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Acta Crystallogr Sect E Struct Rep Online. 2009 February 1; 65(Pt 2): o419.
Published online 2009 January 31. doi:  10.1107/S1600536809003067
PMCID: PMC2968368

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

Abstract

In the title compound, C11H12N2O3·H2O, the water mol­ecule is a hydrogen-bond donor to the double-bond amide and the carbonyl O atoms of two acid mol­ecules; it is also a hydrogen-bond acceptor to the acid –OH and amide –NH– groups. These hydrogen-bonding inter­actions give rise to a layer structure, with the layers parallel to the ab plane.

Related literature

The deprotonated anion of 2-aroylhydrazonopropionic acid furnishes a number of metal complexes; see, for example: Wu, Chen et al. (2006 [triangle]); Liu et al. (2007 [triangle]); Wu & Zeng (2007 [triangle]); Wu et al. (2006a [triangle],b [triangle]); Yang et al. (2004 [triangle]); Yin & Chen (2006 [triangle]); Zhai et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o419-scheme1.jpg

Experimental

Crystal data

  • C11H12N2O3·H2O
  • M r = 238.24
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o419-efi1.jpg
  • a = 6.8464 (1) Å
  • b = 11.9753 (2) Å
  • c = 7.0005 (1) Å
  • β = 102.169 (1)°
  • V = 561.06 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 100 (2) K
  • 0.20 × 0.10 × 0.10 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: none
  • 5272 measured reflections
  • 1335 independent reflections
  • 1211 reflections with I > 2σ(I)
  • R int = 0.029

Refinement

  • R[F 2 > 2σ(F 2)] = 0.030
  • wR(F 2) = 0.083
  • S = 1.02
  • 1335 reflections
  • 172 parameters
  • 5 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.19 e Å−3
  • Δρmin = −0.16 e Å−3
  • Absolute structure: 1126 Friedel pairs were merged

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007 [triangle]); 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: publCIF (Westrip, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809003067/cv2513sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809003067/cv2513Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Experimental

4-Toluihydrazide (1 g, 0.007 mol) and pyruvic acid (0.6 g, 0.007 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 0.93–0.99 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 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 (2) and O—H 0.84 (2) Å]; their temperature factors were freely refined.

Figures

Fig. 1.
Displacement ellipsoids plot (Barbour, 2001) of the title compound at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C11H12N2O3·H2OF(000) = 252
Mr = 238.24Dx = 1.410 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 1743 reflections
a = 6.8464 (1) Åθ = 3.0–26.9°
b = 11.9753 (2) ŵ = 0.11 mm1
c = 7.0005 (1) ÅT = 100 K
β = 102.169 (1)°Irregular block, colourless
V = 561.06 (2) Å30.20 × 0.10 × 0.10 mm
Z = 2

Data collection

Bruker SMART APEX diffractometer1211 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.029
graphiteθmax = 27.5°, θmin = 3.0°
ω scansh = −8→8
5272 measured reflectionsk = −14→15
1335 independent 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)] = 0.030H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.083w = 1/[σ2(Fo2) + (0.0559P)2 + 0.0248P] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
1335 reflectionsΔρmax = 0.19 e Å3
172 parametersΔρmin = −0.16 e Å3
5 restraintsAbsolute structure: 1126 Friedel pairs were merged
Primary atom site location: structure-invariant direct methods

Special details

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.

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

xyzUiso*/Ueq
O11.4450 (2)0.99988 (13)0.8798 (3)0.0255 (4)
O21.2160 (2)1.13156 (13)0.8463 (2)0.0269 (4)
O31.2831 (2)0.64501 (13)0.7200 (2)0.0260 (4)
O1W1.6032 (2)0.78718 (13)0.8663 (3)0.0251 (4)
N11.1624 (2)0.84748 (15)0.7821 (3)0.0192 (4)
N21.0279 (3)0.76060 (15)0.7458 (3)0.0202 (4)
C11.2584 (3)1.03349 (18)0.8395 (3)0.0204 (5)
C21.0961 (3)0.94692 (18)0.7861 (3)0.0183 (4)
C30.8847 (3)0.98625 (18)0.7447 (3)0.0232 (5)
H3A0.81310.94120.66860.035*
H3B0.84000.99510.86510.035*
H3C0.87541.05680.67770.035*
C41.1067 (3)0.65752 (18)0.7236 (3)0.0198 (4)
C50.9684 (3)0.56054 (18)0.7054 (3)0.0178 (4)
C60.7608 (3)0.5709 (2)0.6510 (3)0.0218 (4)
H60.70180.64220.61920.026*
C70.6408 (3)0.47675 (19)0.6437 (3)0.0231 (5)
H70.49980.48450.60670.028*
C80.7226 (3)0.37199 (18)0.6891 (3)0.0214 (5)
C90.9315 (3)0.3617 (2)0.7379 (3)0.0221 (5)
H9A0.99040.29010.76590.026*
C101.0524 (3)0.45480 (19)0.7457 (3)0.0202 (4)
H101.19360.44670.77870.024*
C110.5927 (3)0.27036 (19)0.6870 (4)0.0288 (5)
H11A0.61570.24110.79850.043*
H11B0.45420.29240.66890.043*
H11C0.60710.22110.58150.043*
H111.496 (3)0.755 (3)0.813 (5)0.059 (10)*
H121.653 (4)0.748 (2)0.963 (3)0.052 (10)*
H11.445 (5)0.9307 (9)0.867 (5)0.056 (11)*
H20.906 (2)0.773 (2)0.761 (4)0.031 (7)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0193 (8)0.0198 (9)0.0371 (10)−0.0029 (6)0.0049 (7)−0.0031 (7)
O20.0234 (7)0.0182 (8)0.0384 (9)−0.0001 (6)0.0047 (7)−0.0028 (7)
O30.0171 (7)0.0206 (8)0.0416 (9)−0.0005 (6)0.0094 (6)−0.0039 (7)
O1W0.0205 (7)0.0208 (8)0.0331 (10)−0.0018 (6)0.0036 (7)0.0028 (7)
N10.0186 (9)0.0171 (9)0.0218 (9)−0.0017 (7)0.0042 (7)0.0008 (7)
N20.0139 (8)0.0165 (9)0.0301 (10)−0.0001 (7)0.0048 (7)−0.0012 (7)
C10.0198 (10)0.0212 (11)0.0202 (11)−0.0033 (8)0.0043 (8)−0.0013 (8)
C20.0167 (9)0.0179 (10)0.0209 (10)−0.0012 (8)0.0054 (8)−0.0004 (8)
C30.0174 (10)0.0189 (11)0.0329 (13)0.0007 (8)0.0044 (9)0.0033 (9)
C40.0200 (10)0.0186 (10)0.0207 (10)−0.0004 (8)0.0041 (8)0.0004 (9)
C50.0170 (10)0.0169 (10)0.0201 (10)0.0010 (8)0.0049 (8)−0.0013 (8)
C60.0205 (10)0.0204 (10)0.0240 (11)0.0024 (9)0.0036 (8)−0.0003 (9)
C70.0159 (10)0.0238 (11)0.0289 (12)0.0017 (9)0.0034 (8)−0.0049 (9)
C80.0225 (11)0.0216 (11)0.0211 (11)−0.0046 (9)0.0068 (8)−0.0057 (9)
C90.0260 (11)0.0154 (10)0.0254 (11)0.0042 (9)0.0067 (9)0.0005 (8)
C100.0160 (9)0.0214 (11)0.0226 (11)0.0021 (8)0.0030 (8)−0.0004 (9)
C110.0282 (11)0.0228 (12)0.0370 (14)−0.0050 (10)0.0110 (10)−0.0044 (10)

Geometric parameters (Å, °)

O1—C11.312 (3)C4—C51.487 (3)
O1—H10.83 (2)C5—C101.395 (3)
O2—C11.213 (3)C5—C61.397 (3)
O3—C41.222 (2)C6—C71.390 (3)
O1W—H110.84 (2)C6—H60.9500
O1W—H120.82 (2)C7—C81.383 (3)
N1—C21.277 (3)C7—H70.9500
N1—N21.377 (2)C8—C91.404 (3)
N2—C41.369 (3)C8—C111.506 (3)
N2—H20.87 (2)C9—C101.383 (3)
C1—C21.508 (3)C9—H9A0.9500
C2—C31.491 (3)C10—H100.9500
C3—H3A0.8400C11—H11A0.8400
C3—H3B0.9620C11—H11B0.9663
C3—H3C0.9620C11—H11C0.9662
C1—O1—H1108 (2)C6—C5—C4123.14 (19)
H11—O1W—H12106 (3)C7—C6—C5119.8 (2)
C2—N1—N2118.80 (17)C7—C6—H6120.1
C4—N2—N1116.00 (17)C5—C6—H6120.1
C4—N2—H2124.9 (19)C8—C7—C6121.34 (19)
N1—N2—H2118.1 (19)C8—C7—H7119.3
O2—C1—O1121.2 (2)C6—C7—H7119.3
O2—C1—C2120.35 (19)C7—C8—C9118.5 (2)
O1—C1—C2118.40 (18)C7—C8—C11121.41 (19)
N1—C2—C3128.72 (19)C9—C8—C11120.1 (2)
N1—C2—C1113.55 (17)C10—C9—C8120.6 (2)
C3—C2—C1117.73 (19)C10—C9—H9A119.7
C2—C3—H3A109.5C8—C9—H9A119.7
C2—C3—H3B109.9C9—C10—C5120.40 (18)
H3A—C3—H3B112.0C9—C10—H10119.8
C2—C3—H3C109.5C5—C10—H10119.8
H3A—C3—H3C106.6C8—C11—H11A109.5
H3B—C3—H3C109.3C8—C11—H11B110.0
O3—C4—N2121.82 (19)H11A—C11—H11B102.8
O3—C4—C5121.12 (19)C8—C11—H11C110.2
N2—C4—C5117.06 (17)H11A—C11—H11C115.2
C10—C5—C6119.3 (2)H11B—C11—H11C108.8
C10—C5—C4117.61 (17)
C2—N1—N2—C4173.5 (2)N2—C4—C5—C620.0 (3)
N2—N1—C2—C3−3.9 (3)C10—C5—C6—C72.0 (3)
N2—N1—C2—C1176.43 (17)C4—C5—C6—C7−177.78 (19)
O2—C1—C2—N1179.1 (2)C5—C6—C7—C8−0.1 (3)
O1—C1—C2—N1−1.5 (3)C6—C7—C8—C9−1.8 (3)
O2—C1—C2—C3−0.6 (3)C6—C7—C8—C11178.2 (2)
O1—C1—C2—C3178.78 (19)C7—C8—C9—C101.8 (3)
N1—N2—C4—O3−5.9 (3)C11—C8—C9—C10−178.2 (2)
N1—N2—C4—C5173.67 (17)C8—C9—C10—C50.1 (3)
O3—C4—C5—C1019.8 (3)C6—C5—C10—C9−2.0 (3)
N2—C4—C5—C10−159.73 (19)C4—C5—C10—C9177.77 (19)
O3—C4—C5—C6−160.4 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···O1W0.83 (2)2.03 (2)2.777 (2)149 (3)
O1W—H11···O30.84 (2)1.97 (2)2.794 (2)165 (4)
O1W—H12···O2i0.84 (2)2.00 (1)2.829 (2)168 (3)
N2—H2···O1Wii0.87 (2)2.35 (1)3.210 (2)168 (3)

Symmetry codes: (i) −x+3, y−1/2, −z+2; (ii) x−1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2513).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Liu, F., Wu, W.-T., Zhang, W.-P., Chen, F.-Y. & He, S.-Y. (2007). Acta Cryst. E63, m2450–m2451.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.
  • Wu, W.-T., Chen, F.-Y., He, S.-Y., Hu, H.-M., Yang, M.-L. & Wang, Y.-Y. (2006). Chin. J. Chem.24, 711–713.
  • Wu, W.-T., He, S.-Y., Hu, H.-M., Yang, M.-L., Wang, Y.-Y. & Shi, Q.-Z. (2006a). J. Coord. Chem.59, 1785–1791.
  • Wu, W.-T., He, S.-Y., Hu, H.-M., Yang, M.-L., Wang, Y.-Y. & Shi, Q.-Z. (2006b). J. Coord. Chem.60, 125–130.
  • Wu, W.-P., Zeng, F.-C. & Wu, Y. (2007). Acta Cryst. E63, m2664.
  • Yang, R., He, S.-Y., Wu, W.-T., Wen, Z.-Y., Shi, Q.-Z. & Wang, D.-Q. (2004). Acta Chim. Sin.62, 2040–2044.
  • Yin, H.-D. & Chen, S.-W. (2006). Inorg. Chim. Acta, 359, 3330–3338.
  • Zhai, J., Yin, H., Li, F. & Wang, D. (2007). Acta Cryst. E63, m3066.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography