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Acta Crystallogr Sect E Struct Rep Online. 2009 April 1; 65(Pt 4): o816.
Published online 2009 March 25. doi:  10.1107/S1600536809009544
PMCID: PMC2969080

2-[(4-Chloro­benzo­yl)­hydrazono]­propionic acid monohydrate

Abstract

In the title compound, C10H9ClN2O3·H2O, the water mol­ecule is a hydrogen-bond donor to the amide and carbonyl O atoms of two acid mol­ecules; it is also a hydrogen-bond acceptor to the acid OH group and the amide H atom. The hydrogen-bonding inter­actions give rise to a two-dimensional array.

Related literature

For the structure of 2-[(4-methyl­benzo­yl)hydrazono]propionic acid monohydrate, see: Wong et al. (2009 [triangle]).

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Object name is e-65-0o816-scheme1.jpg

Experimental

Crystal data

  • C10H9ClN2O3·H2O
  • M r = 258.66
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o816-efi1.jpg
  • a = 6.6516 (1) Å
  • b = 6.9345 (1) Å
  • c = 7.0988 (1) Å
  • α = 73.833 (1)°
  • β = 80.182 (1)°
  • γ = 61.613 (1)°
  • V = 276.39 (1) Å3
  • Z = 1
  • Mo Kα radiation
  • μ = 0.35 mm−1
  • T = 118 K
  • 0.45 × 0.35 × 0.15 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.858, T max = 0.949
  • 2247 measured reflections
  • 1965 independent reflections
  • 1952 reflections with I > 2σ(I)
  • R int = 0.011

Refinement

  • R[F 2 > 2σ(F 2)] = 0.026
  • wR(F 2) = 0.070
  • S = 1.00
  • 1965 reflections
  • 171 parameters
  • 7 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.20 e Å−3
  • Δρmin = −0.33 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 733 Friedel pairs
  • Flack parameter: 0.02 (3)

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: pubCIF (Westrip, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809009544/tk2398sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809009544/tk2398Isup2.hkl

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

Acknowledgments

We thank the University of Malaya (grant Nos. FS339/2008 A and PS206/2008 A) for supporting this study.

supplementary crystallographic information

Experimental

4-Chlorobenzoylhydrazide (0.85 g, 0.005 mol) and pyruvic acid (0.43 g, 0.005 mol) were dissolved in methanol (30 ml). The solution was heated for 3 h; slow evaporation of the solvent gave colorless crystals.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C–H 0.95-0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2-1.5U(C). The methyl H-atoms were rotated to fit the electron density.

The oxygen- and nitrogen-bound H-atoms were located in a difference Fourier map, and were refined with distance restraints [N–H 0.88±0.01 and O–H 0.84±0.01 Å]; their Uiso values were freely refined.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of C10H9N2O3.H2O at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C10H9ClN2O3·H2OZ = 1
Mr = 258.66F(000) = 134
Triclinic, P1Dx = 1.554 Mg m3
Hall symbol: P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.6516 (1) ÅCell parameters from 2199 reflections
b = 6.9345 (1) Åθ = 3.0–28.2°
c = 7.0988 (1) ŵ = 0.35 mm1
α = 73.833 (1)°T = 118 K
β = 80.182 (1)°Irregular block, colorless
γ = 61.613 (1)°0.45 × 0.35 × 0.15 mm
V = 276.39 (1) Å3

Data collection

Bruker SMART APEX diffractometer1965 independent reflections
Radiation source: fine-focus sealed tube1952 reflections with I > 2σ(I)
graphiteRint = 0.011
ω scansθmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −8→8
Tmin = 0.858, Tmax = 0.949k = −8→8
2247 measured reflectionsl = −9→9

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.026H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.070w = 1/[σ2(Fo2) + (0.0628P)2 + 0.0013P] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
1965 reflectionsΔρmax = 0.20 e Å3
171 parametersΔρmin = −0.33 e Å3
7 restraintsAbsolute structure: Flack (1983), 733 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.02 (3)

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

xyzUiso*/Ueq
Cl10.50015 (5)0.49992 (5)0.49993 (4)0.02415 (12)
O12.0776 (2)0.41172 (18)−0.23906 (16)0.0184 (2)
O21.9975 (2)0.76916 (19)−0.31287 (18)0.0221 (3)
O31.5700 (2)0.18182 (19)0.11932 (19)0.0228 (3)
O1W1.9830 (2)0.06405 (18)−0.10712 (18)0.0216 (2)
N11.4403 (2)0.5584 (2)−0.0003 (2)0.0168 (3)
N21.6543 (2)0.5201 (2)−0.07703 (19)0.0154 (3)
C11.9322 (3)0.6250 (3)−0.2491 (2)0.0161 (3)
C21.6887 (3)0.6861 (2)−0.1806 (2)0.0165 (3)
C31.5134 (3)0.9273 (3)−0.2314 (3)0.0279 (4)
H3A1.38620.9390−0.29370.042*
H3B1.58301.0164−0.32220.042*
H3C1.45620.9845−0.11150.042*
C41.4131 (3)0.3718 (3)0.1048 (2)0.0169 (3)
C51.1830 (3)0.4130 (3)0.2013 (2)0.0158 (3)
C61.1356 (3)0.2284 (3)0.2676 (2)0.0197 (3)
H61.24830.08450.24920.024*
C70.9270 (3)0.2526 (3)0.3596 (2)0.0200 (3)
H70.89550.12680.40450.024*
C80.7637 (3)0.4649 (3)0.3852 (2)0.0187 (3)
C90.8072 (3)0.6496 (3)0.3209 (2)0.0194 (3)
H90.69340.79340.33850.023*
C101.0168 (3)0.6238 (2)0.2310 (2)0.0184 (3)
H101.04830.74970.18910.022*
H1O2.032 (8)0.321 (6)−0.244 (7)0.115 (18)*
H111.970 (4)−0.004 (3)−0.182 (3)0.029 (5)*
H121.855 (2)0.111 (4)−0.048 (3)0.028 (6)*
H1N1.318 (3)0.689 (2)−0.024 (3)0.013 (4)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0181 (2)0.0375 (2)0.02137 (18)−0.01711 (17)0.00484 (13)−0.00835 (14)
O10.0136 (6)0.0172 (5)0.0225 (6)−0.0068 (4)0.0026 (4)−0.0041 (4)
O20.0191 (6)0.0202 (5)0.0283 (6)−0.0120 (5)0.0068 (5)−0.0066 (4)
O30.0183 (6)0.0153 (5)0.0309 (6)−0.0077 (4)0.0049 (5)−0.0028 (4)
O1W0.0183 (6)0.0182 (5)0.0274 (6)−0.0087 (5)0.0051 (5)−0.0067 (4)
N10.0140 (7)0.0163 (6)0.0188 (6)−0.0074 (5)0.0021 (5)−0.0027 (5)
N20.0120 (7)0.0196 (6)0.0160 (6)−0.0082 (5)0.0032 (5)−0.0064 (5)
C10.0167 (8)0.0171 (6)0.0156 (6)−0.0087 (6)0.0011 (6)−0.0044 (5)
C20.0165 (8)0.0158 (7)0.0176 (7)−0.0080 (6)0.0008 (6)−0.0038 (5)
C30.0177 (8)0.0165 (7)0.0415 (10)−0.0060 (6)0.0068 (7)−0.0028 (6)
C40.0154 (8)0.0191 (7)0.0173 (7)−0.0093 (6)0.0014 (6)−0.0044 (5)
C50.0137 (8)0.0178 (7)0.0153 (7)−0.0081 (6)0.0014 (6)−0.0026 (5)
C60.0197 (8)0.0195 (7)0.0206 (7)−0.0105 (6)0.0010 (6)−0.0036 (5)
C70.0213 (9)0.0222 (7)0.0212 (7)−0.0147 (7)0.0018 (6)−0.0044 (6)
C80.0143 (8)0.0279 (8)0.0151 (7)−0.0123 (7)0.0019 (6)−0.0030 (6)
C90.0168 (8)0.0191 (7)0.0182 (7)−0.0064 (6)−0.0003 (6)−0.0016 (5)
C100.0176 (8)0.0187 (7)0.0185 (7)−0.0098 (6)0.0018 (6)−0.0023 (5)

Geometric parameters (Å, °)

Cl1—C81.7363 (18)C3—H3B0.9800
O1—C11.3161 (19)C3—H3C0.9800
O1—H1O0.829 (10)C4—C51.493 (2)
O2—C11.219 (2)C5—C61.399 (2)
O3—C41.220 (2)C5—C101.400 (2)
O1W—H110.842 (9)C6—C71.382 (2)
O1W—H120.836 (10)C6—H60.9500
N1—N21.360 (2)C7—C81.393 (2)
N1—C41.379 (2)C7—H70.9500
N1—H1N0.878 (9)C8—C91.383 (2)
N2—C21.281 (2)C9—C101.380 (3)
C1—C21.495 (2)C9—H90.9500
C2—C31.497 (2)C10—H100.9500
C3—H3A0.9800
C1—O1—H1O120 (3)N1—C4—C5116.93 (13)
H11—O1W—H12103 (2)C6—C5—C10119.14 (15)
N2—N1—C4116.41 (12)C6—C5—C4117.42 (14)
N2—N1—H1N124.6 (14)C10—C5—C4123.44 (14)
C4—N1—H1N118.6 (14)C7—C6—C5120.85 (14)
C2—N2—N1119.24 (13)C7—C6—H6119.6
O2—C1—O1119.90 (16)C5—C6—H6119.6
O2—C1—C2121.04 (14)C6—C7—C8118.77 (14)
O1—C1—C2119.06 (13)C6—C7—H7120.6
N2—C2—C1114.38 (13)C8—C7—H7120.6
N2—C2—C3126.56 (16)C9—C8—C7121.30 (17)
C1—C2—C3119.03 (14)C9—C8—Cl1119.04 (13)
C2—C3—H3A109.5C7—C8—Cl1119.67 (13)
C2—C3—H3B109.5C10—C9—C8119.64 (15)
H3A—C3—H3B109.5C10—C9—H9120.2
C2—C3—H3C109.5C8—C9—H9120.2
H3A—C3—H3C109.5C9—C10—C5120.28 (14)
H3B—C3—H3C109.5C9—C10—H10119.9
O3—C4—N1121.63 (16)C5—C10—H10119.9
O3—C4—C5121.44 (15)
C4—N1—N2—C2178.11 (13)N1—C4—C5—C10−16.0 (2)
N1—N2—C2—C1177.31 (11)C10—C5—C6—C70.7 (2)
N1—N2—C2—C3−0.7 (2)C4—C5—C6—C7179.58 (13)
O2—C1—C2—N2−164.68 (14)C5—C6—C7—C80.0 (2)
O1—C1—C2—N215.00 (19)C6—C7—C8—C9−0.1 (2)
O2—C1—C2—C313.5 (2)C6—C7—C8—Cl1179.90 (11)
O1—C1—C2—C3−166.78 (14)C7—C8—C9—C10−0.6 (2)
N2—N1—C4—O3−3.7 (2)Cl1—C8—C9—C10179.43 (11)
N2—N1—C4—C5175.94 (11)C8—C9—C10—C51.3 (2)
O3—C4—C5—C6−15.2 (2)C6—C5—C10—C9−1.3 (2)
N1—C4—C5—C6165.12 (13)C4—C5—C10—C9179.82 (13)
O3—C4—C5—C10163.61 (15)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1O···O1W0.83 (1)1.92 (3)2.659 (2)147 (4)
O1W—H11···O2i0.84 (1)1.96 (1)2.784 (2)165 (2)
O1W—H12···O30.84 (1)1.98 (1)2.809 (2)172 (2)
N1—H1N···O1Wii0.88 (1)2.48 (2)3.3596 (18)177 (2)

Symmetry codes: (i) x, y−1, z; (ii) x−1, y+1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2398).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.
  • Wong, H. W., Lo, K. M. & Ng, S. W. (2009). Acta Cryst. E65, o419. [PMC free article] [PubMed]

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