1-(9-Methyl-11-sulfanyl­idene-8-oxa-10,12-diaza­tricyclo­[7.3.1.02,7]trideca-2,4,6-trien-13-yl)ethanone

Kurbanova, M.M.; Maharramov, A.M.; Novruzova, A.B.; Gurbanov, A.V.; Ng, S.W.

doi:10.1107/S1600536811013699

Volume 67
Part 5
Page o1156
May 2011

Received 11 April 2011
Accepted 12 April 2011
Online 16 April 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.007 Å
R = 0.079
wR = 0.211
Data-to-parameter ratio = 14.0
Details

1-(9-Methyl-11-sulfanylidene-8-oxa-10,12-diazatricyclo[7.3.1.0^2,7]trideca-2,4,6-trien-13-yl)ethanone

Malahat M. Kurbanova,^a Abel M. Maharramov,^a Aysel B. Novruzova,^a Atash V. Gurbanov ^a and Seik Weng Ng ^b ^*

^aDepartment of Organic Chemistry, Baku State University, Baku, Azerbaijan, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng@um.edu.my

The six-membered oxacyclohexene ring of the title compound, C₁₃H₁₄N₂O₂S, is fused with the benzene ring and the quarternary C atom lies above the plane of the benzene ring by 0.229 (8) Å, whereas the methine C atom (which bears the acetyl substituent) lies below this plane by 0.595 (8) Å. The oxacyclohexene ring is also fused with the sofa-shaped 2,6-diazacyclohexanone ring. The methine C atom that belongs to both six-membered rings lies above the mean plane of the other five atoms (r.m.s. deviation = 0.077 Å) by 0.759 (5) Å. In the crystal, N-HS hydrogen bonds link adjacent molecules into a linear chain.

Related literature

For related structures, see: Kettmann & Svetlík (1996, 1997); Kurbanova et al. (2009).

Experimental

Crystal data

C₁₃H₁₄N₂O₂S
M_r = 262.32
Monoclinic, P 2₁ /n
a = 8.2382 (5) Å
b = 19.1223 (12) Å
c = 9.2209 (6) Å
= 114.623 (1)°
V = 1320.51 (14) Å³
Z = 4
Mo K radiation
= 0.24 mm^-1
T = 296 K
0.40 × 0.30 × 0.20 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.589, T_max = 1.000
8830 measured reflections
2292 independent reflections
1523 reflections with I > 2(I)
R_int = 0.119

Refinement

R[F² > 2(F²)] = 0.079
wR(F²) = 0.211
S = 0.99
2292 reflections
164 parameters
H-atom parameters constrained
_max = 0.65 e Å^-3
_min = -0.41 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1S1ⁱ	0.88	2.49	3.324 (3)	158
N2-H2S1ⁱⁱ	0.88	2.43	3.259 (3)	158
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+2, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5193 ).

Acknowledgements

We thank Baku State University and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Kettmann, V. & Svetlík, J. (1996). Acta Cryst. C52, 1496-1499.
Kettmann, V. & Svetlík, J. (1997). Acta Cryst. C53, 1493-1495.
Kurbanova, M. M., Kurbanov, A. V., Askerov, R. K., Allakhverdiev, M. A., Khrustalev, V. N. & Magerramov, A. M. (2009). J. Struct. Chem. 50, 505-509.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds

1-(9-Methyl-11-sulfanylidene-8-oxa-10,12-diazatricyclo[7.3.1.02,7]trideca-2,4,6-trien-13-yl)ethanone