4-(1-Naphth­yl)benzonitrile

Carlos F Lima; Ligia R Gomes; Luís M N B F Santos; John Nicolson Low

doi:10.1107/S1600536810042108

. 2010 Nov 24;66(Pt 12):o3289. doi: 10.1107/S1600536810042108

4-(1-Naphthyl)benzonitrile

Carlos F Lima ^a, Ligia R Gomes ^b, Luís M N B F Santos ^a, John Nicolson Low ^c,^*

PMCID: PMC3011424 PMID: 21589568

Abstract

The title compound, C₁₇H₁₁N, crystallizes with two molecules in the asymmetric unit which are linked by a weak C—H⋯N hydrogen bond. The dihedral angles between the benzene ring and the naphthalene ring system in the two molecules are 60.28 (3) and 60.79 (3)°. In the crystal, molecules are linked into a three-dimensional network by weak C—H⋯π interactions.

Related literature

For the structure of the related compound 1-(3,4,5-trimethoxyphenyl)naphthalene, see: Suthar et al. (2005 ▶).

Experimental

Crystal data

C₁₇H₁₁N
M _r = 229.27
Triclinic,
a = 7.3387 (3) Å
b = 11.3461 (5) Å
c = 15.5804 (7) Å
α = 71.237 (2)°
β = 89.981 (2)°
γ = 87.647 (2)°
V = 1227.22 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 150 K
0.40 × 0.18 × 0.06 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T _min = 0.972, T _max = 0.996
17670 measured reflections
7450 independent reflections
5228 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.135
S = 1.02
7450 reflections
325 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and OSCAIL (McArdle et al., 2004 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810042108/fl2322sup1.cif

e-66-o3289-sup1.cif^{(24.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042108/fl2322Isup2.hkl

e-66-o3289-Isup2.hkl^{(364.5KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

Cg1, Cg3, Cg5, Cg6 and Cg7 are the centroids of the C11–C110, C111–C116, C21–C210, C28–C210 and C211–C216 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C113—H113⋯N42	0.95	2.58	3.4804 (17)	158
C14—H14⋯Cg6ⁱ	0.95	2.99	3.9165 (14)	165
C15—H15⋯Cg5ⁱ	0.95	2.51	3.4128 (14)	160
C17—H17⋯Cg3ⁱⁱ	0.95	2.86	3.6648 (15)	144
C25—H25⋯Cg1ⁱⁱⁱ	0.95	2.52	3.4155 (14)	158
C27—H27⋯Cg7^iv	0.95	2.91	3.7205 (15)	144
C115—H115⋯Cg1^v	0.95	2.81	3.5935 (13)	141
C215—H215⋯Cg5^v	0.95	2.77	3.5740 (13)	143

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) .

Acknowledgments

CFL thanks the FCT and the European Social Fund (ESF) under the third Community Support Framework (CSF) for the award of a PhD Research Grant (SRFH/BD/29394/2006).

supplementary crystallographic information

Comment

The title compound crystallizes with two molecules on the asymmetric unit. The asymmetric unit was selected so that the 2 molecules were connected by the weak C113—H113···N42 hydrogen bond with H···N, 2.58 Å, C···N, 3.4804 (17)Å and the angle at H, 158°, Fig.1. Molecule 1 contains atoms C1X and molecule 2 contains atoms C2X. The two molecules show no unusual bonds or angles. The naphthalene rings form dihedral angles of 60.28 (3)° and 60.79 (3)° with the the phenyl rings for molecules 1 and 2 respectively. In the related compound 1-(3,4,5-trimethoxyphenyl)naphthalene, Suthar et al., (2005), which has only one molecule in the asymmetric unit, this dihedral angle is 68.19 (10)°.

Apart from the C—H···N hydrogen bond, seven weak C—H···π interactions stabilize the supramolecular structure linking the molecules into a three dimensional network (Table 1). There are no π···π interactions

Atoms C14 and C15 form weak C—H···π interactions with the C28—C210(Cg6) and C21—C210(Cg5) naphthalene rings at (x,1 + y,-1 + z), forming a dimer. These dimers are linked by the C—H···N hydrogen bond to form a chain which runs parallel to [10–1], Fig. 2.

Atoms C115 and C215 form weak C—H···π interactions with the C11—C110(Cg1) and C21—C210(Cg5) naphthalene rings at (-1 + x,y,z) respectively, forming a ladder which runs along the a axis with the C—H···N hydrogen bond forming the rungs, Fig.3.

Atom C17 forms a weak C—H···π interaction with the phenyl ring C111—C116(Cg3) at (-x,2 - y,1 - z) to give a centrosymmetric dimer. Similarly, C27 forms a centrosymmetric dimer through a C—H···π with the phenyl ring C211—C216(Cg7). These dimers are linked together via the C—H···N hydrogen bond forming a chain which runs parallel to the b axis, Fig 4.

Atom C25 forms a weak C—H···π interaction with the C11—C110(Cg1) phenyl ring at (1 + x,1 - y,1 + z) alternating with the C—H···N hydrogen bond to form a chain which runs parallel to [1–11], Fig. 5.

The related compound 1-(3,4,5-trimethoxyphenyl)naphthalene, Suthar et al., (2005) by contrast is stabilized by one C—H···π interaction. There are no π···π or C—H···O hydrogen bonds.

Experimental

A solution of K₂CO₃ (6.2 mmol) in 20 ml of water was added to a solution of 1-bromonaphthalene (3.1 mmol), 4-cyanophenylboronic acid (4.5 mmol) and Pd(OAc)₂ (1 mol %) in 20 ml of DMF. The resultant mixture was heated at 100°C for 8 h under stirring. The final solution was allowed to cool to room temperature, and extracted with ethyl acetate. The organic layer was washed with water and aqueous 0.1 M NaOH, dried over anhydrous sodium sulfate and evaporated. The brown solid obtained (0.45 g, 58%) was recrystallized from MeOH and sublimed under reduced pressure to yield white crystals of the title compound; ¹H-NMR (400 MHz, CDCl₃, 300 K, TMS) 7.98–7.92 (2H, m, 2-H + 8-H), 7.81 (2H, d, 2-H, J=8.2), 7.84–7.78 (1H, m), 7.64 (2H, d, 3-H, J=8.2), 7.61–7.40 (4H, m); ¹³C-NMR (100.6 MHz, CDCl₃, 300 K) 146.6, 139.1, 134.7, 133.0, 131.9, 131.7, 129.7, 129.5, 127.9,127.6, 127.1, 126.3, 126.1, 119.8, 112.1.