N-(2-Chloro-4-nitro-phen-yl)maleamic acid monohydrate.

The title compound, C(10)H(7)ClN(2)O(5)·H(2)O, crystallizes with a half-mol-ecule each of N-(2-chloro-4-nitro-phen-yl)maleamic acid (located on a mirror plane) and water (located on a twofold rotation axis) in the asymmetric unit. The main mol-ecule is planar by symmetry and its conformation is stabilized by an intra-molecular O-H⋯O hydrogen bond. In the crystal, N-H⋯O and O-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network.

Related literature

For studies on the effects of substituents on the structures and other aspects of N-(ar­yl)-amides, see: Gowda et al. (2000 ▶); Prasad et al. (2002 ▶); Shakuntala et al. (2011 ▶), on N-(ar­yl)-methane­sulfonamides, see: Jayalakshmi & Gowda (2004 ▶) on N-(ar­yl)-aryl­sulfonamides, see: Shetty & Gowda (2005 ▶) and on N-chloro­aryl­sulfonamides, see: Gowda & Kumar (2003 ▶). For modes of inter­linking carb­oxy­lic acids by hydrogen bonds, see: Leiserowitz (1976 ▶).

Experimental

Crystal data

C10H7ClN2O5·H2O

M = 288.64

Orthorhombic,

a = 6.7499 (2) Å

b = 20.3357 (5) Å

c = 17.1671 (4) Å

V = 2356.42 (11) Å3

Z = 8

Mo Kα radiation

μ = 0.35 mm−1

T = 293 K

0.81 × 0.25 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector

Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2009 ▶), based on expressions derived by Clark & Reid (1995 ▶)] T min = 0.860, T max = 0.965

14309 measured reflections

1310 independent reflections

1131 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.128

S = 1.07

1310 reflections

118 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.44 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: Mercury (Macrae et al., 2008 ▶) and DIAMOND (Brandenburg, 2002 ▶); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009 ▶) and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811052573/bt5742sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811052573/bt5742Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811052573/bt5742Isup3.cml

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

C10H7ClN2O5·H2O	F(000) = 1184
Mr = 288.64	Dx = 1.627 Mg m−3
Orthorhombic, Cmca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2bc 2	Cell parameters from 4659 reflections
a = 6.7499 (2) Å	θ = 2.0–29.4°
b = 20.3357 (5) Å	µ = 0.35 mm−1
c = 17.1671 (4) Å	T = 293 K
V = 2356.42 (11) Å3	Prism, colorless
Z = 8	0.81 × 0.25 × 0.12 mm

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector	1310 independent reflections
Radiation source: fine-focus sealed tube	1131 reflections with I > 2σ(I)
graphite	Rint = 0.027
Detector resolution: 10.4340 pixels mm-1	θmax = 26.4°, θmin = 4.1°
ω scans	h = −8→8
Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2009), based on expressions derived by Clark & Reid (1995)]	k = −24→25
Tmin = 0.860, Tmax = 0.965	l = −21→21
14309 measured reflections

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)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.128	w = 1/[σ2(Fo2) + (0.0582P)2 + 3.7851P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
1310 reflections	Δρmax = 0.25 e Å−3
118 parameters	Δρmin = −0.44 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0049 (7)

Experimental. CrysAlisPro (Oxford Diffraction, 2009) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived (Clark & Reid, 1995).

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	0.0000	0.38088 (14)	0.11375 (16)	0.0392 (7)
C2	0.0000	0.31306 (15)	0.08336 (18)	0.0456 (8)
H2A	0.0000	0.2800	0.1208	0.055*
C3	0.0000	0.29270 (15)	0.00997 (17)	0.0450 (8)
H3A	0.0000	0.2472	0.0048	0.054*
C4	0.0000	0.32802 (18)	−0.06507 (19)	0.0546 (9)
C5	0.0000	0.44114 (13)	0.23898 (16)	0.0350 (6)
C6	0.0000	0.43336 (14)	0.32018 (16)	0.0365 (6)
C7	0.0000	0.48666 (15)	0.36958 (17)	0.0435 (7)
H7A	0.0000	0.4810	0.4233	0.052*
C8	0.0000	0.54865 (15)	0.33704 (18)	0.0440 (8)
C9	0.0000	0.55845 (14)	0.25794 (19)	0.0425 (7)
H9A	0.0000	0.6008	0.2377	0.051*
C10	0.0000	0.50500 (15)	0.20906 (17)	0.0405 (7)
H10A	0.0000	0.5114	0.1554	0.049*
Cl1	0.0000	0.35546 (4)	0.36046 (4)	0.0487 (3)
N1	0.0000	0.38484 (12)	0.19242 (14)	0.0431 (6)
H1A	0.0000	0.3480	0.2169	0.052*
N2	0.0000	0.60563 (15)	0.38903 (18)	0.0647 (9)
O1	0.0000	0.42972 (11)	0.07268 (12)	0.0671 (9)
O2	0.0000	0.39196 (13)	−0.06678 (14)	0.0886 (12)
H7W	0.0000	0.4070	−0.0267	0.133*
O3	0.0000	0.29773 (15)	−0.12558 (15)	0.0864 (11)
O4	0.0000	0.59696 (16)	0.45824 (16)	0.1041 (14)
O5	0.0000	0.65986 (14)	0.35994 (18)	0.1049 (15)
O11	0.2500	0.26168 (15)	0.2500	0.0931 (11)
H11	0.319 (5)	0.2243 (11)	0.2174 (17)	0.112*

	U11	U22	U33	U12	U13	U23
C1	0.0580 (18)	0.0330 (15)	0.0266 (13)	0.000	0.000	−0.0002 (11)
C2	0.075 (2)	0.0294 (15)	0.0328 (15)	0.000	0.000	0.0028 (12)
C3	0.070 (2)	0.0306 (15)	0.0349 (16)	0.000	0.000	−0.0042 (12)
C4	0.089 (3)	0.0443 (19)	0.0306 (16)	0.000	0.000	−0.0048 (14)
C5	0.0481 (16)	0.0313 (13)	0.0257 (13)	0.000	0.000	0.0002 (10)
C6	0.0487 (16)	0.0328 (14)	0.0279 (14)	0.000	0.000	0.0032 (11)
C7	0.063 (2)	0.0418 (17)	0.0259 (13)	0.000	0.000	−0.0025 (12)
C8	0.062 (2)	0.0360 (16)	0.0341 (15)	0.000	0.000	−0.0082 (12)
C9	0.0593 (19)	0.0311 (14)	0.0371 (16)	0.000	0.000	0.0002 (12)
C10	0.0587 (18)	0.0357 (15)	0.0270 (14)	0.000	0.000	0.0020 (11)
Cl1	0.0793 (6)	0.0367 (4)	0.0301 (4)	0.000	0.000	0.0070 (3)
N1	0.0757 (18)	0.0288 (12)	0.0248 (11)	0.000	0.000	0.0015 (9)
N2	0.108 (3)	0.0425 (17)	0.0436 (17)	0.000	0.000	−0.0118 (13)
O1	0.144 (3)	0.0313 (12)	0.0258 (11)	0.000	0.000	0.0009 (9)
O2	0.197 (4)	0.0424 (15)	0.0262 (12)	0.000	0.000	0.0001 (10)
O3	0.166 (3)	0.0607 (17)	0.0327 (13)	0.000	0.000	−0.0123 (12)
O4	0.213 (4)	0.0621 (19)	0.0368 (15)	0.000	0.000	−0.0167 (13)
O5	0.218 (5)	0.0353 (14)	0.0618 (19)	0.000	0.000	−0.0111 (13)
O11	0.145 (3)	0.0680 (19)	0.0664 (19)	0.000	0.021 (2)	0.000

C1—O1	1.218 (4)	C6—Cl1	1.728 (3)
C1—N1	1.353 (4)	C7—C8	1.379 (4)
C1—C2	1.474 (4)	C7—H7A	0.9300
C2—C3	1.326 (4)	C8—C9	1.372 (4)
C2—H2A	0.9300	C8—N2	1.463 (4)
C3—C4	1.475 (4)	C9—C10	1.373 (4)
C3—H3A	0.9300	C9—H9A	0.9300
C4—O3	1.208 (4)	C10—H10A	0.9300
C4—O2	1.301 (4)	N1—H1A	0.8600
C5—C10	1.397 (4)	N2—O4	1.201 (4)
C5—N1	1.396 (4)	N2—O5	1.211 (4)
C5—C6	1.403 (4)	O2—H7W	0.7531
C6—C7	1.376 (4)	O11—H11	1.052 (3)
O1—C1—N1	122.0 (3)	C6—C7—H7A	121.0
O1—C1—C2	123.9 (3)	C8—C7—H7A	121.0
N1—C1—C2	114.1 (3)	C9—C8—C7	122.2 (3)
C3—C2—C1	128.9 (3)	C9—C8—N2	119.3 (3)
C3—C2—H2A	115.5	C7—C8—N2	118.5 (3)
C1—C2—H2A	115.5	C10—C9—C8	119.3 (3)
C2—C3—C4	132.7 (3)	C10—C9—H9A	120.3
C2—C3—H3A	113.7	C8—C9—H9A	120.3
C4—C3—H3A	113.7	C9—C10—C5	120.8 (3)
O3—C4—O2	119.4 (3)	C9—C10—H10A	119.6
O3—C4—C3	120.2 (3)	C5—C10—H10A	119.6
O2—C4—C3	120.4 (3)	C1—N1—C5	128.3 (3)
C10—C5—N1	123.5 (3)	C1—N1—H1A	115.9
C10—C5—C6	118.1 (3)	C5—N1—H1A	115.8
N1—C5—C6	118.4 (2)	O4—N2—O5	122.8 (3)
C7—C6—C5	121.6 (3)	O4—N2—C8	119.2 (3)
C7—C6—Cl1	118.4 (2)	O5—N2—C8	118.0 (3)
C5—C6—Cl1	120.1 (2)	C4—O2—H7W	112.6
C6—C7—C8	118.1 (3)
O1—C1—C2—C3	0.0	C7—C8—C9—C10	0.000 (1)
N1—C1—C2—C3	180.0	N2—C8—C9—C10	180.0
C1—C2—C3—C4	0.0	C8—C9—C10—C5	0.0
C2—C3—C4—O3	180.0	N1—C5—C10—C9	180.0
C2—C3—C4—O2	0.0	C6—C5—C10—C9	0.0
C10—C5—C6—C7	0.0	O1—C1—N1—C5	0.0
N1—C5—C6—C7	180.0	C2—C1—N1—C5	180.0
C10—C5—C6—Cl1	180.0	C10—C5—N1—C1	0.0
N1—C5—C6—Cl1	0.0	C6—C5—N1—C1	180.0
C5—C6—C7—C8	0.0	C9—C8—N2—O4	180.0
Cl1—C6—C7—C8	180.0	C7—C8—N2—O4	0.000 (1)
C6—C7—C8—C9	0.000 (1)	C9—C8—N2—O5	0.000 (1)
C6—C7—C8—N2	180.0	C7—C8—N2—O5	180.0

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O11	0.86	2.50	3.178 (3)	136.
O2—H7W···O1	0.75	1.77	2.515 (3)	171.
O11—H11···O3i	1.05 (1)	2.04 (2)	2.978 (2)	146 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O11	0.86	2.50	3.178 (3)	136
O2—H7W⋯O1	0.75	1.77	2.515 (3)	171
O11—H11⋯O3i	1.05 (1)	2.04 (2)	2.978 (2)	146 (3)

Symmetry code: (i) .