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Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): o1700.
Published online 2009 June 27. doi:  10.1107/S1600536809023708
PMCID: PMC2969194

(Z)-2-[(2-Hydr­oxy-1-naphth­yl)methyl­eneamino]benzonitrile

Abstract

The title compound, C18H12N2O, crystallizes in a phenol–imine tautomeric form with a Z conformation for the imine functionality. The dihedral angle between the aromatic rings is 8.98 (9)°. A strong intra­molecular O—H(...)N hydrogen-bond inter­action between the hydroxyl group and imine N atom occurs.

Related literature

For general properties of Schiff base compounds, see: Weber et al. (2007 [triangle]); Chen et al. (2008 [triangle]). For related structures, see: Elmali et al. (2001 [triangle]); Yüce et al. (2006 [triangle]); Petek et al. (2007 [triangle]).

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Object name is e-65-o1700-scheme1.jpg

Experimental

Crystal data

  • C18H12N2O
  • M r = 272.30
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1700-efi1.jpg
  • a = 13.4640 (13) Å
  • b = 7.4450 (6) Å
  • c = 15.4090 (11) Å
  • β = 116.660 (6)°
  • V = 1380.4 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 293 K
  • 0.20 × 0.20 × 0.20 mm

Data collection

  • Rigaku SCXmini diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 [triangle]) T min = 0.973, T max = 0.979
  • 12133 measured reflections
  • 2706 independent reflections
  • 1803 reflections with I > 2σ(I)
  • R int = 0.056

Refinement

  • R[F 2 > 2σ(F 2)] = 0.066
  • wR(F 2) = 0.159
  • S = 1.10
  • 2706 reflections
  • 190 parameters
  • H-atom parameters constrained
  • Δρmax = 0.20 e Å−3
  • Δρmin = −0.18 e Å−3

Data collection: CrystalClear (Rigaku, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; 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 I, global. DOI: 10.1107/S1600536809023708/bh2232sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809023708/bh2232Isup2.hkl

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

supplementary crystallographic information

Comment

Schiff base compounds have received considerable attention for many years because these compounds play an important role in coordination chemistry related to magnetism (Weber et al., 2007) and catalysis (Chen et al., 2008).Our group is interested in the synthesis and preparation of Schiff bases. Here, we report the synthesis and crystal structure of the title compound.

Figure 1 shows an ORTEP plot of the title compound. The molecule adopts the phenol–imine tautomeric form with a strong intramolecular O—H···N hydrogen bond. The C11N1 and C2—O1 bond lengths [1.296 (3) and 1.324 (3) Å, respectively] are comparable to corresponding values observed in a similar phenol–imine tautomeric structures (e.g. Petek et al., 2007), while different geometry is observed in the case of zwitterionic molecules (Elmali et al., 2001; Yüce et al., 2006). Phenyl and naphthalyl rings, A (C12···C17) and B (C1···C10), are, of course, planar, and the dihedral angle between them is 8.98 (9)°. The molecule displays a trans configuration about the central CN imine bond. Molecules are packed in the crystal at van der Waals distances.

Experimental

2-Aminobenzonitrile (0.59 g, 5 mmol) and 2-hydroxynaphthalene-1-carbaldehyde (0.861 g, 5 mmol) were dissolved in ethanol (25 ml). The resulting mixture was refluxed for 5 h and cooled to room temperature. The solid product was collected by filtration. Crystals suitable for X-ray diffraction studies were obtained on slow evaporation at room temperature.

Refinement

The H atoms were placed geometrically and treated as riding atoms with O—H = 0.82 Å and C—H = 0.93 Å, and with Uiso(H) = 1.2Ueq(Carrier C) and Uiso(H1A) = 1.5Ueq(O1).

Figures

Fig. 1.
The molecular structure of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

Crystal data

C18H12N2OF(000) = 568
Mr = 272.30Dx = 1.310 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2198 reflections
a = 13.4640 (13) Åθ = 2.7–27.5°
b = 7.4450 (6) ŵ = 0.08 mm1
c = 15.4090 (11) ÅT = 293 K
β = 116.660 (6)°Block, pale yellow
V = 1380.4 (2) Å30.20 × 0.20 × 0.20 mm
Z = 4

Data collection

Rigaku SCXmini diffractometer2706 independent reflections
Radiation source: fine-focus sealed tube1803 reflections with I > 2σ(I)
graphiteRint = 0.056
Detector resolution: 13.6612 pixels mm-1θmax = 26.0°, θmin = 3.0°
ω scansh = −16→16
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)k = −9→9
Tmin = 0.973, Tmax = 0.979l = −18→18
12133 measured reflections

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)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159H-atom parameters constrained
S = 1.10w = 1/[σ2(Fo2) + (0.0672P)2 + 0.1372P] where P = (Fo2 + 2Fc2)/3
2706 reflections(Δ/σ)max < 0.001
190 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = −0.18 e Å3
0 constraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O10.22890 (15)0.5907 (3)−0.07648 (12)0.0792 (6)
H1A0.17180.6436−0.08520.119*
N10.07487 (14)0.7038 (2)−0.03712 (12)0.0490 (5)
N20.0188 (2)0.7966 (4)−0.27347 (16)0.0894 (8)
C10.24373 (17)0.5812 (3)0.08450 (16)0.0465 (5)
C110.13677 (17)0.6610 (3)0.05282 (16)0.0459 (5)
H11A0.11050.68310.09830.055*
C12−0.03185 (17)0.7809 (3)−0.07090 (15)0.0439 (5)
C13−0.08320 (18)0.8360 (3)−0.16755 (16)0.0500 (6)
C100.30954 (17)0.5267 (3)0.18411 (16)0.0477 (6)
C60.4729 (2)0.3710 (3)0.3064 (2)0.0674 (7)
H6A0.53810.30680.32280.081*
C50.41020 (19)0.4302 (3)0.21022 (18)0.0550 (6)
C90.2793 (2)0.5638 (3)0.25909 (17)0.0582 (6)
H9A0.21500.62900.24510.070*
C20.2839 (2)0.5440 (3)0.01600 (18)0.0569 (6)
C17−0.08801 (19)0.8058 (3)−0.01468 (16)0.0528 (6)
H17A−0.05520.77090.05020.063*
C16−0.1922 (2)0.8823 (3)−0.05539 (18)0.0579 (6)
H16A−0.22920.8983−0.01750.069*
C14−0.1883 (2)0.9135 (3)−0.20763 (18)0.0596 (7)
H14A−0.22160.9502−0.27220.072*
C15−0.2426 (2)0.9355 (3)−0.15123 (19)0.0605 (7)
H15A−0.31330.9862−0.17760.073*
C40.4449 (2)0.3949 (3)0.1372 (2)0.0664 (7)
H4A0.51050.33160.15370.080*
C30.3859 (2)0.4500 (4)0.0453 (2)0.0684 (8)
H3A0.41210.4264−0.00010.082*
C18−0.0262 (2)0.8130 (4)−0.22658 (17)0.0624 (7)
C80.3432 (2)0.5053 (4)0.35194 (19)0.0716 (8)
H8A0.32180.53220.40010.086*
C70.4394 (2)0.4064 (4)0.3755 (2)0.0749 (8)
H7A0.48080.36470.43860.090*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0708 (12)0.1177 (17)0.0570 (11)0.0071 (11)0.0359 (10)−0.0072 (11)
N10.0484 (11)0.0551 (12)0.0439 (11)−0.0048 (9)0.0211 (9)−0.0043 (9)
N20.0851 (17)0.134 (2)0.0598 (15)0.0022 (16)0.0421 (14)0.0019 (14)
C10.0461 (12)0.0447 (12)0.0530 (14)−0.0078 (10)0.0259 (11)−0.0084 (10)
C110.0498 (13)0.0447 (12)0.0473 (13)−0.0059 (10)0.0256 (11)−0.0057 (10)
C120.0428 (12)0.0450 (12)0.0449 (12)−0.0070 (10)0.0205 (10)−0.0072 (10)
C130.0498 (13)0.0542 (14)0.0475 (13)−0.0075 (11)0.0232 (11)−0.0025 (11)
C100.0461 (12)0.0406 (12)0.0559 (14)−0.0069 (10)0.0224 (11)−0.0025 (10)
C60.0505 (14)0.0529 (15)0.083 (2)0.0003 (12)0.0163 (15)0.0074 (14)
C50.0471 (13)0.0417 (12)0.0716 (17)−0.0036 (11)0.0227 (13)−0.0049 (12)
C90.0552 (14)0.0652 (16)0.0542 (15)0.0035 (12)0.0244 (12)0.0035 (12)
C20.0525 (14)0.0638 (16)0.0570 (15)−0.0058 (12)0.0269 (12)−0.0093 (12)
C170.0563 (14)0.0571 (15)0.0495 (13)−0.0069 (12)0.0278 (11)−0.0025 (11)
C160.0577 (15)0.0566 (15)0.0701 (17)−0.0052 (12)0.0383 (13)−0.0092 (13)
C140.0609 (15)0.0595 (15)0.0537 (15)−0.0002 (12)0.0214 (13)0.0031 (12)
C150.0502 (14)0.0540 (15)0.0726 (18)0.0010 (11)0.0233 (13)−0.0023 (13)
C40.0489 (14)0.0572 (16)0.092 (2)0.0015 (12)0.0304 (15)−0.0130 (14)
C30.0612 (16)0.0731 (19)0.084 (2)−0.0025 (14)0.0443 (15)−0.0200 (15)
C180.0610 (15)0.0807 (19)0.0448 (14)−0.0019 (14)0.0231 (12)0.0029 (13)
C80.0692 (17)0.085 (2)0.0578 (16)0.0000 (16)0.0261 (14)0.0081 (14)
C70.0678 (18)0.0729 (19)0.0686 (18)0.0019 (14)0.0169 (15)0.0185 (15)

Geometric parameters (Å, °)

O1—C21.324 (3)C5—C41.423 (3)
O1—H1A0.8200C9—C81.368 (3)
N1—C111.296 (3)C9—H9A0.9300
N1—C121.412 (3)C2—C31.423 (3)
N2—C181.139 (3)C17—C161.377 (3)
C1—C21.412 (3)C17—H17A0.9300
C1—C111.426 (3)C16—C151.378 (3)
C1—C101.444 (3)C16—H16A0.9300
C11—H11A0.9300C14—C151.374 (3)
C12—C171.394 (3)C14—H14A0.9300
C12—C131.393 (3)C15—H15A0.9300
C13—C141.390 (3)C4—C31.340 (4)
C13—C181.439 (3)C4—H4A0.9300
C10—C91.414 (3)C3—H3A0.9300
C10—C51.423 (3)C8—C71.390 (4)
C6—C71.355 (4)C8—H8A0.9300
C6—C51.408 (3)C7—H7A0.9300
C6—H6A0.9300
C2—O1—H1A109.5O1—C2—C3117.6 (2)
C11—N1—C12123.63 (18)C1—C2—C3119.9 (2)
C2—C1—C11119.5 (2)C16—C17—C12119.8 (2)
C2—C1—C10118.8 (2)C16—C17—H17A120.1
C11—C1—C10121.64 (19)C12—C17—H17A120.1
N1—C11—C1122.3 (2)C15—C16—C17121.3 (2)
N1—C11—H11A118.8C15—C16—H16A119.4
C1—C11—H11A118.8C17—C16—H16A119.4
C17—C12—C13118.5 (2)C15—C14—C13119.6 (2)
C17—C12—N1124.8 (2)C15—C14—H14A120.2
C13—C12—N1116.66 (19)C13—C14—H14A120.2
C14—C13—C12121.0 (2)C14—C15—C16119.8 (2)
C14—C13—C18119.6 (2)C14—C15—H15A120.1
C12—C13—C18119.4 (2)C16—C15—H15A120.1
C9—C10—C5117.0 (2)C3—C4—C5122.0 (2)
C9—C10—C1123.3 (2)C3—C4—H4A119.0
C5—C10—C1119.6 (2)C5—C4—H4A119.0
C7—C6—C5120.9 (3)C4—C3—C2121.0 (2)
C7—C6—H6A119.6C4—C3—H3A119.5
C5—C6—H6A119.6C2—C3—H3A119.5
C6—C5—C4121.4 (2)N2—C18—C13179.3 (3)
C6—C5—C10120.0 (2)C9—C8—C7121.1 (3)
C4—C5—C10118.6 (2)C9—C8—H8A119.4
C8—C9—C10121.1 (2)C7—C8—H8A119.4
C8—C9—H9A119.5C6—C7—C8119.8 (3)
C10—C9—H9A119.5C6—C7—H7A120.1
O1—C2—C1122.4 (2)C8—C7—H7A120.1

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1A···N10.821.822.551 (2)147

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2232).

References

  • Chen, Z. H., Morimoto, H., Matsunaga, S. & Shibasaki, M. (2008). J. Am. Chem. Soc.130, 2170–2171. [PubMed]
  • Elmali, A., Elerman, Y. & Svoboda, I. (2001). Acta Cryst. C57, 485–486. [PubMed]
  • Petek, H., Albayrak, Ç., Ağar, E., Ískeleli, N. O. & Şenel, İ. (2007). Acta Cryst. E63, o810–o812.
  • Rigaku (2005). CrystalClear Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Weber, B., Tandon, R. & Himsl, D. (2007). Z. Anorg. Allg. Chem.633, 1159–1162.
  • Yüce, S., Albayrak, Ç., Odabaşoğlu, M. & Büyükgüngör, O. (2006). Acta Cryst. C62, o389–o393. [PubMed]

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