N-(2,3-Dimethyl-phen-yl)succinamic acid.

In the title compound, C(12)H(15)NO(3), the conformations of 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- and meta-methyl groups in the benzene ring. In the crystal, the mol-ecules are linked into infinite chains through inter-molecular O-H⋯O and N-H⋯O hydrogen bonds.

Related literature

For background to our study of the effect of ring and side-chain substitutions on the crystal structures of anilides, see: Gowda et al. (2010a ▶,b ▶,c ▶). For the 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

C12H15NO3

M = 221.25

Triclinic,

a = 4.8379 (4) Å

b = 10.0424 (6) Å

c = 11.9876 (8) Å

α = 90.222 (6)°

β = 99.614 (7)°

γ = 98.506 (6)°

V = 567.67 (7) Å3

Z = 2

Cu Kα radiation

μ = 0.77 mm−1

T = 299 K

0.40 × 0.25 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

3962 measured reflections

2017 independent reflections

1751 reflections with I > 2σ(I)

R int = 0.035

3 standard reflections every 120 min intensity decay: 0.5%

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.183

S = 1.11

2017 reflections

154 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.31 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/S160053681005292X/bq2264sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681005292X/bq2264Isup2.hkl

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

C12H15NO3	Z = 2
Mr = 221.25	F(000) = 236
Triclinic, P1	Dx = 1.294 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54180 Å
a = 4.8379 (4) Å	Cell parameters from 25 reflections
b = 10.0424 (6) Å	θ = 5.9–22.4°
c = 11.9876 (8) Å	µ = 0.77 mm−1
α = 90.222 (6)°	T = 299 K
β = 99.614 (7)°	Prism, colorless
γ = 98.506 (6)°	0.40 × 0.25 × 0.10 mm
V = 567.67 (7) Å3

Enraf–Nonius CAD-4 diffractometer	Rint = 0.035
Radiation source: fine-focus sealed tube	θmax = 66.9°, θmin = 3.7°
graphite	h = −5→5
ω/2θ scans	k = −11→11
3962 measured reflections	l = −14→14
2017 independent reflections	3 standard reflections every 120 min
1751 reflections with I > 2σ(I)	intensity decay: 0.5%

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)] = 0.064	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.183	w = 1/[σ2(Fo2) + (0.1035P)2 + 0.1611P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max = 0.003
2017 reflections	Δρmax = 0.42 e Å−3
154 parameters	Δρmin = −0.31 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: 0.025 (4)

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	−0.0305 (4)	0.17546 (19)	0.88221 (15)	0.0389 (5)
C2	0.0537 (4)	0.21089 (18)	0.77926 (15)	0.0396 (5)
C3	−0.0852 (4)	0.1370 (2)	0.68124 (17)	0.0481 (5)
C4	−0.3018 (5)	0.0324 (2)	0.6889 (2)	0.0597 (6)
H4	−0.3937	−0.0163	0.6236	0.072*
C5	−0.3839 (5)	−0.0011 (2)	0.7909 (2)	0.0655 (7)
H5	−0.5314	−0.0710	0.7942	0.079*
C6	−0.2461 (4)	0.0697 (2)	0.88872 (19)	0.0534 (6)
H6	−0.2976	0.0464	0.9582	0.064*
C7	−0.0169 (4)	0.3000 (2)	1.05958 (16)	0.0502 (6)
C8	0.1749 (4)	0.3738 (3)	1.15994 (17)	0.0560 (6)
H8A	0.3676	0.3570	1.1608	0.067*
H8B	0.1734	0.4699	1.1529	0.067*
C9	0.0814 (5)	0.3293 (2)	1.26929 (17)	0.0545 (6)
H9A	−0.1128	0.3442	1.2677	0.065*
H9B	0.0872	0.2336	1.2772	0.065*
C10	0.2680 (4)	0.4050 (2)	1.36885 (16)	0.0481 (5)
C11	0.2885 (4)	0.3245 (2)	0.77306 (18)	0.0518 (5)
H11A	0.4581	0.2888	0.7655	0.062*
H11B	0.3218	0.3797	0.8409	0.062*
H11C	0.2361	0.3778	0.7088	0.062*
C12	−0.0018 (6)	0.1712 (3)	0.56799 (19)	0.0684 (7)
H12A	0.1952	0.1644	0.5709	0.082*
H12B	−0.0329	0.2615	0.5500	0.082*
H12C	−0.1144	0.1096	0.5109	0.082*
N1	0.1111 (3)	0.24747 (17)	0.98335 (13)	0.0432 (5)
H1N	0.295 (6)	0.262 (2)	0.998 (2)	0.052*
O1	−0.2754 (3)	0.2922 (2)	1.05008 (14)	0.0823 (7)
O2	0.4948 (4)	0.3603 (2)	1.40631 (16)	0.0769 (6)
H2O	0.538 (7)	0.397 (3)	1.472 (3)	0.092*
O3	0.2004 (4)	0.50537 (19)	1.40937 (15)	0.0762 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0239 (9)	0.0495 (10)	0.0406 (9)	0.0034 (7)	−0.0001 (7)	−0.0042 (7)
C2	0.0310 (10)	0.0455 (10)	0.0418 (10)	0.0092 (7)	0.0022 (7)	−0.0021 (7)
C3	0.0462 (12)	0.0536 (11)	0.0440 (11)	0.0177 (9)	−0.0027 (8)	−0.0079 (8)
C4	0.0548 (14)	0.0571 (12)	0.0587 (13)	0.0069 (10)	−0.0133 (10)	−0.0185 (10)
C5	0.0453 (13)	0.0560 (12)	0.0837 (16)	−0.0122 (10)	−0.0043 (11)	−0.0092 (11)
C6	0.0394 (11)	0.0598 (12)	0.0556 (12)	−0.0062 (9)	0.0045 (9)	0.0024 (9)
C7	0.0230 (9)	0.0834 (14)	0.0413 (10)	0.0000 (8)	0.0041 (7)	−0.0105 (9)
C8	0.0285 (10)	0.0906 (16)	0.0439 (11)	−0.0054 (9)	0.0051 (8)	−0.0160 (10)
C9	0.0400 (11)	0.0723 (14)	0.0469 (11)	−0.0019 (9)	0.0045 (8)	−0.0115 (9)
C10	0.0388 (11)	0.0676 (13)	0.0375 (10)	0.0039 (9)	0.0089 (8)	−0.0060 (9)
C11	0.0449 (12)	0.0574 (12)	0.0525 (11)	0.0008 (9)	0.0124 (9)	0.0030 (9)
C12	0.0806 (18)	0.0824 (16)	0.0441 (12)	0.0265 (13)	0.0034 (11)	−0.0066 (10)
N1	0.0196 (8)	0.0677 (11)	0.0391 (8)	−0.0010 (7)	0.0026 (6)	−0.0072 (7)
O1	0.0220 (8)	0.1555 (19)	0.0645 (10)	0.0054 (9)	0.0015 (7)	−0.0449 (11)
O2	0.0544 (11)	0.1007 (14)	0.0710 (11)	0.0252 (9)	−0.0140 (8)	−0.0343 (10)
O3	0.0715 (12)	0.0869 (12)	0.0660 (11)	0.0300 (10)	−0.0155 (9)	−0.0277 (9)

C1—C6	1.387 (3)	C8—H8A	0.9700
C1—C2	1.394 (3)	C8—H8B	0.9700
C1—N1	1.425 (2)	C9—C10	1.499 (3)
C2—C3	1.402 (3)	C9—H9A	0.9700
C2—C11	1.498 (3)	C9—H9B	0.9700
C3—C4	1.385 (3)	C10—O3	1.227 (3)
C3—C12	1.507 (3)	C10—O2	1.261 (3)
C4—C5	1.376 (4)	C11—H11A	0.9600
C4—H4	0.9300	C11—H11B	0.9600
C5—C6	1.384 (3)	C11—H11C	0.9600
C5—H5	0.9300	C12—H12A	0.9600
C6—H6	0.9300	C12—H12B	0.9600
C7—O1	1.227 (2)	C12—H12C	0.9600
C7—N1	1.334 (3)	N1—H1N	0.87 (3)
C7—C8	1.508 (3)	O2—H2O	0.85 (3)
C8—C9	1.505 (3)
C6—C1—C2	121.34 (18)	H8A—C8—H8B	108.0
C6—C1—N1	119.13 (17)	C10—C9—C8	111.26 (17)
C2—C1—N1	119.52 (16)	C10—C9—H9A	109.4
C1—C2—C3	118.49 (18)	C8—C9—H9A	109.4
C1—C2—C11	121.03 (16)	C10—C9—H9B	109.4
C3—C2—C11	120.48 (17)	C8—C9—H9B	109.4
C4—C3—C2	119.54 (19)	H9A—C9—H9B	108.0
C4—C3—C12	119.9 (2)	O3—C10—O2	123.04 (19)
C2—C3—C12	120.5 (2)	O3—C10—C9	120.7 (2)
C5—C4—C3	121.38 (19)	O2—C10—C9	116.29 (19)
C5—C4—H4	119.3	C2—C11—H11A	109.5
C3—C4—H4	119.3	C2—C11—H11B	109.5
C4—C5—C6	119.8 (2)	H11A—C11—H11B	109.5
C4—C5—H5	120.1	C2—C11—H11C	109.5
C6—C5—H5	120.1	H11A—C11—H11C	109.5
C5—C6—C1	119.5 (2)	H11B—C11—H11C	109.5
C5—C6—H6	120.3	C3—C12—H12A	109.5
C1—C6—H6	120.3	C3—C12—H12B	109.5
O1—C7—N1	123.30 (18)	H12A—C12—H12B	109.5
O1—C7—C8	120.46 (18)	C3—C12—H12C	109.5
N1—C7—C8	116.23 (16)	H12A—C12—H12C	109.5
C9—C8—C7	111.27 (17)	H12B—C12—H12C	109.5
C9—C8—H8A	109.4	C7—N1—C1	125.13 (16)
C7—C8—H8A	109.4	C7—N1—H1N	115.0 (16)
C9—C8—H8B	109.4	C1—N1—H1N	119.8 (16)
C7—C8—H8B	109.4	C10—O2—H2O	101 (2)
C6—C1—C2—C3	0.1 (3)	C2—C1—C6—C5	−1.0 (3)
N1—C1—C2—C3	178.85 (16)	N1—C1—C6—C5	−179.77 (19)
C6—C1—C2—C11	−179.43 (19)	O1—C7—C8—C9	49.2 (3)
N1—C1—C2—C11	−0.7 (3)	N1—C7—C8—C9	−131.8 (2)
C1—C2—C3—C4	0.4 (3)	C7—C8—C9—C10	−178.67 (19)
C11—C2—C3—C4	180.00 (19)	C8—C9—C10—O3	95.5 (3)
C1—C2—C3—C12	−179.90 (18)	C8—C9—C10—O2	−83.7 (3)
C11—C2—C3—C12	−0.4 (3)	O1—C7—N1—C1	−0.3 (4)
C2—C3—C4—C5	−0.1 (3)	C8—C7—N1—C1	−179.29 (19)
C12—C3—C4—C5	−179.7 (2)	C6—C1—N1—C7	−51.1 (3)
C3—C4—C5—C6	−0.8 (4)	C2—C1—N1—C7	130.1 (2)
C4—C5—C6—C1	1.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.87 (3)	2.04 (3)	2.909 (2)	174 (2)
O2—H2O···O3ii	0.85 (3)	1.90 (4)	2.679 (2)	152 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.87 (3)	2.04 (3)	2.909 (2)	174 (2)
O2—H2O⋯O3ii	0.85 (3)	1.90 (4)	2.679 (2)	152 (3)

Symmetry codes: (i) ; (ii) .