5-(Phenyl­diazen­yl)tropolone

Hill, T.N.; Mangwaela, M.S.; Steyl, G.

doi:10.1107/S1600536812008677

Volume 68
Part 4
Page o941
April 2012

Received 13 February 2012
Accepted 27 February 2012
Online 3 March 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R = 0.048
wR = 0.128
Data-to-parameter ratio = 17.2
Details

5-(Phenyldiazenyl)tropolone

Tania N. Hill,^a ^* Moeketsi S. Mangwaela ^a and Gideon Steyl ^a

^aDepartment of Chemistry, University of the Free State, PO Box 339, Bloemfontein 9300, South Africa
Correspondence e-mail: tania.hill@gmail.com

The title compound [systematic name: (E)-2-hydroxy-5-(phenyldiazenyl)cyclohepta-2,4,6-trien-1-one], C₁₃H₁₀N₂O₂, is essentially planar with an r.m.s. deviation of 0.036 (2) Å and a dihedral angle of 1.57 (8)° between the phenyl and tropolone rings. In the crystal, molecules are linked by pairs of O-HO hydrogen bonds into inversion dimers. The dimers are further connected by C-HO hydrogen bonds and [pi] - [pi] stacking interactions, with centroid-centroid distances of 3.6934 (9) and 3.6282 (9) Å.

Related literature

For synthetic background, see: Gao & Zheng (2001). For applications of azo-substituted tropolones, see: Mori et al. (2002). For related systems, see: Shimanouchi & Sasada (1973); Steyl & Roodt (2006). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental

Crystal data

C₁₃H₁₀N₂O₂
M_r = 226.23
Monoclinic, P 2₁ /c
a = 6.2838 (2) Å
b = 24.8474 (13) Å
c = 8.0478 (3) Å
= 122.255 (2)°
V = 1062.64 (8) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 100 K
0.35 × 0.32 × 0.05 mm

Data collection

Bruker X8 APEXII 4K KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004) T_min = 0.967, T_max = 0.995
10621 measured reflections
2669 independent reflections
1925 reflections with I > 2(I)
R_int = 0.050

Refinement

R[F² > 2(F²)] = 0.048
wR(F²) = 0.128
S = 1.05
2669 reflections
155 parameters
H-atom parameters constrained
_max = 0.38 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O2	0.84	2.08	2.5754 (15)	117
C5-H5O1ⁱ	0.95	2.40	3.1866 (19)	140
O1-H1O2ⁱⁱ	0.84	1.96	2.6686 (15)	141
Symmetry codes: (i) x-1, y, z-1; (ii) -x+1, -y, -z+3.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5073 ).

Acknowledgements

Financial assistance from the University of the Free State is gratefully acknowledged. We also express our gratitude towards SASOL and the South African National Research Foundation (SA-NRF/THRIP) for financial support of this project. Part of this material is based on work supported by the SA-NRF/THRIP under grant No. GUN 2068915. Opinions, findings, conclusions or recommendations expressed in this material are those of the authors and do not necessarily reflect the views of the SA-NRF.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2004). SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin. USA.
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Gao, W. T. & Zheng, Z. (2001). Chin. Chem. Lett. 12, 103-106.
Mori, A., Uno, K. & Takeshita, H. (2002). Liq. Cryst. 29, 1539-1545.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shimanouchi, H. & Sasada, Y. (1973). Acta Cryst. B29, 81-90.
Steyl, G. & Roodt, A. (2006). S. Afr. J. Chem. 59, 21-27.

organic compounds