proofs

proofs IS2558

Acta Crystallographica Section E

Structure Reports Online ISSN 1600-5368

Cholest-5-en-7-one Khan et al. Synopsis

Queries and comments Please supply or correct as appropriate all bold underlined text. In describing corrections please refer to line numbers where appropriate: these are shown in grey.

Author index Authors’ names will normally be arranged alphabetically under their family name and this is commonly their last name. Prefixes (van, de etc.) will only be taken into account in the alphabetization if they begin with a capital letter. Authors wishing their names to be alphabetized differently should indicate this below. Author names may appear more than once in this list; it is not necessary to mark this correction on your proofs. Khan, M.S. Sulaiman, O. Hashim, R. Quah, C.K. Fun, H.-K.

Important notice This article is in the new shorter format that was introduced in March 2007 for all articles submitted to Acta Crystallographica Section E: Structure Reports Online. For more information, please visit http://journals.iucr.org/e/services/newformat.html.

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organic compounds 1


Experimental

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Structure Reports Online

Crystal data

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ISSN 1600-5368

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Cholest-5-en-7-one Mohd. Shaheen Khan,a Othman Sulaiman,a Rokiah Hashim,a Ching Kheng Quahb‡ and Hoong-Kun Funb*§ a

Bio-resource, Paper and Coatings Technology Division, School of Industrial Technology, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia Correspondence e-mail: [email protected]

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˚3 V = 1145.6 (4) A Z=2 Mo K radiation = 0.07 mm 1 T = 100 K 0.25 0.18 0.03 mm

C27H44O Mr = 384.62 Monoclinic, P21 ˚ a = 6.3468 (13) A ˚ b = 11.517 (3) A ˚ c = 15.678 (3) A = 91.470 (5)

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Data collection

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Bruker SMART APEXII DUO CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009) Tmin = 0.984, Tmax = 0.998

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˚; Key indicators: single-crystal X-ray study; T = 100 K; mean (C–C) = 0.004 A R factor = 0.051; wR factor = 0.132; data-to-parameter ratio = 13.9.

In the decahydrophenanthrenone ring system of the title compound, C27H44O, the two cyclohexane rings adopt chair conformations, whereas the cyclohexene ring adopts an envelope conformation. The cyclopentane ring is twisted. In the crystal structure, molecules are stacked along the a axis, but no significant intermolecular interactions are observed.

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13066 measured reflections 3512 independent reflections 2776 reflections with I > 2(I) Rint = 0.058

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Refinement

Received 2 June 2010; accepted 7 June 2010

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Related literature For general background to and the biological activity of steroid derivatives, see: Drach et al. (2000); Grover et al. (2007); Khan & Yusuf (2009). For the synthesis of title compound, see: Dauben & Takemura (1953); Ruiz (1958). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986). For details of ring conformations, see: Cremer & Pople (1975). For bond-length data, see: Allen et al. (1987).

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R[F > 2(F )] = 0.051 wR(F 2) = 0.132 S = 1.04 3512 reflections 252 parameters

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1 restraint H-atom parameters constrained ˚ 3 max = 0.51 e A ˚ 3 min = 0.44 e A

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Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; 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 and PLATON (Spek, 2009).

The authors thank Universiti Sains Malaysia for providing research facilities. HKF and CKQ thank USM for the Research University Golden Goose Grant (1001/PFIZIK/ 811012). MSK thanks USM for the award of post doctoral fellowship and CKQ thanks USM for the award of USM Fellowship.

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Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2558).

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References

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Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. Dauben, W. G. & Takemura, K. H. (1953). J. Am. Chem. Soc. 75, 6302–6304. Drach, S. V., Litvinovskaya, R. P. & Kripach, V. A. (2000). Chem. Heterocycl. Compd, 36, 233–255. Grover, V. K., Babu, R. & Bedi, S. P. S. (2007). Indian J. Anaesth. 51, 389–393. Khan, S. A. & Yusuf, M. (2009). Eur. J. Med. Chem. 44, 2597–2600. Ruiz, H. J. (1958). Chem. Abstr. 52, 10126a. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Spek, A. L. (2009). Acta Cryst. D65, 148–155.

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‡ Thomson Reuters ResearcherID: A-5525-2009. § Thomson Reuters ResearcherID: A-3561-2009.

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