N-(3,5-Dimethyl-phen-yl)succinamic acid.

In the title compound, C(12)H(15)NO(3), the N-H and C=O bonds are anti to each other. The C=O and O-H bonds of the acid group display an anti-periplanar orientation relative to each other. The crystal packing features a three-dimensional network of molecules held together by O-H⋯O and N-H⋯O hydrogen bonds.

Related literature

For our study of the effect of ring and side-chain substitutions on the crystal structures 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

C12H15NO3

M = 221.25

Monoclinic,

a = 14.346 (2) Å

b = 5.0225 (9) Å

c = 17.860 (3) Å

β = 112.00 (2)°

V = 1193.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.45 × 0.08 × 0.05 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 = 0.996

4452 measured reflections

2419 independent reflections

1593 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.147

S = 1.03

2419 reflections

153 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.18 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/S1600536810053055/bt5440sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810053055/bt5440Isup2.hkl

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

C12H15NO3	F(000) = 472
Mr = 221.25	Dx = 1.232 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1372 reflections
a = 14.346 (2) Å	θ = 2.9–27.7°
b = 5.0225 (9) Å	µ = 0.09 mm−1
c = 17.860 (3) Å	T = 293 K
β = 112.00 (2)°	Needle, colourless
V = 1193.2 (3) Å3	0.45 × 0.08 × 0.05 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2419 independent reflections
Radiation source: fine-focus sealed tube	1593 reflections with I > 2σ(I)
graphite	Rint = 0.019
Rotation method data acquisition using ω scans	θmax = 26.4°, θmin = 3.1°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −17→17
Tmin = 0.961, Tmax = 0.996	k = −6→4
4452 measured reflections	l = −22→12

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0672P)2 + 0.3965P] where P = (Fo2 + 2Fc2)/3
2419 reflections	(Δ/σ)max = 0.018
153 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.18 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
C1	0.59923 (15)	−0.1845 (4)	0.36154 (12)	0.0429 (5)
C2	0.56185 (17)	−0.3031 (5)	0.28576 (13)	0.0490 (6)
H2	0.5005	−0.2483	0.2476	0.059*
C3	0.61608 (19)	−0.5031 (5)	0.26700 (15)	0.0555 (6)
C4	0.70735 (19)	−0.5819 (5)	0.32444 (17)	0.0627 (7)
H4	0.7437	−0.7157	0.3117	0.075*
C5	0.74574 (18)	−0.4675 (5)	0.40004 (16)	0.0583 (7)
C6	0.69101 (16)	−0.2678 (5)	0.41832 (14)	0.0506 (6)
H6	0.7159	−0.1887	0.4691	0.061*
C7	0.45744 (14)	0.1217 (4)	0.34799 (11)	0.0390 (5)
C8	0.42783 (15)	0.3396 (4)	0.39303 (12)	0.0419 (5)
H8A	0.4314	0.2706	0.4448	0.050*
H8B	0.4759	0.4841	0.4035	0.050*
C9	0.32429 (15)	0.4476 (4)	0.34847 (12)	0.0477 (6)
H9A	0.3190	0.5039	0.2951	0.057*
H9B	0.2757	0.3063	0.3418	0.057*
C10	0.29831 (15)	0.6774 (4)	0.39033 (11)	0.0417 (5)
C11	0.5745 (2)	−0.6330 (6)	0.18462 (17)	0.0773 (9)
H11A	0.5206	−0.5267	0.1489	0.093*
H11B	0.5499	−0.8074	0.1893	0.093*
H11C	0.6268	−0.6471	0.1635	0.093*
C12	0.8446 (2)	−0.5577 (7)	0.46246 (19)	0.0861 (10)
H12A	0.8325	−0.6906	0.4964	0.103*
H12B	0.8784	−0.4084	0.4948	0.103*
H12C	0.8858	−0.6316	0.4359	0.103*
N1	0.54859 (13)	0.0184 (4)	0.38637 (10)	0.0446 (5)
H1N	0.5825 (17)	0.090 (5)	0.4335 (14)	0.054*
O1	0.40041 (11)	0.0430 (3)	0.28096 (9)	0.0557 (5)
O2	0.35474 (12)	0.7710 (3)	0.45287 (9)	0.0593 (5)
O3	0.20787 (12)	0.7838 (3)	0.35458 (9)	0.0563 (5)
H3O	0.1771 (19)	0.695 (5)	0.3110 (16)	0.068*

	U11	U22	U33	U12	U13	U23
C1	0.0391 (11)	0.0465 (13)	0.0432 (11)	0.0005 (10)	0.0154 (9)	0.0049 (10)
C2	0.0464 (12)	0.0548 (14)	0.0461 (12)	−0.0005 (11)	0.0178 (10)	−0.0002 (11)
C3	0.0628 (15)	0.0543 (14)	0.0601 (14)	−0.0069 (12)	0.0352 (13)	−0.0027 (12)
C4	0.0632 (16)	0.0578 (15)	0.0810 (19)	0.0093 (13)	0.0429 (15)	0.0059 (14)
C5	0.0473 (13)	0.0631 (16)	0.0691 (16)	0.0074 (12)	0.0271 (12)	0.0175 (13)
C6	0.0446 (12)	0.0580 (14)	0.0477 (12)	0.0015 (11)	0.0158 (10)	0.0075 (11)
C7	0.0361 (10)	0.0416 (12)	0.0323 (10)	−0.0043 (9)	0.0050 (8)	0.0001 (9)
C8	0.0390 (11)	0.0449 (12)	0.0345 (10)	−0.0036 (9)	0.0053 (8)	−0.0026 (9)
C9	0.0436 (12)	0.0479 (13)	0.0375 (11)	0.0041 (10)	−0.0010 (9)	−0.0059 (10)
C10	0.0398 (11)	0.0479 (12)	0.0307 (10)	0.0008 (10)	0.0055 (8)	0.0020 (9)
C11	0.090 (2)	0.0774 (19)	0.0780 (19)	−0.0079 (16)	0.0473 (17)	−0.0227 (16)
C12	0.0632 (17)	0.105 (2)	0.090 (2)	0.0334 (17)	0.0282 (16)	0.0258 (19)
N1	0.0390 (10)	0.0513 (11)	0.0343 (9)	0.0019 (8)	0.0032 (8)	−0.0051 (8)
O1	0.0458 (9)	0.0639 (11)	0.0397 (8)	0.0063 (8)	−0.0042 (7)	−0.0135 (7)
O2	0.0572 (10)	0.0654 (11)	0.0380 (8)	0.0020 (8)	−0.0021 (7)	−0.0156 (8)
O3	0.0492 (9)	0.0673 (11)	0.0414 (8)	0.0137 (8)	0.0043 (7)	−0.0070 (8)

C1—C2	1.389 (3)	C8—H8A	0.9700
C1—C6	1.392 (3)	C8—H8B	0.9700
C1—N1	1.416 (3)	C9—C10	1.496 (3)
C2—C3	1.386 (3)	C9—H9A	0.9700
C2—H2	0.9300	C9—H9B	0.9700
C3—C4	1.385 (3)	C10—O2	1.203 (2)
C3—C11	1.513 (3)	C10—O3	1.325 (2)
C4—C5	1.378 (4)	C11—H11A	0.9600
C4—H4	0.9300	C11—H11B	0.9600
C5—C6	1.386 (3)	C11—H11C	0.9600
C5—C12	1.508 (4)	C12—H12A	0.9600
C6—H6	0.9300	C12—H12B	0.9600
C7—O1	1.235 (2)	C12—H12C	0.9600
C7—N1	1.333 (3)	N1—H1N	0.88 (2)
C7—C8	1.510 (3)	O3—H3O	0.86 (3)
C8—C9	1.499 (3)
C2—C1—C6	119.7 (2)	H8A—C8—H8B	107.7
C2—C1—N1	123.88 (19)	C10—C9—C8	113.35 (17)
C6—C1—N1	116.40 (19)	C10—C9—H9A	108.9
C3—C2—C1	120.0 (2)	C8—C9—H9A	108.9
C3—C2—H2	120.0	C10—C9—H9B	108.9
C1—C2—H2	120.0	C8—C9—H9B	108.9
C4—C3—C2	119.2 (2)	H9A—C9—H9B	107.7
C4—C3—C11	121.1 (2)	O2—C10—O3	119.1 (2)
C2—C3—C11	119.7 (2)	O2—C10—C9	123.95 (19)
C5—C4—C3	121.8 (2)	O3—C10—C9	116.91 (17)
C5—C4—H4	119.1	C3—C11—H11A	109.5
C3—C4—H4	119.1	C3—C11—H11B	109.5
C4—C5—C6	118.6 (2)	H11A—C11—H11B	109.5
C4—C5—C12	121.3 (2)	C3—C11—H11C	109.5
C6—C5—C12	120.1 (3)	H11A—C11—H11C	109.5
C5—C6—C1	120.7 (2)	H11B—C11—H11C	109.5
C5—C6—H6	119.6	C5—C12—H12A	109.5
C1—C6—H6	119.6	C5—C12—H12B	109.5
O1—C7—N1	122.7 (2)	H12A—C12—H12B	109.5
O1—C7—C8	122.14 (18)	C5—C12—H12C	109.5
N1—C7—C8	115.19 (17)	H12A—C12—H12C	109.5
C9—C8—C7	113.56 (16)	H12B—C12—H12C	109.5
C9—C8—H8A	108.9	C7—N1—C1	129.70 (18)
C7—C8—H8A	108.9	C7—N1—H1N	114.7 (15)
C9—C8—H8B	108.9	C1—N1—H1N	115.6 (15)
C7—C8—H8B	108.9	C10—O3—H3O	107.7 (17)
C6—C1—C2—C3	−0.1 (3)	N1—C1—C6—C5	179.3 (2)
N1—C1—C2—C3	−179.2 (2)	O1—C7—C8—C9	−0.1 (3)
C1—C2—C3—C4	−0.1 (3)	N1—C7—C8—C9	−179.09 (19)
C1—C2—C3—C11	179.5 (2)	C7—C8—C9—C10	−175.54 (18)
C2—C3—C4—C5	0.2 (4)	C8—C9—C10—O2	1.1 (3)
C11—C3—C4—C5	−179.3 (2)	C8—C9—C10—O3	180.00 (19)
C3—C4—C5—C6	−0.2 (4)	O1—C7—N1—C1	1.5 (4)
C3—C4—C5—C12	179.2 (2)	C8—C7—N1—C1	−179.56 (19)
C4—C5—C6—C1	0.0 (4)	C2—C1—N1—C7	4.9 (4)
C12—C5—C6—C1	−179.4 (2)	C6—C1—N1—C7	−174.2 (2)
C2—C1—C6—C5	0.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.88 (2)	2.01 (2)	2.881 (2)	171 (2)
O3—H3O···O1ii	0.86 (3)	1.77 (3)	2.630 (2)	172 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.88 (2)	2.01 (2)	2.881 (2)	171 (2)
O3—H3O⋯O1ii	0.86 (3)	1.77 (3)	2.630 (2)	172 (3)

Symmetry codes: (i) ; (ii) .