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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 3| March 2012| Page o873
doi:10.1107/S1600536812008021

N-(4-Chloro-3-nitro­phen­yl)maleamic acid

U. Chaithanya,a Sabine Forob and B. Thimme Gowdaa*

aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
*Correspondence e-mail: gowdabt@yahoo.com

(Received 21 February 2012; accepted 22 February 2012; online 29 February 2012)

In the mol­ecule of the title compound, C10H7ClN2O5, the acyclic C=C double bond is cis configured. The C=O and O—H bonds of the acid group are in a relatively rare anti position to each other, due to the donation of intramolecular hydrogen bond to the amide by the carboxyl group. The nitro group is significantly twisted [dihedral angle = 66.9 (3)°] out of the plane of the remaining atoms, which are almost coplanar (r.m.s. deviation for non-H atoms except the nitro group = 0.202 Å). In the crystal, N—H⋯O hydrogen bonds link the mol­ecules into zigzag chains running along the b axis.

Related literature

For our studies of the effects of substituents on the structures and other aspects of N-(ar­yl)amides, see: Gowda et al. (2000[Gowda, B. T., Kumar, B. H. A. & Fuess, H. (2000). Z. Naturforsch. Teil A, 55, 721-728.], 2003[Gowda, B. T., Usha, K. M. & Jayalakshmi, K. L. (2003). Z. Naturforsch. Teil A, 58, 801-806.]); Chaithanya et al. (2012[Chaithanya, U., Foro, S. & Gowda, B. T. (2012). Acta Cryst. E68. In the press.]); N-(ar­yl)methane­sulfonamides, see: Gowda et al. (2007[Gowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o2337.]); N-chloro­aryl­amides, see: Jyothi & Gowda (2004[Jyothi, K. & Gowda, B. T. (2004). Z. Naturforsch. Teil A, 59, 64-68.]) and N-bromo­aryl­sulfonamides, see: Usha & Gowda (2006[Usha, K. M. & Gowda, B. T. (2006). J. Chem. Sci. 118, 351-359.]).

[Scheme 1]

Experimental

Crystal data

  • C10H7ClN2O5

  • Mr = 270.63

  • Monoclinic, P 21 /c

  • a = 9.7187 (9) Å

  • b = 13.596 (1) Å

  • c = 8.4990 (9) Å

  • β = 99.64 (1)°

  • V = 1107.16 (18) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.36 mm−1

  • T = 293 K

  • 0.42 × 0.12 × 0.06 mm
Data collection

  • Oxford Xcalibur diffractometer with a Sapphire CCD detector

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]) Tmin = 0.863, Tmax = 0.979

  • 4360 measured reflections

  • 2243 independent reflections

  • 1540 reflections with I > 2σ(I)

  • Rint = 0.025
Refinement

  • R[F2 > 2σ(F2)] = 0.063

  • wR(F2) = 0.180

  • S = 0.97

  • 2243 reflections

  • 169 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.38 e Å−3

  • Δρmin = −0.25 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O3—H3O⋯O1 0.82 (2) 1.67 (2) 2.494 (4) 174 (7)
N1—H1N⋯O2i 0.86 (2) 2.01 (2) 2.839 (4) 162 (4)
Symmetry code: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812008021/bt5827sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812008021/bt5827Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812008021/bt5827Isup3.cml

checkCIF report


Comment top

As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Gowda et al., 2000, 2003; Chaithanya et al., 2012), N-(aryl)-methanesulfonamides (Gowda et al., 2007); N-chloroarylsulfonamides (Jyothi & Gowda, 2004) and N-bromoarylsulfonamides (Usha & Gowda, 2006), in the present work, the crystal structure of N-(4-Chloro-3-nitrophenyl)maleamic acid 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. The N—H bond is also anti to the meta–nitro group. Further, the conformation of the amide C═O is anti to the H atom on the adjacent –CH group, while the carboxyl C═O of the acid segment is syn to the adjacent –CH group. Furthermore, the C═O and O—H bond of the acid group are in relatively rare anti position to each other, due to the donation of hydrogen bond to the amide by the carboxyl group, similar to that observed in N-(3-Chloro-4-methylphenyl)maleamic acid (I) (Chaithanya et al., 2012).

The dihedral angle between the phenyl ring and the amide group in the title compound is 11.52 (27)°, compared to the value of 6.55 (99)° in (I).

In the structure, the pairs of O—H···O and N—H···O intermolecular hydrogen bonds pack the molecules into zigzag chains (Table 1, Fig.2).

Related literature top

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

Experimental top

Maleic anhydride (0.025 mol) in toluene (25 ml) was treated dropwise with 4-chloro-3-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 4-chloro-3-nitroaniline. The resultant solid N-(4-Chloro-3-nitrophenyl)maleamic acid 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.

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

Refinement top

The H atoms of the NH group and the OH group were located in a difference map and later restrained to the distance N—H = 0.86 (2) Å and O—H = 0.82 (2) Å, respectively. The other H atoms were positioned with idealized geometry using a riding model with the aromatic C—H = 0.93 Å and methylene C—H = 0.97 Å. All H atoms were refined with isotropic displacement parameters set at 1.2Ueq.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound, showing the atom labelling scheme and with displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.
N-(4-Chloro-3-nitrophenyl)maleamic acid top
Crystal data top
C10H7ClN2O5F(000) = 552
Mr = 270.63Dx = 1.624 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1582 reflections
a = 9.7187 (9) Åθ = 2.6–27.7°
b = 13.596 (1) ŵ = 0.36 mm−1
c = 8.4990 (9) ÅT = 293 K
β = 99.64 (1)°Rod, colourless
V = 1107.16 (18) Å30.42 × 0.12 × 0.06 mm
Z = 4
Data collection top
Oxford Xcalibur
diffractometer with a Sapphire CCD detector		2243 independent reflections
Radiation source: fine-focus sealed tube1540 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
Rotation method data acquisition using ω and ϕ scansθmax = 26.4°, θmin = 2.6°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)		h = −12→6
Tmin = 0.863, Tmax = 0.979k = −16→16
4360 measured reflectionsl = −7→10
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.180H atoms treated by a mixture of independent and constrained refinement
S = 0.97 w = 1/[σ2(Fo2) + (0.0665P)2 + 3.5725P]
where P = (Fo2 + 2Fc2)/3
2243 reflections(Δ/σ)max = 0.034
169 parametersΔρmax = 0.38 e Å−3
2 restraintsΔρmin = −0.25 e Å−3
Crystal data top
C10H7ClN2O5V = 1107.16 (18) Å3
Mr = 270.63Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.7187 (9) ŵ = 0.36 mm−1
b = 13.596 (1) ÅT = 293 K
c = 8.4990 (9) Å0.42 × 0.12 × 0.06 mm
β = 99.64 (1)°
Data collection top
Oxford Xcalibur
diffractometer with a Sapphire CCD detector		2243 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)		1540 reflections with I > 2σ(I)
Tmin = 0.863, Tmax = 0.979Rint = 0.025
4360 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0632 restraints
wR(F2) = 0.180H atoms treated by a mixture of independent and constrained refinement
S = 0.97Δρmax = 0.38 e Å−3
2243 reflectionsΔρmin = −0.25 e Å−3
169 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl1−0.22417 (12)−0.02257 (9)0.06740 (14)0.0526 (4)
O10.3160 (3)0.2207 (2)0.5078 (4)0.0543 (10)
O20.6054 (3)0.3654 (2)0.8733 (4)0.0527 (9)
O30.4475 (4)0.3576 (2)0.6601 (4)0.0582 (10)
H3O0.402 (6)0.315 (3)0.604 (6)0.087*
O4−0.0092 (5)0.2184 (3)0.0224 (5)0.0750 (12)
O5−0.1941 (4)0.1979 (3)0.1206 (6)0.0852 (14)
N10.3025 (3)0.0549 (2)0.5150 (4)0.0353 (8)
H1N0.332 (5)0.004 (2)0.569 (5)0.042*
N2−0.0772 (4)0.1760 (3)0.1083 (4)0.0420 (9)
C10.1800 (4)0.0411 (3)0.4016 (5)0.0320 (9)
C20.1145 (4)0.1155 (3)0.3048 (5)0.0337 (9)
H20.15340.17810.30680.040*
C3−0.0098 (4)0.0945 (3)0.2053 (5)0.0331 (9)
C4−0.0696 (4)0.0024 (3)0.1939 (5)0.0357 (10)
C5−0.0005 (5)−0.0720 (3)0.2858 (5)0.0441 (11)
H5−0.0375−0.13520.27870.053*
C60.1233 (4)−0.0536 (3)0.3887 (5)0.0416 (11)
H60.1688−0.10450.44940.050*
C70.3599 (4)0.1411 (3)0.5669 (5)0.0357 (9)
C80.4800 (4)0.1338 (3)0.6985 (5)0.0379 (10)
H80.50990.07040.72810.046*
C90.5505 (4)0.2064 (3)0.7794 (5)0.0409 (10)
H90.62400.18480.85610.049*
C100.5357 (4)0.3159 (3)0.7725 (5)0.0384 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0429 (6)0.0487 (7)0.0575 (7)−0.0113 (5)−0.0165 (5)−0.0070 (6)
O10.0534 (19)0.0280 (16)0.067 (2)0.0018 (14)−0.0321 (16)−0.0018 (15)
O20.059 (2)0.0404 (18)0.0501 (19)−0.0077 (16)−0.0147 (16)−0.0133 (15)
O30.066 (2)0.0288 (16)0.067 (2)−0.0032 (15)−0.0280 (18)−0.0044 (15)
O40.100 (3)0.053 (2)0.075 (3)0.007 (2)0.020 (2)0.026 (2)
O50.051 (2)0.071 (3)0.126 (4)0.018 (2)−0.008 (2)0.027 (3)
N10.0350 (18)0.0245 (17)0.0408 (19)−0.0004 (14)−0.0095 (15)0.0022 (14)
N20.041 (2)0.0329 (19)0.045 (2)−0.0018 (17)−0.0123 (17)0.0000 (17)
C10.0296 (19)0.028 (2)0.035 (2)−0.0004 (16)−0.0044 (16)−0.0027 (16)
C20.035 (2)0.027 (2)0.035 (2)−0.0060 (16)−0.0063 (17)−0.0014 (16)
C30.036 (2)0.028 (2)0.033 (2)0.0013 (17)−0.0020 (17)−0.0014 (17)
C40.034 (2)0.032 (2)0.038 (2)−0.0053 (16)−0.0063 (17)−0.0078 (17)
C50.050 (2)0.027 (2)0.050 (3)−0.0077 (19)−0.007 (2)−0.0007 (19)
C60.044 (2)0.026 (2)0.048 (2)0.0010 (18)−0.012 (2)0.0027 (18)
C70.032 (2)0.028 (2)0.043 (2)0.0011 (17)−0.0041 (18)−0.0006 (17)
C80.040 (2)0.028 (2)0.041 (2)0.0037 (18)−0.0095 (18)−0.0013 (18)
C90.040 (2)0.039 (2)0.039 (2)0.0034 (19)−0.0092 (19)0.0011 (18)
C100.036 (2)0.035 (2)0.041 (2)−0.0022 (18)−0.0043 (19)−0.0050 (18)
Geometric parameters (Å, º) top
Cl1—C41.729 (4)C2—C31.383 (5)
O1—C71.239 (5)C2—H20.9300
O2—C101.205 (5)C3—C41.377 (5)
O3—C101.302 (5)C4—C51.382 (6)
O3—H3O0.82 (2)C5—C61.386 (6)
O4—N21.209 (5)C5—H50.9300
O5—N21.196 (5)C6—H60.9300
N1—C71.340 (5)C7—C81.479 (5)
N1—C11.413 (5)C8—C91.326 (6)
N1—H1N0.857 (19)C8—H80.9300
N2—C31.469 (5)C9—C101.497 (6)
C1—C21.389 (5)C9—H90.9300
C1—C61.397 (6)
C10—O3—H3O110 (4)C4—C5—C6120.8 (4)
C7—N1—C1126.7 (3)C4—C5—H5119.6
C7—N1—H1N117 (3)C6—C5—H5119.6
C1—N1—H1N115 (3)C5—C6—C1120.4 (4)
O5—N2—O4123.9 (4)C5—C6—H6119.8
O5—N2—C3118.7 (4)C1—C6—H6119.8
O4—N2—C3117.5 (4)O1—C7—N1122.3 (3)
C2—C1—C6119.2 (3)O1—C7—C8122.7 (4)
C2—C1—N1123.8 (3)N1—C7—C8115.0 (3)
C6—C1—N1116.9 (3)C9—C8—C7128.0 (4)
C3—C2—C1118.6 (4)C9—C8—H8116.0
C3—C2—H2120.7C7—C8—H8116.0
C1—C2—H2120.7C8—C9—C10133.0 (4)
C4—C3—C2123.1 (4)C8—C9—H9113.5
C4—C3—N2120.2 (3)C10—C9—H9113.5
C2—C3—N2116.7 (3)O2—C10—O3120.1 (4)
C3—C4—C5117.8 (4)O2—C10—C9119.3 (4)
C3—C4—Cl1122.4 (3)O3—C10—C9120.6 (3)
C5—C4—Cl1119.8 (3)
C7—N1—C1—C212.4 (7)N2—C3—C4—Cl10.0 (6)
C7—N1—C1—C6−167.4 (4)C3—C4—C5—C61.4 (7)
C6—C1—C2—C33.9 (6)Cl1—C4—C5—C6−179.7 (4)
N1—C1—C2—C3−176.0 (4)C4—C5—C6—C10.3 (7)
C1—C2—C3—C4−2.1 (7)C2—C1—C6—C5−3.0 (7)
C1—C2—C3—N2178.4 (4)N1—C1—C6—C5176.8 (4)
O5—N2—C3—C457.7 (6)C1—N1—C7—O1−6.7 (7)
O4—N2—C3—C4−123.7 (5)C1—N1—C7—C8173.9 (4)
O5—N2—C3—C2−122.8 (5)O1—C7—C8—C95.4 (8)
O4—N2—C3—C255.7 (5)N1—C7—C8—C9−175.2 (5)
C2—C3—C4—C5−0.5 (7)C7—C8—C9—C101.3 (9)
N2—C3—C4—C5178.9 (4)C8—C9—C10—O2171.7 (5)
C2—C3—C4—Cl1−179.4 (3)C8—C9—C10—O3−7.5 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3O···O10.82 (2)1.67 (2)2.494 (4)174 (7)
N1—H1N···O2i0.86 (2)2.01 (2)2.839 (4)162 (4)
Symmetry code: (i) −x+1, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formulaC10H7ClN2O5
Mr270.63
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)9.7187 (9), 13.596 (1), 8.4990 (9)
β (°) 99.64 (1)
V (Å3)1107.16 (18)
Z4
Radiation typeMo Kα
µ (mm−1)0.36
Crystal size (mm)0.42 × 0.12 × 0.06
Data collection
DiffractometerOxford Xcalibur
diffractometer with a Sapphire CCD detector
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2009)
Tmin, Tmax0.863, 0.979
No. of measured, independent and
observed [I > 2σ(I)] reflections		4360, 2243, 1540
Rint0.025
(sin θ/λ)max (Å−1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.063, 0.180, 0.97
No. of reflections2243
No. of parameters169
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.38, −0.25

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3O···O10.82 (2)1.67 (2)2.494 (4)174 (7)
N1—H1N···O2i0.857 (19)2.01 (2)2.839 (4)162 (4)
Symmetry code: (i) −x+1, y−1/2, −z+3/2.
 

Acknowledgements

BTG thanks the University Grants Commission, Government of India, New Delhi, for a special grant under a UGC-BSR one-time grant to faculty.

References

First citationChaithanya, U., Foro, S. & Gowda, B. T. (2012). Acta Cryst. E68. In the press.  CrossRef IUCr Journals Google Scholar
 First citationGowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o2337.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationGowda, B. T., Kumar, B. H. A. & Fuess, H. (2000). Z. Naturforsch. Teil A, 55, 721–728.  CAS Google Scholar
 First citationGowda, B. T., Usha, K. M. & Jayalakshmi, K. L. (2003). Z. Naturforsch. Teil A, 58, 801–806.  CAS Google Scholar
 First citationJyothi, K. & Gowda, B. T. (2004). Z. Naturforsch. Teil A, 59, 64–68.  CAS Google Scholar
 First citationOxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationUsha, K. M. & Gowda, B. T. (2006). J. Chem. Sci. 118, 351–359.  Web of Science CrossRef CAS Google Scholar

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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 3| March 2012| Page o873
doi:10.1107/S1600536812008021
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