N-(2-Methyl-phen-yl)maleamic acid.

In the title compound, C(11)H(11)NO(3), the conformation of the N-H bond is anti to the C=O bond in the amide segment, while it is syn to the ortho-methyl group in the phenyl ring. In the maleamic acid unit, the amide C=O bond is anti to the adjacent C-H bond, while the carboxyl C=O bond is syn to the adjacent C-H bond. The C=O and O-H bonds of the acid group are in the relatively rare anti position to each other. This is an obvious consequence of the intra-molecular O-H⋯O hydrogen bond donated to the amide carbonyl group. The ortho-substituted phenyl ring makes a dihedral angle of 12.7 (1)° with the mean plane of the maleamic acid unit. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into zigzag chains parallel to [001]. These chains are further linked into sheet by weak π-π inter-actions [centroid-centroid distance = 3.425 (2) Å].

Related literature

For studies on the effect of ring- and side-chain substitutions on the crystal structures of amides, see: Gowda et al. (2009 ▶); Prasad et al. (2002 ▶). For the modes of inter­linking carb­oxy­lic acids by hydrogen bonds, see: Jagannathan et al. (1994 ▶); Leiserowitz (1976 ▶).

Experimental

Crystal data

C11H11NO3

M = 205.21

Monoclinic,

a = 7.3942 (3) Å

b = 11.5898 (4) Å

c = 12.9903 (3) Å

β = 114.534 (2)°

V = 1012.72 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 295 K

0.58 × 0.42 × 0.42 mm

Data collection

Oxford Diffraction Gemini R CCD diffractometer

Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.922, T max = 0.962

15644 measured reflections

1776 independent reflections

1453 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.098

S = 1.07

1776 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.13 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 I, global. DOI: 10.1107/S160053681002012X/dn2569sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681002012X/dn2569Isup2.hkl

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

C11H11NO3	F(000) = 432
Mr = 205.21	Dx = 1.346 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8927 reflections
a = 7.3942 (3) Å	θ = 2.5–29.5°
b = 11.5898 (4) Å	µ = 0.10 mm−1
c = 12.9903 (3) Å	T = 295 K
β = 114.534 (2)°	Prism, colourless
V = 1012.72 (5) Å3	0.58 × 0.42 × 0.42 mm
Z = 4

Oxford Diffraction Gemini R CCD diffractometer	1776 independent reflections
graphite	1453 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm-1	Rint = 0.027
ω scans	θmax = 25°, θmin = 2.5°
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009)	h = −8→8
Tmin = 0.922, Tmax = 0.962	k = −13→13
15644 measured reflections	l = −15→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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.056P)2 + 0.0996P] where P = (Fo2 + 2Fc2)/3
1776 reflections	(Δ/σ)max < 0.001
137 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.13 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
O1	0.24625 (18)	0.49123 (8)	0.59119 (8)	0.0661 (3)
O2	0.26421 (19)	0.62958 (9)	0.74100 (8)	0.0701 (4)
H2A	0.2600	0.5770	0.6870	0.105*
O3	0.24623 (18)	0.81655 (10)	0.75227 (8)	0.0711 (4)
N1	0.24594 (15)	0.49437 (9)	0.41733 (8)	0.0432 (3)
H1N	0.2368	0.5389	0.3624	0.052*
C1	0.23624 (18)	0.54568 (11)	0.50723 (9)	0.0416 (3)
C2	0.2115 (2)	0.67235 (11)	0.49860 (10)	0.0444 (3)
H2	0.1931	0.7044	0.4293	0.053*
C3	0.2122 (2)	0.74646 (11)	0.57694 (11)	0.0463 (3)
H3	0.1892	0.8224	0.5517	0.056*
C4	0.2424 (2)	0.73222 (12)	0.69681 (11)	0.0488 (4)
C5	0.26967 (19)	0.37432 (11)	0.40204 (11)	0.0432 (3)
C6	0.2264 (2)	0.33549 (12)	0.29220 (11)	0.0502 (4)
C7	0.2520 (2)	0.21851 (13)	0.27818 (14)	0.0614 (4)
H7	0.2247	0.1910	0.2060	0.074*
C8	0.3162 (3)	0.14215 (13)	0.36698 (15)	0.0680 (5)
H8	0.3303	0.0643	0.3547	0.082*
C9	0.3591 (3)	0.18185 (13)	0.47378 (14)	0.0648 (4)
H9	0.4031	0.1307	0.5345	0.078*
C10	0.3376 (2)	0.29766 (12)	0.49199 (12)	0.0550 (4)
H10	0.3688	0.3242	0.5650	0.066*
C11	0.1553 (3)	0.41495 (15)	0.19286 (12)	0.0711 (5)
H11A	0.1342	0.3721	0.1256	0.107*
H11B	0.2532	0.4737	0.2041	0.107*
H11C	0.0326	0.4502	0.1849	0.107*

	U11	U22	U33	U12	U13	U23
O1	0.1258 (10)	0.0400 (6)	0.0506 (6)	0.0030 (6)	0.0547 (6)	0.0022 (5)
O2	0.1294 (10)	0.0507 (6)	0.0420 (5)	0.0101 (6)	0.0472 (6)	0.0033 (4)
O3	0.1142 (10)	0.0573 (7)	0.0486 (6)	0.0083 (6)	0.0406 (6)	−0.0134 (5)
N1	0.0616 (7)	0.0386 (6)	0.0353 (5)	−0.0011 (5)	0.0261 (5)	−0.0029 (5)
C1	0.0547 (8)	0.0400 (7)	0.0348 (6)	−0.0020 (6)	0.0233 (6)	−0.0022 (5)
C2	0.0620 (8)	0.0418 (7)	0.0327 (6)	0.0025 (6)	0.0231 (6)	0.0018 (5)
C3	0.0650 (9)	0.0367 (6)	0.0397 (7)	0.0057 (6)	0.0243 (6)	0.0008 (5)
C4	0.0642 (9)	0.0468 (8)	0.0397 (7)	0.0051 (6)	0.0260 (6)	−0.0044 (6)
C5	0.0500 (8)	0.0392 (7)	0.0474 (7)	−0.0045 (5)	0.0272 (6)	−0.0079 (6)
C6	0.0567 (8)	0.0491 (8)	0.0485 (7)	−0.0072 (6)	0.0254 (6)	−0.0151 (6)
C7	0.0701 (10)	0.0541 (9)	0.0626 (9)	−0.0079 (7)	0.0301 (8)	−0.0254 (8)
C8	0.0793 (11)	0.0406 (8)	0.0926 (13)	−0.0042 (7)	0.0441 (10)	−0.0151 (8)
C9	0.0849 (12)	0.0444 (8)	0.0776 (11)	0.0072 (7)	0.0461 (9)	0.0057 (8)
C10	0.0737 (10)	0.0482 (8)	0.0532 (8)	0.0046 (7)	0.0364 (7)	−0.0016 (6)
C11	0.1050 (13)	0.0666 (10)	0.0427 (8)	0.0016 (9)	0.0316 (9)	−0.0134 (7)

O1—C1	1.2355 (14)	C5—C6	1.4005 (17)
O2—C4	1.3015 (17)	C6—C7	1.391 (2)
O2—H2A	0.9200	C6—C11	1.492 (2)
O3—C4	1.2076 (16)	C7—C8	1.373 (2)
N1—C1	1.3387 (14)	C7—H7	0.9300
N1—C5	1.4265 (16)	C8—C9	1.368 (2)
N1—H1N	0.8602	C8—H8	0.9300
C1—C2	1.4779 (18)	C9—C10	1.384 (2)
C2—C3	1.3301 (18)	C9—H9	0.9300
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.4876 (18)	C11—H11A	0.9600
C3—H3	0.9300	C11—H11B	0.9600
C5—C10	1.3856 (19)	C11—H11C	0.9600
C4—O2—H2A	108.1	C7—C6—C11	120.42 (12)
C1—N1—C5	127.52 (10)	C5—C6—C11	122.15 (12)
C1—N1—H1N	116.3	C8—C7—C6	122.44 (14)
C5—N1—H1N	116.2	C8—C7—H7	118.8
O1—C1—N1	122.54 (11)	C6—C7—H7	118.8
O1—C1—C2	122.32 (10)	C9—C8—C7	119.28 (14)
N1—C1—C2	115.14 (10)	C9—C8—H8	120.4
C3—C2—C1	128.49 (11)	C7—C8—H8	120.4
C3—C2—H2	115.8	C8—C9—C10	120.33 (15)
C1—C2—H2	115.8	C8—C9—H9	119.8
C2—C3—C4	132.88 (12)	C10—C9—H9	119.8
C2—C3—H3	113.6	C9—C10—C5	120.33 (13)
C4—C3—H3	113.6	C9—C10—H10	119.8
O3—C4—O2	120.58 (12)	C5—C10—H10	119.8
O3—C4—C3	119.39 (13)	C6—C11—H11A	109.5
O2—C4—C3	120.03 (11)	C6—C11—H11B	109.5
C10—C5—C6	120.17 (12)	H11A—C11—H11B	109.5
C10—C5—N1	122.04 (11)	C6—C11—H11C	109.5
C6—C5—N1	117.77 (11)	H11A—C11—H11C	109.5
C7—C6—C5	117.43 (13)	H11B—C11—H11C	109.5
C5—N1—C1—O1	−0.5 (2)	N1—C5—C6—C7	179.30 (12)
C5—N1—C1—C2	179.87 (12)	C10—C5—C6—C11	−179.25 (14)
O1—C1—C2—C3	5.8 (2)	N1—C5—C6—C11	−0.7 (2)
N1—C1—C2—C3	−174.52 (14)	C5—C6—C7—C8	0.3 (2)
C1—C2—C3—C4	2.1 (3)	C11—C6—C7—C8	−179.68 (15)
C2—C3—C4—O3	175.97 (16)	C6—C7—C8—C9	−0.8 (2)
C2—C3—C4—O2	−4.1 (3)	C7—C8—C9—C10	0.2 (2)
C1—N1—C5—C10	−17.3 (2)	C8—C9—C10—C5	0.9 (2)
C1—N1—C5—C6	164.21 (12)	C6—C5—C10—C9	−1.4 (2)
C10—C5—C6—C7	0.8 (2)	N1—C5—C10—C9	−179.82 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3i	0.86	2.22	3.0665 (14)	167
O2—H2A···O1	0.92	1.56	2.4822 (13)	178

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3i	0.86	2.22	3.0665 (14)	167
O2—H2A⋯O1	0.92	1.56	2.4822 (13)	178

Symmetry code: (i) .