1-(Benz-yloxy)naphthalene.

In the title compound, C(17)H(14)O, the dihedral angle between the naphthyl ring system and the benzyl group is 83.22 (4)°. Both of these moieties are planar, with mean deviations from their least-squares planes, defined by the naphthyl ring C atoms and the O atom, and the phenyl ring C atoms and the benzyl α-C atom, of 0.0176 (1) and 0.0024 (13) Å, respectively. The crystal structure is stabilized by C-H⋯π and π-π inter-actions [centroid-centroid distance = 3.7817 (10) Å].

Related literature

For the synthesis of benzyl-1-naphthyl ether, see: Mohamed & Arunadevi (2010 ▶); For related structures, see: Hassan et al. (2008a ▶,b ▶,c ▶,d ▶, 2009a ▶,b ▶); Abdullah & Ng (2008 ▶). For applications of naphthyl ethers, see: Fernandes et al. (2011 ▶); Scanu et al. (2007 ▶); He et al. (2008 ▶). For the use of benzyl protecting groups, see: Rao & Senthilkumar (2001 ▶). For the role of benzyl ether inter­mediates in sigmatropic rearrangement reactions, see: Salunkhe et al. (1994 ▶).

Experimental

Crystal data

C17H14O

M = 234.28

Orthorhombic,

a = 13.0210 (6) Å

b = 24.8832 (10) Å

c = 7.9478 (3) Å

V = 2575.12 (19) Å3

Z = 8

Mo Kα radiation

μ = 0.07 mm−1

T = 296 K

0.07 × 0.06 × 0.06 mm

Data collection

Bruker SMART CCD area-detector diffractometer

22084 measured reflections

2418 independent reflections

1609 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.099

S = 1.02

2418 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.12 e Å−3

Data collection: SMART (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811025219/bv2185sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811025219/bv2185Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811025219/bv2185Isup3.cml

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

Enhanced figure: interactive version of Fig. 3

C17H14O	F(000) = 992
Mr = 234.28	Dx = 1.209 Mg m−3
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 2417 reflections
a = 13.0210 (6) Å	θ = 3.1–21.2°
b = 24.8832 (10) Å	µ = 0.07 mm−1
c = 7.9478 (3) Å	T = 296 K
V = 2575.12 (19) Å3	Prism, colourless
Z = 8	0.07 × 0.06 × 0.06 mm

Bruker SMART CCD area-detector diffractometer	1609 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.059
graphite	θmax = 25.6°, θmin = 1.6°
φ and ω scans	h = −15→14
22084 measured reflections	k = −30→30
2418 independent reflections	l = −9→9

Refinement on F2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0378P)2 + 0.3925P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.039	(Δ/σ)max = 0.001
wR(F2) = 0.099	Δρmax = 0.13 e Å−3
S = 1.02	Δρmin = −0.12 e Å−3
2418 reflections	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
164 parameters	Extinction coefficient: 0.0079 (9)
0 restraints

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.

	x	y	z	Uiso*/Ueq
O1	0.03144 (8)	0.60213 (4)	0.09247 (13)	0.0529 (3)
C1	−0.02611 (11)	0.63577 (5)	−0.00569 (18)	0.0420 (4)
C10	0.02903 (11)	0.65924 (5)	−0.14237 (18)	0.0399 (4)
C9	−0.02477 (12)	0.69375 (5)	−0.25359 (19)	0.0464 (4)
C12	0.05778 (12)	0.53982 (6)	0.31348 (18)	0.0473 (4)
C8	0.13464 (12)	0.65015 (6)	−0.16880 (19)	0.0490 (4)
H8	0.1703	0.6273	−0.0972	0.059*
C5	0.02988 (15)	0.71737 (7)	−0.3876 (2)	0.0621 (5)
H5	−0.0045	0.7397	−0.4626	0.075*
C2	−0.12767 (12)	0.64702 (6)	0.0187 (2)	0.0507 (4)
H2	−0.1625	0.6321	0.1096	0.061*
C13	0.12458 (13)	0.56037 (7)	0.4314 (2)	0.0595 (5)
H13	0.1219	0.5967	0.4581	0.071*
C11	−0.01908 (12)	0.57545 (7)	0.2298 (2)	0.0577 (5)
H11A	−0.0763	0.5543	0.1884	0.069*
H11B	−0.0452	0.6017	0.3093	0.069*
C4	−0.13007 (13)	0.70384 (6)	−0.2253 (2)	0.0568 (5)
H4	−0.1658	0.7264	−0.2981	0.068*
C3	−0.17964 (13)	0.68115 (6)	−0.0938 (2)	0.0569 (5)
H3	−0.2491	0.6882	−0.0775	0.068*
C6	0.13163 (16)	0.70813 (7)	−0.4092 (2)	0.0667 (5)
H6	0.1661	0.7242	−0.4984	0.08*
C17	0.06300 (13)	0.48573 (7)	0.2763 (2)	0.0556 (4)
H17	0.0183	0.4711	0.1973	0.067*
C16	0.13394 (14)	0.45329 (7)	0.3553 (2)	0.0618 (5)
H16	0.137	0.4169	0.329	0.074*
C14	0.19522 (13)	0.52779 (7)	0.5101 (2)	0.0660 (5)
H14	0.2399	0.5422	0.5894	0.079*
C7	0.18510 (13)	0.67464 (7)	−0.2986 (2)	0.0600 (5)
H7	0.2551	0.669	−0.3134	0.072*
C15	0.19991 (13)	0.47420 (7)	0.4721 (2)	0.0608 (5)
H15	0.2476	0.4522	0.5252	0.073*

	U11	U22	U33	U12	U13	U23
O1	0.0472 (6)	0.0611 (7)	0.0503 (7)	0.0055 (5)	0.0024 (5)	0.0189 (5)
C1	0.0438 (9)	0.0394 (8)	0.0427 (8)	0.0022 (7)	−0.0049 (7)	0.0000 (7)
C10	0.0463 (9)	0.0340 (7)	0.0394 (8)	−0.0015 (7)	−0.0037 (7)	−0.0035 (6)
C9	0.0608 (11)	0.0349 (8)	0.0434 (9)	0.0011 (7)	−0.0083 (8)	−0.0024 (7)
C12	0.0473 (9)	0.0524 (9)	0.0424 (9)	−0.0019 (8)	0.0040 (7)	0.0094 (8)
C8	0.0501 (10)	0.0525 (9)	0.0445 (9)	−0.0001 (8)	−0.0032 (8)	−0.0007 (7)
C5	0.0854 (14)	0.0488 (10)	0.0521 (10)	0.0012 (9)	−0.0036 (10)	0.0101 (8)
C2	0.0482 (10)	0.0507 (9)	0.0532 (10)	0.0005 (8)	0.0013 (8)	0.0004 (8)
C13	0.0669 (12)	0.0488 (9)	0.0627 (11)	−0.0032 (9)	−0.0085 (10)	0.0010 (9)
C11	0.0535 (11)	0.0673 (11)	0.0523 (10)	0.0006 (8)	0.0067 (8)	0.0184 (9)
C4	0.0632 (12)	0.0502 (9)	0.0570 (11)	0.0143 (8)	−0.0140 (9)	0.0010 (8)
C3	0.0462 (10)	0.0580 (10)	0.0666 (11)	0.0103 (8)	−0.0060 (9)	−0.0043 (9)
C6	0.0868 (15)	0.0621 (11)	0.0513 (11)	−0.0133 (10)	0.0093 (10)	0.0073 (9)
C17	0.0624 (11)	0.0582 (11)	0.0461 (9)	−0.0054 (9)	−0.0026 (8)	0.0010 (8)
C16	0.0750 (12)	0.0508 (10)	0.0597 (11)	0.0070 (9)	0.0035 (10)	0.0013 (9)
C14	0.0633 (12)	0.0729 (12)	0.0619 (12)	−0.0047 (10)	−0.0169 (10)	0.0001 (10)
C7	0.0559 (10)	0.0680 (11)	0.0560 (11)	−0.0078 (9)	0.0076 (9)	−0.0022 (9)
C15	0.0571 (11)	0.0673 (12)	0.0578 (11)	0.0126 (9)	0.0010 (9)	0.0132 (9)

O1—C1	1.3677 (16)	C13—C14	1.377 (2)
O1—C11	1.4372 (17)	C13—H13	0.93
C1—C2	1.366 (2)	C11—H11A	0.97
C1—C10	1.4272 (19)	C11—H11B	0.97
C10—C8	1.409 (2)	C4—C3	1.352 (2)
C10—C9	1.4176 (19)	C4—H4	0.93
C9—C5	1.409 (2)	C3—H3	0.93
C9—C4	1.412 (2)	C6—C7	1.397 (2)
C12—C13	1.377 (2)	C6—H6	0.93
C12—C17	1.380 (2)	C17—C16	1.378 (2)
C12—C11	1.493 (2)	C17—H17	0.93
C8—C7	1.367 (2)	C16—C15	1.367 (2)
C8—H8	0.93	C16—H16	0.93
C5—C6	1.356 (2)	C14—C15	1.369 (2)
C5—H5	0.93	C14—H14	0.93
C2—C3	1.407 (2)	C7—H7	0.93
C2—H2	0.93	C15—H15	0.93
C1—O1—C11	117.72 (12)	O1—C11—H11B	110.1
C2—C1—O1	125.11 (14)	C12—C11—H11B	110.1
C2—C1—C10	120.74 (13)	H11A—C11—H11B	108.5
O1—C1—C10	114.15 (12)	C3—C4—C9	120.82 (15)
C8—C10—C9	119.11 (14)	C3—C4—H4	119.6
C8—C10—C1	122.59 (13)	C9—C4—H4	119.6
C9—C10—C1	118.29 (13)	C4—C3—C2	120.93 (16)
C5—C9—C4	122.44 (15)	C4—C3—H3	119.5
C5—C9—C10	118.31 (15)	C2—C3—H3	119.5
C4—C9—C10	119.24 (14)	C5—C6—C7	120.58 (16)
C13—C12—C17	118.49 (15)	C5—C6—H6	119.7
C13—C12—C11	120.38 (15)	C7—C6—H6	119.7
C17—C12—C11	121.12 (15)	C16—C17—C12	120.45 (16)
C7—C8—C10	120.67 (15)	C16—C17—H17	119.8
C7—C8—H8	119.7	C12—C17—H17	119.8
C10—C8—H8	119.7	C15—C16—C17	120.49 (16)
C6—C5—C9	121.22 (16)	C15—C16—H16	119.8
C6—C5—H5	119.4	C17—C16—H16	119.8
C9—C5—H5	119.4	C15—C14—C13	120.21 (16)
C1—C2—C3	119.97 (15)	C15—C14—H14	119.9
C1—C2—H2	120	C13—C14—H14	119.9
C3—C2—H2	120	C8—C7—C6	120.08 (17)
C14—C13—C12	120.84 (15)	C8—C7—H7	120
C14—C13—H13	119.6	C6—C7—H7	120
C12—C13—H13	119.6	C16—C15—C14	119.51 (16)
O1—C11—C12	107.80 (12)	C16—C15—H15	120.2
O1—C11—H11A	110.1	C14—C15—H15	120.2
C12—C11—H11A	110.1
C11—O1—C1—C2	1.5 (2)	C11—C12—C13—C14	179.53 (15)
C11—O1—C1—C10	−178.07 (12)	C1—O1—C11—C12	177.97 (12)
C2—C1—C10—C8	177.82 (14)	C13—C12—C11—O1	83.11 (18)
O1—C1—C10—C8	−2.56 (19)	C17—C12—C11—O1	−97.56 (17)
C2—C1—C10—C9	−1.1 (2)	C5—C9—C4—C3	−178.92 (15)
O1—C1—C10—C9	178.56 (12)	C10—C9—C4—C3	0.2 (2)
C8—C10—C9—C5	0.5 (2)	C9—C4—C3—C2	0.2 (2)
C1—C10—C9—C5	179.38 (13)	C1—C2—C3—C4	−1.0 (2)
C8—C10—C9—C4	−178.67 (13)	C9—C5—C6—C7	0.2 (3)
C1—C10—C9—C4	0.3 (2)	C13—C12—C17—C16	−0.3 (2)
C9—C10—C8—C7	0.7 (2)	C11—C12—C17—C16	−179.60 (15)
C1—C10—C8—C7	−178.16 (14)	C12—C17—C16—C15	0.2 (3)
C4—C9—C5—C6	178.20 (16)	C12—C13—C14—C15	−0.1 (3)
C10—C9—C5—C6	−0.9 (2)	C10—C8—C7—C6	−1.5 (2)
O1—C1—C2—C3	−178.15 (14)	C5—C6—C7—C8	1.0 (3)
C10—C1—C2—C3	1.4 (2)	C17—C16—C15—C14	−0.1 (3)
C17—C12—C13—C14	0.2 (2)	C13—C14—C15—C16	0.0 (3)

Cg1 is the centroid of the C1–C4/C9/C10 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Cg1i	0.93	2.72	3.6168 (18)	161
C16—H16···Cg1ii	0.93	2.85	3.6847 (18)	149

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C4/C9/C10 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯Cg1i	0.93	2.72	3.6168 (18)	161
C16—H16⋯Cg1ii	0.93	2.85	3.6847 (18)	149

Symmetry codes: (i) ; (ii) .