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Acta Cryst. (2009). E65, o534    [ doi:10.1107/S1600536809004486 ]

2-Benzyloxy-1-naphthaldehyde

R. Gao, W.-H. Li, P. Liu and P.-A. Wang

Abstract top

In the title compound, C18H14O2, the dihedral angle between the phenyl and naphthyl ring systems is 21.8 (3)°. The packing of molecules in the crystal structure is stabilized by weak intermolecular C-H...O hydrogen bonds.

Comment top

The title compound, 2-benzyloxy-1-naphthaldehyde, was obtained by benzylation of 2-hydroxy-1-naphthaldehyde with benzyl bromide (Quideau et al., 2001) and used for alkylation of position 4 in the naphthyl ring system. It has also been used for the intramolecular trapping of benzynes to yield some novel xanthenes (Knight & Little, 2001).

In the title compound, C18H14O2, the dihedral angle between the phenyl and naphthyl ring systems is 21.8 (3)°. The packing of molecules in the crystal structure is stabilized by weak intermolecular C—H···O hydrogen bonds.

Related literature top

For the preparation of 2-benzyloxy-1-naphthaldehyde, see: Quideau et al. (2001). For synthetic use of the title compound, see: Knight & Little (2001).

Experimental top

To a stirred solution of commercially available 2-hydroxy-1-naphthaldehyde (4.30 g, 25.0 mmol) in N,N-dimethylformamide (100.0 cm3) was added potassium carbonate (3.82 g, 27.6 mmol) and benzyl bromide (3.0 cm3, 25.0 mmol), and the mixture was heated for 4 h at 90–100°C. The solution was filtered through celite and the solvent removed in vacuo. The residue was dissolved with Et2O (160 cm3), washed with 1 M NaOH (110 cm3), brine (2× 110 cm3), and dried over Na2SO4. Evaporation of the solvent afforded the title compound as a light yellow powder (6.0 g, 91%). The melting point and the spectroscopic data of the title compound were consisted with the reported literature (Quideau et al., 2001).

Refinement top

All H atoms were placed in calculated positions and refined as riding, with C—H = 0.93–0.97Å and with Uiso(H) = 1.2Ueq(C). The values of R[F2>2σ(F2)] and wR(F2) are 0.084 and 0.285, respectively; these high values may be due to the poor quality of the crystals.

Computing details top

Data collection: SMART(Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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: Mercury (Macrae et al., 2006) and CAMERON (Watkin et al., 1996).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
[Figure 2] Fig. 2. The packing of the title compound, viewed down the b axis. Dotted lines indicate hydrogen bonds.
2-Benzyloxy-1-naphthaldehyde top
Crystal data top
C18H14O2F(000) = 552
Mr = 262.29Dx = 1.307 Mg m−3
Monoclinic, P21/cMelting point: 393(1) K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 10.427 (7) ÅCell parameters from 1554 reflections
b = 8.128 (6) Åθ = 2.6–24.3°
c = 15.787 (11) ŵ = 0.08 mm−1
β = 94.746 (11)°T = 296 K
V = 1333.3 (16) Å3Block, colourless
Z = 40.39 × 0.26 × 0.16 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		2262 independent reflections
Radiation source: fine-focus sealed tube1354 reflections with I > 2σ(I)
graphiteRint = 0.038
φ and ω scansθmax = 25.1°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		h = −7→12
Tmin = 0.968, Tmax = 0.987k = −9→6
5088 measured reflectionsl = −18→17
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.084Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.285H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.18P)2 + 0.612P]
where P = (Fo2 + 2Fc2)/3
2262 reflections(Δ/σ)max < 0.001
181 parametersΔρmax = 0.41 e Å−3
0 restraintsΔρmin = −0.53 e Å−3
Crystal data top
C18H14O2V = 1333.3 (16) Å3
Mr = 262.29Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.427 (7) ŵ = 0.08 mm−1
b = 8.128 (6) ÅT = 296 K
c = 15.787 (11) Å0.39 × 0.26 × 0.16 mm
β = 94.746 (11)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		2262 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		1354 reflections with I > 2σ(I)
Tmin = 0.968, Tmax = 0.987Rint = 0.038
5088 measured reflectionsθmax = 25.1°
Refinement top
R[F2 > 2σ(F2)] = 0.084H-atom parameters constrained
wR(F2) = 0.285Δρmax = 0.41 e Å−3
S = 1.04Δρmin = −0.53 e Å−3
2262 reflectionsAbsolute structure: ?
181 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
O10.6120 (3)0.2057 (4)0.65206 (15)0.0658 (10)
O20.6321 (2)0.1063 (4)0.41483 (14)0.0531 (8)
C10.4002 (3)0.3376 (5)0.5290 (2)0.0411 (9)
C20.3808 (4)0.4033 (5)0.6101 (2)0.0518 (11)
H20.44230.38370.65510.062*
C30.2749 (4)0.4942 (6)0.6241 (3)0.0630 (12)
H30.26410.53350.67840.076*
C40.1821 (4)0.5289 (7)0.5572 (3)0.0716 (14)
H40.11030.59180.56710.086*
C50.1967 (4)0.4710 (5)0.4783 (3)0.0577 (11)
H50.13490.49520.43430.069*
C60.3053 (3)0.3737 (6)0.4616 (2)0.0504 (11)
C70.3228 (3)0.3153 (5)0.3794 (2)0.0523 (11)
H70.26080.33950.33540.063*
C80.4275 (3)0.2244 (6)0.3622 (2)0.0539 (11)
H80.43540.18510.30750.065*
C90.5238 (3)0.1904 (5)0.4280 (2)0.0431 (10)
C100.5100 (3)0.2424 (5)0.5110 (2)0.0392 (9)
C110.6122 (3)0.1927 (6)0.5756 (2)0.0514 (11)
H110.68530.14590.55560.062*
C120.6621 (3)0.0652 (6)0.3305 (2)0.0575 (12)
H12A0.63810.15480.29180.069*
H12B0.6154−0.03260.31080.069*
C130.8049 (3)0.0350 (5)0.3337 (2)0.0468 (10)
C140.8757 (4)0.1189 (6)0.2765 (2)0.0571 (12)
H140.83480.19020.23680.069*
C151.0079 (4)0.0954 (7)0.2792 (3)0.0713 (15)
H151.05490.14840.23970.086*
C161.0699 (4)−0.0047 (6)0.3390 (3)0.0635 (13)
H161.1589−0.01630.34120.076*
C171.0006 (4)−0.0884 (6)0.3960 (3)0.0630 (12)
H171.0423−0.15820.43600.076*
C180.8681 (4)−0.0675 (6)0.3932 (2)0.0579 (12)
H180.8214−0.12320.43190.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0596 (17)0.099 (3)0.0374 (14)0.0078 (16)−0.0065 (11)−0.0031 (14)
O20.0498 (15)0.075 (2)0.0352 (13)0.0178 (14)0.0062 (10)−0.0012 (12)
C10.0352 (18)0.047 (3)0.0415 (17)−0.0085 (16)0.0054 (14)0.0049 (17)
C20.045 (2)0.062 (3)0.050 (2)−0.003 (2)0.0112 (16)−0.0008 (19)
C30.058 (2)0.066 (3)0.068 (3)−0.003 (2)0.023 (2)−0.001 (2)
C40.046 (2)0.082 (4)0.090 (3)0.008 (2)0.024 (2)0.003 (3)
C50.043 (2)0.056 (3)0.075 (3)−0.0013 (19)0.0041 (18)0.008 (2)
C60.0307 (17)0.068 (3)0.052 (2)−0.0035 (17)0.0040 (15)0.011 (2)
C70.040 (2)0.067 (3)0.047 (2)−0.0013 (19)−0.0074 (15)0.010 (2)
C80.045 (2)0.082 (3)0.0340 (18)−0.002 (2)−0.0007 (15)0.0032 (18)
C90.0345 (17)0.055 (3)0.0393 (18)−0.0040 (17)0.0035 (13)0.0078 (17)
C100.0328 (17)0.047 (2)0.0373 (17)−0.0047 (15)0.0012 (13)0.0028 (16)
C110.0386 (19)0.076 (3)0.0386 (19)0.0002 (19)−0.0005 (14)0.0038 (19)
C120.043 (2)0.096 (4)0.0337 (17)−0.003 (2)0.0069 (14)−0.004 (2)
C130.0395 (18)0.066 (3)0.0355 (16)−0.0014 (18)0.0055 (14)−0.0021 (18)
C140.045 (2)0.081 (4)0.047 (2)0.005 (2)0.0070 (16)0.015 (2)
C150.044 (2)0.107 (4)0.064 (3)0.003 (2)0.0155 (19)0.017 (3)
C160.043 (2)0.087 (4)0.061 (2)0.010 (2)0.0049 (18)0.002 (2)
C170.056 (2)0.075 (3)0.057 (2)0.015 (2)−0.0031 (18)0.008 (2)
C180.054 (2)0.071 (3)0.050 (2)−0.002 (2)0.0091 (17)0.010 (2)
Geometric parameters (Å, °) top
O1—C111.211 (4)C8—H80.9300
O2—C91.351 (4)C9—C101.395 (5)
O2—C121.433 (4)C10—C111.471 (5)
C1—C21.417 (5)C11—H110.9300
C1—C61.422 (5)C12—C131.506 (5)
C1—C101.430 (5)C12—H12A0.9700
C2—C31.362 (6)C12—H12B0.9700
C2—H20.9300C13—C181.382 (6)
C3—C41.400 (6)C13—C141.391 (5)
C3—H30.9300C14—C151.389 (5)
C4—C51.351 (6)C14—H140.9300
C4—H40.9300C15—C161.367 (6)
C5—C61.424 (5)C15—H150.9300
C5—H50.9300C16—C171.380 (6)
C6—C71.407 (5)C16—H160.9300
C7—C81.365 (5)C17—C181.389 (5)
C7—H70.9300C17—H170.9300
C8—C91.412 (5)C18—H180.9300
C9—O2—C12120.7 (3)C9—C10—C11116.3 (3)
C2—C1—C6117.1 (3)C1—C10—C11123.8 (3)
C2—C1—C10124.1 (3)O1—C11—C10127.3 (4)
C6—C1—C10118.8 (3)O1—C11—H11116.3
C3—C2—C1121.9 (4)C10—C11—H11116.3
C3—C2—H2119.0O2—C12—C13107.3 (3)
C1—C2—H2119.0O2—C12—H12A110.2
C2—C3—C4120.4 (4)C13—C12—H12A110.2
C2—C3—H3119.8O2—C12—H12B110.2
C4—C3—H3119.8C13—C12—H12B110.2
C5—C4—C3120.1 (4)H12A—C12—H12B108.5
C5—C4—H4120.0C18—C13—C14119.2 (3)
C3—C4—H4120.0C18—C13—C12122.4 (3)
C4—C5—C6121.1 (4)C14—C13—C12118.3 (3)
C4—C5—H5119.5C15—C14—C13119.4 (4)
C6—C5—H5119.5C15—C14—H14120.3
C7—C6—C1119.0 (3)C13—C14—H14120.3
C7—C6—C5121.6 (3)C16—C15—C14121.0 (4)
C1—C6—C5119.4 (4)C16—C15—H15119.5
C8—C7—C6122.2 (3)C14—C15—H15119.5
C8—C7—H7118.9C15—C16—C17120.0 (4)
C6—C7—H7118.9C15—C16—H16120.0
C7—C8—C9119.4 (3)C17—C16—H16120.0
C7—C8—H8120.3C16—C17—C18119.5 (4)
C9—C8—H8120.3C16—C17—H17120.2
O2—C9—C10116.8 (3)C18—C17—H17120.2
O2—C9—C8122.5 (3)C13—C18—C17120.8 (4)
C10—C9—C8120.6 (3)C13—C18—H18119.6
C9—C10—C1119.9 (3)C17—C18—H18119.6
C6—C1—C2—C31.4 (6)O2—C9—C10—C11−2.9 (5)
C10—C1—C2—C3179.6 (4)C8—C9—C10—C11176.6 (4)
C1—C2—C3—C4−1.4 (7)C2—C1—C10—C9−176.6 (4)
C2—C3—C4—C50.5 (7)C6—C1—C10—C91.5 (5)
C3—C4—C5—C60.4 (7)C2—C1—C10—C114.0 (6)
C2—C1—C6—C7178.0 (4)C6—C1—C10—C11−177.9 (3)
C10—C1—C6—C7−0.2 (6)C9—C10—C11—O1−169.9 (4)
C2—C1—C6—C5−0.5 (5)C1—C10—C11—O19.6 (7)
C10—C1—C6—C5−178.8 (3)C9—O2—C12—C13158.2 (3)
C4—C5—C6—C7−178.8 (4)O2—C12—C13—C1849.5 (6)
C4—C5—C6—C1−0.3 (6)O2—C12—C13—C14−127.9 (4)
C1—C6—C7—C80.3 (6)C18—C13—C14—C151.4 (6)
C5—C6—C7—C8178.8 (4)C12—C13—C14—C15178.8 (4)
C6—C7—C8—C9−1.6 (6)C13—C14—C15—C16−2.2 (7)
C12—O2—C9—C10−172.4 (3)C14—C15—C16—C172.2 (8)
C12—O2—C9—C88.1 (6)C15—C16—C17—C18−1.3 (7)
C7—C8—C9—O2−177.6 (4)C14—C13—C18—C17−0.6 (7)
C7—C8—C9—C102.9 (6)C12—C13—C18—C17−177.9 (4)
O2—C9—C10—C1177.6 (3)C16—C17—C18—C130.5 (7)
C8—C9—C10—C1−2.8 (6)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C12—H12A···O1i0.972.483.381 (4)155
C14—H14···O1i0.932.723.544 (5)148
Symmetry codes: (i) x, −y+1/2, z−1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C12—H12A···O1i0.972.483.381 (4)155
C14—H14···O1i0.932.723.544 (5)148
Symmetry codes: (i) x, −y+1/2, z−1/2.
Acknowledgements top

We thank the Natural Science Foundation of China (grant No. 20802092) for financial support.

references
References top

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