N-(2-Chloro-4-nitro­phen­yl)maleamic acid monohydrate

Shakuntala, K.; Fronc, M.; Gowda, B.T.; Kožíšek, J.

doi:10.1107/S1600536811052573

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Pages o99-o100

doi:10.1107/S1600536811052573

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N-(2-Chloro-4-nitrophenyl)maleamic acid monohydrate

K. Shakuntala,^a Marek Fronc,^b B. Thimme Gowda ^a ^* and Jozef Kožíšek ^b

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bInstitute of Physical Chemistry and Chemical Physics, Slovak University of Technology, Radlinského 9, SK-812 37 Bratislava, Slovak Republic
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 3 December 2011; accepted 6 December 2011; online 14 December 2011)

The title compound, C₁₀H₇ClN₂O₅·H₂O, crystallizes with a half-molecule each of N-(2-chloro-4-nitrophenyl)maleamic acid (located on a mirror plane) and water (located on a twofold rotation axis) in the asymmetric unit. The main molecule is planar by symmetry and its conformation is stabilized by an intramolecular O—H⋯O hydrogen bond. In the crystal, N—H⋯O and O—H⋯O hydrogen bonds link the molecules 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_r = 288.64
Orthorhombic, C m c a
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 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ), 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[F² > 2σ(F²)] = 0.044
wR(F²) = 0.128
S = 1.07
1310 reflections
118 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.44 e Å⁻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) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811052573/bt5742sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811052573/bt5742Isup3.cml

checkCIF report

Comment top

The amide moiety is a constituent of many biologically significant compounds. As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Gowda et al., 2000; Prasad et al., 2002; Shakuntala et al., 2011), N-(aryl)-methanesulfonamides (Jayalakshmi & Gowda, 2004), N-(aryl)-arylsulfonamides (Shetty & Gowda, 2005) and N-chloroarylsulfoamides (Gowda & Kumar, 2003), in the present work, the crystal structure of N-(2-chloro-4-nitrophenyl)-maleamic acid monohydrate(I) has been determined (Fig.1).

The conformations of the N—H and the C=O bonds in the amide segment are anti to each other. But the conformation of the N—H bond is syn to the ortho-Cl atom in the phenyl ring, similar to that observed between the N—H bond and ortho-methyl group in N-(4-Chloro-2-methylphenyl)-maleamic acid (II) (Shakuntala et al., 2011).

In the maleamic acid moiety, the amide C=O bond is anti to the adjacent C—H bond, while the carboxyl C=O bond is syn to the adjacent C—H bond. The observed rare anti conformation of the C=O and O—H bonds of the acid group is similar to that observed in (II). This may be due to the hydrogen bond donated to the amide carbonyl group by the carboxyl group. The C2–C3 bond length of 1.327 (4)Å indicates the double bond character.

The various modes of interlinking carboxylic acids by hydrogen bonds is described elsewhere (Leiserowitz, 1976).

In (I), both the intramolecular O–H···O and N—H···Cl, and intermolecular N–H···O and O–H···O hydrogen bonds have been observed. The packing of molecules linked by intermolecular N–H···O and O–H···O hydrogen bonds into infinite chains is shown in Fig. 2.

Related literature top

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 top

The solution of maleic anhydride (0.025 mol) in toluene (25 ml) was treated dropwise with the solution of 2-chloro-4-nitroaniline (0.025 mol) also in toluene (20 ml) with constant stirring. The resulting mixture was stirred for about 30 min and set aside for an additional 30 min at room temperature for the completion of reaction. The mixture was then treated with dilute hydrochloric acid to remove the unreacted 2-chloro-4-nitroaniline. The resultant solid N-(2-chloro-4-nitrophenyl)-maleamic acid monohydrate was filtered under suction and washed thoroughly with water to remove the unreacted maleic anhydride and maleic acid. It was recrystallized to constant melting point from ethanol. The purity of the compound was checked and characterized by its infrared spectra.

Prism like colorless single crystals of the title compound used in X-ray diffraction studies were grown in an ethanol solution by slow evaporation (0.5 g in about 30 ml of ethanol) at room temperature.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); 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 (Sheldrick, 2008), PLATON (Spek, 2009) and WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Molecular structure of the title compound showing the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Packing view of the title compound. Molecular chains along a-axis are generated by N–H···O hydrogen bonds which are shown as dashed lines. H atoms not involved in H-bonding have been omitted.

3-[(2-chloro-4-nitrophenyl)carbamoyl]prop-2-enoic acid monohydrate top

Crystal data top

C₁₀H₇ClN₂O₅·H₂O	F(000) = 1184
M_r = 288.64	D_x = 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

Data collection top

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 monochromator	R_int = 0.027
Detector resolution: 10.4340 pixels mm^-1	θ_max = 26.4°, θ_min = 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
T_min = 0.860, T_max = 0.965	l = −21→21
14309 measured reflections

Refinement top

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(F_o²) + (0.0582P)² + 3.7851P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
1310 reflections	Δρ_max = 0.25 e Å⁻³
118 parameters	Δρ_min = −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)

Crystal data top

C₁₀H₇ClN₂O₅·H₂O	V = 2356.42 (11) Å³
M_r = 288.64	Z = 8
Orthorhombic, Cmca	Mo Kα radiation
a = 6.7499 (2) Å	µ = 0.35 mm⁻¹
b = 20.3357 (5) Å	T = 293 K
c = 17.1671 (4) Å	0.81 × 0.25 × 0.12 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector	1310 independent reflections
Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2009), based on expressions derived by Clark & Reid (1995)]	1131 reflections with I > 2σ(I)
T_min = 0.860, T_max = 0.965	R_int = 0.027
14309 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	1 restraint
wR(F²) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.25 e Å⁻³
1310 reflections	Δρ_min = −0.44 e Å⁻³
118 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) −x+1/2, −y+1/2, −z.

Experimental details

Crystal data
Chemical formula	C₁₀H₇ClN₂O₅·H₂O
M_r	288.64
Crystal system, space group	Orthorhombic, Cmca
Temperature (K)	293
a, b, c (Å)	6.7499 (2), 20.3357 (5), 17.1671 (4)
V (Å³)	2356.42 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.81 × 0.25 × 0.12

Data collection
Diffractometer	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, T_max	0.860, 0.965
No. of measured, independent and observed [I > 2σ(I)] reflections	14309, 1310, 1131
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.128, 1.07
No. of reflections	1310
No. of parameters	118
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.44

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), Mercury (Macrae et al., 2008) and DIAMOND (Brandenburg, 2002), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O11	0.86	2.50	3.178 (3)	136.3
O2—H7W···O1	0.75	1.77	2.515 (3)	171.2
O11—H11···O3ⁱ	1.052 (3)	2.044 (18)	2.978 (2)	146 (3)

Symmetry code: (i) −x+1/2, −y+1/2, −z.

Acknowledgements

MF and JK thank the VEGA Grant Agency of the Slovak Ministry of Education (1/0679/11) and the Research and Development Agency of Slovakia (APVV-0202–10) for financial support and the Structural Funds, Interreg IIIA, for financial support in purchasing the diffractometer. KS thanks the University Grants Commission, Government of India, New Delhi, for award of a research fellowship under its faculty improvement program.

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