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

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 14 March 2009; accepted 16 March 2009; online 25 March 2009)

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[Wong, H. W., Lo, K. M. & Ng, S. W. (2009). Acta Cryst. E65, o419.]).

[Scheme 1]

Experimental

Crystal data
  • C10H9ClN2O3·H2O

  • Mr = 258.66

  • Triclinic, P 1

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.858, Tmax = 0.949

  • 2247 measured reflections

  • 1965 independent reflections

  • 1952 reflections with I > 2σ(I)

  • Rint = 0.011

Refinement
  • R[F2 > 2σ(F2)] = 0.026

  • wR(F2) = 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[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 733 Friedel pairs

  • Flack parameter: 0.02 (3)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1O⋯O1W 0.83 (1) 1.92 (3) 2.659 (2) 147 (4)
O1W—H11⋯O2i 0.84 (1) 1.96 (1) 2.784 (2) 165 (2)
O1W—H12⋯O3 0.84 (1) 1.98 (1) 2.809 (2) 172 (2)
N1—H1N⋯O1Wii 0.88 (1) 2.48 (2) 3.3596 (18) 177 (2)
Symmetry codes: (i) x, y-1, z; (ii) x-1, y+1, z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: pubCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


Related literature top

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

Experimental top

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 top

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.

Computing details top

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

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C10H9N2O3.H2O at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
2-[(4-Chlorobenzoyl)hydrazono]propionic acid monohydrate top
Crystal data top
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 top
Bruker SMART APEX
diffractometer
1965 independent reflections
Radiation source: fine-focus sealed tube1952 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.011
ω scansθmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 88
Tmin = 0.858, Tmax = 0.949k = 88
2247 measured reflectionsl = 99
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)] = 0.026H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.070 w = 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 methodsAbsolute structure parameter: 0.02 (3)
Crystal data top
C10H9ClN2O3·H2Oγ = 61.613 (1)°
Mr = 258.66V = 276.39 (1) Å3
Triclinic, P1Z = 1
a = 6.6516 (1) ÅMo Kα radiation
b = 6.9345 (1) ŵ = 0.35 mm1
c = 7.0988 (1) ÅT = 118 K
α = 73.833 (1)°0.45 × 0.35 × 0.15 mm
β = 80.182 (1)°
Data collection top
Bruker SMART APEX
diffractometer
1965 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1952 reflections with I > 2σ(I)
Tmin = 0.858, Tmax = 0.949Rint = 0.011
2247 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.026H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.070Δρmax = 0.20 e Å3
S = 1.00Δρmin = 0.33 e Å3
1965 reflectionsAbsolute structure: Flack (1983), 733 Friedel pairs
171 parametersAbsolute structure parameter: 0.02 (3)
7 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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)
H3A1.38620.93900.29370.042*
H3B1.58301.01640.32220.042*
H3C1.45620.98450.11150.042*
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) top
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, º) top
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—C1016.0 (2)
N1—N2—C2—C1177.31 (11)C10—C5—C6—C70.7 (2)
N1—N2—C2—C30.7 (2)C4—C5—C6—C7179.58 (13)
O2—C1—C2—N2164.68 (14)C5—C6—C7—C80.0 (2)
O1—C1—C2—N215.00 (19)C6—C7—C8—C90.1 (2)
O2—C1—C2—C313.5 (2)C6—C7—C8—Cl1179.90 (11)
O1—C1—C2—C3166.78 (14)C7—C8—C9—C100.6 (2)
N2—N1—C4—O33.7 (2)Cl1—C8—C9—C10179.43 (11)
N2—N1—C4—C5175.94 (11)C8—C9—C10—C51.3 (2)
O3—C4—C5—C615.2 (2)C6—C5—C10—C91.3 (2)
N1—C4—C5—C6165.12 (13)C4—C5—C10—C9179.82 (13)
O3—C4—C5—C10163.61 (15)
Hydrogen-bond geometry (Å, º) top
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, y1, z; (ii) x1, y+1, z.

Experimental details

Crystal data
Chemical formulaC10H9ClN2O3·H2O
Mr258.66
Crystal system, space groupTriclinic, P1
Temperature (K)118
a, b, c (Å)6.6516 (1), 6.9345 (1), 7.0988 (1)
α, β, γ (°)73.833 (1), 80.182 (1), 61.613 (1)
V3)276.39 (1)
Z1
Radiation typeMo Kα
µ (mm1)0.35
Crystal size (mm)0.45 × 0.35 × 0.15
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.858, 0.949
No. of measured, independent and
observed [I > 2σ(I)] reflections
2247, 1965, 1952
Rint0.011
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.026, 0.070, 1.00
No. of reflections1965
No. of parameters171
No. of restraints7
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.20, 0.33
Absolute structureFlack (1983), 733 Friedel pairs
Absolute structure parameter0.02 (3)

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), pubCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top
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, y1, z; (ii) x1, y+1, z.
 

Acknowledgements

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

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2009). publCIF. In preparation.  Google Scholar
First citationWong, H. W., Lo, K. M. & Ng, S. W. (2009). Acta Cryst. E65, o419.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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