(2Z)-2-(4-Methyl-phen-yl)-3-(2-naphth-yl)prop-2-enenitrile.

In the title compound, C(20)H(15)N, the dihedral angle between the naphthalene and benzene rings is 60.30 (16)°. The crystal packing features very weak inter-molecular C-H⋯π inter-actions.

Related literature

For background on the commercial importance and applications of styryl dyes, see: Haidekker et al. (2001 ▶); Hamer (1964 ▶); Li et al. (1998 ▶); Makoto et al. (2000a ▶,b ▶); Mousnier et al. (2004 ▶); Park et al. (2001 ▶); Pommeret et al. (1995 ▶); Spalletti (2004 ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C20H15N

M = 269.33

Orthorhombic,

a = 12.3194 (11) Å

b = 16.4796 (16) Å

c = 7.2596 (7) Å

V = 1473.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 296 K

0.37 × 0.28 × 0.13 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: none

16248 measured reflections

3659 independent reflections

1549 reflections with I > 2σ(I)

R int = 0.092

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.174

S = 0.95

3659 reflections

192 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809034229/hb5070sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809034229/hb5070Isup2.hkl

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

C20H15N	F(000) = 568
Mr = 269.33	Dx = 1.214 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 1202 reflections
a = 12.3194 (11) Å	θ = 3.3–19.2°
b = 16.4796 (16) Å	µ = 0.07 mm−1
c = 7.2596 (7) Å	T = 296 K
V = 1473.8 (2) Å3	Prism, pale yellow
Z = 4	0.37 × 0.28 × 0.13 mm

Bruker Kappa APEXII CCD diffractometer	1549 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.092
graphite	θmax = 28.3°, θmin = 1.2°
φ and ω scans	h = −16→16
16248 measured reflections	k = −21→21
3659 independent reflections	l = −9→9

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.174	H-atom parameters constrained
S = 0.95	w = 1/[σ2(Fo2) + (0.0732P)2] where P = (Fo2 + 2Fc2)/3
3659 reflections	(Δ/σ)max < 0.001
192 parameters	Δρmax = 0.21 e Å−3
1 restraint	Δρmin = −0.21 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F^2^ for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > σ(F^2^) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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
N1	0.2102 (3)	0.2374 (2)	0.2270 (6)	0.0755 (18)
C1	0.4123 (2)	0.4123 (2)	0.3160 (5)	0.0387 (11)
C2	0.4702 (2)	0.4813 (2)	0.2783 (5)	0.0384 (11)
C3	0.4291 (3)	0.5598 (2)	0.3140 (5)	0.0371 (11)
C4	0.4872 (3)	0.6316 (2)	0.2717 (5)	0.0459 (14)
C5	0.4449 (3)	0.7059 (2)	0.3090 (5)	0.0510 (14)
C6	0.3431 (3)	0.7129 (2)	0.3916 (6)	0.0537 (14)
C7	0.2845 (3)	0.6454 (2)	0.4337 (5)	0.0477 (16)
C8	0.3250 (3)	0.5669 (2)	0.3945 (5)	0.0374 (11)
C9	0.2669 (3)	0.4948 (2)	0.4371 (5)	0.0448 (14)
C10	0.3079 (3)	0.4205 (2)	0.3993 (6)	0.0426 (11)
C11	0.4613 (2)	0.3337 (2)	0.2763 (5)	0.0424 (11)
C12	0.4168 (2)	0.2602 (2)	0.2486 (5)	0.0420 (11)
C13	0.4813 (3)	0.1865 (2)	0.2136 (5)	0.0422 (14)
C14	0.4457 (3)	0.1283 (2)	0.0903 (6)	0.0543 (14)
C15	0.5086 (3)	0.0608 (2)	0.0502 (7)	0.0633 (17)
C16	0.6068 (3)	0.0487 (2)	0.1335 (6)	0.0550 (16)
C17	0.6417 (3)	0.1063 (2)	0.2582 (7)	0.0620 (18)
C18	0.5807 (3)	0.1741 (2)	0.2980 (6)	0.0543 (14)
C19	0.6730 (4)	−0.0271 (2)	0.0951 (8)	0.0840 (19)
C20	0.3006 (3)	0.2492 (2)	0.2411 (7)	0.0503 (14)
H2	0.53910	0.47630	0.22730	0.0460*
H4	0.55540	0.62770	0.21750	0.0550*
H5	0.48410	0.75230	0.27940	0.0610*
H6	0.31510	0.76400	0.41800	0.0640*
H7	0.21680	0.65090	0.48910	0.0570*
H9	0.19910	0.49870	0.49250	0.0540*
H10	0.26780	0.37440	0.42780	0.0510*
H11	0.53670	0.33460	0.26870	0.0510*
H14	0.37860	0.13450	0.03350	0.0650*
H15	0.48350	0.02310	−0.03500	0.0750*
H17	0.70810	0.09910	0.31690	0.0750*
H18	0.60650	0.21190	0.38240	0.0650*
H19A	0.64500	−0.07140	0.16670	0.1260*
H19B	0.74750	−0.01760	0.12780	0.1260*
H19C	0.66850	−0.04030	−0.03350	0.1260*

	U11	U22	U33	U12	U13	U23
N1	0.0474 (19)	0.072 (3)	0.107 (4)	−0.0020 (18)	0.000 (2)	−0.009 (2)
C1	0.0332 (17)	0.047 (2)	0.036 (2)	0.0056 (17)	0.0002 (16)	−0.0009 (19)
C2	0.0332 (17)	0.048 (2)	0.034 (2)	0.0018 (16)	−0.0001 (16)	−0.0039 (18)
C3	0.0353 (17)	0.048 (2)	0.028 (2)	0.0005 (16)	−0.0054 (16)	−0.0042 (17)
C4	0.0437 (19)	0.047 (2)	0.047 (3)	−0.0043 (18)	−0.001 (2)	0.000 (2)
C5	0.058 (2)	0.044 (2)	0.051 (3)	−0.005 (2)	−0.006 (2)	−0.004 (2)
C6	0.056 (2)	0.045 (2)	0.060 (3)	0.006 (2)	−0.005 (2)	−0.011 (2)
C7	0.042 (2)	0.054 (3)	0.047 (3)	0.0066 (19)	−0.0003 (18)	−0.007 (2)
C8	0.0392 (19)	0.044 (2)	0.029 (2)	0.0072 (17)	−0.0026 (16)	−0.0033 (18)
C9	0.0374 (19)	0.058 (2)	0.039 (3)	0.0041 (19)	0.0064 (18)	0.001 (2)
C10	0.0418 (19)	0.046 (2)	0.040 (2)	−0.0020 (17)	0.0063 (17)	0.0063 (19)
C11	0.0363 (17)	0.046 (2)	0.045 (2)	0.0053 (17)	0.0031 (17)	−0.0007 (19)
C12	0.0411 (18)	0.041 (2)	0.044 (2)	−0.0011 (17)	−0.0014 (19)	0.0056 (19)
C13	0.0407 (19)	0.036 (2)	0.050 (3)	−0.0034 (16)	−0.0008 (18)	0.0054 (18)
C14	0.049 (2)	0.047 (2)	0.067 (3)	0.002 (2)	−0.007 (2)	−0.006 (2)
C15	0.076 (3)	0.047 (3)	0.067 (3)	0.002 (2)	−0.007 (3)	−0.005 (2)
C16	0.063 (3)	0.041 (2)	0.061 (3)	0.007 (2)	0.014 (2)	0.008 (2)
C17	0.051 (2)	0.053 (3)	0.082 (4)	0.005 (2)	−0.010 (2)	0.000 (3)
C18	0.054 (2)	0.044 (2)	0.065 (3)	0.0016 (19)	−0.010 (2)	−0.008 (2)
C19	0.102 (3)	0.058 (3)	0.092 (4)	0.024 (3)	0.017 (3)	−0.006 (3)
C20	0.047 (2)	0.051 (2)	0.053 (3)	0.001 (2)	0.005 (2)	0.002 (2)

N1—C20	1.135 (5)	C15—C16	1.367 (6)
C1—C2	1.370 (4)	C16—C17	1.380 (6)
C1—C10	1.428 (5)	C16—C19	1.518 (5)
C1—C11	1.458 (5)	C17—C18	1.377 (5)
C2—C3	1.413 (5)	C2—H2	0.9300
C3—C4	1.417 (5)	C4—H4	0.9300
C3—C8	1.414 (5)	C5—H5	0.9300
C4—C5	1.358 (5)	C6—H6	0.9300
C5—C6	1.395 (5)	C7—H7	0.9300
C6—C7	1.361 (5)	C9—H9	0.9300
C7—C8	1.415 (5)	C10—H10	0.9300
C8—C9	1.421 (5)	C11—H11	0.9300
C9—C10	1.353 (5)	C14—H14	0.9300
C11—C12	1.345 (5)	C15—H15	0.9300
C12—C13	1.474 (5)	C17—H17	0.9300
C12—C20	1.444 (4)	C18—H18	0.9300
C13—C14	1.383 (5)	C19—H19A	0.9600
C13—C18	1.384 (5)	C19—H19B	0.9600
C14—C15	1.387 (5)	C19—H19C	0.9600
N1···H10	2.7800	H2···C8iv	3.0200
N1···H4i	2.9300	H4···H2	2.5000
N1···H5i	2.8200	H4···C1iv	3.0100
N1···H19Aii	2.8800	H4···C10iv	2.9700
C5···C13iii	3.549 (5)	H4···N1vii	2.9300
C6···C13iii	3.591 (5)	H5···N1vii	2.8200
C10···C20	3.049 (5)	H7···H9	2.5200
C13···C5iv	3.549 (5)	H9···H7	2.5200
C13···C6iv	3.591 (5)	H9···C1viii	3.0700
C20···C10	3.049 (5)	H9···C2viii	2.9600
C1···H9v	3.0700	H9···C3viii	2.9900
C1···H4iii	3.0100	H10···N1	2.7800
C2···H9v	2.9600	H10···C12	2.9300
C3···H9v	2.9900	H10···C20	2.5000
C3···H2iii	3.0800	H11···C18	2.7100
C8···H2iii	3.0200	H11···H2	2.3500
C10···H4iii	2.9700	H11···H18	2.3500
C11···H18	2.8000	H14···C20	2.6000
C12···H10	2.9300	H15···H19C	2.5100
C14···H19Bii	3.0600	H15···C16ix	2.9000
C16···H15vi	2.9000	H15···C17ix	3.0300
C17···H15vi	3.0300	H17···H19B	2.4100
C18···H11	2.7100	H18···C11	2.8000
C20···H10	2.5000	H18···H11	2.3500
C20···H14	2.6000	H19A···N1x	2.8800
H2···H4	2.5000	H19B···H17	2.4100
H2···H11	2.3500	H19B···C14x	3.0600
H2···C3iv	3.0800	H19C···H15	2.5100
C2—C1—C10	118.4 (3)	C1—C2—H2	119.00
C2—C1—C11	118.8 (2)	C3—C2—H2	119.00
C10—C1—C11	122.7 (3)	C3—C4—H4	119.00
C1—C2—C3	122.5 (3)	C5—C4—H4	120.00
C2—C3—C4	123.0 (3)	C4—C5—H5	120.00
C2—C3—C8	118.5 (3)	C6—C5—H5	120.00
C4—C3—C8	118.6 (3)	C5—C6—H6	120.00
C3—C4—C5	121.1 (3)	C7—C6—H6	120.00
C4—C5—C6	120.4 (3)	C6—C7—H7	120.00
C5—C6—C7	120.4 (3)	C8—C7—H7	119.00
C6—C7—C8	121.0 (3)	C8—C9—H9	119.00
C3—C8—C7	118.6 (3)	C10—C9—H9	119.00
C3—C8—C9	118.5 (3)	C1—C10—H10	120.00
C7—C8—C9	122.9 (3)	C9—C10—H10	120.00
C8—C9—C10	121.6 (3)	C1—C11—H11	114.00
C1—C10—C9	120.5 (3)	C12—C11—H11	114.00
C1—C11—C12	131.4 (2)	C13—C14—H14	120.00
C11—C12—C13	123.3 (3)	C15—C14—H14	119.00
C11—C12—C20	121.5 (3)	C14—C15—H15	119.00
C13—C12—C20	115.1 (3)	C16—C15—H15	119.00
C12—C13—C14	120.8 (3)	C16—C17—H17	119.00
C12—C13—C18	121.5 (3)	C18—C17—H17	119.00
C14—C13—C18	117.7 (3)	C13—C18—H18	120.00
C13—C14—C15	121.0 (4)	C17—C18—H18	120.00
C14—C15—C16	121.2 (4)	C16—C19—H19A	109.00
C15—C16—C17	117.7 (3)	C16—C19—H19B	110.00
C15—C16—C19	121.0 (4)	C16—C19—H19C	110.00
C17—C16—C19	121.3 (4)	H19A—C19—H19B	109.00
C16—C17—C18	121.7 (4)	H19A—C19—H19C	109.00
C13—C18—C17	120.6 (4)	H19B—C19—H19C	109.00
N1—C20—C12	176.0 (5)
C10—C1—C2—C3	−1.8 (5)	C3—C8—C9—C10	−1.3 (6)
C11—C1—C2—C3	−179.5 (3)	C7—C8—C9—C10	−179.5 (4)
C2—C1—C10—C9	1.0 (6)	C8—C9—C10—C1	0.5 (6)
C11—C1—C10—C9	178.5 (4)	C1—C11—C12—C13	−178.6 (4)
C2—C1—C11—C12	−158.4 (4)	C1—C11—C12—C20	4.9 (7)
C10—C1—C11—C12	24.1 (6)	C11—C12—C13—C14	−142.5 (4)
C1—C2—C3—C4	−178.5 (3)	C11—C12—C13—C18	35.5 (6)
C1—C2—C3—C8	1.1 (5)	C20—C12—C13—C14	34.2 (5)
C2—C3—C4—C5	−179.7 (4)	C20—C12—C13—C18	−147.8 (4)
C8—C3—C4—C5	0.7 (5)	C12—C13—C14—C15	176.8 (4)
C2—C3—C8—C7	178.8 (3)	C18—C13—C14—C15	−1.3 (6)
C2—C3—C8—C9	0.5 (5)	C12—C13—C18—C17	−177.5 (4)
C4—C3—C8—C7	−1.6 (5)	C14—C13—C18—C17	0.6 (6)
C4—C3—C8—C9	−179.9 (3)	C13—C14—C15—C16	1.2 (6)
C3—C4—C5—C6	0.5 (6)	C14—C15—C16—C17	−0.4 (6)
C4—C5—C6—C7	−0.8 (6)	C14—C15—C16—C19	177.4 (4)
C5—C6—C7—C8	−0.2 (6)	C15—C16—C17—C18	−0.3 (6)
C6—C7—C8—C3	1.4 (6)	C19—C16—C17—C18	−178.1 (4)
C6—C7—C8—C9	179.6 (4)	C16—C17—C18—C13	0.2 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cg1iv	0.93	2.98	3.682 (4)	134
C7—H7···Cg2viii	0.93	2.93	3.695 (4)	140
C9—H9···Cg1viii	0.93	2.78	3.473 (4)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯Cg1i	0.93	2.98	3.682 (4)	134
C7—H7⋯Cg2ii	0.93	2.93	3.695 (4)	140
C9—H9⋯Cg1ii	0.93	2.78	3.473 (4)	133

Symmetry codes: (i) ; (ii) . Cg1 and Cg2 are the centroids of the C1–C3/C8–C10 and C3–C8 rings, respectively.