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

In the amide segment of the title compound, C(12)H(15)NO(3) {systematic name: 3-[(2,6-dimethyl-phen-yl)amino-carbon-yl]propionic acid}, the N-H and C=O bonds are anti to each other. The mol-ecules are packed into a two-dimensional array via N-H⋯O and O-H⋯O hydrogen bonds.

Related literature

For related structures, see: Gowda et al. (2007 ▶, 2008 ▶, 2009 ▶).

Experimental

Crystal data

C12H15NO3

M = 221.25

Monoclinic,

a = 7.9633 (8) Å

b = 19.889 (2) Å

c = 7.9822 (8) Å

β = 111.16 (1)°

V = 1179.0 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 299 (2) K

0.50 × 0.48 × 0.40 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.958, T max = 0.966

6777 measured reflections

2391 independent reflections

1826 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.135

S = 1.05

2391 reflections

154 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2004 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); 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, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809003833/tk2369sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809003833/tk2369Isup2.hkl

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

C12H15NO3	F(000) = 472
Mr = 221.25	Dx = 1.246 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3013 reflections
a = 7.9633 (8) Å	θ = 2.7–28.0°
b = 19.889 (2) Å	µ = 0.09 mm−1
c = 7.9822 (8) Å	T = 299 K
β = 111.16 (1)°	Prism, colourless
V = 1179.0 (2) Å3	0.50 × 0.48 × 0.40 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2391 independent reflections
Radiation source: fine-focus sealed tube	1826 reflections with I > 2σ(I)
graphite	Rint = 0.017
Rotation method data acquisition using ω and φ scans	θmax = 26.4°, θmin = 2.9°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	h = −9→9
Tmin = 0.958, Tmax = 0.966	k = −24→24
6777 measured reflections	l = −8→9

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)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.135	w = 1/[σ2(Fo2) + (0.0691P)2 + 0.3248P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.03
2391 reflections	Δρmax = 0.19 e Å−3
154 parameters	Δρmin = −0.17 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: 0.017 (4)

Experimental. CrysAlis RED, Oxford Diffraction Ltd., 2007 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	0.12966 (19)	0.18528 (8)	0.03678 (19)	0.0379 (4)
C2	0.0916 (2)	0.11993 (8)	0.0772 (2)	0.0480 (4)
C3	0.2273 (3)	0.07205 (10)	0.1098 (3)	0.0688 (6)
H3	0.2062	0.0282	0.1376	0.083*
C4	0.3924 (3)	0.08854 (14)	0.1016 (3)	0.0799 (8)
H4	0.4816	0.0559	0.1241	0.096*
C5	0.4251 (3)	0.15276 (13)	0.0604 (3)	0.0693 (6)
H5	0.5369	0.1632	0.0552	0.083*
C6	0.2949 (2)	0.20310 (10)	0.0260 (2)	0.0483 (4)
C7	0.00487 (18)	0.28812 (7)	0.11169 (19)	0.0353 (3)
C8	−0.1610 (2)	0.33204 (8)	0.0593 (2)	0.0434 (4)
H8A	−0.2293	0.3264	−0.0679	0.052*
H8B	−0.2363	0.3174	0.1245	0.052*
C9	−0.1168 (2)	0.40548 (8)	0.0976 (2)	0.0467 (4)
H9A	−0.0409	0.4109	0.2229	0.056*
H9B	−0.0499	0.4212	0.0250	0.056*
C10	−0.2830 (2)	0.44735 (8)	0.0582 (2)	0.0473 (4)
C11	−0.0877 (3)	0.10257 (10)	0.0884 (3)	0.0637 (5)
H11A	−0.1803	0.1074	−0.0280	0.076*
H11B	−0.1120	0.1323	0.1717	0.076*
H11C	−0.0854	0.0570	0.1287	0.076*
C12	0.3334 (3)	0.27264 (12)	−0.0218 (3)	0.0662 (6)
H12A	0.3733	0.3001	0.0843	0.079*
H12B	0.2258	0.2916	−0.1077	0.079*
H12C	0.4256	0.2709	−0.0727	0.079*
N1	−0.00837 (16)	0.23498 (6)	0.00415 (17)	0.0368 (3)
H1N	−0.111 (2)	0.2276 (9)	−0.079 (2)	0.044*
O1	0.13819 (13)	0.30009 (6)	0.24524 (15)	0.0469 (3)
O2	−0.25948 (19)	0.51129 (6)	0.0379 (2)	0.0750 (5)
H2O	−0.363 (4)	0.5325 (13)	0.012 (3)	0.090*
O3	−0.42763 (16)	0.42371 (6)	0.0464 (2)	0.0714 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0333 (7)	0.0407 (8)	0.0329 (7)	0.0075 (6)	0.0038 (6)	−0.0065 (6)
C2	0.0541 (10)	0.0393 (9)	0.0399 (9)	0.0074 (7)	0.0042 (7)	−0.0068 (7)
C3	0.0865 (16)	0.0462 (11)	0.0573 (12)	0.0256 (10)	0.0061 (10)	−0.0063 (8)
C4	0.0731 (15)	0.0875 (17)	0.0666 (13)	0.0504 (13)	0.0101 (11)	−0.0078 (12)
C5	0.0444 (10)	0.0996 (18)	0.0593 (12)	0.0256 (11)	0.0134 (9)	−0.0131 (11)
C6	0.0358 (8)	0.0675 (11)	0.0385 (8)	0.0078 (7)	0.0096 (7)	−0.0073 (8)
C7	0.0270 (7)	0.0371 (8)	0.0365 (8)	0.0034 (6)	0.0052 (6)	0.0009 (6)
C8	0.0307 (7)	0.0399 (8)	0.0491 (9)	0.0082 (6)	0.0018 (6)	−0.0039 (7)
C9	0.0341 (8)	0.0415 (9)	0.0577 (10)	0.0060 (6)	0.0084 (7)	−0.0013 (7)
C10	0.0385 (9)	0.0376 (8)	0.0576 (10)	0.0057 (7)	0.0075 (7)	−0.0053 (7)
C11	0.0671 (12)	0.0449 (10)	0.0697 (13)	−0.0105 (9)	0.0132 (10)	0.0004 (9)
C12	0.0486 (10)	0.0862 (15)	0.0702 (13)	−0.0092 (10)	0.0291 (10)	0.0006 (11)
N1	0.0258 (6)	0.0367 (7)	0.0384 (7)	0.0032 (5)	0.0001 (5)	−0.0047 (5)
O1	0.0325 (6)	0.0498 (7)	0.0436 (6)	0.0089 (5)	−0.0042 (5)	−0.0094 (5)
O2	0.0473 (8)	0.0376 (7)	0.1347 (15)	0.0076 (6)	0.0263 (8)	−0.0008 (8)
O3	0.0415 (7)	0.0434 (7)	0.1276 (13)	0.0085 (5)	0.0284 (8)	0.0044 (7)

C1—C6	1.395 (2)	C8—H8A	0.9700
C1—C2	1.398 (2)	C8—H8B	0.9700
C1—N1	1.4306 (18)	C9—C10	1.498 (2)
C2—C3	1.393 (2)	C9—H9A	0.9700
C2—C11	1.503 (3)	C9—H9B	0.9700
C3—C4	1.379 (3)	C10—O3	1.216 (2)
C3—H3	0.9300	C10—O2	1.304 (2)
C4—C5	1.367 (4)	C11—H11A	0.9600
C4—H4	0.9300	C11—H11B	0.9600
C5—C6	1.395 (3)	C11—H11C	0.9600
C5—H5	0.9300	C12—H12A	0.9600
C6—C12	1.495 (3)	C12—H12B	0.9600
C7—O1	1.2260 (17)	C12—H12C	0.9600
C7—N1	1.3415 (19)	N1—H1N	0.859 (18)
C7—C8	1.5115 (19)	O2—H2O	0.88 (3)
C8—C9	1.508 (2)
C6—C1—C2	122.55 (15)	H8A—C8—H8B	107.8
C6—C1—N1	119.54 (15)	C10—C9—C8	111.83 (13)
C2—C1—N1	117.91 (14)	C10—C9—H9A	109.3
C3—C2—C1	117.43 (18)	C8—C9—H9A	109.3
C3—C2—C11	121.43 (18)	C10—C9—H9B	109.3
C1—C2—C11	121.12 (15)	C8—C9—H9B	109.3
C4—C3—C2	121.1 (2)	H9A—C9—H9B	107.9
C4—C3—H3	119.4	O3—C10—O2	122.82 (15)
C2—C3—H3	119.4	O3—C10—C9	122.82 (15)
C5—C4—C3	120.05 (18)	O2—C10—C9	114.37 (15)
C5—C4—H4	120.0	C2—C11—H11A	109.5
C3—C4—H4	120.0	C2—C11—H11B	109.5
C4—C5—C6	121.7 (2)	H11A—C11—H11B	109.5
C4—C5—H5	119.1	C2—C11—H11C	109.5
C6—C5—H5	119.1	H11A—C11—H11C	109.5
C1—C6—C5	117.12 (19)	H11B—C11—H11C	109.5
C1—C6—C12	122.35 (15)	C6—C12—H12A	109.5
C5—C6—C12	120.53 (18)	C6—C12—H12B	109.5
O1—C7—N1	123.55 (13)	H12A—C12—H12B	109.5
O1—C7—C8	121.63 (13)	C6—C12—H12C	109.5
N1—C7—C8	114.79 (12)	H12A—C12—H12C	109.5
C9—C8—C7	112.76 (12)	H12B—C12—H12C	109.5
C9—C8—H8A	109.0	C7—N1—C1	123.37 (12)
C7—C8—H8A	109.0	C7—N1—H1N	117.7 (12)
C9—C8—H8B	109.0	C1—N1—H1N	118.3 (12)
C7—C8—H8B	109.0	C10—O2—H2O	109.4 (16)
C6—C1—C2—C3	0.9 (2)	C4—C5—C6—C1	0.5 (3)
N1—C1—C2—C3	−179.61 (14)	C4—C5—C6—C12	−178.95 (19)
C6—C1—C2—C11	179.75 (15)	O1—C7—C8—C9	36.3 (2)
N1—C1—C2—C11	−0.8 (2)	N1—C7—C8—C9	−145.43 (15)
C1—C2—C3—C4	−0.3 (3)	C7—C8—C9—C10	−175.54 (14)
C11—C2—C3—C4	−179.12 (18)	C8—C9—C10—O3	19.1 (3)
C2—C3—C4—C5	−0.2 (3)	C8—C9—C10—O2	−161.05 (17)
C3—C4—C5—C6	0.1 (3)	O1—C7—N1—C1	2.0 (2)
C2—C1—C6—C5	−1.0 (2)	C8—C7—N1—C1	−176.22 (14)
N1—C1—C6—C5	179.54 (14)	C6—C1—N1—C7	−66.5 (2)
C2—C1—C6—C12	178.40 (16)	C2—C1—N1—C7	114.05 (17)
N1—C1—C6—C12	−1.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.859 (18)	2.059 (19)	2.9120 (16)	171.8 (17)
O2—H2O···O3ii	0.88 (3)	1.79 (3)	2.6686 (18)	178 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.859 (18)	2.059 (19)	2.9120 (16)	171.8 (17)
O2—H2O⋯O3ii	0.88 (3)	1.79 (3)	2.6686 (18)	178 (3)

Symmetry codes: (i) ; (ii) .