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

In the crystal structure of the title compound, C(10)H(6)Cl(3)NO(3), the conformation of the amide bond is trans. The C=O and O-H bonds of the acid group are in the relatively rare anti position to each other. This is a consequence of the intra-molecular O-H⋯O hydrogen bond donated to the amide carbonyl group stabilizing the mol-ecular structure. In the crystal, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into zigzag chains along the c axis.

Related literature

For studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Arjunan et al. (2004 ▶); Bhat & Gowda (2000 ▶); Gowda et al. (2000 ▶, 2009 ▶); Lo & Ng (2009 ▶); Prasad et al. (2002 ▶), and on N-(ar­yl)-methane­sulfonamides, see: Jayalakshmi & Gowda (2004 ▶). For modes of inter­linking carb­oxy­lic acids by hydrogen bonds, see: Leiserowitz (1976 ▶).

Experimental

Crystal data

C10H6Cl3NO3

M = 294.51

Monoclinic,

a = 21.928 (3) Å

b = 8.2678 (8) Å

c = 13.248 (2) Å

β = 99.08 (1)°

V = 2371.7 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.77 mm−1

T = 293 K

0.44 × 0.44 × 0.40 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.729, T max = 0.749

4862 measured reflections

2436 independent reflections

2000 reflections with I > 2σ(I)

R int = 0.012

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.094

S = 1.08

2436 reflections

161 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.55 e Å−3

Δρmin = −0.44 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 datablock(s) I, global. DOI: 10.1107/S1600536811029436/bt5581sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029436/bt5581Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811029436/bt5581Isup3.cml

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

C10H6Cl3NO3	F(000) = 1184
Mr = 294.51	Dx = 1.650 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2201 reflections
a = 21.928 (3) Å	θ = 2.6–27.9°
b = 8.2678 (8) Å	µ = 0.77 mm−1
c = 13.248 (2) Å	T = 293 K
β = 99.08 (1)°	Prism, colourless
V = 2371.7 (5) Å3	0.44 × 0.44 × 0.40 mm
Z = 8

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2436 independent reflections
Radiation source: fine-focus sealed tube	2000 reflections with I > 2σ(I)
graphite	Rint = 0.012
Rotation method data acquisition using ω and φ scans	θmax = 26.3°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −21→27
Tmin = 0.729, Tmax = 0.749	k = −9→10
4862 measured reflections	l = −14→16

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)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.094	w = 1/[σ2(Fo2) + (0.0453P)2 + 2.1238P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.008
2436 reflections	Δρmax = 0.55 e Å−3
161 parameters	Δρmin = −0.44 e Å−3
2 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: 0.0069 (5)

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
Cl1	0.01367 (3)	0.14374 (7)	0.38180 (5)	0.0547 (2)
Cl2	−0.05298 (3)	0.76688 (8)	0.35643 (5)	0.0546 (2)
Cl3	0.18696 (3)	0.61105 (7)	0.44095 (6)	0.0594 (2)
O1	0.13622 (8)	0.26049 (19)	0.24188 (11)	0.0489 (4)
O2	0.20438 (7)	−0.1698 (2)	0.11143 (12)	0.0491 (4)
O3	0.15810 (9)	0.0634 (2)	0.10918 (12)	0.0554 (5)
H3O	0.1526 (15)	0.138 (3)	0.147 (2)	0.083*
N1	0.14268 (8)	0.2673 (2)	0.41225 (12)	0.0356 (4)
H1N	0.1593 (10)	0.234 (3)	0.4704 (14)	0.043*
C1	0.09629 (9)	0.3880 (2)	0.40607 (13)	0.0325 (4)
C2	0.03409 (10)	0.3452 (2)	0.38660 (14)	0.0355 (4)
C3	−0.01220 (9)	0.4607 (3)	0.37139 (15)	0.0389 (5)
H3	−0.0535	0.4305	0.3569	0.047*
C4	0.00448 (9)	0.6214 (3)	0.37825 (14)	0.0362 (5)
C5	0.06509 (10)	0.6697 (3)	0.40216 (16)	0.0394 (5)
H5	0.0753	0.7787	0.4096	0.047*
C6	0.11040 (9)	0.5516 (2)	0.41482 (15)	0.0358 (4)
C7	0.15744 (9)	0.2035 (2)	0.32652 (15)	0.0344 (4)
C8	0.19895 (10)	0.0623 (3)	0.34006 (15)	0.0391 (5)
H8	0.2183	0.0426	0.4066	0.047*
C9	0.21238 (10)	−0.0406 (3)	0.26948 (16)	0.0407 (5)
H9	0.2405	−0.1206	0.2950	0.049*
C10	0.19092 (9)	−0.0518 (3)	0.15725 (15)	0.0371 (5)

	U11	U22	U33	U12	U13	U23
Cl1	0.0623 (4)	0.0373 (3)	0.0631 (4)	−0.0113 (3)	0.0060 (3)	−0.0095 (3)
Cl2	0.0499 (3)	0.0574 (4)	0.0557 (4)	0.0228 (3)	0.0064 (3)	−0.0018 (3)
Cl3	0.0376 (3)	0.0433 (3)	0.0960 (5)	−0.0025 (2)	0.0072 (3)	0.0033 (3)
O1	0.0625 (10)	0.0509 (10)	0.0327 (8)	0.0257 (8)	0.0056 (7)	0.0070 (7)
O2	0.0507 (9)	0.0483 (9)	0.0485 (9)	0.0001 (7)	0.0086 (7)	−0.0150 (7)
O3	0.0717 (12)	0.0589 (11)	0.0340 (8)	0.0200 (9)	0.0034 (7)	−0.0018 (7)
N1	0.0442 (10)	0.0324 (9)	0.0292 (8)	0.0089 (7)	0.0026 (7)	0.0037 (7)
C1	0.0398 (10)	0.0322 (10)	0.0263 (9)	0.0039 (8)	0.0073 (7)	0.0011 (8)
C2	0.0437 (11)	0.0346 (10)	0.0288 (9)	−0.0037 (8)	0.0075 (8)	−0.0044 (8)
C3	0.0345 (10)	0.0498 (13)	0.0330 (10)	−0.0009 (9)	0.0073 (8)	−0.0067 (9)
C4	0.0391 (11)	0.0403 (11)	0.0302 (10)	0.0108 (9)	0.0085 (8)	−0.0009 (8)
C5	0.0453 (12)	0.0307 (10)	0.0433 (11)	0.0040 (9)	0.0108 (9)	0.0018 (9)
C6	0.0351 (10)	0.0341 (10)	0.0390 (11)	0.0007 (8)	0.0082 (8)	0.0021 (8)
C7	0.0379 (10)	0.0326 (10)	0.0322 (10)	0.0033 (8)	0.0039 (8)	0.0019 (8)
C8	0.0456 (12)	0.0380 (11)	0.0315 (10)	0.0102 (9)	−0.0006 (8)	0.0018 (8)
C9	0.0425 (12)	0.0352 (11)	0.0429 (11)	0.0107 (9)	0.0018 (9)	0.0007 (9)
C10	0.0320 (10)	0.0415 (11)	0.0387 (11)	−0.0035 (9)	0.0087 (8)	−0.0040 (9)

Cl1—C2	1.723 (2)	C2—C3	1.385 (3)
Cl2—C4	1.733 (2)	C3—C4	1.377 (3)
Cl3—C6	1.731 (2)	C3—H3	0.9300
O1—C7	1.237 (2)	C4—C5	1.376 (3)
O2—C10	1.210 (3)	C5—C6	1.384 (3)
O3—C10	1.299 (3)	C5—H5	0.9300
O3—H3O	0.819 (18)	C7—C8	1.473 (3)
N1—C7	1.338 (3)	C8—C9	1.331 (3)
N1—C1	1.418 (2)	C8—H8	0.9300
N1—H1N	0.843 (16)	C9—C10	1.490 (3)
C1—C6	1.388 (3)	C9—H9	0.9300
C1—C2	1.393 (3)
C10—O3—H3O	112 (2)	C4—C5—H5	120.9
C7—N1—C1	119.74 (16)	C6—C5—H5	120.9
C7—N1—H1N	121.4 (16)	C5—C6—C1	122.08 (19)
C1—N1—H1N	118.8 (16)	C5—C6—Cl3	118.60 (16)
C6—C1—C2	117.51 (18)	C1—C6—Cl3	119.32 (15)
C6—C1—N1	122.16 (18)	O1—C7—N1	120.82 (18)
C2—C1—N1	120.28 (18)	O1—C7—C8	123.28 (18)
C3—C2—C1	121.69 (19)	N1—C7—C8	115.89 (17)
C3—C2—Cl1	118.74 (16)	C9—C8—C7	128.44 (19)
C1—C2—Cl1	119.58 (16)	C9—C8—H8	115.8
C4—C3—C2	118.33 (19)	C7—C8—H8	115.8
C4—C3—H3	120.8	C8—C9—C10	132.11 (19)
C2—C3—H3	120.8	C8—C9—H9	113.9
C5—C4—C3	122.17 (19)	C10—C9—H9	113.9
C5—C4—Cl2	119.15 (16)	O2—C10—O3	120.37 (19)
C3—C4—Cl2	118.69 (16)	O2—C10—C9	119.2 (2)
C4—C5—C6	118.12 (19)	O3—C10—C9	120.47 (18)
C7—N1—C1—C6	−98.7 (2)	C4—C5—C6—Cl3	178.00 (15)
C7—N1—C1—C2	78.7 (2)	C2—C1—C6—C5	−1.7 (3)
C6—C1—C2—C3	3.1 (3)	N1—C1—C6—C5	175.71 (18)
N1—C1—C2—C3	−174.36 (17)	C2—C1—C6—Cl3	179.01 (14)
C6—C1—C2—Cl1	−176.52 (14)	N1—C1—C6—Cl3	−3.5 (3)
N1—C1—C2—Cl1	6.0 (2)	C1—N1—C7—O1	8.1 (3)
C1—C2—C3—C4	−1.5 (3)	C1—N1—C7—C8	−170.97 (18)
Cl1—C2—C3—C4	178.18 (15)	O1—C7—C8—C9	−11.8 (4)
C2—C3—C4—C5	−1.7 (3)	N1—C7—C8—C9	167.2 (2)
C2—C3—C4—Cl2	178.53 (14)	C7—C8—C9—C10	−1.0 (4)
C3—C4—C5—C6	3.0 (3)	C8—C9—C10—O2	−170.9 (2)
Cl2—C4—C5—C6	−177.20 (15)	C8—C9—C10—O3	9.0 (4)
C4—C5—C6—C1	−1.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.84 (2)	2.04 (2)	2.884 (2)	175 (2)
O3—H3O···O1	0.82 (2)	1.69 (2)	2.498 (2)	168 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.84 (2)	2.04 (2)	2.884 (2)	175 (2)
O3—H3O⋯O1	0.82 (2)	1.69 (2)	2.498 (2)	168 (3)

Symmetry code: (i) .