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Acta Crystallogr Sect E Struct Rep Online. 2009 April 1; 65(Pt 4): o666.
Published online 2009 March 6. doi:  10.1107/S1600536809006941
PMCID: PMC2968967

(E)-N′-(3-Fluoro­benzyl­idene)-2-hydroxy­benzohydrazide

Abstract

The title compound, C14H11FN2O2, adopts an E or trans configuration with respect to the C=N bond. An intra­molecular N—H(...)O hydrogen bond contributes to the relatively planarity of the mol­ecular conformation; the two benzene rings are inclined to one another by 12.5 (2)°. In the crystal structure, inter­molecular O—H(...)O hydrogen bonds link the mol­ecules into chains running parallel to the c axis.

Related literature

For the potential pharmacological and anti­tumor properties of hydrazones and Schiff bases, see: Karthikeyan et al. (2006 [triangle]); Khattab (2005 [triangle]); Kucukguzel et al. (2006 [triangle]); Okabe et al. (1993 [triangle]).

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Object name is e-65-0o666-scheme1.jpg

Experimental

Crystal data

  • C14H11FN2O2
  • M r = 258.25
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o666-efi1.jpg
  • a = 4.8751 (15) Å
  • b = 22.188 (7) Å
  • c = 11.323 (3) Å
  • β = 96.717 (5)°
  • V = 1216.4 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 297 K
  • 0.20 × 0.10 × 0.10 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.979, T max = 0.989
  • 8534 measured reflections
  • 2152 independent reflections
  • 1205 reflections with I > 2σ(I)
  • R int = 0.081

Refinement

  • R[F 2 > 2σ(F 2)] = 0.088
  • wR(F 2) = 0.240
  • S = 1.05
  • 2152 reflections
  • 170 parameters
  • H-atom parameters constrained
  • Δρmax = 0.20 e Å−3
  • Δρmin = −0.30 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/S1600536809006941/su2098sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006941/su2098Isup2.hkl

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

Acknowledgments

This work was supported by the Key Project of Science and Technology of Anhui, P. R. China (grant No. 08010302218).

supplementary crystallographic information

Comment

Hydrazones and Schiff bases have attracted much attention for their excellent biological properties, especially for their potential pharmacological and antitumor properties (Kucukguzel et al., 2006; Khattab, 2005; Karthikeyan et al., 2006; Okabe et al., 1993). As part of an ongoing study of such compounds, we report here on the crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1. It can be seen to display a trans configuration about the C=N bond. There is an intramolecular N-H···O hydrogen bond, involving the NH H-atom and the O-atom of the hydroxyl substituent (Table 1), and the dihedral angle between the two benzene rings is 12.5 (2)°.

In the crystal molecules are linked by intermolecular O—H···O hydrongen bonds to form chains running parallel to the c axis (Fig. 2 and Table 1).

Experimental

Equimolar amounts of 2-Hydroxybenzohydrazide and 3-fluorobenzohydrazide were reacted in ethanol (10 ml) for 1 h. After allowing the resulting solution to stand in air for 10 days yellow block-shaped crystals were formed, on slow evaporation of the solvent.

Refinement

Phenyl ring C9-C14 was treated as a regular hexagon, and refined as a rigid body. The F-atom was found to be disordered over two positions, F1/F1', and given occupancies of 0.5/0.5. The H-atoms at C11 and C13 were also given occupancies of 0.5/0.5. All the H-atoms were placed in calculated positions and treated as riding: O-H = 0.82 Å, N-H = 0.86 Å, C-H = 0.93 Å, with Uiso(H) = 1.5Ueq(parent O and N-atom, and = 1.2Ueq(parent C-atom).

Figures

Fig. 1.
The molecular structure of the title compound, showing 30% probability displacement ellipsoids. H-atoms have been omitted for clarity.
Fig. 2.
Crystal packing viewed along the A axis. The intra- and intermolecular hydrogen bonds are shown as dashed lines (details are given in Table 1).

Crystal data

C14H11FN2O2F(000) = 536
Mr = 258.25Dx = 1.410 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 589 reflections
a = 4.8751 (15) Åθ = 2.3–15°
b = 22.188 (7) ŵ = 0.11 mm1
c = 11.323 (3) ÅT = 297 K
β = 96.717 (5)°Block, yellow
V = 1216.4 (6) Å30.20 × 0.10 × 0.10 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer2152 independent reflections
Radiation source: fine-focus sealed tube1205 reflections with I > 2σ(I)
graphiteRint = 0.081
[var phi] and ω scansθmax = 25.1°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −5→5
Tmin = 0.979, Tmax = 0.989k = −26→26
8534 measured reflectionsl = −13→13

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)] = 0.088Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.240H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.1113P)2 + 0.2945P] where P = (Fo2 + 2Fc2)/3
2152 reflections(Δ/σ)max = 0.002
170 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = −0.30 e Å3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles
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)
F1−0.2554 (15)0.0383 (3)0.4844 (5)0.103 (3)0.500
F1'−0.3673 (19)0.0122 (3)0.0916 (6)0.136 (4)0.500
O10.8661 (7)0.26546 (15)0.1078 (3)0.0638 (11)
O20.7116 (7)0.27530 (14)0.4613 (2)0.0643 (11)
N10.5969 (8)0.23163 (16)0.2828 (3)0.0518 (12)
N20.4125 (7)0.19142 (17)0.3234 (3)0.0490 (12)
C10.9330 (8)0.31131 (19)0.3001 (4)0.0443 (12)
C21.0667 (10)0.3559 (2)0.3713 (4)0.0563 (16)
C31.2548 (11)0.3939 (2)0.3302 (4)0.0658 (19)
C41.3165 (10)0.3890 (2)0.2158 (4)0.0601 (17)
C51.1869 (9)0.34596 (19)0.1418 (4)0.0527 (17)
C60.9959 (8)0.30710 (19)0.1824 (3)0.0433 (14)
C70.7399 (9)0.27175 (19)0.3545 (4)0.0465 (17)
C80.2866 (9)0.1604 (2)0.2415 (4)0.0524 (17)
C90.0844 (6)0.11357 (12)0.2623 (3)0.0497 (17)
C100.0213 (6)0.09879 (13)0.3754 (2)0.0520 (16)
C11−0.1728 (7)0.05426 (14)0.3894 (3)0.067 (2)
C12−0.3037 (6)0.02449 (13)0.2905 (4)0.0750 (19)
C13−0.2406 (7)0.03926 (15)0.1774 (3)0.083 (2)
C14−0.0466 (7)0.08380 (16)0.1634 (2)0.073 (2)
H1N0.621000.230900.208700.0620*
H1O0.962100.257700.055000.0950*
H21.026900.360100.449300.0680*
H31.341300.423200.380300.0790*
H41.445600.414700.188100.0720*
H51.227700.342900.063800.0630*
H80.323000.167400.163900.0630*
H100.108900.118700.441600.0620*
H11−0.215000.044400.465100.0800*0.500
H12−0.43350−0.005300.299900.0900*
H13−0.328200.019300.111200.0990*0.500
H14−0.004400.093700.087700.0870*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
F10.145 (6)0.094 (5)0.080 (4)−0.033 (5)0.054 (4)0.006 (4)
F1'0.184 (8)0.138 (6)0.075 (4)−0.103 (6)−0.026 (5)−0.006 (4)
O10.076 (2)0.075 (2)0.0473 (19)−0.0178 (19)0.0363 (16)−0.0120 (17)
O20.081 (2)0.075 (2)0.0416 (18)−0.0068 (18)0.0274 (17)−0.0018 (15)
N10.063 (2)0.056 (2)0.041 (2)−0.005 (2)0.0255 (19)0.0029 (18)
N20.051 (2)0.053 (2)0.047 (2)0.003 (2)0.0222 (18)0.0074 (19)
C10.045 (2)0.042 (2)0.048 (2)0.011 (2)0.014 (2)0.006 (2)
C20.074 (3)0.053 (3)0.044 (2)0.001 (3)0.016 (2)−0.002 (2)
C30.080 (4)0.053 (3)0.064 (3)−0.013 (3)0.007 (3)0.000 (3)
C40.061 (3)0.062 (3)0.059 (3)−0.008 (3)0.014 (2)0.011 (3)
C50.061 (3)0.050 (3)0.051 (3)−0.002 (2)0.023 (2)0.007 (2)
C60.047 (3)0.045 (2)0.040 (2)0.004 (2)0.014 (2)−0.004 (2)
C70.054 (3)0.048 (3)0.041 (3)0.013 (2)0.021 (2)0.001 (2)
C80.058 (3)0.059 (3)0.042 (3)0.009 (3)0.014 (2)0.009 (2)
C90.052 (3)0.047 (3)0.052 (3)0.009 (2)0.014 (2)0.005 (2)
C100.061 (3)0.041 (2)0.057 (3)0.002 (2)0.019 (2)0.000 (2)
C110.076 (4)0.049 (3)0.080 (4)0.001 (3)0.031 (3)0.006 (3)
C120.060 (3)0.055 (3)0.111 (4)−0.004 (3)0.014 (3)0.008 (3)
C130.085 (4)0.077 (4)0.085 (4)−0.017 (3)0.004 (3)0.001 (3)
C140.078 (4)0.084 (4)0.055 (3)−0.012 (3)0.003 (3)−0.005 (3)

Geometric parameters (Å, °)

F1'—C131.243 (8)C9—C101.3908
F1—C111.243 (7)C9—C141.3896
O1—C61.357 (5)C10—C111.3899
O2—C71.236 (5)C11—C121.3894
O1—H1O0.8200C12—C131.3908
N1—N21.383 (5)C13—C141.3897
N1—C71.344 (6)C2—H20.9300
N2—C81.256 (6)C3—H30.9300
N1—H1N0.8600C4—H40.9300
C1—C71.474 (6)C5—H50.9300
C1—C21.390 (6)C8—H80.9300
C1—C61.405 (6)C10—H100.9300
C2—C31.367 (7)C11—H110.9300
C3—C41.368 (6)C12—H120.9300
C4—C51.375 (6)C13—H130.9300
C5—C61.386 (6)C14—H140.9300
C8—C91.470 (5)
C6—O1—H1O109.00C11—C12—C13120.00
N2—N1—C7122.6 (3)C12—C13—C14119.96
N1—N2—C8112.9 (3)F1'—C13—C12117.6 (5)
C7—N1—H1N119.00F1'—C13—C14122.5 (4)
N2—N1—H1N119.00C9—C14—C13120.06
C6—C1—C7125.3 (4)C1—C2—H2119.00
C2—C1—C7117.4 (4)C3—C2—H2119.00
C2—C1—C6117.3 (4)C2—C3—H3120.00
C1—C2—C3122.0 (4)C4—C3—H3120.00
C2—C3—C4120.3 (4)C3—C4—H4120.00
C3—C4—C5119.7 (4)C5—C4—H4120.00
C4—C5—C6120.6 (4)C4—C5—H5120.00
C1—C6—C5120.2 (4)C6—C5—H5120.00
O1—C6—C1119.9 (4)N2—C8—H8118.00
O1—C6—C5120.0 (3)C9—C8—H8118.00
O2—C7—N1121.6 (4)C9—C10—H10120.00
O2—C7—C1121.4 (4)C11—C10—H10120.00
N1—C7—C1117.0 (4)C10—C11—H11120.00
N2—C8—C9123.2 (4)C12—C11—H11120.00
C10—C9—C14119.98C11—C12—H12120.00
C8—C9—C14117.4 (3)C13—C12—H12120.00
C8—C9—C10122.6 (3)C12—C13—H13120.00
C9—C10—C11119.97C14—C13—H13120.00
F1—C11—C10126.5 (4)C9—C14—H14120.00
C10—C11—C12120.04C13—C14—H14120.00
F1—C11—C12113.4 (4)
C7—N1—N2—C8175.7 (4)C4—C5—C6—O1178.9 (4)
N2—N1—C7—O2−0.8 (7)C4—C5—C6—C1−0.1 (6)
N2—N1—C7—C1179.0 (4)N2—C8—C9—C10−1.7 (6)
N1—N2—C8—C9178.6 (4)N2—C8—C9—C14178.1 (4)
C2—C1—C6—C50.8 (6)C8—C9—C10—C11179.7 (3)
C7—C1—C6—O12.7 (6)C14—C9—C10—C11−0.02
C7—C1—C6—C5−178.3 (4)C8—C9—C14—C13−179.7 (3)
C2—C1—C7—O2−4.8 (6)C10—C9—C14—C13−0.03
C2—C1—C7—N1175.4 (4)C9—C10—C11—F1−177.2 (5)
C6—C1—C7—O2174.3 (4)C9—C10—C11—C120.03
C6—C1—C7—N1−5.5 (6)F1—C11—C12—C13177.5 (4)
C2—C1—C6—O1−178.2 (4)C10—C11—C12—C13−0.02
C6—C1—C2—C3−0.8 (7)C11—C12—C13—F1'−178.6 (5)
C7—C1—C2—C3178.3 (4)C11—C12—C13—C14−0.02
C1—C2—C3—C40.2 (7)F1'—C13—C14—C9178.5 (5)
C2—C3—C4—C50.5 (7)C12—C13—C14—C90.03
C3—C4—C5—C6−0.6 (7)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1N···O10.861.912.612 (5)138
O1—H1O···O2i0.821.862.657 (5)166

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: SU2098).

References

  • Karthikeyan, M. S., Prasad, D. J., Poojary, B., Bhat, K. S., Holla, B. S. & Kumari, N. S. (2006). Bioorg. Med. Chem.14, 7482–7489. [PubMed]
  • Khattab, S. N. (2005). Molecules, 10, 1218–1228. [PubMed]
  • Kucukguzel, G., Kocatepe, A., De Clercq, E., Sahi, F. & Gulluce, M. (2006). Eur. J. Med. Chem.41, 353–359. [PubMed]
  • Okabe, N., Nakamura, T. & Fukuda, H. (1993). Acta Cryst. C49, 1678–1680.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

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