2-Benz­yloxy-1-naphthaldehyde

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

doi:10.1107/S1600536809004486

organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o534

doi:10.1107/S1600536809004486

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2-Benzyloxy-1-naphthaldehyde

Rong Gao,^a Wen-Hong Li,^a Peng Liu ^b and Ping-An Wang ^b ^*

^aDepartment of Chemical Engineering, Northwest University, Taibai North Road 229, 710069 Xi-An, People's Republic of China, and ^bDepartment of Chemistry, School of Pharmacy, Fourth Military Medical University, Changle West Road 17, 710032 Xi-An, People's Republic of China
^*Correspondence e-mail: ping_an1718@yahoo.com.cn

(Received 25 December 2008; accepted 7 February 2009; online 18 February 2009)

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

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

Crystal data

C₁₈H₁₄O₂
M_r = 262.29
Monoclinic, P 2₁ /c
a = 10.427 (7) Å
b = 8.128 (6) Å
c = 15.787 (11) Å
β = 94.746 (11)°
V = 1333.3 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.39 × 0.26 × 0.16 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.968, T_max = 0.987
5088 measured reflections
2262 independent reflections
1354 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.084
wR(F²) = 0.285
S = 1.04
2262 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.53 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯O1ⁱ	0.97	2.48	3.381 (4)	155
C14—H14⋯O1ⁱ	0.93	2.72	3.544 (5)	148
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; 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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809004486/wn2303sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809004486/wn2303Isup2.hkl

checkCIF report

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).

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).

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

	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.
	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

C₁₈H₁₄O₂	F(000) = 552
M_r = 262.29	D_x = 1.307 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 393(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.427 (7) Å	Cell parameters from 1554 reflections
b = 8.128 (6) Å	θ = 2.6–24.3°
c = 15.787 (11) Å	µ = 0.08 mm⁻¹
β = 94.746 (11)°	T = 296 K
V = 1333.3 (16) Å³	Block, colourless
Z = 4	0.39 × 0.26 × 0.16 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2262 independent reflections
Radiation source: fine-focus sealed tube	1354 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ϕ and ω scans	θ_max = 25.1°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −7→12
T_min = 0.968, T_max = 0.987	k = −9→6
5088 measured reflections	l = −18→17

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.084	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.285	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.18P)² + 0.612P] where P = (F_o² + 2F_c²)/3
2262 reflections	(Δ/σ)_max < 0.001
181 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.53 e Å⁻³

Crystal data top

C₁₈H₁₄O₂	V = 1333.3 (16) Å³
M_r = 262.29	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.427 (7) Å	µ = 0.08 mm⁻¹
b = 8.128 (6) Å	T = 296 K
c = 15.787 (11) Å	0.39 × 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)
T_min = 0.968, T_max = 0.987	R_int = 0.038
5088 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.084	0 restraints
wR(F²) = 0.285	H-atom parameters constrained
S = 1.04	Δρ_max = 0.41 e Å⁻³
2262 reflections	Δρ_min = −0.53 e Å⁻³
181 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.6120 (3)	0.2057 (4)	0.65206 (15)	0.0658 (10)
O2	0.6321 (2)	0.1063 (4)	0.41483 (14)	0.0531 (8)
C1	0.4002 (3)	0.3376 (5)	0.5290 (2)	0.0411 (9)
C2	0.3808 (4)	0.4033 (5)	0.6101 (2)	0.0518 (11)
H2	0.4423	0.3837	0.6551	0.062*
C3	0.2749 (4)	0.4942 (6)	0.6241 (3)	0.0630 (12)
H3	0.2641	0.5335	0.6784	0.076*
C4	0.1821 (4)	0.5289 (7)	0.5572 (3)	0.0716 (14)
H4	0.1103	0.5918	0.5671	0.086*
C5	0.1967 (4)	0.4710 (5)	0.4783 (3)	0.0577 (11)
H5	0.1349	0.4952	0.4343	0.069*
C6	0.3053 (3)	0.3737 (6)	0.4616 (2)	0.0504 (11)
C7	0.3228 (3)	0.3153 (5)	0.3794 (2)	0.0523 (11)
H7	0.2608	0.3395	0.3354	0.063*
C8	0.4275 (3)	0.2244 (6)	0.3622 (2)	0.0539 (11)
H8	0.4354	0.1851	0.3075	0.065*
C9	0.5238 (3)	0.1904 (5)	0.4280 (2)	0.0431 (10)
C10	0.5100 (3)	0.2424 (5)	0.5110 (2)	0.0392 (9)
C11	0.6122 (3)	0.1927 (6)	0.5756 (2)	0.0514 (11)
H11	0.6853	0.1459	0.5556	0.062*
C12	0.6621 (3)	0.0652 (6)	0.3305 (2)	0.0575 (12)
H12A	0.6381	0.1548	0.2918	0.069*
H12B	0.6154	−0.0326	0.3108	0.069*
C13	0.8049 (3)	0.0350 (5)	0.3337 (2)	0.0468 (10)
C14	0.8757 (4)	0.1189 (6)	0.2765 (2)	0.0571 (12)
H14	0.8348	0.1902	0.2368	0.069*
C15	1.0079 (4)	0.0954 (7)	0.2792 (3)	0.0713 (15)
H15	1.0549	0.1484	0.2397	0.086*
C16	1.0699 (4)	−0.0047 (6)	0.3390 (3)	0.0635 (13)
H16	1.1589	−0.0163	0.3412	0.076*
C17	1.0006 (4)	−0.0884 (6)	0.3960 (3)	0.0630 (12)
H17	1.0423	−0.1582	0.4360	0.076*
C18	0.8681 (4)	−0.0675 (6)	0.3932 (2)	0.0579 (12)
H18	0.8214	−0.1232	0.4319	0.069*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0596 (17)	0.099 (3)	0.0374 (14)	0.0078 (16)	−0.0065 (11)	−0.0031 (14)
O2	0.0498 (15)	0.075 (2)	0.0352 (13)	0.0178 (14)	0.0062 (10)	−0.0012 (12)
C1	0.0352 (18)	0.047 (3)	0.0415 (17)	−0.0085 (16)	0.0054 (14)	0.0049 (17)
C2	0.045 (2)	0.062 (3)	0.050 (2)	−0.003 (2)	0.0112 (16)	−0.0008 (19)
C3	0.058 (2)	0.066 (3)	0.068 (3)	−0.003 (2)	0.023 (2)	−0.001 (2)
C4	0.046 (2)	0.082 (4)	0.090 (3)	0.008 (2)	0.024 (2)	0.003 (3)
C5	0.043 (2)	0.056 (3)	0.075 (3)	−0.0013 (19)	0.0041 (18)	0.008 (2)
C6	0.0307 (17)	0.068 (3)	0.052 (2)	−0.0035 (17)	0.0040 (15)	0.011 (2)
C7	0.040 (2)	0.067 (3)	0.047 (2)	−0.0013 (19)	−0.0074 (15)	0.010 (2)
C8	0.045 (2)	0.082 (3)	0.0340 (18)	−0.002 (2)	−0.0007 (15)	0.0032 (18)
C9	0.0345 (17)	0.055 (3)	0.0393 (18)	−0.0040 (17)	0.0035 (13)	0.0078 (17)
C10	0.0328 (17)	0.047 (2)	0.0373 (17)	−0.0047 (15)	0.0012 (13)	0.0028 (16)
C11	0.0386 (19)	0.076 (3)	0.0386 (19)	0.0002 (19)	−0.0005 (14)	0.0038 (19)
C12	0.043 (2)	0.096 (4)	0.0337 (17)	−0.003 (2)	0.0069 (14)	−0.004 (2)
C13	0.0395 (18)	0.066 (3)	0.0355 (16)	−0.0014 (18)	0.0055 (14)	−0.0021 (18)
C14	0.045 (2)	0.081 (4)	0.047 (2)	0.005 (2)	0.0070 (16)	0.015 (2)
C15	0.044 (2)	0.107 (4)	0.064 (3)	0.003 (2)	0.0155 (19)	0.017 (3)
C16	0.043 (2)	0.087 (4)	0.061 (2)	0.010 (2)	0.0049 (18)	0.002 (2)
C17	0.056 (2)	0.075 (3)	0.057 (2)	0.015 (2)	−0.0031 (18)	0.008 (2)
C18	0.054 (2)	0.071 (3)	0.050 (2)	−0.002 (2)	0.0091 (17)	0.010 (2)

Geometric parameters (Å, º) top

O1—C11	1.211 (4)	C8—H8	0.9300
O2—C9	1.351 (4)	C9—C10	1.395 (5)
O2—C12	1.433 (4)	C10—C11	1.471 (5)
C1—C2	1.417 (5)	C11—H11	0.9300
C1—C6	1.422 (5)	C12—C13	1.506 (5)
C1—C10	1.430 (5)	C12—H12A	0.9700
C2—C3	1.362 (6)	C12—H12B	0.9700
C2—H2	0.9300	C13—C18	1.382 (6)
C3—C4	1.400 (6)	C13—C14	1.391 (5)
C3—H3	0.9300	C14—C15	1.389 (5)
C4—C5	1.351 (6)	C14—H14	0.9300
C4—H4	0.9300	C15—C16	1.367 (6)
C5—C6	1.424 (5)	C15—H15	0.9300
C5—H5	0.9300	C16—C17	1.380 (6)
C6—C7	1.407 (5)	C16—H16	0.9300
C7—C8	1.365 (5)	C17—C18	1.389 (5)
C7—H7	0.9300	C17—H17	0.9300
C8—C9	1.412 (5)	C18—H18	0.9300

C9—O2—C12	120.7 (3)	C9—C10—C11	116.3 (3)
C2—C1—C6	117.1 (3)	C1—C10—C11	123.8 (3)
C2—C1—C10	124.1 (3)	O1—C11—C10	127.3 (4)
C6—C1—C10	118.8 (3)	O1—C11—H11	116.3
C3—C2—C1	121.9 (4)	C10—C11—H11	116.3
C3—C2—H2	119.0	O2—C12—C13	107.3 (3)
C1—C2—H2	119.0	O2—C12—H12A	110.2
C2—C3—C4	120.4 (4)	C13—C12—H12A	110.2
C2—C3—H3	119.8	O2—C12—H12B	110.2
C4—C3—H3	119.8	C13—C12—H12B	110.2
C5—C4—C3	120.1 (4)	H12A—C12—H12B	108.5
C5—C4—H4	120.0	C18—C13—C14	119.2 (3)
C3—C4—H4	120.0	C18—C13—C12	122.4 (3)
C4—C5—C6	121.1 (4)	C14—C13—C12	118.3 (3)
C4—C5—H5	119.5	C15—C14—C13	119.4 (4)
C6—C5—H5	119.5	C15—C14—H14	120.3
C7—C6—C1	119.0 (3)	C13—C14—H14	120.3
C7—C6—C5	121.6 (3)	C16—C15—C14	121.0 (4)
C1—C6—C5	119.4 (4)	C16—C15—H15	119.5
C8—C7—C6	122.2 (3)	C14—C15—H15	119.5
C8—C7—H7	118.9	C15—C16—C17	120.0 (4)
C6—C7—H7	118.9	C15—C16—H16	120.0
C7—C8—C9	119.4 (3)	C17—C16—H16	120.0
C7—C8—H8	120.3	C16—C17—C18	119.5 (4)
C9—C8—H8	120.3	C16—C17—H17	120.2
O2—C9—C10	116.8 (3)	C18—C17—H17	120.2
O2—C9—C8	122.5 (3)	C13—C18—C17	120.8 (4)
C10—C9—C8	120.6 (3)	C13—C18—H18	119.6
C9—C10—C1	119.9 (3)	C17—C18—H18	119.6

C6—C1—C2—C3	1.4 (6)	O2—C9—C10—C11	−2.9 (5)
C10—C1—C2—C3	179.6 (4)	C8—C9—C10—C11	176.6 (4)
C1—C2—C3—C4	−1.4 (7)	C2—C1—C10—C9	−176.6 (4)
C2—C3—C4—C5	0.5 (7)	C6—C1—C10—C9	1.5 (5)
C3—C4—C5—C6	0.4 (7)	C2—C1—C10—C11	4.0 (6)
C2—C1—C6—C7	178.0 (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—O1	9.6 (7)
C10—C1—C6—C5	−178.8 (3)	C9—O2—C12—C13	158.2 (3)
C4—C5—C6—C7	−178.8 (4)	O2—C12—C13—C18	49.5 (6)
C4—C5—C6—C1	−0.3 (6)	O2—C12—C13—C14	−127.9 (4)
C1—C6—C7—C8	0.3 (6)	C18—C13—C14—C15	1.4 (6)
C5—C6—C7—C8	178.8 (4)	C12—C13—C14—C15	178.8 (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—C17	2.2 (8)
C12—O2—C9—C8	8.1 (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—C10	2.9 (6)	C12—C13—C18—C17	−177.9 (4)
O2—C9—C10—C1	177.6 (3)	C16—C17—C18—C13	0.5 (7)
C8—C9—C10—C1	−2.8 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O1ⁱ	0.97	2.48	3.381 (4)	155
C14—H14···O1ⁱ	0.93	2.72	3.544 (5)	148

Symmetry code: (i) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₄O₂
M_r	262.29
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	10.427 (7), 8.128 (6), 15.787 (11)
β (°)	94.746 (11)
V (Å³)	1333.3 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.39 × 0.26 × 0.16

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.968, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	5088, 2262, 1354
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.084, 0.285, 1.04
No. of reflections	2262
No. of parameters	181
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.53

Computer programs: SMART(Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), Mercury (Macrae et al., 2006) and CAMERON (Watkin et al., 1996).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O1ⁱ	0.97	2.48	3.381 (4)	155.4
C14—H14···O1ⁱ	0.93	2.72	3.544 (5)	148.3

Symmetry code: (i) x, −y+1/2, z−1/2.

Acknowledgements

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

References

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