4-(Naphthalen-1-yl)pyridine.

In the title compound, C15H11N, the mean planes of the aromatic moieties are inclined to one another by 72.9 (1)°. The crystal is stabilized by π-π stacking inter-actions between the pyridine rings of inversion-related mol-ecules, with a centroid-centroid distance of 3.772 (2) Å. In addition, C-H⋯π contacts involving an α-C-H group of the pyridine ring and the nonsubstituted ring of the naphthalene unit are observed, giving rise to a herringbone-type supramolecular architecture of the naphthalene moiety being contained in the molecule.

Related literature

For preparative methods and the characterization of the title compound, see: Miyaura et al. (1981 ▶); Broutin & Colobert (2005 ▶); Molander & Beaumard (2010 ▶). For π–π stacking inter­actions, see: James (2004 ▶). For C—H⋯π inter­actions, see: Nishio et al. (2009 ▶). For non-classic hydrogen bonds, see: Desiraju & Steiner (1999 ▶). For related structures, see: Boeyens et al. (1988 ▶); Fabbiani et al. (2006 ▶); Suthar et al. (2005 ▶). For aspects of organic crystal engineering, see: Tiekink et al. (2010 ▶).

Experimental

Crystal data

C15H11N

M = 205.25

Monoclinic,

a = 6.8487 (2) Å

b = 7.4436 (2) Å

c = 21.8378 (5) Å

β = 91.833 (1)°

V = 1112.70 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 193 K

0.53 × 0.43 × 0.43 mm

Data collection

Bruker X8 APEX CCD diffractometer

14800 measured reflections

2831 independent reflections

2302 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.147

S = 1.05

2831 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT-NT (Bruker, 2007 ▶); data reduction: SAINT-NT; 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, 2012 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813014372/fj2629sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813014372/fj2629Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813014372/fj2629Isup3.cml

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

C15H11N	F(000) = 432
Mr = 205.25	Dx = 1.225 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7291 reflections
a = 6.8487 (2) Å	θ = 2.9–32.2°
b = 7.4436 (2) Å	µ = 0.07 mm−1
c = 21.8378 (5) Å	T = 193 K
β = 91.833 (1)°	Irregular, colourless
V = 1112.70 (5) Å3	0.53 × 0.43 × 0.43 mm
Z = 4

Bruker X8 APEX CCD diffractometer	2302 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
Graphite monochromator	θmax = 28.6°, θmin = 1.9°
φ and ω scans	h = −7→9
14800 measured reflections	k = −10→9
2831 independent reflections	l = −29→28

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0714P)2 + 0.2598P] where P = (Fo2 + 2Fc2)/3
2831 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.18 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
C1	0.12887 (17)	0.13749 (16)	0.10279 (5)	0.0377 (3)
C2	0.2963 (2)	0.1121 (2)	0.07098 (6)	0.0502 (3)
H2	0.3218	0.1859	0.0378	0.060*
C3	0.4299 (2)	−0.0245 (2)	0.08800 (7)	0.0568 (4)
H3	0.5416	−0.0412	0.0656	0.068*
C4	0.3968 (2)	−0.13166 (19)	0.13686 (7)	0.0517 (3)
H4	0.4867	−0.2206	0.1477	0.062*
C5	0.22727 (18)	−0.10975 (16)	0.17143 (6)	0.0405 (3)
C6	0.1913 (2)	−0.21677 (19)	0.22348 (7)	0.0521 (3)
H6	0.2814	−0.3045	0.2354	0.063*
C7	0.0282 (2)	−0.1939 (2)	0.25625 (7)	0.0587 (4)
H7	0.0089	−0.2637	0.2908	0.070*
C8	−0.1115 (2)	−0.0647 (2)	0.23796 (7)	0.0552 (4)
H8	−0.2247	−0.0516	0.2600	0.066*
C9	−0.08234 (18)	0.04175 (17)	0.18808 (6)	0.0433 (3)
H9	−0.1765	0.1262	0.1764	0.052*
C10	0.08913 (16)	0.02542 (15)	0.15386 (5)	0.0356 (3)
C11	−0.00895 (17)	0.28518 (16)	0.08512 (5)	0.0383 (3)
C12	−0.1289 (2)	0.27550 (19)	0.03312 (6)	0.0519 (3)
H12	−0.1247	0.1757	0.0076	0.062*
C13	−0.2554 (2)	0.4160 (2)	0.01943 (7)	0.0603 (4)
H13	−0.3365	0.4058	−0.0154	0.072*
C14	−0.1506 (2)	0.5733 (2)	0.10206 (8)	0.0595 (4)
H14	−0.1552	0.6763	0.1261	0.071*
C15	−0.0213 (2)	0.43915 (19)	0.11996 (7)	0.0537 (4)
H15	0.0569	0.4526	0.1553	0.064*
N1	−0.26865 (18)	0.56431 (17)	0.05271 (6)	0.0572 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0399 (6)	0.0367 (6)	0.0362 (5)	0.0064 (4)	−0.0017 (4)	−0.0047 (4)
C2	0.0521 (8)	0.0563 (8)	0.0428 (6)	0.0127 (6)	0.0091 (6)	0.0022 (6)
C3	0.0486 (8)	0.0686 (9)	0.0540 (8)	0.0212 (7)	0.0123 (6)	−0.0027 (7)
C4	0.0460 (7)	0.0516 (8)	0.0571 (8)	0.0194 (6)	−0.0029 (6)	−0.0033 (6)
C5	0.0402 (6)	0.0373 (6)	0.0435 (6)	0.0048 (5)	−0.0073 (5)	−0.0031 (5)
C6	0.0531 (8)	0.0455 (7)	0.0569 (8)	0.0037 (6)	−0.0104 (6)	0.0099 (6)
C7	0.0618 (9)	0.0573 (9)	0.0568 (8)	−0.0067 (7)	−0.0005 (7)	0.0170 (7)
C8	0.0471 (8)	0.0601 (8)	0.0589 (8)	−0.0050 (6)	0.0105 (6)	0.0056 (7)
C9	0.0369 (6)	0.0428 (6)	0.0504 (7)	0.0027 (5)	0.0015 (5)	−0.0007 (5)
C10	0.0350 (6)	0.0331 (5)	0.0383 (6)	0.0021 (4)	−0.0043 (4)	−0.0050 (4)
C11	0.0381 (6)	0.0386 (6)	0.0383 (6)	0.0045 (5)	0.0027 (4)	0.0011 (4)
C12	0.0523 (8)	0.0491 (7)	0.0536 (7)	0.0098 (6)	−0.0100 (6)	−0.0085 (6)
C13	0.0536 (8)	0.0660 (9)	0.0603 (8)	0.0133 (7)	−0.0156 (7)	0.0007 (7)
C14	0.0652 (9)	0.0452 (7)	0.0681 (9)	0.0169 (7)	−0.0011 (7)	−0.0076 (7)
C15	0.0608 (9)	0.0479 (7)	0.0516 (7)	0.0134 (6)	−0.0114 (6)	−0.0087 (6)
N1	0.0518 (7)	0.0529 (7)	0.0669 (8)	0.0175 (5)	−0.0010 (6)	0.0064 (6)

C1—C2	1.3723 (17)	C8—C9	1.367 (2)
C1—C10	1.4259 (17)	C8—H8	0.9300
C1—C11	1.4916 (16)	C9—C10	1.4172 (17)
C2—C3	1.4098 (19)	C9—H9	0.9300
C2—H2	0.9300	C11—C15	1.3797 (18)
C3—C4	1.357 (2)	C11—C12	1.3823 (17)
C3—H3	0.9300	C12—C13	1.3849 (19)
C4—C5	1.4144 (19)	C12—H12	0.9300
C4—H4	0.9300	C13—N1	1.326 (2)
C5—C6	1.4161 (19)	C13—H13	0.9300
C5—C10	1.4252 (16)	C14—N1	1.328 (2)
C6—C7	1.356 (2)	C14—C15	1.3828 (19)
C6—H6	0.9300	C14—H14	0.9300
C7—C8	1.405 (2)	C15—H15	0.9300
C7—H7	0.9300
C2—C1—C10	119.92 (11)	C7—C8—H8	119.7
C2—C1—C11	120.16 (11)	C8—C9—C10	121.00 (12)
C10—C1—C11	119.90 (10)	C8—C9—H9	119.5
C1—C2—C3	120.78 (13)	C10—C9—H9	119.5
C1—C2—H2	119.6	C9—C10—C5	118.21 (11)
C3—C2—H2	119.6	C9—C10—C1	122.98 (10)
C4—C3—C2	120.51 (13)	C5—C10—C1	118.81 (11)
C4—C3—H3	119.7	C15—C11—C12	116.81 (12)
C2—C3—H3	119.7	C15—C11—C1	121.27 (11)
C3—C4—C5	120.82 (12)	C12—C11—C1	121.92 (11)
C3—C4—H4	119.6	C11—C12—C13	119.29 (13)
C5—C4—H4	119.6	C11—C12—H12	120.4
C4—C5—C6	122.03 (12)	C13—C12—H12	120.4
C4—C5—C10	119.14 (11)	N1—C13—C12	124.30 (14)
C6—C5—C10	118.83 (12)	N1—C13—H13	117.8
C7—C6—C5	121.34 (13)	C12—C13—H13	117.8
C7—C6—H6	119.3	N1—C14—C15	124.12 (14)
C5—C6—H6	119.3	N1—C14—H14	117.9
C6—C7—C8	120.05 (13)	C15—C14—H14	117.9
C6—C7—H7	120.0	C11—C15—C14	119.60 (13)
C8—C7—H7	120.0	C11—C15—H15	120.2
C9—C8—C7	120.51 (13)	C14—C15—H15	120.2
C9—C8—H8	119.7	C13—N1—C14	115.86 (12)
C10—C1—C2—C3	0.3 (2)	C2—C1—C10—C9	−178.79 (12)
C11—C1—C2—C3	178.62 (13)	C11—C1—C10—C9	2.86 (17)
C1—C2—C3—C4	−1.1 (2)	C2—C1—C10—C5	1.02 (17)
C2—C3—C4—C5	0.5 (2)	C11—C1—C10—C5	−177.32 (10)
C3—C4—C5—C6	−178.45 (14)	C2—C1—C11—C15	−105.67 (15)
C3—C4—C5—C10	0.8 (2)	C10—C1—C11—C15	72.68 (16)
C4—C5—C6—C7	179.85 (14)	C2—C1—C11—C12	73.83 (17)
C10—C5—C6—C7	0.6 (2)	C10—C1—C11—C12	−107.83 (14)
C5—C6—C7—C8	1.5 (2)	C15—C11—C12—C13	−1.2 (2)
C6—C7—C8—C9	−1.6 (2)	C1—C11—C12—C13	179.30 (13)
C7—C8—C9—C10	−0.3 (2)	C11—C12—C13—N1	1.1 (3)
C8—C9—C10—C5	2.34 (18)	C12—C11—C15—C14	0.4 (2)
C8—C9—C10—C1	−177.84 (12)	C1—C11—C15—C14	179.90 (13)
C4—C5—C10—C9	178.26 (11)	N1—C14—C15—C11	0.6 (3)
C6—C5—C10—C9	−2.44 (17)	C12—C13—N1—C14	−0.1 (2)
C4—C5—C10—C1	−1.57 (17)	C15—C14—N1—C13	−0.8 (2)
C6—C5—C10—C1	177.74 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···Cg1i	0.93	2.69	3.577 (2)	161
C14—H14···Cg1ii	0.93	2.84	3.648 (2)	146

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C5–C10 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯Cg1i	0.93	2.69	3.577 (2)	161
C14—H14⋯Cg1ii	0.93	2.84	3.648 (2)	146

Symmetry codes: (i) ; (ii) .