N-(3-Chloro-4-methyl-phen-yl)maleamic acid.

In the title compound, C(11)H(10)ClNO(3), the dihedral angle between the benzene ring and the amide group is 6.6 (10)° and an intramolecular O-H⋯O hydrogen bond occurs. In the crystal, molecules are linked by N-H⋯O hydrogen bonds, generating C(7) zigzag chains.

Related literature

For our studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Gowda et al. (2000 ▶, 2003 ▶, 2007 ▶); Chaithanya et al. (2012 ▶). For N-chloro­aryl­amides, see: Jyothi & Gowda (2004 ▶). For N-bromo­aryl­sulfonamides, see: Usha & Gowda (2006 ▶).

Experimental

Crystal data

C11H10ClNO3

M = 239.65

Monoclinic,

a = 9.005 (1) Å

b = 13.491 (2) Å

c = 8.757 (1) Å

β = 97.91 (1)°

V = 1053.7 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.35 mm−1

T = 293 K

0.48 × 0.40 × 0.34 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.849, T max = 0.890

4069 measured reflections

2147 independent reflections

1798 reflections with I > 2σ(I)

R int = 0.011

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.105

S = 1.04

2147 reflections

152 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.27 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/S1600536812007842/kp2391sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812007842/kp2391Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812007842/kp2391Isup3.cml

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

C11H10ClNO3	F(000) = 496
Mr = 239.65	Dx = 1.511 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1538 reflections
a = 9.005 (1) Å	θ = 2.8–27.9°
b = 13.491 (2) Å	µ = 0.35 mm−1
c = 8.757 (1) Å	T = 293 K
β = 97.91 (1)°	Prism, yellow
V = 1053.7 (2) Å3	0.48 × 0.40 × 0.34 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2147 independent reflections
Radiation source: fine-focus sealed tube	1798 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.011
Rotation method data acquisition using ω and phi scans	θmax = 26.4°, θmin = 2.8°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −11→8
Tmin = 0.849, Tmax = 0.890	k = −16→14
4069 measured reflections	l = −7→10

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0582P)2 + 0.2934P] where P = (Fo2 + 2Fc2)/3
2147 reflections	(Δ/σ)max < 0.001
152 parameters	Δρmax = 0.33 e Å−3
2 restraints	Δρmin = −0.27 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
C1	0.66874 (17)	0.04762 (11)	0.39541 (18)	0.0309 (3)
C2	0.59803 (18)	0.12392 (11)	0.30833 (19)	0.0359 (4)
H2	0.6327	0.1887	0.3217	0.043*
C3	0.47494 (18)	0.10217 (11)	0.20120 (19)	0.0355 (4)
C4	0.41627 (17)	0.00764 (12)	0.17621 (18)	0.0332 (4)
C5	0.49161 (19)	−0.06669 (12)	0.2641 (2)	0.0398 (4)
H5	0.4571	−0.1315	0.2503	0.048*
C6	0.61566 (18)	−0.04879 (12)	0.3714 (2)	0.0381 (4)
H6	0.6637	−0.1009	0.4275	0.046*
C7	0.85614 (17)	0.14437 (12)	0.56761 (18)	0.0324 (3)
C8	0.98127 (18)	0.13165 (12)	0.69471 (19)	0.0351 (4)
H8	1.0081	0.0665	0.7197	0.042*
C9	1.06040 (18)	0.20092 (13)	0.77789 (19)	0.0378 (4)
H9	1.1357	0.1758	0.8509	0.045*
C10	1.05105 (18)	0.31142 (12)	0.77605 (19)	0.0366 (4)
C11	0.27987 (18)	−0.01421 (14)	0.0625 (2)	0.0434 (4)
H11A	0.2960	0.0081	−0.0380	0.052*
H11B	0.1949	0.0196	0.0930	0.052*
H11C	0.2614	−0.0843	0.0598	0.052*
N1	0.79351 (15)	0.06004 (10)	0.51139 (16)	0.0338 (3)
H1N	0.827 (2)	0.0067 (12)	0.560 (2)	0.041*
O1	0.81351 (14)	0.22693 (9)	0.51661 (15)	0.0483 (3)
O2	1.13005 (15)	0.35781 (10)	0.87433 (15)	0.0507 (4)
O3	0.95988 (16)	0.35732 (9)	0.67213 (17)	0.0537 (4)
H3O	0.911 (2)	0.3136 (16)	0.611 (2)	0.064*
Cl1	0.38990 (6)	0.19890 (3)	0.09113 (6)	0.0620 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0306 (7)	0.0240 (7)	0.0350 (8)	−0.0015 (6)	−0.0065 (6)	−0.0020 (6)
C2	0.0396 (8)	0.0203 (7)	0.0427 (9)	−0.0025 (6)	−0.0119 (7)	−0.0008 (6)
C3	0.0381 (8)	0.0234 (7)	0.0407 (9)	0.0018 (6)	−0.0099 (7)	−0.0006 (7)
C4	0.0324 (8)	0.0264 (8)	0.0375 (8)	−0.0021 (6)	−0.0064 (6)	−0.0040 (6)
C5	0.0425 (9)	0.0218 (8)	0.0503 (10)	−0.0058 (6)	−0.0112 (7)	−0.0008 (7)
C6	0.0421 (9)	0.0219 (8)	0.0453 (9)	−0.0008 (6)	−0.0118 (7)	0.0024 (7)
C7	0.0323 (7)	0.0259 (7)	0.0359 (8)	−0.0011 (6)	−0.0064 (6)	−0.0018 (6)
C8	0.0372 (8)	0.0264 (8)	0.0378 (9)	0.0012 (6)	−0.0083 (7)	0.0009 (6)
C9	0.0374 (8)	0.0341 (9)	0.0368 (8)	0.0010 (7)	−0.0125 (7)	0.0008 (7)
C10	0.0370 (8)	0.0322 (8)	0.0376 (8)	−0.0037 (7)	−0.0051 (7)	−0.0042 (7)
C11	0.0395 (9)	0.0356 (9)	0.0497 (10)	−0.0037 (7)	−0.0135 (8)	−0.0050 (8)
N1	0.0354 (7)	0.0229 (6)	0.0385 (7)	−0.0005 (5)	−0.0115 (6)	0.0022 (5)
O1	0.0517 (7)	0.0246 (6)	0.0584 (8)	−0.0014 (5)	−0.0286 (6)	0.0011 (5)
O2	0.0559 (8)	0.0382 (7)	0.0511 (8)	−0.0093 (6)	−0.0174 (6)	−0.0103 (6)
O3	0.0593 (8)	0.0273 (6)	0.0638 (9)	−0.0037 (6)	−0.0298 (6)	−0.0009 (6)
Cl1	0.0708 (4)	0.0261 (2)	0.0743 (4)	0.00032 (19)	−0.0426 (3)	0.0058 (2)

C1—C2	1.383 (2)	C7—N1	1.334 (2)
C1—C6	1.392 (2)	C7—C8	1.481 (2)
C1—N1	1.4170 (19)	C8—C9	1.330 (2)
C2—C3	1.382 (2)	C8—H8	0.9300
C2—H2	0.9300	C9—C10	1.493 (2)
C3—C4	1.386 (2)	C9—H9	0.9300
C3—Cl1	1.7364 (16)	C10—O2	1.212 (2)
C4—C5	1.384 (2)	C10—O3	1.296 (2)
C4—C11	1.500 (2)	C11—H11A	0.9600
C5—C6	1.378 (2)	C11—H11B	0.9600
C5—H5	0.9300	C11—H11C	0.9600
C6—H6	0.9300	N1—H1N	0.869 (15)
C7—O1	1.2410 (19)	O3—H3O	0.871 (16)
C2—C1—C6	119.32 (14)	N1—C7—C8	114.71 (13)
C2—C1—N1	124.51 (13)	C9—C8—C7	128.69 (15)
C6—C1—N1	116.16 (13)	C9—C8—H8	115.7
C3—C2—C1	118.80 (14)	C7—C8—H8	115.7
C3—C2—H2	120.6	C8—C9—C10	132.10 (15)
C1—C2—H2	120.6	C8—C9—H9	113.9
C2—C3—C4	123.73 (14)	C10—C9—H9	113.9
C2—C3—Cl1	117.95 (12)	O2—C10—O3	120.32 (16)
C4—C3—Cl1	118.31 (12)	O2—C10—C9	118.75 (16)
C5—C4—C3	115.58 (14)	O3—C10—C9	120.92 (14)
C5—C4—C11	121.39 (14)	C4—C11—H11A	109.5
C3—C4—C11	123.03 (14)	C4—C11—H11B	109.5
C6—C5—C4	122.79 (15)	H11A—C11—H11B	109.5
C6—C5—H5	118.6	C4—C11—H11C	109.5
C4—C5—H5	118.6	H11A—C11—H11C	109.5
C5—C6—C1	119.74 (15)	H11B—C11—H11C	109.5
C5—C6—H6	120.1	C7—N1—C1	128.23 (13)
C1—C6—H6	120.1	C7—N1—H1N	115.1 (13)
O1—C7—N1	122.59 (14)	C1—N1—H1N	116.2 (13)
O1—C7—C8	122.70 (14)	C10—O3—H3O	108.9 (16)
C6—C1—C2—C3	0.9 (3)	C2—C1—C6—C5	−1.5 (3)
N1—C1—C2—C3	−178.44 (16)	N1—C1—C6—C5	177.89 (15)
C1—C2—C3—C4	0.6 (3)	O1—C7—C8—C9	3.8 (3)
C1—C2—C3—Cl1	−178.99 (13)	N1—C7—C8—C9	−176.65 (18)
C2—C3—C4—C5	−1.5 (3)	C7—C8—C9—C10	1.3 (3)
Cl1—C3—C4—C5	178.12 (13)	C8—C9—C10—O2	173.92 (19)
C2—C3—C4—C11	178.21 (16)	C8—C9—C10—O3	−5.7 (3)
Cl1—C3—C4—C11	−2.2 (2)	O1—C7—N1—C1	−3.5 (3)
C3—C4—C5—C6	0.9 (3)	C8—C7—N1—C1	177.01 (15)
C11—C4—C5—C6	−178.86 (17)	C2—C1—N1—C7	6.7 (3)
C4—C5—C6—C1	0.6 (3)	C6—C1—N1—C7	−172.69 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.87 (2)	2.11 (2)	2.9546 (19)	164 (2)
O3—H3O···O1	0.87 (2)	1.62 (2)	2.4885 (17)	173 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.87 (2)	2.11 (2)	2.9546 (19)	164 (2)
O3—H3O⋯O1	0.87 (2)	1.62 (2)	2.4885 (17)	173 (2)

Symmetry code: (i) .