4,4′-(1,8-Naphthalene-1,8-di­yl)dibenzonitrile

Lima, C.F.; Gomes, L.R.; Santos, L.M.N.B.F.; Low, J.N.

doi:10.1107/S160053681005083X

Volume 67
Part 1
Page o66
January 2011

Received 29 November 2010
Accepted 3 December 2010
Online 11 December 2010

Key indicators
Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.002 Å
R = 0.048
wR = 0.131
Data-to-parameter ratio = 19.7
Details

4,4'-(1,8-Naphthalene-1,8-diyl)dibenzonitrile

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

^aCentro de Investigação em Química, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, Rua do Campo Alegre, 687, P-4169 007 Porto, Portugal,^bREQUIMTE, Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, Rua do Campo Alegre, 687, P-4169 007 Porto, Portugal, and ^cDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland
Correspondence e-mail: jnlow111@gmail.com

In the title molecule, C₂₄H₁₄N₂, the exterior C-C-C angle of the naphthalene ring system involving the two phenyl-substituted C atoms is 126.06 (11)° and the dihedral angles between the mean plane of the naphthalene ring system and those of the benzene rings are 66.63 (5) and 67.89 (5)°. In the crystal, molecules are linked into a ladders by four weak C-H [pi] interactions.

Related literature

For the structure of the related compound 4-(1-naphtyl)benzonitrile, see: Lima et al. (2010).

Experimental

Crystal data

C₂₄H₁₄N₂
M_r = 330.37
Monoclinic, C 2/c
a = 17.0872 (9) Å
b = 8.2997 (4) Å
c = 24.3656 (13) Å
= 93.795 (2)°
V = 3447.9 (3) Å³
Z = 8
Mo K radiation
= 0.08 mm^-1
T = 150 K
0.40 × 0.30 × 0.02 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004) T_min = 0.971, T_max = 0.999
11422 measured reflections
4634 independent reflections
3482 reflections with I > 2(I)
R_int = 0.031

Refinement

R[F² > 2(F²)] = 0.048
wR(F²) = 0.131
S = 1.04
4634 reflections
235 parameters
H-atom parameters constrained
_max = 0.38 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1-C10 and C8-C10 rings, respectively.

D-HA	D-H	HA	DA	D-HA
C12-H12Cg2ⁱ	0.95	2.75	3.6147 (13)	152
C16-H16Cg2ⁱⁱ	0.95	2.92	3.6539 (15)	135
C82-H82Cg1ⁱ	0.95	2.83	3.6180 (15)	141
C86-H86Cg1ⁱⁱ	0.95	2.83	3.6614 (13)	147
Symmetry codes: (i) $[-x+{\script{3\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (ii) $[x+{\script{3\over 2}}, y+{\script{3\over 2}}, z+1]$ .

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 data and figures for this paper are available from the IUCr electronic archives (Reference: LH5183 ).

Acknowledgements

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).

References

Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Lima, C. F., Gomes, L. R., Santos, L. M. N. B. F. & Low, J. N. (2010). Acta Cryst. E66, o3289.
McArdle, P., Gilligan, K., Cunningham, D., Dark, R. & Mahon, M. (2004). CrystEngComm, 6, 303-309.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds