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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 65| Part 8| August 2009| Page o1722
doi:10.1107/S1600536809024519

3-[(3,4-Di­chloro­phen­yl)amino­carbon­yl]propionic acid monohydrate

B. Thimme Gowda,a* Sabine Foro,b B. S. Saraswathia and Hartmut Fuessb

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 24 June 2009; accepted 25 June 2009; online 1 July 2009)

In the crystal structure of the title compound, C10H9Cl2NO3·H2O, the conformations of the amide O atom and the carbonyl O atom of the acid segment are anti to the H atoms of adjacent –CH2 groups. In the crystal, the mol­ecules are linked into a three-dimensional network through N—H⋯O and O—H⋯O inter­molecular hydrogen bonds.

Related literature

For related structures, see: Gowda et al. (2009a[Gowda, B. T., Foro, S., Saraswathi, B. S., Terao, H. & Fuess, H. (2009a). Acta Cryst. E65, o399.],b[Gowda, B. T., Foro, S., Saraswathi, B. S., Terao, H. & Fuess, H. (2009b). Acta Cryst. E65, o466.],c[Gowda, B. T., Foro, S., Saraswathi, B. S., Terao, H. & Fuess, H. (2009c). Acta Cryst. E65, o873.]). For hydrogen bonds involving carboxylic acids, see: Jagannathan et al. (1994[Jagannathan, N. R., Rajan, S. S. & Subramanian, E. (1994). J. Chem. Crystallogr. 24, 75-78.]); Leiserowitz (1976[Leiserowitz, L. (1976). Acta Cryst. B32, 775-802.]). For the modeling of water H atoms, see: Nardelli (1999[Nardelli, M. (1999). J. Appl. Cryst. 32, 563-571.]).

[Scheme 1]

Experimental

Crystal data

  • C10H9Cl2NO3·H2O

  • Mr = 280.10

  • Monoclinic, P 21 /c

  • a = 9.5634 (9) Å

  • b = 7.4527 (7) Å

  • c = 17.292 (2) Å

  • β = 104.35 (2)°

  • V = 1194.0 (2) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 4.95 mm−1

  • T = 299 K

  • 0.55 × 0.50 × 0.40 mm
Data collection

  • Enraf–Nonius CAD-4 diffractometer

  • Absorption correction: ψ scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.098, Tmax = 0.138

  • 2508 measured reflections

  • 2129 independent reflections

  • 2052 reflections with I > 2σ(I)

  • Rint = 0.072

  • 3 standard reflections frequency: 120 min intensity decay: 1.0%
Refinement

  • R[F2 > 2σ(F2)] = 0.083

  • wR(F2) = 0.212

  • S = 1.08

  • 2129 reflections

  • 167 parameters

  • 5 restraints

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

  • Δρmax = 0.92 e Å−3

  • Δρmin = −0.69 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O2—H2O⋯O4i 0.88 (3) 1.79 (3) 2.672 (4) 177 (5)
N1—H1N⋯O3ii 0.84 (3) 2.11 (3) 2.941 (4) 168 (4)
O4—H41⋯O1iii 0.82 (3) 2.11 (4) 2.894 (4) 162 (5)
O4—H42⋯O1iv 0.84 (3) 2.09 (3) 2.881 (4) 156 (5)
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) -x+1, -y+1, -z+1; (iii) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iv) x, y+1, z.

Data collection: CAD-4-PC (Enraf–Nonius, 1996[Enraf-Nonius (1996). CAD-4-PC. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987[Stoe & Cie (1987). REDU4. Stoe & Cie GmbH, Darmstadt, Germany.]); 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/S1600536809024519/ci2838sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809024519/ci2838Isup2.hkl

checkCIF report


Comment top

As a part of studying the effect of ring and side chain substitutions on the structures of aromatic amides (Gowda et al., 2009a,b,c), the crystal structure of N-(3,4-dichlorophenyl)succinamic acid monohydrate (I), systematic name: 3-[(3,4-dichloro)-aminocarbonyl]propionic acid monohydrate has been determined. The conformation of the N—H bond is anti to both the 3-chloro substituent in the aromatic ring and the C═O bond in the amide segment of the structure. Further, the amide O atom and the carbonyl O atom of the acid segment are anti to each other and are also anti to H atoms attached to the adjacent C atoms (Fig.1). Further, C═O and O—H bonds of the acid group are syn to each other, contrary to the anti position observed in 3-[(3,5-dichloro)-aminocarbonyl]propionic acid (Gowda et al., 2009c). The observed anti position with the latter may be due to the hydrogen bond donated to the amide carbonyl group by the acid segment, which is prevented in the present structure due to the H-bonding effect of hydration. The N—H···O and O—H···O intermolecular hydrogen bonds link the molecules into a three-dimensional network (Table 1 and Fig.2).

The modes of interlinking carboxylic acids by hydrogen bonds is described elsewhere (Leiserowitz, 1976). The packing of molecules involving dimeric hydrogen-bonded association of each carboxyl group with a centrosymmetrically related neighbor has also been observed (Jagannathan et al., 1994).

Related literature top

For related structures, see: Gowda et al. (2009a,b,c). For hydrogen bonds involving carboxylic acids, see: Jagannathan et al. (1994); Leiserowitz (1976). For the modeling of water H atoms, see: Nardelli (1999).

Experimental top

The solution of succinic anhydride (0.02 mol) in toluene (25 ml) was treated dropwise with the solution of 3,4-dichloroaniline (0.02 mol) also in toluene (20 ml) with constant stirring. The resulting mixture was stirred for about 1 h and set aside for an additional hour at room temperature for the completion of reaction. The mixture was then treated with dilute hydrochloric acid to remove the unreacted 3,4-dichloroaniline. The resultant solid N-(3,4-dichlorophenyl)-succinamic acid was filtered under suction and washed thoroughly with water to remove the unreacted succinic anhydride and succinic acid. It was recrystallized to constant melting point from ethanol. The purity of the compound was checked by elemental analysis and characterized by its infrared spectra. Single crystals used in X-ray diffraction studies were grown in an ethanol solution by slow evaporation at room temperature.

Refinement top

The O-bound and N-bound H atoms were located in a difference map. The positional parameters of the N-bound H atom were refined with N-H = 0.86 (4) Å and those of the O-bound (hydroxyl) H atom were refined with O-H distance restrained to 0.82 (4) Å. The positions of water H atoms were refined with restrained geometry (Nardelli, 1999) viz. O-H = 0.85 (4) Å and H···H = 1.365 (4) Å. The other H atoms were positioned with idealized geometry using a riding model [C-H = 0.93–0.97 Å]. The isotropic displacement parameters of all H atoms were set to 1.2 times of the Ueq of the parent atom.

Computing details top

Data collection: CAD-4-PC (Enraf–Nonius, 1996); cell refinement: CAD-4-PC (Enraf–Nonius, 1996); data reduction: REDU4 (Stoe & Cie, 1987); 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. The molecular structure of the title compound, showing the atom labelling and the displacement ellipsoids are at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.
[Figure 2] Fig. 2. The crystal packing of the title compound, with hydrogen bonds shown as dashed lines.
3-[(3,4-Dichlorophenyl)aminocarbonyl]propionic acid monohydrate top
Crystal data top
C10H9Cl2NO3·H2OF(000) = 576
Mr = 280.10Dx = 1.558 Mg m−3
Monoclinic, P21/cCu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 9.5634 (9) Åθ = 4.8–20.7°
b = 7.4527 (7) ŵ = 4.95 mm−1
c = 17.292 (2) ÅT = 299 K
β = 104.35 (2)°Prism, colourless
V = 1194.0 (2) Å30.55 × 0.50 × 0.40 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer		2052 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.072
Graphite monochromatorθmax = 67.0°, θmin = 4.8°
ω/2θ scansh = −11→1
Absorption correction: ψ scan
(North et al., 1968)		k = −8→0
Tmin = 0.098, Tmax = 0.138l = −19→20
2508 measured reflections3 standard reflections every 120 min
2129 independent reflections intensity decay: 1.0%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.083H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.212 w = 1/[σ2(Fo2) + (0.1684P)2 + 0.6399P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.003
2129 reflectionsΔρmax = 0.92 e Å−3
167 parametersΔρmin = −0.69 e Å−3
5 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.014 (2)
Crystal data top
C10H9Cl2NO3·H2OV = 1194.0 (2) Å3
Mr = 280.10Z = 4
Monoclinic, P21/cCu Kα radiation
a = 9.5634 (9) ŵ = 4.95 mm−1
b = 7.4527 (7) ÅT = 299 K
c = 17.292 (2) Å0.55 × 0.50 × 0.40 mm
β = 104.35 (2)°
Data collection top
Enraf–Nonius CAD-4
diffractometer		2052 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)		Rint = 0.072
Tmin = 0.098, Tmax = 0.1383 standard reflections every 120 min
2508 measured reflections intensity decay: 1.0%
2129 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0835 restraints
wR(F2) = 0.212H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.92 e Å−3
2129 reflectionsΔρmin = −0.69 e Å−3
167 parameters
Special details top

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
Cl1−0.35278 (8)0.10598 (12)0.56662 (5)0.0441 (4)
Cl2−0.33021 (8)0.03602 (12)0.38996 (4)0.0449 (4)
O10.1190 (2)0.2952 (3)0.33626 (13)0.0417 (6)
O20.5845 (3)0.4233 (4)0.26373 (15)0.0534 (7)
H2O0.674 (4)0.448 (6)0.262 (3)0.064*
O30.6264 (3)0.5188 (4)0.38871 (15)0.0543 (7)
N10.1755 (3)0.3197 (3)0.47092 (15)0.0331 (6)
H1N0.240 (4)0.353 (5)0.511 (2)0.040*
C10.0452 (3)0.2667 (4)0.48923 (17)0.0301 (7)
C20.0368 (3)0.2923 (4)0.56697 (18)0.0345 (7)
H20.11380.34460.60360.041*
C3−0.0840 (3)0.2416 (4)0.59077 (18)0.0367 (7)
H3−0.08790.25820.64350.044*
C4−0.2005 (3)0.1652 (4)0.53626 (17)0.0319 (7)
C5−0.1905 (3)0.1364 (4)0.45895 (17)0.0315 (7)
C6−0.0693 (3)0.1877 (4)0.43433 (17)0.0325 (7)
H6−0.06460.16960.38180.039*
C70.2060 (3)0.3302 (4)0.39971 (17)0.0311 (7)
C80.3601 (3)0.3889 (4)0.40446 (18)0.0360 (7)
H8A0.37730.50340.43190.043*
H8B0.42600.30220.43590.043*
C90.3923 (4)0.4068 (7)0.3247 (2)0.0566 (11)
H9A0.32940.49730.29390.068*
H9B0.37170.29380.29630.068*
C100.5465 (3)0.4577 (5)0.33053 (19)0.0400 (8)
O40.1421 (3)0.9875 (5)0.23932 (16)0.0570 (8)
H410.070 (4)0.945 (6)0.209 (3)0.068*
H420.116 (5)1.059 (6)0.271 (3)0.068*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0340 (5)0.0587 (6)0.0425 (6)−0.0077 (3)0.0149 (4)0.0020 (3)
Cl20.0329 (5)0.0645 (7)0.0332 (6)−0.0134 (3)0.0003 (4)−0.0034 (3)
O10.0306 (11)0.0668 (15)0.0259 (11)−0.0049 (10)0.0035 (9)−0.0020 (9)
O20.0391 (13)0.0936 (19)0.0297 (13)−0.0109 (13)0.0123 (10)0.0014 (12)
O30.0375 (13)0.0839 (19)0.0395 (14)−0.0159 (13)0.0058 (11)−0.0119 (13)
N10.0270 (12)0.0455 (14)0.0256 (13)−0.0077 (10)0.0045 (10)−0.0018 (10)
C10.0263 (13)0.0343 (14)0.0291 (15)0.0006 (10)0.0057 (11)0.0034 (11)
C20.0326 (15)0.0411 (15)0.0279 (15)−0.0056 (12)0.0039 (12)−0.0048 (11)
C30.0392 (16)0.0438 (16)0.0281 (15)−0.0024 (12)0.0103 (12)−0.0045 (12)
C40.0273 (14)0.0380 (14)0.0310 (14)−0.0010 (11)0.0085 (11)0.0037 (11)
C50.0265 (14)0.0372 (14)0.0272 (14)−0.0027 (11)−0.0001 (11)0.0022 (11)
C60.0313 (14)0.0417 (16)0.0237 (14)−0.0022 (11)0.0055 (11)0.0017 (11)
C70.0255 (14)0.0359 (14)0.0301 (14)0.0002 (11)0.0039 (11)0.0017 (11)
C80.0299 (15)0.0489 (17)0.0288 (16)−0.0071 (12)0.0063 (12)0.0003 (12)
C90.0322 (18)0.110 (3)0.0274 (17)−0.0167 (18)0.0062 (13)−0.0016 (17)
C100.0315 (16)0.060 (2)0.0281 (15)−0.0061 (13)0.0071 (12)0.0040 (13)
O40.0364 (13)0.094 (2)0.0387 (14)−0.0004 (13)0.0064 (11)−0.0163 (14)
Geometric parameters (Å, º) top
Cl1—C41.723 (3)C3—H30.93
Cl2—C51.726 (3)C4—C51.381 (4)
O1—C71.229 (4)C5—C61.384 (4)
O2—C101.319 (4)C6—H60.93
O2—H2O0.88 (3)C7—C81.520 (4)
O3—C101.193 (4)C8—C91.492 (5)
N1—C71.337 (4)C8—H8A0.97
N1—C11.415 (4)C8—H8B0.97
N1—H1N0.84 (3)C9—C101.501 (4)
C1—C21.380 (4)C9—H9A0.97
C1—C61.390 (4)C9—H9B0.97
C2—C31.372 (4)O4—H410.82 (3)
C2—H20.93O4—H420.84 (3)
C3—C41.390 (4)
C10—O2—H2O118 (3)C1—C6—H6120.5
C7—N1—C1128.9 (2)O1—C7—N1123.8 (3)
C7—N1—H1N117 (3)O1—C7—C8122.8 (3)
C1—N1—H1N114 (3)N1—C7—C8113.4 (3)
C2—C1—C6119.8 (3)C9—C8—C7113.3 (3)
C2—C1—N1116.5 (3)C9—C8—H8A108.9
C6—C1—N1123.6 (3)C7—C8—H8A108.9
C3—C2—C1120.7 (3)C9—C8—H8B108.9
C3—C2—H2119.6C7—C8—H8B108.9
C1—C2—H2119.6H8A—C8—H8B107.7
C2—C3—C4120.2 (3)C8—C9—C10112.6 (3)
C2—C3—H3119.9C8—C9—H9A109.1
C4—C3—H3119.9C10—C9—H9A109.1
C5—C4—C3118.9 (3)C8—C9—H9B109.1
C5—C4—Cl1121.4 (2)C10—C9—H9B109.1
C3—C4—Cl1119.6 (2)H9A—C9—H9B107.8
C4—C5—C6121.3 (3)O3—C10—O2123.7 (3)
C4—C5—Cl2120.6 (2)O3—C10—C9124.5 (3)
C6—C5—Cl2118.1 (2)O2—C10—C9111.8 (3)
C5—C6—C1119.0 (3)H41—O4—H42109 (4)
C5—C6—H6120.5
C7—N1—C1—C2−171.2 (3)C4—C5—C6—C11.2 (4)
C7—N1—C1—C610.6 (5)Cl2—C5—C6—C1−179.2 (2)
C6—C1—C2—C3−0.3 (5)C2—C1—C6—C50.1 (4)
N1—C1—C2—C3−178.6 (3)N1—C1—C6—C5178.3 (3)
C1—C2—C3—C4−0.8 (5)C1—N1—C7—O11.1 (5)
C2—C3—C4—C52.1 (5)C1—N1—C7—C8−178.6 (3)
C2—C3—C4—Cl1−178.8 (3)O1—C7—C8—C92.4 (5)
C3—C4—C5—C6−2.3 (4)N1—C7—C8—C9−177.9 (3)
Cl1—C4—C5—C6178.6 (2)C7—C8—C9—C10−177.7 (3)
C3—C4—C5—Cl2178.1 (2)C8—C9—C10—O3−16.9 (6)
Cl1—C4—C5—Cl2−1.0 (4)C8—C9—C10—O2161.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2O···O4i0.88 (3)1.79 (3)2.672 (4)177 (5)
N1—H1N···O3ii0.84 (3)2.11 (3)2.941 (4)168 (4)
O4—H41···O1iii0.82 (3)2.11 (4)2.894 (4)162 (5)
O4—H42···O1iv0.84 (3)2.09 (3)2.881 (4)156 (5)
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z+1; (iii) −x, y+1/2, −z+1/2; (iv) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC10H9Cl2NO3·H2O
Mr280.10
Crystal system, space groupMonoclinic, P21/c
Temperature (K)299
a, b, c (Å)9.5634 (9), 7.4527 (7), 17.292 (2)
β (°) 104.35 (2)
V (Å3)1194.0 (2)
Z4
Radiation typeCu Kα
µ (mm−1)4.95
Crystal size (mm)0.55 × 0.50 × 0.40
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.098, 0.138
No. of measured, independent and
observed [I > 2σ(I)] reflections		2508, 2129, 2052
Rint0.072
(sin θ/λ)max (Å−1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.083, 0.212, 1.08
No. of reflections2129
No. of parameters167
No. of restraints5
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.92, −0.69

Computer programs: CAD-4-PC (Enraf–Nonius, 1996), REDU4 (Stoe & Cie, 1987), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2O···O4i0.88 (3)1.79 (3)2.672 (4)177 (5)
N1—H1N···O3ii0.84 (3)2.11 (3)2.941 (4)168 (4)
O4—H41···O1iii0.82 (3)2.11 (4)2.894 (4)162 (5)
O4—H42···O1iv0.84 (3)2.09 (3)2.881 (4)156 (5)
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z+1; (iii) −x, y+1/2, −z+1/2; (iv) x, y+1, z.
 

Acknowledgements

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions of his research fellowship.

References

First citationEnraf–Nonius (1996). CAD-4-PC. Enraf–Nonius, Delft, The Netherlands.  Google Scholar
 First citationGowda, B. T., Foro, S., Saraswathi, B. S., Terao, H. & Fuess, H. (2009a). Acta Cryst. E65, o399.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationGowda, B. T., Foro, S., Saraswathi, B. S., Terao, H. & Fuess, H. (2009b). Acta Cryst. E65, o466.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationGowda, B. T., Foro, S., Saraswathi, B. S., Terao, H. & Fuess, H. (2009c). Acta Cryst. E65, o873.  Web of Science CSD CrossRef IUCr Journals Google Scholar
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ISSN: 2056-9890
Volume 65| Part 8| August 2009| Page o1722
doi:10.1107/S1600536809024519
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