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Volume 69 
Part 9 
Page o1392  
September 2013  

Received 18 June 2013
Accepted 1 August 2013
Online 7 August 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.003 Å
R = 0.051
wR = 0.171
Data-to-parameter ratio = 16.1
Details
Open access

Lacinilene C 7-methyl ether

aA.S. Sadykov Institute of Bioorganic Chemistry, Academy of Sciences of Uzbekistan, Mirzo Ulugbek str. 83, Tashkent 100125, Uzbekistan, and bSouthern Plains Agricultural Research Center, Agricultural Research Service, USDA, College Station, TX 77845, USA
Correspondence e-mail: via74@yandex.ru

The title compound, C16H20O3 [systematic name: 1-hydroxy-7-methoxy-1,6-dimethyl-4-(propan-2-yl)naphthalen-2(1H)-one], is a sesquiterpene isolated from foliar tissues of the cotton plant and is of interest with respect to its antibacterial properties. Its phenyl ring is ideally planar, and the maximum of deviation in the second ring is 0.386 (3) Å. The hydroxy group and the methyl group are oriented in an equatorial fashion and axial, respectively, to the second ring. In the crystal, inversion dimers are formed through pairs of O-H...O hydrogen bonds. Weak C-H...O hydrogen bonds link the dimers into columns along the c axis. These columns form a crystal structure with a crystal packing factor of 0.66.

Related literature

For the original isolation from Ulmus laciniata Mayr and proposed structure, see: Suzuki et al. (1972[Suzuki, H., Yasuda, S. & Hanzawa, M. (1972). Mokuzai Gakkaishi, 18, 617-622.]). For isolation from cotton bracts (Gossypium), identification and structure definition, see: Stipanovic et al. (1975[Stipanovic, R. D., Wakelyn, P. J. & Bell, A. A. (1975). Phytochemistry, 14, 1041-1043.], 1981[Stipanovic, R. D., Greenblatt, G. A., Beier, R. C. & Bell, A. A. (1981). Phytochemistry, 20, 729-730.]). For information on the biological activity, see: Essenberg et al. (1982[Essenberg, M., Doherty, M. d'A., Hamilton, B. K., Henning, V. T., Cover, E. C., Mcfaul, S. J. & Johnson, W. M. (1982). Phytopathology, 72, 1349-1356.]). For biosynthetic studies, see: Stipanovic et al. (1981[Stipanovic, R. D., Greenblatt, G. A., Beier, R. C. & Bell, A. A. (1981). Phytochemistry, 20, 729-730.]); Essenberg et al. (1985[Essenberg, M., Stoessl, A. & Stothers, J. B. (1985). J. Chem. Soc. Chem. Commun. 9, 556-557.]).

[Scheme 1]

Experimental

Crystal data
  • C16H20O3

  • Mr = 260.32

  • Triclinic, [P \overline 1]

  • a = 8.285 (2) Å

  • b = 8.987 (2) Å

  • c = 10.665 (3) Å

  • [alpha] = 68.58 (2)°

  • [beta] = 78.95 (2)°

  • [gamma] = 88.87 (2)°

  • V = 724.4 (3) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 0.65 mm-1

  • T = 295 K

  • 0.34 × 0.27 × 0.20 mm

Data collection
  • Oxford Diffraction Xcalibur Ruby CCD diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.809, Tmax = 0.878

  • 6210 measured reflections

  • 2927 independent reflections

  • 1928 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.171

  • S = 1.06

  • 2927 reflections

  • 182 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H3...O2i 0.87 (3) 2.08 (3) 2.892 (2) 156.3
C13-H13B...O2ii 0.96 2.51 3.467 (2) 177
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) x, y, z-1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2406 ).


Acknowledgements

The authors thank the Academy of Sciences of the Republic of Uzbekistan for supporting this work (project Nos. F7-T048 and I5-FA-18897)

References

Essenberg, M., Doherty, M. d'A., Hamilton, B. K., Henning, V. T., Cover, E. C., Mcfaul, S. J. & Johnson, W. M. (1982). Phytopathology, 72, 1349-1356.  [CrossRef] [ChemPort]
Essenberg, M., Stoessl, A. & Stothers, J. B. (1985). J. Chem. Soc. Chem. Commun. 9, 556-557.  [CrossRef] [ISI]
Oxford Diffraction (2009). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Stipanovic, R. D., Greenblatt, G. A., Beier, R. C. & Bell, A. A. (1981). Phytochemistry, 20, 729-730.  [CrossRef] [ChemPort] [ISI]
Stipanovic, R. D., Wakelyn, P. J. & Bell, A. A. (1975). Phytochemistry, 14, 1041-1043.  [CrossRef] [ChemPort] [ISI]
Suzuki, H., Yasuda, S. & Hanzawa, M. (1972). Mokuzai Gakkaishi, 18, 617-622.  [ChemPort]


Acta Cryst (2013). E69, o1392  [ doi:10.1107/S1600536813021430 ]

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