8-(Naphthalen-1-yl)quinoline.

In the title mol-ecule, C(19)H(13)N, the angle between the mean planes of the naphthalene and quinoline ring systems is 68.59 (2)°. The compound is of inter-est with respect to its potential for spontaneous resolution. In the crystal structure, the R and S isomers are arranged in alternating homochiral layers. The mol-ecules of a given layer are oriented with their major axes (i.e. the axis perpendicular to the interannular bond) in the same direction and their naphthalene and quinoline ring systems are arranged parallel. Like the configurations, this orientation alternates in adjacent layers.

Related literature

For spontanteous-resolution experiments, see: Asakura & Plasson (2006 ▶); Kondipudi et al. (1999 ▶); Kranz et al. (1993 ▶); Sainz-Diaz et al. (2005 ▶); Wilson & Pincock (1974 ▶). For related structures, see: Kerr & Robertson (1969 ▶); Kuroda & Manson (1981 ▶). For details of the synthesis, see: Huff et al. (1998 ▶).

Experimental

Crystal data

C19H13N

M = 255.30

Triclinic,

a = 6.1778 (1) Å

b = 10.0392 (2) Å

c = 10.8828 (2) Å

α = 104.537 (1)°

β = 106.435 (1)°

γ = 90.002 (1)°

V = 624.80 (2) Å3

Z = 2

Cu Kα radiation

μ = 0.61 mm−1

T = 100 K

0.37 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD APEXII diffractometer

Absorption correction: numerical (SADABS; Sheldrick, 2008 ▶) T min = 0.806, T max = 0.942

5783 measured reflections

2058 independent reflections

1678 reflections with I > 2σ(I)

R int = 0.011

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.131

S = 1.06

2058 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811034052/lh5298sup1.cif

Supplementary material file. DOI: 10.1107/S1600536811034052/lh5298Isup2.mol

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034052/lh5298Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536811034052/lh5298Isup4.cml

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

C19H13N	Z = 2
Mr = 255.30	F(000) = 268
Triclinic, P1	Dx = 1.357 Mg m−3
Hall symbol: -P 1	Melting point = 436.0–437.5 K
a = 6.1778 (1) Å	Cu Kα radiation, λ = 1.54178 Å
b = 10.0392 (2) Å	Cell parameters from 3661 reflections
c = 10.8828 (2) Å	θ = 4.4–66.7°
α = 104.537 (1)°	µ = 0.61 mm−1
β = 106.435 (1)°	T = 100 K
γ = 90.002 (1)°	Plate, colourless
V = 624.80 (2) Å3	0.37 × 0.20 × 0.10 mm

Bruker SMART CCD APEXII diffractometer	2058 independent reflections
Radiation source: fine-focus sealed tube	1678 reflections with I > 2σ(I)
graphite	Rint = 0.011
φ and ω scans	θmax = 67.5°, θmin = 4.4°
Absorption correction: numerical (SADABS; Sheldrick, 2008)	h = −7→7
Tmin = 0.806, Tmax = 0.942	k = −11→11
5783 measured reflections	l = −12→12

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0654P)2 + 0.348P] where P = (Fo2 + 2Fc2)/3
2058 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

Experimental. crystal mounted on a Cryoloop using Paratone-N

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
N1	0.9761 (3)	0.89896 (16)	1.10848 (15)	0.0304 (4)
C2	1.1692 (3)	0.96964 (18)	1.19213 (17)	0.0269 (4)
H2	1.2610	1.0176	1.1579	0.032*
C3	1.2400 (3)	0.97528 (18)	1.32817 (17)	0.0268 (4)
H3	1.3785	1.0249	1.3839	0.032*
C4	1.1084 (3)	0.90897 (17)	1.37947 (16)	0.0233 (4)
H4	1.1549	0.9126	1.4713	0.028*
C4A	0.9019 (3)	0.83446 (16)	1.29589 (15)	0.0207 (4)
C5	0.7566 (3)	0.76657 (17)	1.34510 (16)	0.0230 (4)
H5	0.7968	0.7702	1.4369	0.028*
C6	0.5598 (3)	0.69612 (17)	1.26156 (16)	0.0243 (4)
H6	0.4636	0.6510	1.2954	0.029*
C7	0.4982 (3)	0.68992 (17)	1.12520 (16)	0.0236 (4)
H7	0.3602	0.6406	1.0684	0.028*
C8	0.6333 (3)	0.75369 (17)	1.07236 (16)	0.0211 (4)
C8A	0.8399 (3)	0.82928 (16)	1.15855 (15)	0.0197 (4)
C1'	0.5605 (3)	0.74639 (17)	0.92755 (16)	0.0210 (4)
C2'	0.3732 (3)	0.81036 (17)	0.87514 (16)	0.0234 (4)
H2'	0.2924	0.8601	0.9321	0.028*
C3'	0.2981 (3)	0.80380 (17)	0.73857 (16)	0.0244 (4)
H3'	0.1677	0.8487	0.7048	0.029*
C4'	0.4114 (3)	0.73338 (17)	0.65465 (16)	0.0229 (4)
H4'	0.3598	0.7297	0.5628	0.027*
C4A'	0.6059 (3)	0.66569 (16)	0.70394 (15)	0.0207 (4)
C5'	0.7289 (3)	0.59114 (17)	0.62054 (16)	0.0234 (4)
H5'	0.6837	0.5877	0.5287	0.028*
C6'	0.9118 (3)	0.52436 (18)	0.67111 (17)	0.0263 (4)
H6'	0.9937	0.4743	0.6150	0.032*
C7'	0.9774 (3)	0.53047 (18)	0.80697 (17)	0.0274 (4)
H7'	1.1039	0.4830	0.8413	0.033*
C8'	0.8677 (2)	0.60111 (16)	0.89035 (15)	0.0173 (4)
H8'	0.9166	0.6033	0.9819	0.021*
C8A'	0.6816 (3)	0.67103 (16)	0.84112 (15)	0.0204 (4)

	U11	U22	U33	U12	U13	U23
N1	0.0366 (9)	0.0240 (8)	0.0316 (8)	0.0013 (6)	0.0141 (7)	0.0046 (6)
C2	0.0307 (9)	0.0211 (9)	0.0313 (9)	−0.0011 (7)	0.0153 (8)	0.0041 (7)
C3	0.0238 (9)	0.0213 (9)	0.0309 (10)	0.0001 (7)	0.0059 (7)	0.0016 (7)
C4	0.0276 (9)	0.0201 (9)	0.0197 (8)	0.0061 (7)	0.0044 (7)	0.0039 (7)
C4A	0.0249 (8)	0.0154 (9)	0.0210 (8)	0.0051 (6)	0.0070 (7)	0.0034 (6)
C5	0.0314 (9)	0.0201 (9)	0.0191 (8)	0.0057 (7)	0.0093 (7)	0.0058 (6)
C6	0.0285 (9)	0.0217 (9)	0.0261 (9)	0.0020 (7)	0.0128 (7)	0.0071 (7)
C7	0.0226 (8)	0.0221 (9)	0.0250 (9)	0.0006 (6)	0.0064 (7)	0.0049 (7)
C8	0.0240 (8)	0.0173 (9)	0.0220 (9)	0.0042 (6)	0.0074 (7)	0.0043 (6)
C8A	0.0227 (8)	0.0163 (9)	0.0211 (8)	0.0039 (6)	0.0085 (7)	0.0043 (6)
C1'	0.0215 (8)	0.0195 (9)	0.0214 (8)	−0.0026 (6)	0.0061 (7)	0.0046 (6)
C2'	0.0236 (8)	0.0229 (9)	0.0235 (9)	0.0015 (7)	0.0082 (7)	0.0043 (7)
C3'	0.0224 (8)	0.0230 (10)	0.0258 (9)	0.0017 (7)	0.0024 (7)	0.0081 (7)
C4'	0.0272 (9)	0.0209 (9)	0.0189 (8)	−0.0029 (7)	0.0035 (7)	0.0060 (6)
C4A'	0.0237 (8)	0.0162 (9)	0.0211 (8)	−0.0036 (6)	0.0046 (7)	0.0052 (6)
C5'	0.0295 (9)	0.0213 (9)	0.0197 (8)	−0.0041 (7)	0.0079 (7)	0.0051 (7)
C6'	0.0274 (9)	0.0225 (10)	0.0288 (9)	0.0004 (7)	0.0116 (7)	0.0028 (7)
C7'	0.0247 (9)	0.0210 (10)	0.0323 (10)	0.0024 (7)	0.0025 (7)	0.0061 (7)
C8'	0.0193 (8)	0.0148 (8)	0.0147 (7)	0.0006 (6)	0.0011 (6)	0.0026 (6)
C8A'	0.0222 (8)	0.0159 (9)	0.0217 (8)	−0.0033 (6)	0.0048 (7)	0.0044 (6)

N1—C2	1.348 (2)	C1'—C2'	1.374 (2)
N1—C8A	1.395 (2)	C1'—C8A'	1.434 (2)
C2—C3	1.406 (2)	C2'—C3'	1.410 (2)
C2—H2	0.9500	C2'—H2'	0.9500
C3—C4	1.364 (2)	C3'—C4'	1.364 (2)
C3—H3	0.9500	C3'—H3'	0.9500
C4—C4A	1.420 (2)	C4'—C4A'	1.418 (2)
C4—H4	0.9500	C4'—H4'	0.9500
C4A—C5	1.418 (2)	C4A'—C5'	1.418 (2)
C4A—C8A	1.421 (2)	C4A'—C8A'	1.419 (2)
C5—C6	1.363 (2)	C5'—C6'	1.364 (2)
C5—H5	0.9500	C5'—H5'	0.9500
C6—C7	1.409 (2)	C6'—C7'	1.403 (2)
C6—H6	0.9500	C6'—H6'	0.9500
C7—C8	1.376 (2)	C7'—C8'	1.346 (2)
C7—H7	0.9500	C7'—H7'	0.9500
C8—C8A	1.432 (2)	C8'—C8A'	1.393 (2)
C8—C1'	1.494 (2)	C8'—H8'	0.9500
C2—N1—C8A	118.89 (15)	C2'—C1'—C8	120.02 (15)
N1—C2—C3	122.60 (15)	C8A'—C1'—C8	120.85 (14)
N1—C2—H2	118.7	C1'—C2'—C3'	121.44 (15)
C3—C2—H2	118.7	C1'—C2'—H2'	119.3
C4—C3—C2	119.48 (15)	C3'—C2'—H2'	119.3
C4—C3—H3	120.3	C4'—C3'—C2'	120.43 (15)
C2—C3—H3	120.3	C4'—C3'—H3'	119.8
C3—C4—C4A	120.15 (15)	C2'—C3'—H3'	119.8
C3—C4—H4	119.9	C3'—C4'—C4A'	120.27 (15)
C4A—C4—H4	119.9	C3'—C4'—H4'	119.9
C5—C4A—C4	122.25 (15)	C4A'—C4'—H4'	119.9
C5—C4A—C8A	119.47 (15)	C5'—C4A'—C4'	122.28 (15)
C4—C4A—C8A	118.27 (15)	C5'—C4A'—C8A'	118.09 (15)
C6—C5—C4A	120.44 (15)	C4'—C4A'—C8A'	119.63 (15)
C6—C5—H5	119.8	C6'—C5'—C4A'	120.54 (15)
C4A—C5—H5	119.8	C6'—C5'—H5'	119.7
C5—C6—C7	120.34 (15)	C4A'—C5'—H5'	119.7
C5—C6—H6	119.8	C5'—C6'—C7'	119.23 (15)
C7—C6—H6	119.8	C5'—C6'—H6'	120.4
C8—C7—C6	121.54 (15)	C7'—C6'—H6'	120.4
C8—C7—H7	119.2	C8'—C7'—C6'	122.44 (15)
C6—C7—H7	119.2	C8'—C7'—H7'	118.8
C7—C8—C8A	119.05 (15)	C6'—C7'—H7'	118.8
C7—C8—C1'	119.94 (15)	C7'—C8'—C8A'	119.33 (15)
C8A—C8—C1'	120.99 (14)	C7'—C8'—H8'	120.3
N1—C8A—C4A	120.58 (15)	C8A'—C8'—H8'	120.3
N1—C8A—C8	120.26 (14)	C8'—C8A'—C4A'	120.35 (15)
C4A—C8A—C8	119.15 (15)	C8'—C8A'—C1'	120.53 (14)
C2'—C1'—C8A'	119.12 (15)	C4A'—C8A'—C1'	119.10 (15)
C8A—N1—C2—C3	0.4 (3)	C7—C8—C1'—C8A'	−112.47 (18)
N1—C2—C3—C4	−1.1 (3)	C8A—C8—C1'—C8A'	69.1 (2)
C2—C3—C4—C4A	0.2 (2)	C8A'—C1'—C2'—C3'	−0.2 (2)
C3—C4—C4A—C5	−178.48 (15)	C8—C1'—C2'—C3'	−179.08 (15)
C3—C4—C4A—C8A	1.1 (2)	C1'—C2'—C3'—C4'	−0.2 (2)
C4—C4A—C5—C6	179.99 (15)	C2'—C3'—C4'—C4A'	0.1 (2)
C8A—C4A—C5—C6	0.4 (2)	C3'—C4'—C4A'—C5'	179.92 (15)
C4A—C5—C6—C7	0.0 (2)	C3'—C4'—C4A'—C8A'	0.3 (2)
C5—C6—C7—C8	0.2 (3)	C4'—C4A'—C5'—C6'	−178.28 (15)
C6—C7—C8—C8A	−0.7 (2)	C8A'—C4A'—C5'—C6'	1.4 (2)
C6—C7—C8—C1'	−179.14 (15)	C4A'—C5'—C6'—C7'	−0.1 (2)
C2—N1—C8A—C4A	1.0 (2)	C5'—C6'—C7'—C8'	−0.6 (3)
C2—N1—C8A—C8	179.75 (15)	C6'—C7'—C8'—C8A'	0.1 (2)
C5—C4A—C8A—N1	177.87 (14)	C7'—C8'—C8A'—C4A'	1.2 (2)
C4—C4A—C8A—N1	−1.7 (2)	C7'—C8'—C8A'—C1'	179.58 (14)
C5—C4A—C8A—C8	−0.9 (2)	C5'—C4A'—C8A'—C8'	−1.9 (2)
C4—C4A—C8A—C8	179.47 (14)	C4'—C4A'—C8A'—C8'	177.77 (14)
C7—C8—C8A—N1	−177.73 (14)	C5'—C4A'—C8A'—C1'	179.69 (13)
C1'—C8—C8A—N1	0.7 (2)	C4'—C4A'—C8A'—C1'	−0.7 (2)
C7—C8—C8A—C4A	1.1 (2)	C2'—C1'—C8A'—C8'	−177.81 (14)
C1'—C8—C8A—C4A	179.50 (14)	C8—C1'—C8A'—C8'	1.1 (2)
C7—C8—C1'—C2'	66.4 (2)	C2'—C1'—C8A'—C4A'	0.6 (2)
C8A—C8—C1'—C2'	−112.04 (18)	C8—C1'—C8A'—C4A'	179.48 (14)