PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): o2007.
Published online 2009 July 29. doi:  10.1107/S160053680902892X
PMCID: PMC2977428

N′-(4-Hydroxy­benzyl­idene)aceto­hydrazide monohydrate

Abstract

In the title compound, C9H10N2O2·H2O, the mol­ecular skeleton of the acetohydrazide mol­ecule is nearly planar [within 0.014 (1) Å]. The mol­ecule adopts a trans configuration with respect to the C=N bond, while the side chain is slightly twisted away from the attached ring, forming a dihedral angle of 9.975 (8)°. The crystal packing exhibits a three-dimensional network composed from alternating acetohydrazide mol­ecules and uncoordinated water mol­ecules, which inter­act via N—H(...)O, O—H(...)O and O—H(...)N hydrogen bonds. A C—H(...)π inter­action is also present.

Related literature

For general background to the analytical applications of Schiff bases, see: Ciemerman et al. (1997 [triangle]). For their mild bacteriostatic activity and potential use as oral iron-chelating drugs for the treatment of genetic disorders such as thalassemia, see: Offe et al. (1952 [triangle]); Richardson et al. (1988 [triangle]). For a related structure, see: Li & Jian (2008 [triangle]); Tamboura et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2007-scheme1.jpg

Experimental

Crystal data

  • C9H10N2O2·H2O
  • M r = 196.21
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2007-efi1.jpg
  • a = 8.352 (2) Å
  • b = 10.146 (3) Å
  • c = 12.328 (3) Å
  • β = 105.353 (3)°
  • V = 1007.3 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 223 K
  • 0.23 × 0.21 × 0.20 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2002 [triangle]) T min = 0.969, T max = 0.976
  • 4820 measured reflections
  • 1764 independent reflections
  • 1569 reflections with I > 2σ(I)
  • R int = 0.015

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.100
  • S = 1.06
  • 1764 reflections
  • 147 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2002 [triangle]); cell refinement: SAINT (Bruker, 2002 [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: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680902892X/bg2278sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680902892X/bg2278Isup2.hkl

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

Acknowledgments

The authors thank the Science and Technology Project of Zhejiang Province (grant No. 2007 F70077) for financial support.

supplementary crystallographic information

Comment

Schiff bases have attracted much attention due to their possibility of analytical application (Ciemerman et al., 1997). They are also important ligands, which have been reported to have mild bacteriostatic activity and potential oral iron-chelating drugs for genetic disorders such as thalassemia (Offe et al., 1952, Richardson et al., 1988). Metal complexes based on Schiff bases have received considerable attention because they can be utilized as model compounds of active centres in various complexes (Tamboura et al., 2009). We report here the crystal structure of the title compound (Fig. 1).

In the title compound,C9H10N2O2 .H2O, (I) the molecular skeleton is nearly planar. The molecule adopts a trans configuration with respect to the C═N bond, while the side chain is slightly twisted away from the attached ring. The dihedral angle between these two essentially planar units is 9.975 (8)°. Bond lengths and angles are comparable to those observed for N'-[1-(4-methoxyphenyl)ethylidene]acetohydrazide (Li et al., 2008).

The crystal packing exhibits a three-dimensional network composed from alternating molecules of (I) and crystalline water, which interact via N-H···O, O-H···O and O-H···N hydrogen bonds. In addition, a intermolecular C—H···π interactions is observed (Table 1 and Fig 2).

Experimental

4-Hydroxybenzaldehyde (1.22 g, 0.01 mol) and acetohydrazide (0.74 g, 0.01 mol) were dissolved in stirred methanol (20 ml) and left for 2.5 h at room temperature. The resulting solid was filtered off and recrystallized from ethanol to give the title compound in 95% yield. Single crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution at room temperature (m.p. 435–437 K).

Refinement

H atoms of the water molecule were located in a difference map and were refined with O-H distances restrained to 0.84 (2) Å and 0.88 (2) Å, Other H atoms were positioned geometrically (N-H = 0.86 Å , O-H=0.82Å and C-H = 0.93 or 0.96Å) and refined using a riding model, with Uiso(H) =1.2Ueq(C,N) and 1.5Ueq(Cmethyl). In the absence of significant anomalous scattering effects, Friedel pairs were averaged.

Figures

Fig. 1.
The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 40% probability level. Dashed lines indicate hydrogen bonds.
Fig. 2.
Crystal packing of the title compound. Hydrogen bonds are shown as dashed lines.

Crystal data

C9H10N2O2·H2OF(000) = 416
Mr = 196.21Dx = 1.294 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1764 reflections
a = 8.352 (2) Åθ = 2.6–25.0°
b = 10.146 (3) ŵ = 0.10 mm1
c = 12.328 (3) ÅT = 223 K
β = 105.353 (3)°Block, colourless
V = 1007.3 (5) Å30.23 × 0.21 × 0.20 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer1764 independent reflections
Radiation source: fine-focus sealed tube1569 reflections with I > 2σ(I)
graphiteRint = 0.015
[var phi] and ω scansθmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2002)h = −9→9
Tmin = 0.969, Tmax = 0.976k = −10→12
4820 measured reflectionsl = −14→14

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H atoms treated by a mixture of independent and constrained refinement
S = 1.06w = 1/[σ2(Fo2) + (0.0527P)2 + 0.2585P] where P = (Fo2 + 2Fc2)/3
1764 reflections(Δ/σ)max < 0.001
147 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = −0.22 e Å3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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)

xyzUiso*/UeqOcc. (<1)
C10.96500 (16)0.24160 (13)0.32475 (11)0.0320 (3)
C20.86072 (18)0.34460 (14)0.27501 (11)0.0376 (3)
H20.83810.35870.19790.046 (4)*
C30.79116 (17)0.42545 (14)0.33983 (12)0.0370 (3)
H30.72210.49410.30600.046 (4)*
C40.82307 (16)0.40561 (13)0.45606 (11)0.0319 (3)
C50.92557 (17)0.30058 (14)0.50398 (11)0.0348 (5)0.998 (6)
H50.94730.28530.58090.040 (4)*
C60.99522 (17)0.21901 (13)0.43931 (11)0.0352 (3)
H61.06230.14900.47250.041 (4)*
C70.75676 (16)0.49358 (13)0.52741 (11)0.0337 (3)
H70.78520.47930.60470.041 (4)*
C80.51412 (16)0.77123 (13)0.52939 (11)0.0321 (3)
C90.47333 (19)0.85289 (14)0.61982 (12)0.0408 (4)
H9A0.52760.81650.69210.094 (7)*
H9B0.35540.85280.61000.104 (8)*
H9C0.51090.94160.61530.086 (7)*
N10.66075 (13)0.58964 (11)0.48641 (9)0.0333 (3)
N20.61346 (14)0.66803 (11)0.56438 (9)0.0329 (3)
H2A0.64790.65040.63500.045 (4)*
O11.04051 (13)0.16176 (10)0.26415 (8)0.0421 (3)
H11.01350.18440.19790.080 (7)*
O20.45976 (13)0.79883 (10)0.42813 (8)0.0436 (3)
O1W0.17157 (17)0.90361 (12)0.29134 (10)0.0527 (3)
H1E0.146 (3)0.984 (2)0.2989 (18)0.075 (7)*
H1F0.260 (3)0.886 (2)0.3465 (19)0.078 (7)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0344 (7)0.0292 (7)0.0343 (7)−0.0020 (5)0.0123 (6)−0.0026 (5)
C20.0447 (8)0.0401 (8)0.0294 (7)0.0043 (6)0.0122 (6)0.0036 (6)
C30.0396 (7)0.0355 (7)0.0367 (7)0.0061 (6)0.0117 (6)0.0040 (6)
C40.0313 (7)0.0317 (7)0.0338 (7)−0.0048 (5)0.0106 (5)−0.0023 (5)
C50.0381 (8)0.0378 (9)0.0289 (7)−0.0024 (6)0.0096 (6)0.0011 (6)
C60.0372 (7)0.0315 (7)0.0366 (7)0.0026 (6)0.0091 (6)0.0035 (6)
C70.0343 (7)0.0361 (7)0.0314 (7)−0.0043 (6)0.0101 (5)−0.0026 (5)
C80.0319 (7)0.0313 (7)0.0350 (7)−0.0061 (5)0.0121 (6)−0.0004 (5)
C90.0474 (9)0.0345 (8)0.0435 (8)−0.0027 (6)0.0173 (7)−0.0066 (6)
N10.0350 (6)0.0347 (6)0.0324 (6)−0.0024 (5)0.0129 (5)−0.0048 (5)
N20.0363 (6)0.0352 (6)0.0281 (6)−0.0004 (5)0.0103 (5)−0.0035 (4)
O10.0545 (7)0.0391 (6)0.0353 (6)0.0119 (5)0.0164 (5)−0.0007 (4)
O20.0534 (6)0.0448 (6)0.0349 (5)0.0090 (5)0.0155 (5)0.0055 (4)
O1W0.0697 (8)0.0430 (7)0.0384 (6)0.0116 (6)0.0019 (6)−0.0018 (5)

Geometric parameters (Å, °)

C1—O11.3644 (16)C7—H70.9300
C1—C61.3864 (19)C8—O21.2421 (17)
C1—C21.3941 (19)C8—O21.2421 (17)
C2—C31.377 (2)C8—N21.3346 (18)
C2—H20.9300C8—C91.4988 (19)
C3—C41.4009 (19)C9—H9A0.9600
C3—H30.9300C9—H9B0.9600
C4—C51.3962 (19)C9—H9C0.9600
C4—C71.4611 (19)N1—N21.3832 (16)
C5—C61.380 (2)N2—H2A0.8600
C5—H50.9300O1—H10.8200
C6—H60.9300O1W—H1E0.85 (2)
C7—N11.2782 (18)O1W—H1F0.88 (2)
O1—C1—C6118.28 (12)N1—C7—H7119.1
O1—C1—C2121.98 (12)C4—C7—H7119.1
C6—C1—C2119.74 (12)O2—C8—N2122.15 (12)
C3—C2—C1120.12 (12)O2—C8—N2122.15 (12)
C3—C2—H2119.9O2—C8—C9121.90 (13)
C1—C2—H2119.9O2—C8—C9121.90 (13)
C2—C3—C4120.85 (13)N2—C8—C9115.95 (12)
C2—C3—H3119.6C8—C9—H9A109.5
C4—C3—H3119.6C8—C9—H9B109.5
C5—C4—C3118.15 (12)H9A—C9—H9B109.5
C5—C4—C7119.94 (12)C8—C9—H9C109.5
C3—C4—C7121.88 (12)H9A—C9—H9C109.5
C6—C5—C4121.22 (12)H9B—C9—H9C109.5
C6—C5—H5119.4C7—N1—N2115.36 (11)
C4—C5—H5119.4C8—N2—N1119.60 (11)
C5—C6—C1119.90 (13)C8—N2—H2A120.2
C5—C6—H6120.1N1—N2—H2A120.2
C1—C6—H6120.1C1—O1—H1109.5
N1—C7—C4121.72 (12)H1E—O1W—H1F107 (2)
O1—C1—C2—C3−177.94 (13)C2—C1—C6—C5−1.7 (2)
C6—C1—C2—C31.5 (2)C5—C4—C7—N1−179.03 (12)
C1—C2—C3—C4−0.2 (2)C3—C4—C7—N13.0 (2)
C2—C3—C4—C5−0.8 (2)C4—C7—N1—N2−177.28 (11)
C2—C3—C4—C7177.21 (13)O2—C8—N2—N11.12 (19)
C3—C4—C5—C60.6 (2)O2—C8—N2—N11.12 (19)
C7—C4—C5—C6−177.44 (12)C9—C8—N2—N1−178.27 (11)
C4—C5—C6—C10.6 (2)C7—N1—N2—C8179.57 (12)
O1—C1—C6—C5177.77 (12)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.822.002.7477 (15)152
N2—H2A···O1Wii0.861.962.8060 (17)166
O1W—H1F···O20.88 (2)1.92 (2)2.7600 (17)159 (2)
O1W—H1E···O1iii0.85 (2)2.01 (2)2.8241 (17)161 (2)
O1—H1···N1i0.822.543.1864 (16)137
C9—H9B···Cg1iv0.962.743.519 (2)138

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2278).

References

  • Bruker (2002). SMART, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Ciemerman, Z., Galic, N. & Bosner, B. (1997). Anal Chim. Acta, 343, 145–153.
  • Li, Y.-F. & Jian, F.-F. (2008). Acta Cryst. E64, o2409. [PMC free article] [PubMed]
  • Offe, H. A., Siefen, W. & Domagk, G. (1952). Z. Naturforsch. Teil B, 7, 446–447.
  • Richardson, D., Baker, E., Ponka, P., Wilairat, P., Vitolo, M. L. & Webb, J. (1988). Thalassemia: Pathophysiology and Management, Part B, p. 81. New York: Alan R. Liss.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Tamboura, F. B., Gaye, M., Sall, A. S., Barry, A. H. & Bah, Y. (2009). Acta Cryst. E65, m160–m161. [PMC free article] [PubMed]

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