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Volume 69 
Part 7 
Page o1186  
July 2013  

Received 1 June 2013
Accepted 22 June 2013
Online 29 June 2013

Key indicators
Single-crystal X-ray study
T = 294 K
Mean [sigma](C-C) = 0.004 Å
R = 0.050
wR = 0.118
Data-to-parameter ratio = 17.4
Details
Open access

Methyl 3-[(chloro­meth­oxy)carbon­yloxy]-7-hy­droxy­cholan-24-oate

aShanghai Institute of Pharmaceutical Industry, Shanghai 200040, People's Republic of China, and bBeijing Chao-Yang Hospital Affiliated with Beijing Capital Medical University, Beijing 100020, People's Republic of China
Correspondence e-mail: liuheliuhe@126.com

The title compound, C27H43ClO6, is a derivative of urso­deoxy­cholic acid, in which the OH group at the 3-position is substituted by a chloro­meth­oxy­carbon­yloxy substituent and the carb­oxy­lic acid group at the 24-position is methyl­ated. The A and B rings are cis-fused, while all other rings are trans-fused. In the crystal, two adjacent mol­ecules located along the b-axis direction are inter­locked head-to-tail due to weak C-H...O hydrogen bonds. Therefore each mol­ecule is linked to four neighbouring mol­ecules by four C-H...O hydrogen bonds, with the OH group at the 7-position and the carbonyl O atom of the ester group acting as the acceptor sites.

Related literature

For the synthesis of the title compound, see: von Geldern et al. (2004[Geldern, T. W. von, Tu, N., Kym, P. R., Link, J. T., Jae, H.-S., Lai, C., Apelqvist, T., Rhonnstad, P., Hagberg, L., Koehler, K., Grynfarb, M., Goos-Nilsson, A., Sandberg, J., Österlund, M., Barkhem, T., Höglund, M., Färnegårdh, M., Kauppi, B., Öhman, L. & Jacobson, P. B. (2004). J. Med. Chem. 47, 4213-4230.]); For similar structures, see: Kannan et al. (2001[Kannan, A., De Clercq, E., Pannecouque, C., Witvrouw, M., Hartman, T. L., Turpin, J. A., Buckheit, R. W. Jr & Cushman, M. (2001). Tetrahedron, 57, 9385-9391.]); Lindley & Carey et al. (1987[Lindley, P. F. & Carey, M. C. (1987). J. Crystallogr. Spectrosc. Res. 17, 231-249.]).

[Scheme 1]

Experimental

Crystal data
  • C27H43ClO6

  • Mr = 499.06

  • Orthorhombic, P 21 21 21

  • a = 7.8896 (13) Å

  • b = 10.9493 (17) Å

  • c = 30.683 (5) Å

  • V = 2650.6 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.18 mm-1

  • T = 294 K

  • 0.24 × 0.20 × 0.12 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • 15292 measured reflections

  • 5411 independent reflections

  • 3191 reflections with I > 2[sigma](I)

  • Rint = 0.054

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.118

  • S = 0.94

  • 5411 reflections

  • 311 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.15 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2309 Friedel pairs

  • Flack parameter: -0.10 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C11-H11B...O2i 0.97 2.49 3.339 (4) 146
C27-H27B...O5ii 0.97 2.40 3.270 (4) 149
Symmetry codes: (i) x+1, y, z; (ii) [-x+{\script{1\over 2}}, -y, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: publCIF (Westrip, 2010)[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.].


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2434 ).


Acknowledgements

We gratefully acknowledge financial support from the National Natural Science Foundation of China (Nos. 81072530 and 30772653).

References

Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [IUCr Journals]
Geldern, T. W. von, Tu, N., Kym, P. R., Link, J. T., Jae, H.-S., Lai, C., Apelqvist, T., Rhonnstad, P., Hagberg, L., Koehler, K., Grynfarb, M., Goos-Nilsson, A., Sandberg, J., Österlund, M., Barkhem, T., Höglund, M., Färnegårdh, M., Kauppi, B., Öhman, L. & Jacobson, P. B. (2004). J. Med. Chem. 47, 4213-4230.  [PubMed]
Kannan, A., De Clercq, E., Pannecouque, C., Witvrouw, M., Hartman, T. L., Turpin, J. A., Buckheit, R. W. Jr & Cushman, M. (2001). Tetrahedron, 57, 9385-9391.  [CrossRef] [ChemPort]
Lindley, P. F. & Carey, M. C. (1987). J. Crystallogr. Spectrosc. Res. 17, 231-249.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1186  [ doi:10.1107/S160053681301725X ]

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