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Acta Crystallogr Sect E Struct Rep Online. 2009 June 1; 65(Pt 6): o1282.
Published online 2009 May 14. doi:  10.1107/S1600536809017280
PMCID: PMC2969562

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

Abstract

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.

Related literature

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

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Object name is e-65-o1282-scheme1.jpg

Experimental

Crystal data

  • C12H9FN2O
  • M r = 216.21
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1282-efi1.jpg
  • a = 13.1635 (11) Å
  • b = 6.2252 (6) Å
  • c = 13.8235 (17) Å
  • β = 113.33 (3)°
  • V = 1040.1 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 293 K
  • 0.40 × 0.25 × 0.15 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: ψ scan (North et al., 1968 [triangle]) T min = 0.960, T max = 0.985
  • 1907 measured reflections
  • 1825 independent reflections
  • 1210 reflections with I > 2σ(I)
  • R int = 0.064

Refinement

  • R[F 2 > 2σ(F 2)] = 0.053
  • wR(F 2) = 0.145
  • S = 1.05
  • 1825 reflections
  • 147 parameters
  • H-atom parameters constrained
  • Δρmax = 0.16 e Å−3
  • Δρmin = −0.17 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 [triangle]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 [triangle]); 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: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809017280/hb2968sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809017280/hb2968Isup2.hkl

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

Acknowledgments

We thank the Measurement Foundation of Nanjing University, and Dr Rui-Qin Fang for her support.

supplementary crystallographic information

Comment

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)°.

Experimental

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

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).

Figures

Fig. 1.
The molecular structure of (I) showing 30% probability displacement ellipsoids.

Crystal data

C12H9FN2OF(000) = 448
Mr = 216.21Dx = 1.381 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 13.1635 (11) Åθ = 9–12°
b = 6.2252 (6) ŵ = 0.10 mm1
c = 13.8235 (17) ÅT = 293 K
β = 113.33 (3)°Block, yellow
V = 1040.1 (3) Å30.40 × 0.25 × 0.15 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometer1825 independent reflections
Radiation source: fine-focus sealed tube1210 reflections with I > 2σ(I)
graphiteRint = 0.064
ω/2θ scansθmax = 25.0°, θmin = 1.8°
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

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053H-atom parameters constrained
wR(F2) = 0.145w = 1/[σ2(Fo2) + (0.0657P)2 + 0.1652P] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
1825 reflectionsΔρmax = 0.16 e Å3
147 parametersΔρmin = −0.17 e Å3
0 restraintsExtinction 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)

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
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)

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, °)

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, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.862.588 (2)147

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2968).

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.
  • 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. [PubMed]

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