2,3-Bis(prop-2-yn­yloxy)naphthalene

Yang, G.-Z.; Li, F.-A.

doi:10.1107/S1600536808037549

Volume 64
Part 12
Page o2383
December 2008

Received 30 September 2008
Accepted 12 November 2008
Online 20 November 2008

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.002 Å
R = 0.039
wR = 0.101
Data-to-parameter ratio = 13.4
Details

2,3-Bis(prop-2-ynyloxy)naphthalene

Guo-Zhong Yang ^a ^* and Fu-An Li ^b

^aCollege of Civil and Architectural Engineering, Henan University, Kaifeng 475001, Henan, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Pingdingshan University, Pingdingshan 467000, Henan, People's Republic of China
Correspondence e-mail: zhw@henu.edu.cn

In the crystal structure of the title compound, C₁₆H₁₂O₂, no classical hydrogen bonds or aromatic [pi] - [pi] stacking interactions were observed. The molecules are linked into a three-dimensional framework by a combination of C-HO and C-H [pi] (arene) hydrogen bonds.

Related literature

For related structures, see: Zhang et al. (2008); Ghosh et al. (2007); Wang & Kong (2007). For the synthesis, see: Burchell et al. (2006). For bond-length data, see: Allen et al. (1987). For [pi] - [pi] stacking interactions, see: Steed & Atwood (2000).

Experimental

Crystal data

C₁₆H₁₂O₂
M_r = 236.26
Orthorhombic, P b c a
a = 8.2921 (12) Å
b = 9.0457 (14) Å
c = 33.070 (5) Å
V = 2480.5 (6) Å³
Z = 8
Mo K radiation
= 0.08 mm^-1
T = 298 (2) K
0.18 × 0.16 × 0.15 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.984, T_max = 0.989
12468 measured reflections
2182 independent reflections
1782 reflections with I > 2(I)
R_int = 0.033

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.101
S = 1.04
2182 reflections
163 parameters
H-atom parameters constrained
_max = 0.17 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C4-C6/C11-C13 ring.

D-HA	D-H	HA	DA	D-HA
C16-H16O2ⁱ	0.93	2.48	3.409 (2)	177
C3-H3ACg1ⁱⁱ	0.97	2.95	3.634 (2)	129
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x-{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BV2111 ).

Acknowledgements

The authors are grateful for financial support from the Henan Administration of Science and Technology (grant No. 0111030700).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Burchell, T. J., Jennings, M. C. & Puddephatt, R. J. (2006). Inorg. Chim. Acta, 359, 2812-2818.
Ghosh, S., Mukhopadhyay, R., Helliwell, M. & Mukherjee, A. K. (2007). Acta Cryst. C63, o496-o500.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Steed, J. W. & Atwood, J. L. (2000). Supramolecular Chemistry, p. 26. Chichester: John Wiley & Sons.
Wang, X.-B. & Kong, L.-Y. (2007). Acta Cryst. E63, o4340.
Zhang, W., Cui, Q. & Yu, Z. (2008). Acta Cryst. E64, o317.

organic compounds