Naphthalene-2,3-diol–imidazole (1/1)

Wang, Y.-T.; Tang, G.-M.; Wan, W.-Z.

doi:10.1107/S1600536808025555

Volume 64
Part 9
Page o1754
September 2008

Received 5 August 2008
Accepted 8 August 2008
Online 13 August 2008

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.002 Å
R = 0.041
wR = 0.125
Data-to-parameter ratio = 16.7
Details

Naphthalene-2,3-diol-imidazole (1/1)

Yong-Tao Wang,^a ^* Gui-Mei Tang ^a and Wen-Zhu Wan ^a

^aDepartment of Chemical Engineering, Shandong Institute of Light Industry, Jinan, Shandong 250353, People's Republic of China
Correspondence e-mail: ceswyt@sohu.com

In the title cocrystal, C₁₀H₈O₂·C₃H₄N₂, intermolecular O-HO and N-HO hydrogen bonds connect the naphthalene-2,3-diol and imidazole molecules into a two-dimensional supramolecular framework.

Related literature

For other cocrystals of naphthalene-2,3-diol, see: Fritchie & Johnston (1975); Wang & Tang (2006); Wang, Tang & Ng (2006); Wang, Tang & Wan (2006); Wells et al. (1974).

Experimental

Crystal data

C₁₀H₈O₂·C₃H₄N₂
M_r = 228.25
Orthorhombic, P b c a
a = 12.0003 (17) Å
b = 7.7862 (11) Å
c = 25.863 (4) Å
V = 2416.6 (6) Å³
Z = 8
Mo K radiation
= 0.09 mm^-1
T = 296 (2) K
0.30 × 0.30 × 0.20 mm

Data collection

Bruker SMART diffractometer
Absorption correction: none
18637 measured reflections
2777 independent reflections
2142 reflections with I > 2(I)
R_int = 0.031

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.125
S = 1.04
2777 reflections
166 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.16 e Å^-3
_min = -0.20 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1BO2ⁱ	0.92 (2)	1.78 (2)	2.6877 (14)	166 (2)
O2-H2AN1	1.03 (2)	1.57 (2)	2.5947 (15)	170 (2)
N2-H2BO1ⁱⁱ	0.89 (2)	2.09 (3)	2.9185 (19)	156 (2)
Symmetry codes: (i) $[x+2, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x-1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART; cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; 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: NG2483 ).

Acknowledgements

This work was supported by the Starting Fund of Shandong Institute of Light Industry (to Y-TW).

References

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Fritchie, C. J. & Johnston, R. M. (1975). Acta Cryst. B31, 454-461.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wang, Y.-T. & Tang, G.-M. (2006). Acta Cryst. E62, o3833-o3834.
Wang, Y.-T., Tang, G.-M. & Ng, S. W. (2006). Acta Cryst. E62, o4429-o4430.
Wang, Y.-T., Tang, G.-M. & Wan, W.-Z. (2006). Acta Cryst. E62, o3396-o3397.
Wells, J. L., Trus, B. L., Johnston, R. M., Marsh, R. E. & Fritchie, C. J. (1974). Acta Cryst. B30, 1127-1134.

organic compounds