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Acta Cryst. (2009). E65, o1282    [ doi:10.1107/S1600536809017280 ]

4-Fluoro-2-[(E)-2-pyridyliminomethyl]phenol

P. Cui and L. Shi

Abstract top

In the title compound, C12H9FN2O, the dihedral angle between the benzene ring and the pyridine ring is 4.35 (16)°. The molecular conformation is stabilized by an intramolecular O-H...N hydrogen bond.

Comment top

Recently, we have reported the structural characterization of one Schiff base compound derived from the condensation of 5-chloro-salicylaldehyde and primary amines (Li et al., 2006). As an extension of this work, we report here the crystal structure of the title compound, (I). In (I), all bond lengths are within normal ranges (Allen et al., 1987) (Fig. 1). There is an intramolecular O—H···N hydrogen bond in (I). The dihedral angle between the two aromatic rings is 4.35(0.16)°.

Related literature top

For a related structure, see: Li et al. (2006). For reference strutural data, see: Allen et al. (1987).

Experimental top

Pyridin-2-amine (94 mg, 1 mmol) and 5-fluoro-salicylaldehyde (140 mg, 1 mmol) were dissolved in methanol (10 ml) at 323 K. The mixture was stirred for 2 h to give a clear yellow solution. After keeping the solution in air for 7 d by slow evaporation of the solvent, yellow blocks of (I) were formed at the bottom of the vessel, with 80% yield. The crystals were isolated, washed three times with methanol and dried in a vacuum desiccator containing anhydrous CaCl2.

Refinement top

All H atoms were positioned geometrically (C—H = 0.93–0.96 Å, O—H = 0.82Å) and refined as riding, with Uiso(H) = 1.2Ueq(carrier).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing 30% probability displacement ellipsoids.
4-Fluoro-2-[(E)-2-pyridyliminomethyl]phenol top
Crystal data top
C12H9FN2OF000 = 448
Mr = 216.21Dx = 1.381 Mg m−3
Monoclinic, P21/nMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 13.1635 (11) Åθ = 9–12º
b = 6.2252 (6) ŵ = 0.10 mm−1
c = 13.8235 (17) ÅT = 293 K
β = 113.33 (3)ºBlock, yellow
V = 1040.1 (3) Å30.40 × 0.25 × 0.15 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer		1825 independent reflections
Radiation source: fine-focus sealed tube1210 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.064
T = 293 Kθmax = 25.0º
ω/2θ scansθmin = 1.8º
Absorption correction: ψ scan
(North et al., 1968)		h = 0→15
Tmin = 0.960, Tmax = 0.985k = 0→7
1907 measured reflectionsl = −16→15
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.053  w = 1/[σ2(Fo2) + (0.0657P)2 + 0.1652P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.145(Δ/σ)max < 0.001
S = 1.05Δρmax = 0.16 e Å−3
1825 reflectionsΔρmin = −0.17 e Å−3
147 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.089 (10)
Secondary atom site location: difference Fourier map
Crystal data top
C12H9FN2OV = 1040.1 (3) Å3
Mr = 216.21Z = 4
Monoclinic, P21/nMo Kα
a = 13.1635 (11) ŵ = 0.10 mm−1
b = 6.2252 (6) ÅT = 293 K
c = 13.8235 (17) Å0.40 × 0.25 × 0.15 mm
β = 113.33 (3)º
Data collection top
Enraf–Nonius CAD-4
diffractometer		1825 independent reflections
Absorption correction: ψ scan
(North et al., 1968)		1210 reflections with I > 2σ(I)
Tmin = 0.960, Tmax = 0.985Rint = 0.064
1907 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.053147 parameters
wR(F2) = 0.145H-atom parameters constrained
S = 1.05Δρmax = 0.16 e Å−3
1825 reflectionsΔρmin = −0.17 e Å−3
Special details top

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) top
xyzUiso*/Ueq
C10.96836 (16)0.2734 (3)0.23488 (17)0.0457 (6)
C21.06679 (18)0.2492 (4)0.21918 (18)0.0529 (6)
C31.1349 (2)0.0730 (4)0.2622 (2)0.0633 (7)
H31.19960.05680.25100.076*
C41.1080 (2)−0.0767 (4)0.3207 (2)0.0658 (7)
H41.1540−0.19360.34960.079*
C51.0116 (2)−0.0506 (4)0.3357 (2)0.0619 (7)
C60.94233 (19)0.1189 (3)0.29492 (19)0.0548 (6)
H60.87790.13180.30690.066*
C70.89393 (17)0.4506 (3)0.18913 (17)0.0484 (6)
H70.83010.46320.20220.058*
C80.83993 (18)0.7650 (3)0.08721 (17)0.0488 (6)
C90.8652 (2)0.9050 (4)0.02246 (19)0.0591 (7)
H90.92690.88160.00700.071*
C100.7981 (2)1.0788 (4)−0.01873 (19)0.0673 (7)
H100.81411.1762−0.06180.081*
C110.7071 (2)1.1067 (4)0.0045 (2)0.0677 (7)
H110.66001.2231−0.02230.081*
C120.6870 (2)0.9583 (4)0.0684 (2)0.0660 (7)
H120.62470.97720.08350.079*
F10.98419 (14)−0.2003 (2)0.39318 (14)0.0938 (6)
N10.91366 (15)0.5906 (3)0.13106 (15)0.0514 (5)
N20.75169 (16)0.7888 (3)0.11012 (15)0.0582 (6)
O11.09729 (14)0.3937 (3)0.16264 (16)0.0721 (6)
H11.04760.48180.13640.108*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0411 (11)0.0435 (12)0.0504 (13)−0.0015 (10)0.0159 (10)−0.0095 (10)
C20.0488 (13)0.0527 (13)0.0569 (14)−0.0022 (11)0.0206 (11)−0.0129 (12)
C30.0499 (14)0.0678 (17)0.0690 (16)0.0094 (13)0.0201 (13)−0.0160 (14)
C40.0655 (17)0.0503 (15)0.0676 (17)0.0120 (13)0.0116 (13)−0.0067 (13)
C50.0649 (16)0.0453 (13)0.0677 (16)−0.0035 (12)0.0181 (13)0.0006 (12)
C60.0502 (13)0.0500 (14)0.0638 (15)−0.0036 (11)0.0221 (11)−0.0062 (12)
C70.0439 (12)0.0493 (13)0.0539 (14)−0.0027 (10)0.0216 (11)−0.0089 (11)
C80.0513 (13)0.0479 (13)0.0462 (13)−0.0020 (11)0.0181 (11)−0.0058 (11)
C90.0651 (16)0.0579 (15)0.0577 (15)−0.0051 (12)0.0280 (13)−0.0030 (12)
C100.0829 (19)0.0613 (16)0.0551 (15)−0.0051 (15)0.0248 (14)0.0088 (13)
C110.0761 (18)0.0572 (16)0.0582 (15)0.0115 (14)0.0143 (14)0.0083 (13)
C120.0631 (16)0.0661 (16)0.0678 (16)0.0146 (13)0.0249 (13)0.0088 (14)
F10.1042 (13)0.0645 (10)0.1094 (13)0.0031 (9)0.0390 (10)0.0279 (9)
N10.0525 (11)0.0486 (11)0.0553 (12)−0.0021 (9)0.0237 (9)−0.0043 (10)
N20.0564 (12)0.0585 (12)0.0618 (13)0.0107 (10)0.0257 (10)0.0087 (10)
O10.0616 (11)0.0784 (13)0.0899 (14)0.0050 (9)0.0444 (10)0.0052 (11)
Geometric parameters (Å, °) top
C1—C61.399 (3)C7—H70.9300
C1—C21.404 (3)C8—N21.328 (3)
C1—C71.444 (3)C8—C91.381 (3)
C2—O11.353 (3)C8—N11.422 (3)
C2—C31.392 (3)C9—C101.370 (3)
C3—C41.369 (3)C9—H90.9300
C3—H30.9300C10—C111.368 (4)
C4—C51.375 (3)C10—H100.9300
C4—H40.9300C11—C121.375 (3)
C5—C61.362 (3)C11—H110.9300
C5—F11.363 (3)C12—N21.335 (3)
C6—H60.9300C12—H120.9300
C7—N11.279 (3)O1—H10.8200
C6—C1—C2118.4 (2)C1—C7—H7119.2
C6—C1—C7120.12 (19)N2—C8—C9122.8 (2)
C2—C1—C7121.5 (2)N2—C8—N1119.8 (2)
O1—C2—C3118.8 (2)C9—C8—N1117.3 (2)
O1—C2—C1121.4 (2)C10—C9—C8119.1 (2)
C3—C2—C1119.7 (2)C10—C9—H9120.4
C4—C3—C2121.0 (2)C8—C9—H9120.4
C4—C3—H3119.5C11—C10—C9118.9 (2)
C2—C3—H3119.5C11—C10—H10120.6
C3—C4—C5118.6 (2)C9—C10—H10120.6
C3—C4—H4120.7C10—C11—C12118.4 (2)
C5—C4—H4120.7C10—C11—H11120.8
C6—C5—F1118.9 (2)C12—C11—H11120.8
C6—C5—C4122.4 (2)N2—C12—C11123.8 (2)
F1—C5—C4118.8 (2)N2—C12—H12118.1
C5—C6—C1119.8 (2)C11—C12—H12118.1
C5—C6—H6120.1C7—N1—C8120.91 (19)
C1—C6—H6120.1C8—N2—C12117.0 (2)
N1—C7—C1121.6 (2)C2—O1—H1109.5
N1—C7—H7119.2
C6—C1—C2—O1−179.5 (2)C6—C1—C7—N1−177.70 (19)
C7—C1—C2—O11.6 (3)C2—C1—C7—N11.2 (3)
C6—C1—C2—C30.7 (3)N2—C8—C9—C101.3 (3)
C7—C1—C2—C3−178.2 (2)N1—C8—C9—C10−178.0 (2)
O1—C2—C3—C4179.5 (2)C8—C9—C10—C11−0.9 (4)
C1—C2—C3—C4−0.6 (3)C9—C10—C11—C120.0 (4)
C2—C3—C4—C50.4 (4)C10—C11—C12—N20.6 (4)
C3—C4—C5—C6−0.2 (4)C1—C7—N1—C8−179.53 (19)
C3—C4—C5—F1179.5 (2)N2—C8—N1—C72.8 (3)
F1—C5—C6—C1−179.4 (2)C9—C8—N1—C7−177.8 (2)
C4—C5—C6—C10.3 (4)C9—C8—N2—C12−0.8 (3)
C2—C1—C6—C5−0.5 (3)N1—C8—N2—C12178.5 (2)
C7—C1—C6—C5178.4 (2)C11—C12—N2—C8−0.2 (4)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.862.588 (2)147
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.862.588 (2)147
references
References top

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.

Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands.

Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.

Li, Y.-G., Huang, K.-X., Ai, L. & Zhu, H.-L. (2006). Acta Cryst. E62, o2219–o2220.

North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.