N-(3,4-Dimethyl-phen-yl)succinamic acid.

The asymmetric unit of the title compound, C(12)H(15)NO(3), contains two independent mol-ecules. In both mol-ecules, the conformations of the amide oxygen and the carbonyl O atom of the acid segment are anti to the adjacent CH(2) groups. In the crystal, both molecules form inversion dimers linked by pairs of O-H⋯O hydrogen bonds and N-H⋯O interactions link the dimers into [100] chains.

Related literature

For the crystal structures of related anilides, see: Gowda et al. (2007 ▶); Gowda, Foro, Saraswathi & Fuess (2009 ▶); Gowda, Foro, Saraswathi et al. (2009 ▶). For the modes of inter­linking carboxylic acids by hydrogen bonds, see: Leiserowitz (1976 ▶); Jagannathan et al. (1994 ▶).

Experimental

Crystal data

C12H15NO3

M = 221.25

Triclinic,

a = 9.736 (1) Å

b = 9.919 (1) Å

c = 12.601 (2) Å

α = 106.42 (1)°

β = 100.98 (1)°

γ = 99.81 (1)°

V = 1112.9 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 299 K

0.44 × 0.40 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.959, T max = 0.985

7776 measured reflections

4538 independent reflections

3173 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.118

S = 1.03

4538 reflections

305 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.17 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/S1600536810002084/rz2408sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810002084/rz2408Isup2.hkl

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

C12H15NO3	Z = 4
Mr = 221.25	F(000) = 472
Triclinic, P1	Dx = 1.320 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.736 (1) Å	Cell parameters from 2369 reflections
b = 9.919 (1) Å	θ = 3.1–27.7°
c = 12.601 (2) Å	µ = 0.10 mm−1
α = 106.42 (1)°	T = 299 K
β = 100.98 (1)°	Rod, colourless
γ = 99.81 (1)°	0.44 × 0.40 × 0.16 mm
V = 1112.9 (2) Å3

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	4538 independent reflections
Radiation source: fine-focus sealed tube	3173 reflections with I > 2σ(I)
graphite	Rint = 0.013
Rotation method data acquisition using ω and φ scans.	θmax = 26.4°, θmin = 3.1°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −11→12
Tmin = 0.959, Tmax = 0.985	k = −12→10
7776 measured reflections	l = −14→15

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0517P)2 + 0.2735P] where P = (Fo2 + 2Fc2)/3
4538 reflections	(Δ/σ)max < 0.001
305 parameters	Δρmax = 0.17 e Å−3
2 restraints	Δρmin = −0.17 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
O1	0.25568 (12)	0.46649 (13)	0.13575 (10)	0.0454 (3)
O2	0.15120 (14)	0.11617 (14)	0.05553 (10)	0.0529 (3)
O3	0.20038 (15)	0.09014 (14)	−0.11316 (10)	0.0530 (3)
H3O	0.243 (2)	0.030 (2)	−0.0934 (17)	0.064*
N1	0.08150 (14)	0.53340 (15)	0.22197 (11)	0.0380 (3)
H1N	−0.013 (2)	0.5115 (19)	0.2162 (14)	0.046*
C1	0.16800 (16)	0.63065 (16)	0.32941 (13)	0.0344 (4)
C2	0.11108 (17)	0.64457 (17)	0.42386 (14)	0.0382 (4)
H2	0.0170	0.5949	0.4138	0.046*
C3	0.19110 (18)	0.73073 (17)	0.53296 (14)	0.0395 (4)
C4	0.33168 (18)	0.80814 (18)	0.54764 (14)	0.0409 (4)
C5	0.38529 (18)	0.79638 (18)	0.45219 (15)	0.0436 (4)
H5	0.4780	0.8489	0.4613	0.052*
C6	0.30594 (17)	0.70921 (17)	0.34342 (14)	0.0409 (4)
H6	0.3448	0.7036	0.2808	0.049*
C7	0.12894 (16)	0.45212 (17)	0.13761 (13)	0.0344 (3)
C8	0.01037 (17)	0.33813 (18)	0.04349 (13)	0.0404 (4)
H8A	−0.0624	0.3841	0.0153	0.048*
H8B	−0.0348	0.2689	0.0750	0.048*
C9	0.06420 (18)	0.25797 (19)	−0.05577 (13)	0.0423 (4)
H9A	−0.0173	0.2094	−0.1214	0.051*
H9B	0.1280	0.3278	−0.0758	0.051*
C10	0.14225 (17)	0.14906 (17)	−0.03140 (13)	0.0386 (4)
C11	0.1276 (2)	0.7378 (2)	0.63389 (15)	0.0568 (5)
H11A	0.0286	0.6851	0.6075	0.068*
H11B	0.1334	0.8370	0.6751	0.068*
H11C	0.1804	0.6960	0.6834	0.068*
C12	0.4230 (2)	0.9026 (2)	0.66431 (15)	0.0592 (5)
H12A	0.5170	0.9429	0.6584	0.071*
H12B	0.4315	0.8457	0.7144	0.071*
H12C	0.3788	0.9794	0.6945	0.071*
O4	0.75949 (12)	0.46145 (14)	0.15126 (10)	0.0545 (4)
O5	0.66192 (15)	0.10463 (14)	0.06567 (10)	0.0548 (3)
O6	0.71268 (15)	0.07822 (14)	−0.10294 (10)	0.0524 (3)
H6O	0.756 (2)	0.015 (2)	−0.0837 (17)	0.063*
N2	0.57898 (15)	0.50597 (17)	0.23359 (12)	0.0478 (4)
H2N	0.486 (2)	0.484 (2)	0.2237 (16)	0.057*
C13	0.66100 (17)	0.61991 (18)	0.33598 (13)	0.0390 (4)
C14	0.66191 (17)	0.60174 (18)	0.44074 (14)	0.0398 (4)
H14	0.6180	0.5122	0.4434	0.048*
C15	0.72698 (17)	0.71425 (18)	0.54223 (13)	0.0385 (4)
C16	0.79482 (17)	0.84812 (17)	0.53795 (14)	0.0387 (4)
C17	0.79743 (19)	0.86189 (18)	0.43201 (15)	0.0448 (4)
H17	0.8453	0.9495	0.4286	0.054*
C18	0.73127 (19)	0.7499 (2)	0.33125 (14)	0.0457 (4)
H18	0.7342	0.7623	0.2612	0.055*
C19	0.63180 (17)	0.43683 (17)	0.14927 (13)	0.0363 (4)
C20	0.51791 (18)	0.32399 (19)	0.05010 (14)	0.0434 (4)
H20A	0.4690	0.2529	0.0782	0.052*
H20B	0.4470	0.3706	0.0201	0.052*
C21	0.57788 (19)	0.24675 (19)	−0.04634 (13)	0.0441 (4)
H21A	0.4993	0.1993	−0.1143	0.053*
H21B	0.6441	0.3182	−0.0629	0.053*
C22	0.65414 (17)	0.13717 (17)	−0.02138 (13)	0.0389 (4)
C23	0.7220 (2)	0.6912 (2)	0.65422 (15)	0.0559 (5)
H23A	0.6822	0.5908	0.6411	0.067*
H23B	0.6628	0.7483	0.6900	0.067*
H23C	0.8177	0.7199	0.7031	0.067*
C24	0.8606 (2)	0.9755 (2)	0.64499 (15)	0.0536 (5)
H24A	0.9336	0.9518	0.6945	0.064*
H24B	0.7873	0.9991	0.6833	0.064*
H24C	0.9029	1.0570	0.6255	0.064*

	U11	U22	U33	U12	U13	U23
O1	0.0328 (6)	0.0520 (7)	0.0422 (7)	0.0089 (5)	0.0099 (5)	0.0014 (5)
O2	0.0701 (9)	0.0541 (8)	0.0409 (7)	0.0255 (7)	0.0226 (6)	0.0134 (6)
O3	0.0680 (9)	0.0579 (8)	0.0407 (7)	0.0301 (7)	0.0231 (6)	0.0127 (6)
N1	0.0285 (7)	0.0405 (8)	0.0367 (7)	0.0091 (6)	0.0057 (6)	0.0011 (6)
C1	0.0318 (8)	0.0303 (8)	0.0355 (8)	0.0101 (7)	0.0051 (6)	0.0031 (7)
C2	0.0330 (8)	0.0350 (8)	0.0421 (9)	0.0073 (7)	0.0106 (7)	0.0054 (7)
C3	0.0425 (9)	0.0358 (9)	0.0386 (9)	0.0148 (7)	0.0092 (7)	0.0073 (7)
C4	0.0394 (9)	0.0362 (9)	0.0393 (9)	0.0115 (7)	0.0026 (7)	0.0039 (7)
C5	0.0324 (8)	0.0384 (9)	0.0493 (10)	0.0036 (7)	0.0069 (7)	0.0032 (8)
C6	0.0382 (9)	0.0389 (9)	0.0419 (9)	0.0079 (7)	0.0134 (7)	0.0062 (7)
C7	0.0327 (8)	0.0348 (8)	0.0335 (8)	0.0098 (7)	0.0056 (6)	0.0085 (7)
C8	0.0340 (8)	0.0410 (9)	0.0378 (9)	0.0092 (7)	0.0041 (7)	0.0032 (7)
C9	0.0414 (9)	0.0450 (10)	0.0316 (8)	0.0101 (8)	0.0041 (7)	0.0022 (7)
C10	0.0394 (9)	0.0354 (9)	0.0303 (8)	0.0037 (7)	0.0069 (7)	−0.0012 (7)
C11	0.0591 (12)	0.0626 (13)	0.0442 (11)	0.0140 (10)	0.0158 (9)	0.0091 (9)
C12	0.0544 (12)	0.0601 (12)	0.0453 (11)	0.0113 (10)	−0.0011 (9)	0.0001 (9)
O4	0.0315 (6)	0.0638 (8)	0.0517 (8)	0.0084 (6)	0.0116 (5)	−0.0053 (6)
O5	0.0720 (9)	0.0607 (8)	0.0413 (7)	0.0297 (7)	0.0245 (6)	0.0165 (6)
O6	0.0651 (9)	0.0557 (8)	0.0399 (7)	0.0249 (7)	0.0220 (6)	0.0093 (6)
N2	0.0291 (7)	0.0580 (9)	0.0406 (8)	0.0045 (7)	0.0091 (6)	−0.0046 (7)
C13	0.0322 (8)	0.0439 (9)	0.0348 (9)	0.0094 (7)	0.0093 (7)	0.0029 (7)
C14	0.0379 (9)	0.0368 (9)	0.0439 (9)	0.0088 (7)	0.0129 (7)	0.0105 (7)
C15	0.0391 (9)	0.0415 (9)	0.0354 (8)	0.0146 (7)	0.0099 (7)	0.0099 (7)
C16	0.0355 (8)	0.0386 (9)	0.0384 (9)	0.0113 (7)	0.0075 (7)	0.0065 (7)
C17	0.0470 (10)	0.0371 (9)	0.0489 (10)	0.0056 (8)	0.0138 (8)	0.0136 (8)
C18	0.0479 (10)	0.0553 (11)	0.0353 (9)	0.0117 (9)	0.0126 (8)	0.0159 (8)
C19	0.0325 (8)	0.0383 (9)	0.0351 (8)	0.0104 (7)	0.0072 (7)	0.0071 (7)
C20	0.0353 (9)	0.0443 (10)	0.0405 (9)	0.0095 (7)	0.0049 (7)	0.0016 (8)
C21	0.0449 (9)	0.0467 (10)	0.0313 (9)	0.0100 (8)	0.0037 (7)	0.0029 (7)
C22	0.0380 (9)	0.0377 (9)	0.0309 (8)	0.0038 (7)	0.0072 (7)	−0.0005 (7)
C23	0.0693 (13)	0.0605 (12)	0.0423 (10)	0.0198 (10)	0.0161 (9)	0.0195 (9)
C24	0.0522 (11)	0.0458 (10)	0.0491 (11)	0.0100 (9)	0.0061 (9)	−0.0003 (9)

O1—C7	1.2233 (18)	O4—C19	1.2194 (18)
O2—C10	1.2203 (19)	O5—C22	1.221 (2)
O3—C10	1.3106 (19)	O6—C22	1.3115 (19)
O3—H3O	0.850 (15)	O6—H6O	0.875 (15)
N1—C7	1.3500 (19)	N2—C19	1.334 (2)
N1—C1	1.4224 (19)	N2—C13	1.434 (2)
N1—H1N	0.894 (18)	N2—H2N	0.87 (2)
C1—C6	1.385 (2)	C13—C18	1.376 (2)
C1—C2	1.388 (2)	C13—C14	1.381 (2)
C2—C3	1.389 (2)	C14—C15	1.388 (2)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.401 (2)	C15—C16	1.399 (2)
C3—C11	1.506 (2)	C15—C23	1.500 (2)
C4—C5	1.383 (2)	C16—C17	1.384 (2)
C4—C12	1.506 (2)	C16—C24	1.503 (2)
C5—C6	1.386 (2)	C17—C18	1.381 (2)
C5—H5	0.9300	C17—H17	0.9300
C6—H6	0.9300	C18—H18	0.9300
C7—C8	1.514 (2)	C19—C20	1.517 (2)
C8—C9	1.517 (2)	C20—C21	1.517 (2)
C8—H8A	0.9700	C20—H20A	0.9700
C8—H8B	0.9700	C20—H20B	0.9700
C9—C10	1.489 (2)	C21—C22	1.487 (2)
C9—H9A	0.9700	C21—H21A	0.9700
C9—H9B	0.9700	C21—H21B	0.9700
C11—H11A	0.9600	C23—H23A	0.9600
C11—H11B	0.9600	C23—H23B	0.9600
C11—H11C	0.9600	C23—H23C	0.9600
C12—H12A	0.9600	C24—H24A	0.9600
C12—H12B	0.9600	C24—H24B	0.9600
C12—H12C	0.9600	C24—H24C	0.9600
C10—O3—H3O	108.4 (14)	C22—O6—H6O	109.0 (14)
C7—N1—C1	126.35 (13)	C19—N2—C13	125.70 (14)
C7—N1—H1N	116.8 (11)	C19—N2—H2N	117.3 (13)
C1—N1—H1N	115.6 (11)	C13—N2—H2N	116.9 (13)
C6—C1—C2	119.26 (14)	C18—C13—C14	119.74 (15)
C6—C1—N1	122.85 (14)	C18—C13—N2	120.78 (15)
C2—C1—N1	117.89 (14)	C14—C13—N2	119.36 (15)
C1—C2—C3	121.68 (15)	C13—C14—C15	121.39 (16)
C1—C2—H2	119.2	C13—C14—H14	119.3
C3—C2—H2	119.2	C15—C14—H14	119.3
C2—C3—C4	119.12 (15)	C14—C15—C16	119.12 (15)
C2—C3—C11	120.02 (16)	C14—C15—C23	119.71 (16)
C4—C3—C11	120.84 (15)	C16—C15—C23	121.16 (15)
C5—C4—C3	118.47 (15)	C17—C16—C15	118.37 (15)
C5—C4—C12	120.40 (16)	C17—C16—C24	120.35 (16)
C3—C4—C12	121.13 (16)	C15—C16—C24	121.26 (15)
C4—C5—C6	122.41 (16)	C18—C17—C16	122.22 (16)
C4—C5—H5	118.8	C18—C17—H17	118.9
C6—C5—H5	118.8	C16—C17—H17	118.9
C1—C6—C5	119.02 (15)	C13—C18—C17	119.08 (16)
C1—C6—H6	120.5	C13—C18—H18	120.5
C5—C6—H6	120.5	C17—C18—H18	120.5
O1—C7—N1	124.17 (14)	O4—C19—N2	123.43 (15)
O1—C7—C8	121.87 (14)	O4—C19—C20	122.88 (14)
N1—C7—C8	113.96 (13)	N2—C19—C20	113.68 (14)
C7—C8—C9	113.04 (13)	C21—C20—C19	113.63 (14)
C7—C8—H8A	109.0	C21—C20—H20A	108.8
C9—C8—H8A	109.0	C19—C20—H20A	108.8
C7—C8—H8B	109.0	C21—C20—H20B	108.8
C9—C8—H8B	109.0	C19—C20—H20B	108.8
H8A—C8—H8B	107.8	H20A—C20—H20B	107.7
C10—C9—C8	113.76 (14)	C22—C21—C20	114.09 (14)
C10—C9—H9A	108.8	C22—C21—H21A	108.7
C8—C9—H9A	108.8	C20—C21—H21A	108.7
C10—C9—H9B	108.8	C22—C21—H21B	108.7
C8—C9—H9B	108.8	C20—C21—H21B	108.7
H9A—C9—H9B	107.7	H21A—C21—H21B	107.6
O2—C10—O3	122.68 (16)	O5—C22—O6	123.06 (16)
O2—C10—C9	123.86 (15)	O5—C22—C21	123.93 (15)
O3—C10—C9	113.46 (15)	O6—C22—C21	113.01 (15)
C3—C11—H11A	109.5	C15—C23—H23A	109.5
C3—C11—H11B	109.5	C15—C23—H23B	109.5
H11A—C11—H11B	109.5	H23A—C23—H23B	109.5
C3—C11—H11C	109.5	C15—C23—H23C	109.5
H11A—C11—H11C	109.5	H23A—C23—H23C	109.5
H11B—C11—H11C	109.5	H23B—C23—H23C	109.5
C4—C12—H12A	109.5	C16—C24—H24A	109.5
C4—C12—H12B	109.5	C16—C24—H24B	109.5
H12A—C12—H12B	109.5	H24A—C24—H24B	109.5
C4—C12—H12C	109.5	C16—C24—H24C	109.5
H12A—C12—H12C	109.5	H24A—C24—H24C	109.5
H12B—C12—H12C	109.5	H24B—C24—H24C	109.5
C7—N1—C1—C6	33.1 (2)	C19—N2—C13—C18	63.8 (2)
C7—N1—C1—C2	−145.84 (16)	C19—N2—C13—C14	−120.24 (19)
C6—C1—C2—C3	−2.7 (2)	C18—C13—C14—C15	2.9 (2)
N1—C1—C2—C3	176.29 (14)	N2—C13—C14—C15	−173.11 (15)
C1—C2—C3—C4	1.5 (2)	C13—C14—C15—C16	−1.0 (2)
C1—C2—C3—C11	−177.34 (15)	C13—C14—C15—C23	178.29 (15)
C2—C3—C4—C5	0.4 (2)	C14—C15—C16—C17	−1.6 (2)
C11—C3—C4—C5	179.24 (16)	C23—C15—C16—C17	179.16 (16)
C2—C3—C4—C12	−179.75 (16)	C14—C15—C16—C24	177.00 (15)
C11—C3—C4—C12	−0.9 (3)	C23—C15—C16—C24	−2.2 (2)
C3—C4—C5—C6	−1.1 (3)	C15—C16—C17—C18	2.3 (3)
C12—C4—C5—C6	179.05 (16)	C24—C16—C17—C18	−176.32 (16)
C2—C1—C6—C5	2.0 (2)	C14—C13—C18—C17	−2.2 (2)
N1—C1—C6—C5	−176.97 (15)	N2—C13—C18—C17	173.74 (15)
C4—C5—C6—C1	−0.1 (3)	C16—C17—C18—C13	−0.4 (3)
C1—N1—C7—O1	−10.9 (3)	C13—N2—C19—O4	1.7 (3)
C1—N1—C7—C8	168.62 (15)	C13—N2—C19—C20	−178.33 (16)
O1—C7—C8—C9	−6.0 (2)	O4—C19—C20—C21	−0.8 (2)
N1—C7—C8—C9	174.42 (14)	N2—C19—C20—C21	179.30 (15)
C7—C8—C9—C10	75.78 (18)	C19—C20—C21—C22	75.46 (19)
C8—C9—C10—O2	6.6 (2)	C20—C21—C22—O5	4.0 (2)
C8—C9—C10—O3	−173.82 (14)	C20—C21—C22—O6	−176.04 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O5i	0.85 (2)	1.82 (2)	2.6681 (18)	174 (2)
N1—H1N···O4ii	0.894 (18)	2.127 (18)	2.9909 (18)	162.5 (15)
O6—H6O···O2i	0.88 (2)	1.78 (2)	2.6555 (18)	175 (2)
N2—H2N···O1	0.87 (2)	2.26 (2)	3.0676 (19)	154.7 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯O5i	0.85 (2)	1.82 (2)	2.6681 (18)	174 (2)
N1—H1N⋯O4ii	0.894 (18)	2.127 (18)	2.9909 (18)	162.5 (15)
O6—H6O⋯O2i	0.88 (2)	1.78 (2)	2.6555 (18)	175 (2)
N2—H2N⋯O1	0.87 (2)	2.26 (2)	3.0676 (19)	154.7 (17)

Symmetry codes: (i) ; (ii) .