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

The asymmetric unit of the title compound, C(12)H(13)NO(3), contains two independent mol-ecules. The conformation of the N-H bond and the C=O bond in the amide segment are anti to each other. The mol-ecular conformation of each mol-ecule is stabilized by an intra-molecular O-H⋯O hydrogen bond. In the crystal, mol-ecules are connected through intermolecular N-H⋯O hydrogen bonds. In addition, there is a carbon-yl-carbonyl dipolar inter-action with an O⋯C contact of 2.926 (3) Å.

Related literature

For our sudies on the effect of ring- and side-chain substitutions on the crystal structures of amides, see: Gowda et al. (2009a ▶,b ▶,c ▶); Prasad et al. (2002 ▶). For bond-length data, see: Allen et al. (1998 ▶). For modes of inter­linking carboxylic acids by hydrogen bonds, see: Leiserowitz (1976 ▶); Jagannathan et al. (1994 ▶).

Experimental

Crystal data

C12H13NO3

M = 219.23

Orthorhombic,

a = 12.5268 (4) Å

b = 12.9226 (4) Å

c = 14.6835 (5) Å

V = 2376.95 (13) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.56 × 0.54 × 0.48 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer

Absorption correction: multi-scan (CrysAlis Pro; Oxford Diffraction, 2009 ▶) T min = 0.940, T max = 0.955

38472 measured reflections

2533 independent reflections

2201 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.089

S = 1.07

2533 reflections

305 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.12 e Å−3

Data collection: CrysAlis Pro (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis Pro; data reduction: CrysAlis Pro; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2002 ▶); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009 ▶) and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809042470/bt5099sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809042470/bt5099Isup2.hkl

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

C12H13NO3	F(000) = 928
Mr = 219.23	Dx = 1.225 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 20238 reflections
a = 12.5268 (4) Å	θ = 2.1–29.4°
b = 12.9226 (4) Å	µ = 0.09 mm−1
c = 14.6835 (5) Å	T = 295 K
V = 2376.95 (13) Å3	Prism, colourless
Z = 8	0.56 × 0.54 × 0.48 mm

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2533 independent reflections
graphite	2201 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm-1	Rint = 0.025
ω scans	θmax = 25.6°, θmin = 2.1°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	h = −15→15
Tmin = 0.940, Tmax = 0.955	k = −15→15
38472 measured reflections	l = −17→17

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0646P)2] where P = (Fo2 + 2Fc2)/3
2533 reflections	(Δ/σ)max < 0.001
305 parameters	Δρmax = 0.14 e Å−3
2 restraints	Δρmin = −0.12 e Å−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	0.25341 (16)	0.39170 (14)	0.10573 (14)	0.0489 (5)
C2	0.34832 (18)	0.37146 (16)	0.15245 (15)	0.0570 (5)
C3	0.44161 (19)	0.3689 (2)	0.10282 (19)	0.0703 (7)
H3	0.5057	0.3534	0.1317	0.084*
C4	0.4408 (2)	0.3891 (2)	0.0114 (2)	0.0824 (8)
H4	0.5045	0.3875	−0.0211	0.099*
C5	0.3477 (2)	0.4115 (2)	−0.03281 (17)	0.0767 (7)
H5	0.3494	0.4271	−0.0946	0.092*
C6	0.2509 (2)	0.41152 (16)	0.01250 (16)	0.0617 (6)
C7	0.10578 (16)	0.47012 (14)	0.18861 (14)	0.0486 (5)
C8	0.00863 (15)	0.44838 (14)	0.24183 (14)	0.0475 (4)
H8	−0.0079	0.3787	0.2493	0.057*
C9	−0.05843 (15)	0.51409 (14)	0.28054 (14)	0.0469 (5)
H9	−0.1152	0.4829	0.3107	0.056*
C10	−0.05898 (16)	0.62944 (15)	0.28426 (14)	0.0483 (5)
C11	0.3486 (3)	0.3555 (2)	0.25411 (18)	0.0814 (7)
H11A	0.4185	0.3342	0.2734	0.122*
H11B	0.2976	0.303	0.2698	0.122*
H11C	0.3299	0.4191	0.2839	0.122*
C12	0.1475 (3)	0.4315 (3)	−0.0362 (2)	0.0929 (9)
H12A	0.1169	0.495	−0.0146	0.139*
H12B	0.0989	0.3755	−0.0246	0.139*
H12C	0.1605	0.4365	−0.1005	0.139*
N1	0.15528 (13)	0.38779 (12)	0.15561 (12)	0.0514 (4)
H1N	0.1307 (18)	0.3268 (17)	0.1688 (16)	0.062*
O1	0.14060 (13)	0.55904 (11)	0.17420 (12)	0.0726 (5)
O2	0.01844 (12)	0.68259 (10)	0.24839 (12)	0.0591 (4)
H2A	0.067 (2)	0.640 (2)	0.2168 (18)	0.071*
O3	−0.13208 (14)	0.67180 (12)	0.32315 (12)	0.0728 (5)
C21	0.69266 (14)	0.49032 (15)	0.15611 (12)	0.0432 (4)
C22	0.64858 (15)	0.48672 (16)	0.24349 (13)	0.0500 (5)
C23	0.65844 (19)	0.39448 (19)	0.29159 (15)	0.0641 (6)
H23	0.6292	0.3896	0.3496	0.077*
C24	0.7103 (2)	0.3108 (2)	0.25536 (18)	0.0734 (7)
H24	0.7175	0.2504	0.2893	0.088*
C25	0.7512 (2)	0.31594 (19)	0.16950 (16)	0.0676 (6)
H25	0.7851	0.2581	0.1453	0.081*
C26	0.74363 (16)	0.40489 (16)	0.11727 (14)	0.0517 (5)
C27	0.76542 (15)	0.64136 (16)	0.07866 (12)	0.0452 (4)
C28	0.73911 (15)	0.73479 (15)	0.02517 (12)	0.0455 (4)
H28	0.6669	0.7505	0.0205	0.055*
C29	0.80542 (15)	0.79940 (14)	−0.01721 (13)	0.0459 (4)
H29	0.7718	0.8548	−0.0457	0.055*
C30	0.92344 (16)	0.79890 (17)	−0.02710 (16)	0.0556 (5)
C31	0.5931 (2)	0.5778 (2)	0.28480 (16)	0.0700 (6)
H31A	0.5664	0.5593	0.3439	0.105*
H31B	0.5347	0.5982	0.2465	0.105*
H31C	0.6425	0.6342	0.2906	0.105*
C32	0.7872 (2)	0.4054 (2)	0.02141 (17)	0.0750 (7)
H32A	0.8546	0.4408	0.0205	0.112*
H32B	0.7379	0.4403	−0.0181	0.112*
H32C	0.7969	0.3355	0.0009	0.112*
N2	0.68287 (12)	0.58427 (13)	0.10535 (11)	0.0455 (4)
H2N	0.6232 (16)	0.6091 (17)	0.0914 (15)	0.055*
O4	0.85813 (11)	0.61612 (13)	0.09830 (11)	0.0665 (4)
O5	0.96486 (13)	0.85754 (14)	−0.08053 (13)	0.0768 (5)
O6	0.98128 (12)	0.73556 (19)	0.02073 (15)	0.0970 (8)
H6A	0.944 (3)	0.685 (3)	0.057 (3)	0.116*

	U11	U22	U33	U12	U13	U23
C1	0.0508 (11)	0.0374 (9)	0.0585 (11)	−0.0027 (9)	0.0129 (10)	−0.0054 (9)
C2	0.0592 (12)	0.0494 (12)	0.0623 (12)	−0.0093 (10)	0.0059 (11)	−0.0118 (10)
C3	0.0507 (12)	0.0769 (16)	0.0835 (17)	−0.0117 (12)	0.0087 (12)	−0.0201 (14)
C4	0.0672 (16)	0.0939 (19)	0.0861 (19)	−0.0245 (15)	0.0330 (15)	−0.0243 (16)
C5	0.0903 (19)	0.0815 (17)	0.0581 (13)	−0.0216 (15)	0.0227 (14)	−0.0082 (12)
C6	0.0706 (14)	0.0523 (12)	0.0622 (13)	−0.0056 (11)	0.0079 (12)	−0.0023 (10)
C7	0.0476 (11)	0.0342 (10)	0.0641 (12)	−0.0011 (9)	0.0063 (9)	0.0024 (9)
C8	0.0450 (10)	0.0319 (9)	0.0654 (11)	−0.0024 (8)	0.0027 (9)	0.0004 (9)
C9	0.0408 (10)	0.0411 (10)	0.0587 (11)	−0.0007 (8)	0.0003 (9)	0.0018 (9)
C10	0.0509 (11)	0.0404 (10)	0.0536 (11)	0.0064 (10)	−0.0065 (10)	−0.0059 (9)
C11	0.0836 (17)	0.0905 (18)	0.0702 (15)	0.0041 (15)	−0.0008 (14)	−0.0064 (14)
C12	0.096 (2)	0.107 (2)	0.0757 (17)	0.0050 (18)	−0.0048 (17)	0.0136 (16)
N1	0.0520 (9)	0.0336 (8)	0.0688 (10)	−0.0028 (7)	0.0148 (8)	0.0015 (8)
O1	0.0681 (10)	0.0378 (7)	0.1120 (13)	−0.0057 (7)	0.0323 (10)	0.0003 (8)
O2	0.0579 (9)	0.0351 (7)	0.0843 (10)	−0.0007 (7)	0.0032 (8)	−0.0074 (7)
O3	0.0757 (11)	0.0502 (8)	0.0924 (12)	0.0134 (8)	0.0203 (10)	−0.0100 (8)
C21	0.0318 (8)	0.0537 (11)	0.0440 (9)	−0.0060 (8)	−0.0052 (8)	0.0082 (8)
C22	0.0418 (10)	0.0618 (12)	0.0464 (10)	−0.0055 (9)	−0.0012 (9)	0.0078 (9)
C23	0.0655 (14)	0.0739 (14)	0.0528 (11)	−0.0056 (13)	−0.0001 (11)	0.0197 (11)
C24	0.0832 (17)	0.0629 (14)	0.0742 (15)	0.0040 (13)	−0.0054 (14)	0.0225 (13)
C25	0.0729 (14)	0.0562 (12)	0.0738 (14)	0.0096 (12)	−0.0027 (14)	0.0035 (11)
C26	0.0468 (10)	0.0558 (11)	0.0525 (10)	−0.0011 (10)	−0.0035 (9)	0.0008 (9)
C27	0.0366 (10)	0.0582 (11)	0.0407 (9)	−0.0030 (9)	−0.0040 (8)	0.0062 (8)
C28	0.0344 (9)	0.0538 (11)	0.0484 (10)	0.0008 (9)	0.0007 (9)	0.0040 (9)
C29	0.0424 (9)	0.0460 (10)	0.0494 (10)	−0.0002 (8)	0.0023 (9)	0.0035 (9)
C30	0.0449 (11)	0.0578 (12)	0.0643 (12)	−0.0118 (10)	0.0003 (10)	0.0091 (11)
C31	0.0711 (14)	0.0823 (16)	0.0565 (12)	0.0068 (13)	0.0147 (11)	0.0056 (12)
C32	0.0820 (17)	0.0803 (16)	0.0626 (13)	0.0058 (14)	0.0126 (13)	−0.0049 (13)
N2	0.0311 (7)	0.0567 (10)	0.0486 (8)	0.0000 (7)	0.0006 (7)	0.0115 (8)
O4	0.0365 (7)	0.0845 (11)	0.0784 (10)	−0.0085 (8)	−0.0110 (7)	0.0377 (9)
O5	0.0529 (9)	0.0795 (11)	0.0979 (13)	−0.0113 (8)	0.0134 (8)	0.0336 (10)
O6	0.0379 (8)	0.1251 (17)	0.1281 (16)	−0.0123 (10)	−0.0069 (9)	0.0741 (15)

C1—C6	1.393 (3)	C21—C26	1.397 (3)
C1—C2	1.397 (3)	C21—C22	1.398 (3)
C1—N1	1.432 (3)	C21—N2	1.430 (2)
C2—C3	1.378 (3)	C22—C23	1.391 (3)
C2—C11	1.507 (4)	C22—C31	1.495 (3)
C3—C4	1.368 (4)	C23—C24	1.369 (4)
C3—H3	0.93	C23—H23	0.93
C4—C5	1.365 (4)	C24—C25	1.362 (4)
C4—H4	0.93	C24—H24	0.93
C5—C6	1.383 (4)	C25—C26	1.385 (3)
C5—H5	0.93	C25—H25	0.93
C6—C12	1.502 (4)	C26—C32	1.510 (3)
C7—O1	1.247 (2)	C27—O4	1.240 (2)
C7—N1	1.323 (3)	C27—N2	1.329 (2)
C7—C8	1.473 (3)	C27—C28	1.478 (3)
C8—C9	1.323 (3)	C28—C29	1.332 (3)
C8—H8	0.93	C28—H28	0.93
C9—C10	1.492 (3)	C29—C30	1.486 (3)
C9—H9	0.93	C29—H29	0.93
C10—O3	1.210 (2)	C30—O5	1.208 (2)
C10—O2	1.300 (3)	C30—O6	1.299 (3)
C11—H11A	0.96	C31—H31A	0.96
C11—H11B	0.96	C31—H31B	0.96
C11—H11C	0.96	C31—H31C	0.96
C12—H12A	0.96	C32—H32A	0.96
C12—H12B	0.96	C32—H32B	0.96
C12—H12C	0.96	C32—H32C	0.96
N1—H1N	0.87 (2)	N2—H2N	0.839 (19)
O2—H2A	0.94 (3)	O6—H6A	0.96 (4)
C6—C1—C2	122.42 (19)	C26—C21—C22	121.93 (17)
C6—C1—N1	119.32 (19)	C26—C21—N2	119.83 (16)
C2—C1—N1	118.21 (18)	C22—C21—N2	118.22 (18)
C3—C2—C1	117.8 (2)	C23—C22—C21	117.4 (2)
C3—C2—C11	121.3 (2)	C23—C22—C31	120.63 (18)
C1—C2—C11	120.9 (2)	C21—C22—C31	122.01 (18)
C4—C3—C2	120.5 (3)	C24—C23—C22	121.5 (2)
C4—C3—H3	119.7	C24—C23—H23	119.3
C2—C3—H3	119.7	C22—C23—H23	119.3
C5—C4—C3	120.9 (2)	C25—C24—C23	119.9 (2)
C5—C4—H4	119.5	C25—C24—H24	120
C3—C4—H4	119.5	C23—C24—H24	120
C4—C5—C6	121.3 (2)	C24—C25—C26	121.8 (2)
C4—C5—H5	119.3	C24—C25—H25	119.1
C6—C5—H5	119.3	C26—C25—H25	119.1
C5—C6—C1	116.9 (2)	C25—C26—C21	117.45 (19)
C5—C6—C12	121.8 (2)	C25—C26—C32	119.7 (2)
C1—C6—C12	121.3 (2)	C21—C26—C32	122.85 (19)
O1—C7—N1	120.98 (18)	O4—C27—N2	120.93 (17)
O1—C7—C8	123.68 (17)	O4—C27—C28	123.18 (17)
N1—C7—C8	115.34 (16)	N2—C27—C28	115.89 (16)
C9—C8—C7	129.05 (17)	C29—C28—C27	128.42 (18)
C9—C8—H8	115.5	C29—C28—H28	115.8
C7—C8—H8	115.5	C27—C28—H28	115.8
C8—C9—C10	131.31 (19)	C28—C29—C30	131.57 (18)
C8—C9—H9	114.3	C28—C29—H29	114.2
C10—C9—H9	114.3	C30—C29—H29	114.2
O3—C10—O2	121.11 (18)	O5—C30—O6	120.45 (19)
O3—C10—C9	118.2 (2)	O5—C30—C29	119.2 (2)
O2—C10—C9	120.65 (18)	O6—C30—C29	120.32 (19)
C2—C11—H11A	109.5	C22—C31—H31A	109.5
C2—C11—H11B	109.5	C22—C31—H31B	109.5
H11A—C11—H11B	109.5	H31A—C31—H31B	109.5
C2—C11—H11C	109.5	C22—C31—H31C	109.5
H11A—C11—H11C	109.5	H31A—C31—H31C	109.5
H11B—C11—H11C	109.5	H31B—C31—H31C	109.5
C6—C12—H12A	109.5	C26—C32—H32A	109.5
C6—C12—H12B	109.5	C26—C32—H32B	109.5
H12A—C12—H12B	109.5	H32A—C32—H32B	109.5
C6—C12—H12C	109.5	C26—C32—H32C	109.5
H12A—C12—H12C	109.5	H32A—C32—H32C	109.5
H12B—C12—H12C	109.5	H32B—C32—H32C	109.5
C7—N1—C1	124.14 (16)	C27—N2—C21	123.92 (16)
C7—N1—H1N	118.8 (16)	C27—N2—H2N	114.2 (16)
C1—N1—H1N	116.8 (15)	C21—N2—H2N	121.9 (16)
C10—O2—H2A	111.5 (15)	C30—O6—H6A	117 (2)
C6—C1—C2—C3	−1.6 (3)	C26—C21—C22—C23	0.8 (3)
N1—C1—C2—C3	175.98 (19)	N2—C21—C22—C23	179.67 (18)
C6—C1—C2—C11	177.0 (2)	C26—C21—C22—C31	−179.38 (19)
N1—C1—C2—C11	−5.4 (3)	N2—C21—C22—C31	−0.5 (3)
C1—C2—C3—C4	2.1 (3)	C21—C22—C23—C24	0.7 (3)
C11—C2—C3—C4	−176.5 (3)	C31—C22—C23—C24	−179.1 (2)
C2—C3—C4—C5	−0.4 (4)	C22—C23—C24—C25	−1.7 (4)
C3—C4—C5—C6	−2.0 (4)	C23—C24—C25—C26	1.1 (4)
C4—C5—C6—C1	2.5 (4)	C24—C25—C26—C21	0.3 (4)
C4—C5—C6—C12	−177.3 (3)	C24—C25—C26—C32	−178.1 (2)
C2—C1—C6—C5	−0.7 (3)	C22—C21—C26—C25	−1.3 (3)
N1—C1—C6—C5	−178.2 (2)	N2—C21—C26—C25	179.84 (18)
C2—C1—C6—C12	179.1 (2)	C22—C21—C26—C32	177.0 (2)
N1—C1—C6—C12	1.5 (3)	N2—C21—C26—C32	−1.8 (3)
O1—C7—C8—C9	1.8 (4)	O4—C27—C28—C29	7.2 (3)
N1—C7—C8—C9	−177.9 (2)	N2—C27—C28—C29	−172.82 (19)
C7—C8—C9—C10	−0.4 (4)	C27—C28—C29—C30	1.7 (4)
C8—C9—C10—O3	178.4 (2)	C28—C29—C30—O5	168.9 (2)
C8—C9—C10—O2	−3.2 (3)	C28—C29—C30—O6	−10.7 (4)
O1—C7—N1—C1	3.2 (3)	O4—C27—N2—C21	−1.2 (3)
C8—C7—N1—C1	−177.03 (18)	C28—C27—N2—C21	178.79 (17)
C6—C1—N1—C7	−84.2 (3)	C26—C21—N2—C27	−64.1 (3)
C2—C1—N1—C7	98.2 (2)	C22—C21—N2—C27	117.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3i	0.87 (2)	2.01 (2)	2.824 (2)	156 (2)
N2—H2N···O5ii	0.84 (2)	2.04 (2)	2.856 (2)	166 (2)
O2—H2A···O1	0.94 (3)	1.53 (3)	2.465 (2)	173 (2)
O6—H6A···O4	0.96 (4)	1.52 (4)	2.462 (2)	163 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3i	0.87 (2)	2.01 (2)	2.824 (2)	156 (2)
N2—H2N⋯O5ii	0.839 (19)	2.04 (2)	2.856 (2)	166 (2)
O2—H2A⋯O1	0.94 (3)	1.53 (3)	2.465 (2)	173 (2)
O6—H6A⋯O4	0.96 (4)	1.52 (4)	2.462 (2)	163 (4)

Symmetry codes: (i) ; (ii) .