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

In the title compound, C(10)H(8)ClNO(3), the molecular conformation is stabilized by two intra-molecular hydrogen bonds. The first is a short O-H⋯O hydrogen bond within the maleamic acid unit and the second is a C-H⋯O hydrogen bond which connects the amide group with the phenyl ring. The maleamic acid unit is essentially planar, with an r.m.s. deviation of 0.044 Å, and makes a dihedral angle of 15.2 (1)° with the phenyl ring. In the crystal, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into C(7) chains running [010].

Related literature

For studies on the effect of ring- and side-chain substitutions on the crystal structures of amides, see: Gowda et al. (2010 ▶); Prasad et al. (2002 ▶); Shakuntala et al. (2009 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C10H8ClNO3

M = 225.62

Monoclinic,

a = 10.7779 (3) Å

b = 13.2103 (4) Å

c = 7.1372 (2) Å

β = 104.976 (3)°

V = 981.69 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.37 mm−1

T = 295 K

0.55 × 0.09 × 0.06 mm

Data collection

Oxford Diffraction Gemini R, CCD diffractometer

Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.852, T max = 0.982

15632 measured reflections

1829 independent reflections

1533 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.081

S = 1.08

1829 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.16 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/S1600536810021446/bx2280sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810021446/bx2280Isup2.hkl

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

C10H8ClNO3	F(000) = 464
Mr = 225.62	Dx = 1.527 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8764 reflections
a = 10.7779 (3) Å	θ = 2.0–29.5°
b = 13.2103 (4) Å	µ = 0.37 mm−1
c = 7.1372 (2) Å	T = 295 K
β = 104.976 (3)°	Rod, colourless
V = 981.69 (5) Å3	0.55 × 0.09 × 0.06 mm
Z = 4

Oxford Diffraction Gemini R, CCD diffractometer	1829 independent reflections
graphite	1533 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm-1	Rint = 0.027
ω scans	θmax = 25.5°, θmin = 2.0°
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009)	h = −13→13
Tmin = 0.852, Tmax = 0.982	k = −16→16
15632 measured reflections	l = −8→8

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0488P)2 + 0.0776P] where P = (Fo2 + 2Fc2)/3
1829 reflections	(Δ/σ)max = 0.001
136 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.16 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	0.31064 (12)	0.29347 (9)	0.57205 (19)	0.0320 (3)
C2	0.44462 (13)	0.28772 (10)	0.6940 (2)	0.0372 (3)
H2	0.4774	0.2228	0.7228	0.045*
C3	0.52416 (13)	0.36307 (11)	0.7676 (2)	0.0401 (3)
H3	0.6043	0.3415	0.8403	0.048*
C4	0.50988 (14)	0.47472 (11)	0.7564 (2)	0.0426 (4)
C5	0.12674 (13)	0.18104 (10)	0.42427 (19)	0.0319 (3)
C6	0.03012 (12)	0.25287 (10)	0.38134 (18)	0.0328 (3)
H6	0.0463	0.3197	0.4214	0.039*
C7	−0.09097 (13)	0.22302 (11)	0.27750 (19)	0.0367 (3)
C8	−0.11862 (14)	0.12464 (12)	0.2179 (2)	0.0444 (4)
H8	−0.201	0.1061	0.149	0.053*
C9	−0.02125 (16)	0.05452 (12)	0.2627 (2)	0.0509 (4)
H9	−0.0383	−0.0123	0.2236	0.061*
C10	0.10121 (14)	0.08138 (11)	0.3646 (2)	0.0432 (4)
H10	0.1662	0.0331	0.3932	0.052*
N1	0.25350 (10)	0.20331 (8)	0.53348 (16)	0.0346 (3)
H1N	0.2998	0.1519	0.5813	0.042*
O1	0.25666 (9)	0.37411 (7)	0.51038 (16)	0.0479 (3)
O2	0.40462 (10)	0.51612 (8)	0.65145 (18)	0.0565 (3)
H2A	0.3485	0.4673	0.5973	0.085*
O3	0.59801 (11)	0.52618 (9)	0.84566 (19)	0.0666 (4)
Cl1	−0.21185 (3)	0.31393 (3)	0.22262 (6)	0.05280 (16)

	U11	U22	U33	U12	U13	U23
C1	0.0286 (7)	0.0273 (7)	0.0383 (7)	0.0013 (5)	0.0054 (6)	0.0006 (6)
C2	0.0316 (7)	0.0292 (7)	0.0465 (8)	0.0040 (6)	0.0023 (6)	0.0016 (6)
C3	0.0284 (7)	0.0370 (8)	0.0484 (8)	0.0011 (6)	−0.0016 (6)	0.0001 (6)
C4	0.0387 (8)	0.0345 (8)	0.0524 (9)	−0.0072 (6)	0.0080 (7)	−0.0053 (6)
C5	0.0306 (7)	0.0300 (7)	0.0336 (7)	−0.0038 (5)	0.0054 (6)	0.0015 (5)
C6	0.0314 (7)	0.0286 (7)	0.0358 (7)	−0.0026 (6)	0.0042 (6)	0.0003 (5)
C7	0.0307 (7)	0.0427 (8)	0.0344 (7)	−0.0021 (6)	0.0045 (6)	0.0031 (6)
C8	0.0362 (8)	0.0462 (9)	0.0461 (8)	−0.0128 (7)	0.0019 (6)	−0.0033 (7)
C9	0.0523 (10)	0.0333 (8)	0.0626 (10)	−0.0119 (7)	0.0069 (8)	−0.0096 (7)
C10	0.0411 (8)	0.0294 (7)	0.0560 (9)	−0.0008 (6)	0.0070 (7)	−0.0021 (6)
N1	0.0293 (6)	0.0257 (6)	0.0444 (7)	0.0022 (5)	0.0014 (5)	0.0023 (5)
O1	0.0340 (5)	0.0281 (5)	0.0707 (7)	0.0001 (4)	−0.0058 (5)	0.0070 (5)
O2	0.0445 (6)	0.0282 (6)	0.0871 (9)	−0.0008 (5)	−0.0004 (6)	−0.0016 (5)
O3	0.0538 (7)	0.0450 (7)	0.0886 (9)	−0.0191 (6)	−0.0038 (6)	−0.0113 (6)
Cl1	0.0326 (2)	0.0540 (3)	0.0625 (3)	0.00544 (16)	−0.00438 (17)	0.00293 (18)

C1—O1	1.2389 (16)	C6—C7	1.3813 (18)
C1—N1	1.3364 (17)	C6—H6	0.93
C1—C2	1.4828 (19)	C7—C8	1.376 (2)
C2—C3	1.330 (2)	C7—Cl1	1.7404 (15)
C2—H2	0.93	C8—C9	1.374 (2)
C3—C4	1.483 (2)	C8—H8	0.93
C3—H3	0.93	C9—C10	1.379 (2)
C4—O3	1.2073 (18)	C9—H9	0.93
C4—O2	1.3069 (18)	C10—H10	0.93
C5—C6	1.3834 (19)	N1—H1N	0.86
C5—C10	1.3891 (19)	O2—H2A	0.90
C5—N1	1.4178 (17)
O1—C1—N1	122.96 (12)	C5—C6—H6	120.8
O1—C1—C2	123.32 (12)	C8—C7—C6	122.32 (13)
N1—C1—C2	113.72 (11)	C8—C7—Cl1	119.50 (11)
C3—C2—C1	128.61 (13)	C6—C7—Cl1	118.19 (11)
C3—C2—H2	115.7	C9—C8—C7	118.25 (13)
C1—C2—H2	115.7	C9—C8—H8	120.9
C2—C3—C4	132.50 (13)	C7—C8—H8	120.9
C2—C3—H3	113.7	C8—C9—C10	121.25 (14)
C4—C3—H3	113.7	C8—C9—H9	119.4
O3—C4—O2	120.99 (14)	C10—C9—H9	119.4
O3—C4—C3	118.36 (14)	C9—C10—C5	119.50 (14)
O2—C4—C3	120.65 (13)	C9—C10—H10	120.2
C6—C5—C10	120.27 (12)	C5—C10—H10	120.2
C6—C5—N1	122.87 (11)	C1—N1—C5	128.71 (11)
C10—C5—N1	116.85 (12)	C1—N1—H1N	115.6
C7—C6—C5	118.41 (12)	C5—N1—H1N	115.6
C7—C6—H6	120.8	C4—O2—H2A	109.5
O1—C1—C2—C3	5.1 (2)	Cl1—C7—C8—C9	179.82 (12)
N1—C1—C2—C3	−175.30 (14)	C7—C8—C9—C10	0.0 (2)
C1—C2—C3—C4	0.0 (3)	C8—C9—C10—C5	0.4 (2)
C2—C3—C4—O3	177.02 (16)	C6—C5—C10—C9	−0.2 (2)
C2—C3—C4—O2	−3.3 (3)	N1—C5—C10—C9	178.16 (13)
C10—C5—C6—C7	−0.4 (2)	O1—C1—N1—C5	−1.2 (2)
N1—C5—C6—C7	−178.62 (12)	C2—C1—N1—C5	179.26 (12)
C5—C6—C7—C8	0.8 (2)	C6—C5—N1—C1	−17.6 (2)
C5—C6—C7—Cl1	−179.60 (10)	C10—C5—N1—C1	164.11 (13)
C6—C7—C8—C9	−0.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1	0.90	1.60	2.4992 (14)	176
N1—H1N···O3i	0.86	1.99	2.8403 (15)	172
C6—H6···O1	0.93	2.31	2.8658 (16)	118

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O1	0.90	1.60	2.4992 (14)	176
N1—H1N⋯O3i	0.86	1.99	2.8403 (15)	172
C6—H6⋯O1	0.93	2.31	2.8658 (16)	118

Symmetry code: (i) .