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Acta Crystallogr Sect E Struct Rep Online. 2008 October 1; 64(Pt 10): o1918.
Published online 2008 September 13. doi:  10.1107/S1600536808028481
PMCID: PMC2959358

2-Hydr­oxy-N′-[(1E,2E)-3-phenyl­prop-2-enyl­idene]benzohydrazide

Abstract

In mol­ecule of the title compound, C16H14N2O2, the two aromatic rings form a dihedral angle of 6.93 (3)° and an intramolecular N—H(...)O hydrogen bond occurs. In the crystal structure, inter­molecular O—H(...)O hydrogen bonds link the mol­ecules into zigzag chains running in the [10An external file that holds a picture, illustration, etc.
Object name is e-64-o1918-efi1.jpg] direction.

Related literature

For the coordination chemistry of Schiff bases, see: Garnovskii et al. (1993 [triangle]); Musie et al. (2001 [triangle]); Paul et al. (2002 [triangle]); Shi et al. (2007 [triangle]). For Schiff bases and biological systems, see: Anderson et al. (1997 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1918-scheme1.jpg

Experimental

Crystal data

  • C16H14N2O2
  • M r = 266.29
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1918-efi2.jpg
  • a = 4.8892 (6) Å
  • b = 26.563 (3) Å
  • c = 10.7367 (13) Å
  • β = 102.305 (2)°
  • V = 1362.4 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 295 K
  • 0.15 × 0.12 × 0.10 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.987, T max = 0.991
  • 7141 measured reflections
  • 2395 independent reflections
  • 1354 reflections with I > 2σ(I)
  • R int = 0.038

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.123
  • S = 1.05
  • 2395 reflections
  • 183 parameters
  • H-atom parameters constrained
  • Δρmax = 0.14 e Å−3
  • Δρmin = −0.13 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [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 global, I. DOI: 10.1107/S1600536808028481/cv2440sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808028481/cv2440Isup2.hkl

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

Acknowledgments

This project was supported by the Postgraduate Foundation of Taishan University (grant No. Y06-2-08).

supplementary crystallographic information

Comment

In recent years, a number of Schiff-bases have been investigated in terms of their coordination chemistry (Garnovskii et al., 1993; Musie et al., 2001; Paul et al., 2002; Shi et al., 2007;) and biological systems (Anderson et al., 1997). In order to search for new Schiff-bases with higher bioactivity, the title compound, (I), was synthesized and its crystal structure determined.

In (I) (Fig. 1), the bond lengths and angles are in good agreement with the expected values (Allen et al., 1987). The intramolecular N—H···O hydrogen bond (Table 1) influences the molecular conformation. In the crystal, the molecules are linked into infinite chains along direction [10-1] by O—H···O hydrogen bonds (Table 1).

Experimental

The title compound was synthesized by the reaction of 2-Hydroxy-benzoic acid hydrazide(1 mmol, 152.2 mg) with 3-Phenyl-propenal (1 mmol, 132.2 mg) in ethanol(20 ml) under reflux conditions (348 K) for 6 h. The solvent was removed and the solid product recrystallized from tetrahydrofuran. After six days colorless crystals suitable for X-ray diffraction study were obtained. Yield, 226.3 mg, 85%. m.p. 239–241 K. Analysis calculated for C16H14N2O2: C 72.16, H 5.30, N 10.52%; found: C 71.73, H 5.34, N 10.48%.

Refinement

All H atoms were placed in idealized positions (C—H = 0.93— 0.97 Å, N—H = 0.86 Å) and refined as riding, with Uiso(H) = 1.2 or 1.5Ueq(C, N).

Figures

Fig. 1.
The molecular structure of (I), with displacement ellipsoids drawn at the 50% probability level.

Crystal data

C16H14N2O2F(000) = 560
Mr = 266.29Dx = 1.298 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 932 reflections
a = 4.8892 (6) Åθ = 3.6–21.4°
b = 26.563 (3) ŵ = 0.09 mm1
c = 10.7367 (13) ÅT = 295 K
β = 102.305 (2)°Block, colourless
V = 1362.4 (3) Å30.15 × 0.12 × 0.10 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer2395 independent reflections
Radiation source: fine-focus sealed tube1354 reflections with I > 2σ(I)
graphiteRint = 0.038
[var phi] and ω scansθmax = 25.1°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −5→5
Tmin = 0.987, Tmax = 0.991k = −21→31
7141 measured reflectionsl = −12→12

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.124w = 1/[σ2(Fo2) + (0.0505P)2] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
2395 reflectionsΔρmax = 0.14 e Å3
183 parametersΔρmin = −0.13 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997a), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.008 (2)

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.
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)

xyzUiso*/Ueq
O10.5440 (4)0.26610 (6)0.08347 (14)0.0702 (5)
H10.62010.26330.02270.105*
O20.4213 (4)0.27755 (6)0.45173 (13)0.0687 (5)
N10.2766 (4)0.24015 (6)0.26236 (15)0.0508 (5)
H1A0.28610.23780.18350.061*
N20.1041 (4)0.20892 (7)0.31262 (16)0.0513 (5)
C10.6656 (4)0.30391 (8)0.15959 (19)0.0483 (6)
C20.6118 (4)0.30864 (8)0.28157 (18)0.0450 (5)
C30.7379 (5)0.34777 (9)0.3569 (2)0.0634 (7)
H30.70480.35130.43860.076*
C40.9102 (6)0.38164 (9)0.3154 (2)0.0736 (8)
H40.98980.40800.36760.088*
C50.9638 (5)0.37611 (9)0.1959 (2)0.0662 (7)
H51.08260.39860.16740.079*
C60.8438 (5)0.33774 (9)0.1184 (2)0.0606 (7)
H60.88180.33430.03750.073*
C70.4304 (5)0.27445 (8)0.33872 (19)0.0476 (6)
C8−0.0380 (5)0.17709 (8)0.2358 (2)0.0529 (6)
H8−0.02200.17660.15100.064*
C9−0.2215 (5)0.14220 (8)0.2788 (2)0.0530 (6)
H9−0.24160.14420.36280.064*
C10−0.3630 (5)0.10743 (9)0.2044 (2)0.0576 (6)
H10−0.34190.10720.12030.069*
C11−0.5490 (5)0.06929 (8)0.2383 (2)0.0529 (6)
C12−0.6805 (5)0.03509 (10)0.1480 (2)0.0739 (8)
H12−0.64990.03690.06550.089*
C13−0.8563 (6)−0.00161 (11)0.1777 (3)0.0842 (9)
H13−0.9404−0.02440.11560.101*
C14−0.9071 (6)−0.00457 (10)0.2973 (3)0.0761 (8)
H14−1.0287−0.02880.31690.091*
C15−0.7772 (6)0.02847 (10)0.3879 (3)0.0807 (8)
H15−0.80840.02640.47020.097*
C16−0.6002 (5)0.06496 (9)0.3590 (2)0.0670 (7)
H16−0.51370.08710.42230.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0858 (13)0.0893 (13)0.0482 (9)−0.0339 (10)0.0428 (9)−0.0229 (9)
O20.0900 (14)0.0857 (12)0.0392 (9)−0.0137 (9)0.0337 (8)−0.0060 (8)
N10.0615 (13)0.0615 (12)0.0363 (9)−0.0068 (10)0.0257 (9)0.0017 (9)
N20.0587 (13)0.0596 (12)0.0424 (10)−0.0030 (10)0.0263 (9)0.0069 (9)
C10.0531 (15)0.0568 (14)0.0384 (12)−0.0055 (11)0.0174 (10)−0.0034 (10)
C20.0509 (15)0.0505 (13)0.0366 (11)0.0016 (11)0.0158 (10)0.0003 (10)
C30.083 (2)0.0703 (17)0.0416 (13)−0.0132 (14)0.0247 (12)−0.0088 (12)
C40.097 (2)0.0700 (18)0.0568 (16)−0.0233 (15)0.0219 (15)−0.0121 (13)
C50.0740 (19)0.0696 (17)0.0575 (15)−0.0225 (14)0.0192 (14)0.0020 (13)
C60.0701 (18)0.0765 (17)0.0412 (12)−0.0134 (13)0.0252 (12)0.0026 (12)
C70.0552 (15)0.0547 (14)0.0383 (12)0.0047 (11)0.0218 (11)0.0002 (11)
C80.0614 (17)0.0631 (15)0.0377 (12)−0.0015 (12)0.0183 (11)0.0042 (11)
C90.0580 (16)0.0613 (15)0.0440 (13)−0.0030 (12)0.0205 (11)0.0068 (11)
C100.0613 (17)0.0687 (16)0.0444 (13)−0.0007 (13)0.0151 (12)0.0044 (12)
C110.0528 (16)0.0563 (15)0.0501 (14)0.0024 (12)0.0118 (11)0.0029 (12)
C120.079 (2)0.086 (2)0.0571 (16)−0.0149 (16)0.0147 (14)−0.0071 (14)
C130.082 (2)0.082 (2)0.085 (2)−0.0215 (16)0.0086 (17)−0.0090 (16)
C140.0696 (19)0.0665 (19)0.093 (2)−0.0088 (14)0.0189 (16)0.0139 (16)
C150.092 (2)0.082 (2)0.0768 (18)−0.0177 (16)0.0376 (17)0.0056 (16)
C160.076 (2)0.0684 (17)0.0609 (16)−0.0142 (13)0.0244 (14)−0.0028 (12)

Geometric parameters (Å, °)

O1—C11.350 (2)C8—C91.433 (3)
O1—H10.8200C8—H80.9300
O2—C71.226 (2)C9—C101.317 (3)
N1—C71.344 (2)C9—H90.9300
N1—N21.373 (2)C10—C111.458 (3)
N1—H1A0.8600C10—H100.9300
N2—C81.278 (2)C11—C161.376 (3)
C1—C61.388 (3)C11—C121.383 (3)
C1—C21.395 (3)C12—C131.381 (3)
C2—C31.379 (3)C12—H120.9300
C2—C71.490 (3)C13—C141.361 (3)
C3—C41.370 (3)C13—H130.9300
C3—H30.9300C14—C151.362 (3)
C4—C51.371 (3)C14—H140.9300
C4—H40.9300C15—C161.378 (3)
C5—C61.366 (3)C15—H150.9300
C5—H50.9300C16—H160.9300
C6—H60.9300
C1—O1—H1109.5N2—C8—H8119.6
C7—N1—N2118.73 (17)C9—C8—H8119.6
C7—N1—H1A120.6C10—C9—C8122.9 (2)
N2—N1—H1A120.6C10—C9—H9118.6
C8—N2—N1116.17 (17)C8—C9—H9118.6
O1—C1—C6120.93 (18)C9—C10—C11127.6 (2)
O1—C1—C2119.23 (18)C9—C10—H10116.2
C6—C1—C2119.8 (2)C11—C10—H10116.2
C3—C2—C1117.9 (2)C16—C11—C12117.0 (2)
C3—C2—C7116.66 (18)C16—C11—C10122.8 (2)
C1—C2—C7125.41 (19)C12—C11—C10120.2 (2)
C4—C3—C2122.2 (2)C13—C12—C11121.4 (2)
C4—C3—H3118.9C13—C12—H12119.3
C2—C3—H3118.9C11—C12—H12119.3
C3—C4—C5119.2 (2)C14—C13—C12120.4 (3)
C3—C4—H4120.4C14—C13—H13119.8
C5—C4—H4120.4C12—C13—H13119.8
C6—C5—C4120.5 (2)C13—C14—C15119.0 (3)
C6—C5—H5119.8C13—C14—H14120.5
C4—C5—H5119.8C15—C14—H14120.5
C5—C6—C1120.4 (2)C14—C15—C16120.8 (3)
C5—C6—H6119.8C14—C15—H15119.6
C1—C6—H6119.8C16—C15—H15119.6
O2—C7—N1121.0 (2)C11—C16—C15121.3 (2)
O2—C7—C2121.1 (2)C11—C16—H16119.3
N1—C7—C2117.84 (17)C15—C16—H16119.3
N2—C8—C9120.8 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O10.861.972.6348 (19)133.
O1—H1···O2i0.822.102.804 (3)144.
O1—H1···N2i0.822.363.057 (3)144.

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2440).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Anderson, O. P., Cour, A. L., Findeisen, M., Hennig, L., Simonsen, O., Taylor, L. & Toflund, H. (1997). J. Chem. Soc. Dalton Trans. pp. 111–120.
  • Garnovskii, A. D., Nivorozhkin, A. L. & Minkin, V. I. (1993). Coord. Chem. Rev.126, 1–69.
  • Musie, G. T., Wei, M., Subramaniam, B. & Busch, D. H. (2001). Inorg. Chem.40, 3336–3341. [PubMed]
  • Paul, S., Barik, A. K., Peng, S. M. & Kar, S. K. (2002). Inorg. Chem.41, 5803–5809. [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Shi, Z.-Q., Ji, N.-N., Zheng, Z.-B. & Li, J.-K. (2007). Acta Cryst. E63, o4561.
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

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