N-(2,4,6-Trimethyl-phen-yl)maleamic acid.

The mol-ecular structure of the title compound, C(13)H(15)NO(3), is stabilized by a short intra-molecular O-H⋯O hydrogen bond within the maleamic unit. In the crystal, inter-molecular N-H⋯O hydrogen bonds link mol-ecules into zigzag chains propagating in [010].

Related literature

For our sudies on the effect of ring- and side-chain substitutions on the crystal structures of amides, see: Gowda, Foro et al. (2009 ▶); Gowda, Tokarčík et al. (2009 ▶); Lo & Ng (2009 ▶). For hydrogen bonds in carboxylic acids, see: Leiserowitz (1976 ▶).

Experimental

Crystal data

C13H15NO3

M = 233.26

Monoclinic,

a = 10.8789 (3) Å

b = 11.9095 (2) Å

c = 20.1004 (5) Å

β = 103.014 (2)°

V = 2537.36 (10) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.56 × 0.48 × 0.35 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer

Absorption correction: analytical (CrysAlis Pro; Oxford Diffraction, 2009 ▶) T min = 0.933, T max = 0.965

26868 measured reflections

2386 independent reflections

2029 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.102

S = 1.04

2386 reflections

159 parameters

H-atom parameters constrained

Δρmax = 0.17 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 I, global. DOI: 10.1107/S1600536809044754/bt5119sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044754/bt5119Isup2.hkl

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

C13H15NO3	F(000) = 992
Mr = 233.26	Dx = 1.221 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 17006 reflections
a = 10.8789 (3) Å	θ = 1.9–29.4°
b = 11.9095 (2) Å	µ = 0.09 mm−1
c = 20.1004 (5) Å	T = 295 K
β = 103.014 (2)°	Block, colourless
V = 2537.36 (10) Å3	0.56 × 0.48 × 0.35 mm
Z = 8

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2386 independent reflections
graphite	2029 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm-1	Rint = 0.023
ω scans	θmax = 25.6°, θmin = 2.1°
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009)	h = −13→13
Tmin = 0.933, Tmax = 0.965	k = −14→14
26868 measured reflections	l = −24→24

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)] = 0.037	H-atom parameters constrained
wR(F2) = 0.102	w = 1/[σ2(Fo2) + (0.0469P)2 + 1.3266P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
2386 reflections	Δρmax = 0.17 e Å−3
159 parameters	Δρmin = −0.12 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: 0.0142 (9)

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	Occ. (<1)
C1	0.35967 (13)	0.14861 (11)	0.17051 (7)	0.0419 (3)
C2	0.28501 (17)	0.17469 (12)	0.22158 (8)	0.0576 (4)
H2	0.2547	0.2478	0.2206	0.069*
C3	0.25517 (19)	0.10848 (13)	0.26854 (8)	0.0634 (5)
H3	0.2108	0.1445	0.2968	0.076*
C4	0.27916 (15)	−0.01212 (12)	0.28450 (7)	0.0486 (4)
C5	0.42558 (11)	0.23129 (11)	0.07158 (6)	0.0379 (3)
C6	0.51419 (13)	0.31543 (12)	0.06931 (7)	0.0456 (3)
C7	0.56646 (14)	0.31987 (13)	0.01267 (8)	0.0542 (4)
H7	0.6248	0.376	0.0104	0.065*
C8	0.53555 (14)	0.24425 (13)	−0.04058 (8)	0.0523 (4)
C9	0.44899 (14)	0.16118 (12)	−0.03596 (7)	0.0490 (4)
H9	0.4288	0.1084	−0.0708	0.059*
C10	0.39115 (12)	0.15365 (11)	0.01878 (7)	0.0402 (3)
C11	0.55135 (18)	0.39999 (15)	0.12605 (9)	0.0693 (5)
H11A	0.6218	0.4432	0.119	0.104*
H11B	0.5744	0.3615	0.169	0.104*
H11C	0.4815	0.4491	0.1263	0.104*
C12	0.5918 (2)	0.25320 (19)	−0.10259 (10)	0.0801 (6)
H12A	0.5606	0.1931	−0.1336	0.12*	0.56 (3)
H12B	0.6821	0.2483	−0.0887	0.12*	0.56 (3)
H12C	0.5686	0.3239	−0.1248	0.12*	0.56 (3)
H12D	0.6469	0.3171	−0.0978	0.12*	0.44 (3)
H12E	0.5255	0.2619	−0.1428	0.12*	0.44 (3)
H12F	0.6389	0.1863	−0.1066	0.12*	0.44 (3)
C13	0.29160 (14)	0.06565 (12)	0.01791 (8)	0.0519 (4)
H13A	0.2615	0.0387	−0.0279	0.078*
H13B	0.2227	0.0977	0.034	0.078*
H13C	0.327	0.0044	0.047	0.078*
N1	0.36385 (11)	0.23264 (9)	0.12731 (6)	0.0424 (3)
H1N	0.3257	0.2937	0.1335	0.051*
O1	0.41359 (10)	0.05741 (8)	0.16796 (5)	0.0508 (3)
O2	0.34725 (10)	−0.07126 (8)	0.25195 (5)	0.0521 (3)
H2A	0.3763	−0.0267	0.2227	0.062*
O3	0.23146 (13)	−0.05442 (9)	0.32755 (6)	0.0693 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0520 (8)	0.0339 (7)	0.0424 (7)	0.0010 (6)	0.0165 (6)	0.0039 (5)
C2	0.0900 (12)	0.0343 (7)	0.0601 (9)	0.0118 (7)	0.0415 (9)	0.0074 (6)
C3	0.1035 (13)	0.0422 (8)	0.0594 (10)	0.0066 (8)	0.0497 (10)	0.0029 (7)
C4	0.0692 (9)	0.0397 (7)	0.0379 (7)	−0.0098 (7)	0.0143 (7)	0.0026 (6)
C5	0.0387 (7)	0.0361 (7)	0.0401 (7)	−0.0004 (5)	0.0114 (5)	0.0075 (5)
C6	0.0452 (8)	0.0414 (7)	0.0498 (8)	−0.0081 (6)	0.0098 (6)	0.0039 (6)
C7	0.0474 (8)	0.0531 (9)	0.0658 (10)	−0.0150 (7)	0.0209 (7)	0.0091 (7)
C8	0.0515 (8)	0.0575 (9)	0.0531 (9)	−0.0009 (7)	0.0225 (7)	0.0095 (7)
C9	0.0556 (9)	0.0491 (8)	0.0440 (8)	−0.0036 (7)	0.0149 (6)	−0.0009 (6)
C10	0.0402 (7)	0.0364 (7)	0.0441 (7)	−0.0030 (5)	0.0099 (6)	0.0052 (5)
C11	0.0781 (12)	0.0590 (10)	0.0706 (11)	−0.0267 (9)	0.0163 (9)	−0.0111 (8)
C12	0.0877 (13)	0.0929 (15)	0.0740 (12)	−0.0034 (11)	0.0480 (11)	0.0131 (10)
C13	0.0547 (9)	0.0453 (8)	0.0546 (9)	−0.0148 (7)	0.0101 (7)	0.0023 (6)
N1	0.0534 (7)	0.0323 (6)	0.0459 (6)	0.0032 (5)	0.0204 (5)	0.0065 (5)
O1	0.0653 (6)	0.0409 (5)	0.0518 (6)	0.0141 (5)	0.0252 (5)	0.0110 (4)
O2	0.0692 (7)	0.0352 (5)	0.0546 (6)	−0.0021 (5)	0.0197 (5)	0.0072 (4)
O3	0.1074 (10)	0.0511 (7)	0.0589 (7)	−0.0122 (6)	0.0390 (7)	0.0112 (5)

C1—O1	1.2409 (16)	C9—C10	1.3880 (19)
C1—N1	1.3325 (16)	C9—H9	0.93
C1—C2	1.4784 (19)	C10—C13	1.5044 (18)
C2—C3	1.325 (2)	C11—H11A	0.96
C2—H2	0.93	C11—H11B	0.96
C3—C4	1.482 (2)	C11—H11C	0.96
C3—H3	0.93	C12—H12A	0.96
C4—O3	1.2140 (17)	C12—H12B	0.96
C4—O2	1.3004 (18)	C12—H12C	0.96
C5—C10	1.3937 (19)	C12—H12D	0.96
C5—C6	1.3983 (18)	C12—H12E	0.96
C5—N1	1.4300 (16)	C12—H12F	0.96
C6—C7	1.383 (2)	C13—H13A	0.96
C6—C11	1.507 (2)	C13—H13B	0.96
C7—C8	1.381 (2)	C13—H13C	0.96
C7—H7	0.93	N1—H1N	0.86
C8—C9	1.383 (2)	O2—H2A	0.9
C8—C12	1.511 (2)
O1—C1—N1	123.00 (12)	C9—C10—C13	119.30 (13)
O1—C1—C2	123.46 (12)	C5—C10—C13	122.71 (12)
N1—C1—C2	113.55 (12)	C6—C11—H11A	109.5
C3—C2—C1	129.10 (14)	C6—C11—H11B	109.5
C3—C2—H2	115.5	H11A—C11—H11B	109.5
C1—C2—H2	115.5	C6—C11—H11C	109.5
C2—C3—C4	132.18 (14)	H11A—C11—H11C	109.5
C2—C3—H3	113.9	H11B—C11—H11C	109.5
C4—C3—H3	113.9	C8—C12—H12A	109.5
O3—C4—O2	121.14 (14)	C8—C12—H12B	109.5
O3—C4—C3	118.28 (14)	C8—C12—H12C	109.5
O2—C4—C3	120.56 (12)	C8—C12—H12D	109.5
C10—C5—C6	121.31 (12)	C8—C12—H12E	109.5
C10—C5—N1	120.72 (11)	H12D—C12—H12E	109.5
C6—C5—N1	117.79 (12)	C8—C12—H12F	109.5
C7—C6—C5	117.93 (13)	H12D—C12—H12F	109.5
C7—C6—C11	120.49 (13)	H12E—C12—H12F	109.5
C5—C6—C11	121.58 (13)	C10—C13—H13A	109.5
C8—C7—C6	122.64 (13)	C10—C13—H13B	109.5
C8—C7—H7	118.7	H13A—C13—H13B	109.5
C6—C7—H7	118.7	C10—C13—H13C	109.5
C7—C8—C9	117.71 (13)	H13A—C13—H13C	109.5
C7—C8—C12	121.33 (15)	H13B—C13—H13C	109.5
C9—C8—C12	120.95 (15)	C1—N1—C5	126.37 (11)
C8—C9—C10	122.43 (14)	C1—N1—H1N	116.8
C8—C9—H9	118.8	C5—N1—H1N	116.8
C10—C9—H9	118.8	C4—O2—H2A	109.5
C9—C10—C5	117.95 (12)
O1—C1—C2—C3	−4.9 (3)	C7—C8—C9—C10	1.6 (2)
N1—C1—C2—C3	175.19 (19)	C12—C8—C9—C10	−176.99 (15)
C1—C2—C3—C4	−3.2 (4)	C8—C9—C10—C5	−2.0 (2)
C2—C3—C4—O3	−174.0 (2)	C8—C9—C10—C13	175.94 (14)
C2—C3—C4—O2	4.5 (3)	C6—C5—C10—C9	0.9 (2)
C10—C5—C6—C7	0.4 (2)	N1—C5—C10—C9	176.00 (12)
N1—C5—C6—C7	−174.81 (12)	C6—C5—C10—C13	−176.92 (13)
C10—C5—C6—C11	179.69 (14)	N1—C5—C10—C13	−1.86 (19)
N1—C5—C6—C11	4.5 (2)	O1—C1—N1—C5	1.9 (2)
C5—C6—C7—C8	−0.8 (2)	C2—C1—N1—C5	−178.23 (13)
C11—C6—C7—C8	179.93 (16)	C10—C5—N1—C1	59.84 (18)
C6—C7—C8—C9	−0.2 (2)	C6—C5—N1—C1	−124.94 (15)
C6—C7—C8—C12	178.41 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1	0.90	1.61	2.5037 (13)	174
N1—H1N···O3i	0.86	2.12	2.9587 (15)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O1	0.90	1.61	2.5037 (13)	174
N1—H1N⋯O3i	0.86	2.12	2.9587 (15)	165

Symmetry code: (i) .