2-(7-Meth-oxy-1-naphth-yl)acetonitrile.

The mol-ecule of the title compound, C(13)H(11)NO, is almost planar (r.m.s. deviation = 0.013 Å), apart from the cyanide group, for which the C and N atoms deviate from the mean plane of the other atoms by 0.341 (3) and 0.571 (4) Å, respectively. In the crystal, weak aromatic π-π stacking [centroid-centroid distance = 3.758 (3) Å] may help to stabilize the structure.

Related literature

For background to the use of naphthyl­ethyl acetonitrile as an inter­mediate for the synthesisis of N-naphthyl­ethyl amide derivatives, see: Depreux & Lesieur (1994 ▶). For further synthetic details, see: Yous & Andrieux (1992 ▶).

Experimental

Crystal data

C13H11NO

M = 197.23

Monoclinic,

a = 7.5110 (15) Å

b = 9.6170 (19) Å

c = 14.731 (3) Å

β = 101.03 (3)°

V = 1044.4 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.976, T max = 0.992

1971 measured reflections

1897 independent reflections

1045 reflections with I > 2σ(I)

R int = 0.011

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.163

S = 1.00

1897 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.14 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (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 datablocks global, I. DOI: 10.1107/S1600536810024372/hb5505sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024372/hb5505Isup2.hkl

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

C13H11NO	F(000) = 416
Mr = 197.23	Dx = 1.254 Mg m−3
Monoclinic, P21/n	Melting point: 353 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 7.5110 (15) Å	Cell parameters from 25 reflections
b = 9.6170 (19) Å	θ = 9–13°
c = 14.731 (3) Å	µ = 0.08 mm−1
β = 101.03 (3)°	T = 293 K
V = 1044.4 (4) Å3	Block, colorless
Z = 4	0.30 × 0.20 × 0.10 mm

Enraf–Nonius CAD-4 diffractometer	1045 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.011
graphite	θmax = 25.3°, θmin = 2.5°
ω/2θ scans	h = −9→8
Absorption correction: ψ scan (North et al., 1968)	k = −11→0
Tmin = 0.976, Tmax = 0.992	l = 0→17
1971 measured reflections	3 standard reflections every 200 reflections
1897 independent reflections	intensity decay: 1%

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.069P)2] where P = (Fo2 + 2Fc2)/3
1897 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.14 e Å−3

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.

	x	y	z	Uiso*/Ueq
O	0.8616 (3)	−0.2547 (2)	0.13823 (13)	0.0718 (6)
N	0.7349 (5)	0.1342 (3)	−0.3297 (2)	0.1076 (12)
C1	0.7327 (4)	0.0786 (3)	−0.2623 (2)	0.0691 (9)
C2	0.7316 (4)	0.0085 (3)	−0.17484 (17)	0.0565 (7)
H2A	0.8471	−0.0380	−0.1550	0.068*
H2B	0.6376	−0.0620	−0.1842	0.068*
C3	0.6992 (3)	0.1069 (3)	−0.09873 (18)	0.0484 (7)
C4	0.6435 (4)	0.2412 (3)	−0.1174 (2)	0.0622 (8)
H4A	0.6228	0.2727	−0.1782	0.075*
C5	0.6171 (4)	0.3319 (3)	−0.0472 (3)	0.0716 (9)
H5A	0.5794	0.4227	−0.0613	0.086*
C6	0.6466 (4)	0.2874 (3)	0.0411 (2)	0.0685 (9)
H6A	0.6293	0.3486	0.0876	0.082*
C7	0.7028 (4)	0.1504 (3)	0.06461 (19)	0.0552 (8)
C8	0.7346 (4)	0.1027 (3)	0.1570 (2)	0.0675 (9)
H8A	0.7200	0.1635	0.2042	0.081*
C9	0.7857 (4)	−0.0299 (4)	0.1779 (2)	0.0685 (9)
H9A	0.8060	−0.0596	0.2391	0.082*
C10	0.8086 (4)	−0.1236 (3)	0.10760 (19)	0.0564 (7)
C11	0.7816 (3)	−0.0820 (3)	0.01827 (18)	0.0495 (7)
H11A	0.7979	−0.1448	−0.0275	0.059*
C12	0.7285 (3)	0.0571 (3)	−0.00618 (18)	0.0471 (7)
C13	0.8857 (4)	−0.3548 (3)	0.0708 (2)	0.0723 (9)
H13A	0.9233	−0.4415	0.1007	0.108*
H13B	0.9768	−0.3229	0.0380	0.108*
H13C	0.7733	−0.3677	0.0280	0.108*

	U11	U22	U33	U12	U13	U23
O	0.0897 (16)	0.0689 (14)	0.0570 (12)	0.0037 (12)	0.0148 (11)	0.0088 (11)
N	0.177 (4)	0.085 (2)	0.062 (2)	−0.005 (2)	0.024 (2)	0.0025 (17)
C1	0.092 (2)	0.064 (2)	0.0507 (18)	−0.0084 (18)	0.0111 (16)	−0.0041 (16)
C2	0.0636 (19)	0.0525 (17)	0.0549 (17)	−0.0034 (14)	0.0150 (14)	−0.0016 (14)
C3	0.0441 (15)	0.0478 (16)	0.0553 (17)	−0.0072 (13)	0.0142 (13)	−0.0041 (13)
C4	0.065 (2)	0.0532 (18)	0.070 (2)	−0.0012 (15)	0.0164 (15)	0.0030 (16)
C5	0.074 (2)	0.0490 (18)	0.097 (3)	0.0035 (16)	0.0285 (19)	−0.0043 (18)
C6	0.073 (2)	0.057 (2)	0.084 (2)	−0.0069 (16)	0.0352 (18)	−0.0222 (17)
C7	0.0506 (17)	0.0552 (19)	0.0636 (19)	−0.0093 (14)	0.0210 (14)	−0.0135 (15)
C8	0.074 (2)	0.073 (2)	0.062 (2)	−0.0102 (18)	0.0293 (16)	−0.0217 (17)
C9	0.078 (2)	0.082 (2)	0.0499 (17)	−0.0113 (19)	0.0234 (16)	−0.0027 (17)
C10	0.0572 (18)	0.0583 (18)	0.0552 (18)	−0.0043 (14)	0.0141 (14)	0.0006 (15)
C11	0.0491 (16)	0.0508 (17)	0.0519 (17)	−0.0058 (13)	0.0182 (13)	−0.0061 (13)
C12	0.0384 (15)	0.0485 (16)	0.0565 (17)	−0.0098 (12)	0.0142 (12)	−0.0069 (13)
C13	0.078 (2)	0.0579 (19)	0.079 (2)	0.0039 (16)	0.0087 (18)	0.0028 (17)

O—C10	1.372 (3)	C6—H6A	0.9300
O—C13	1.419 (3)	C7—C8	1.413 (4)
N—C1	1.130 (4)	C7—C12	1.417 (3)
C1—C2	1.456 (4)	C8—C9	1.350 (4)
C2—C3	1.522 (3)	C8—H8A	0.9300
C2—H2A	0.9700	C9—C10	1.407 (4)
C2—H2B	0.9700	C9—H9A	0.9300
C3—C4	1.369 (4)	C10—C11	1.353 (4)
C3—C12	1.422 (3)	C11—C12	1.422 (4)
C4—C5	1.396 (4)	C11—H11A	0.9300
C4—H4A	0.9300	C13—H13A	0.9600
C5—C6	1.347 (4)	C13—H13B	0.9600
C5—H5A	0.9300	C13—H13C	0.9600
C6—C7	1.406 (4)
C10—O—C13	117.4 (2)	C8—C7—C12	118.8 (3)
N—C1—C2	179.1 (4)	C9—C8—C7	120.9 (3)
C1—C2—C3	113.2 (2)	C9—C8—H8A	119.5
C1—C2—H2A	108.9	C7—C8—H8A	119.5
C3—C2—H2A	108.9	C8—C9—C10	120.4 (3)
C1—C2—H2B	108.9	C8—C9—H9A	119.8
C3—C2—H2B	108.9	C10—C9—H9A	119.8
H2A—C2—H2B	107.8	C11—C10—O	124.9 (3)
C4—C3—C12	119.7 (3)	C11—C10—C9	120.6 (3)
C4—C3—C2	121.6 (3)	O—C10—C9	114.5 (3)
C12—C3—C2	118.7 (2)	C10—C11—C12	120.5 (3)
C3—C4—C5	121.5 (3)	C10—C11—H11A	119.8
C3—C4—H4A	119.2	C12—C11—H11A	119.8
C5—C4—H4A	119.2	C7—C12—C3	118.3 (3)
C6—C5—C4	119.8 (3)	C7—C12—C11	118.7 (2)
C6—C5—H5A	120.1	C3—C12—C11	123.0 (2)
C4—C5—H5A	120.1	O—C13—H13A	109.5
C5—C6—C7	121.4 (3)	O—C13—H13B	109.5
C5—C6—H6A	119.3	H13A—C13—H13B	109.5
C7—C6—H6A	119.3	O—C13—H13C	109.5
C6—C7—C8	121.9 (3)	H13A—C13—H13C	109.5
C6—C7—C12	119.3 (3)	H13B—C13—H13C	109.5