rac-1-(6-Hy­droxy-3,6-dimethyl-4-phenyl-4,5,6,7-tetra­hydro-2,1-benzoxazol-5-yl)ethanone

Maharramov, A.M.; Ismiyev, A.I.; Rashidov, B.A.

doi:10.1107/S1600536810043667

Volume 66
Part 11
Page o3030
November 2010

Received 8 October 2010
Accepted 26 October 2010
Online 31 October 2010

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.002 Å
R = 0.046
wR = 0.141
Data-to-parameter ratio = 19.6
Details

rac-1-(6-Hydroxy-3,6-dimethyl-4-phenyl-4,5,6,7-tetrahydro-2,1-benzoxazol-5-yl)ethanone

Abel M. Maharramov,^a Arif I. Ismiyev ^a and Bahruz A. Rashidov ^a ^*

^aBaku State University, Z. Khalilov Street 23, Baku AZ-1148, Azerbaijan
Correspondence e-mail: Bahruz_81@mail.ru

The structure of the title compound, C₁₇H₁₉NO₃, is of interest with respect to antibacterial properties, antibiotic properties and biological activity. The structure displays intermolecular O-HN hydrogen bonding.

Related literature

For general background to Schiff bases and their uses, see: Lau et al. (1999); Shawali et al. (1985); Raman et al. (2003); Yuxia et al. (2002).

Experimental

Crystal data

C₁₇H₁₉NO₃
M_r = 285.33
Monoclinic, P 2₁ /c
a = 16.1518 (9) Å
b = 5.5353 (3) Å
c = 17.2956 (9) Å
= 103.496 (1)°
V = 1503.61 (14) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 296 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1998) T_min = 0.975, T_max = 0.983
16629 measured reflections
3724 independent reflections
2840 reflections with I > 2(I)
R_int = 0.021

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.141
S = 1.00
3724 reflections
190 parameters
H-atom parameters constrained
_max = 0.28 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O3-H3BN1ⁱ	0.82	2.08	2.8689 (17)	162
Symmetry code: (i) -x, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PB2043 ).

Acknowledgements

The authors thank Professor Victor N. Khrustalev for fruitful discussions and help in this work.

References

Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Lau, K. Y., Mayr, A. & Cheung, K. K. (1999). Inorg. Chim. Acta, 285, 223-232.
Raman, N., Muthuraj, V., Ravichandran, S. & Kulandaisamy, A. (2003). Proc. Indian Acad. Sci. 115, 161-167.
Shawali, A. S., Harb, N. M. S. & Badahdah, K. O. (1985). J. Heterocycl. Chem. 22, 1397-1403.
Sheldrick, G. M. (1998). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Yuxia, Z., Tao, Z., Wanshan, M., Haibin, Z. & Suifeng, C. (2002). Hauxue Shiji, 24, 117.

organic compounds