C6—C13—H13C	109.5
C9—C8—H8A	107.8 (13)	H13A—C13—H13C	109.5
C7—C8—H8B	105.4 (13)	H13B—C13—H13C	109.5
C9—C8—H8B	112.3 (13)	C7—N1—C1	123.64 (14)
H8A—C8—H8B	111.7 (18)	C7—N1—H1N	117.1 (14)
C10—C9—C8	114.18 (18)	C1—N1—H1N	118.7 (14)
C10—C9—H9A	106.1 (14)	C10—O2—H2O	111.1 (18)
C6—C1—C2—C3	−2.6 (3)	N1—C1—C6—C5	−179.01 (15)
N1—C1—C2—C3	178.60 (16)	C2—C1—C6—C13	−177.02 (16)
C6—C1—C2—C11	175.73 (18)	N1—C1—C6—C13	1.8 (2)
N1—C1—C2—C11	−3.1 (3)	O1—C7—C8—C9	20.7 (3)
C1—C2—C3—C4	1.1 (3)	N1—C7—C8—C9	−160.51 (18)
C11—C2—C3—C4	−177.3 (2)	C7—C8—C9—C10	63.5 (3)
C2—C3—C4—C5	0.9 (3)	C8—C9—C10—O3	4.2 (3)
C2—C3—C4—C12	−179.8 (2)	C8—C9—C10—O2	−174.88 (17)
C3—C4—C5—C6	−1.3 (3)	O1—C7—N1—C1	−1.2 (3)
C12—C4—C5—C6	179.3 (2)	C8—C7—N1—C1	179.97 (16)
C4—C5—C6—C1	−0.2 (3)	C6—C1—N1—C7	116.28 (19)
C4—C5—C6—C13	179.05 (18)	C2—C1—N1—C7	−64.9 (2)
C2—C1—C6—C5	2.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.86 (2)	2.10 (2)	2.9368 (18)	163.6 (19)
O2—H2O···O3ii	0.88 (3)	1.80 (3)	2.679 (2)	172 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.86 (2)	2.10 (2)	2.9368 (18)	163.6 (19)
O2—H2O⋯O3ii	0.88 (3)	1.80 (3)	2.679 (2)	172 (3)

Symmetry codes: (i) ; (ii) .