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Volume 68 
Part 1 
Page o69  
January 2012  

Received 12 November 2011
Accepted 3 December 2011
Online 10 December 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.041
wR = 0.110
Data-to-parameter ratio = 14.7
Details
Open access

Dihydroallocryptopine

aCollege of Science, Northwest Agriculture and Forestry University, Yangling 712100, People's Republic of China
Correspondence e-mail: zhoulechem@yahoo.com.cn

In the title compound [systematic name: 7,8-dimethoxy-11-methyl-17,19-dioxa-11-azatetracyclo[12.7.0.04,9.016,20]henicosa-1(21),4,6,8,14,16 (20)-hexaen-2-ol], C21H25NO5, the benzene rings are inclined at a dihedral angle of 23.16 (5)°. One of the methoxy C atoms is close to coplanar with its attached ring [deviation = 0.129 (3) Å], whereas the other is orientated away from the ring [deviation = -1.124 (2) Å]. The 10-membered ring is highly puckered, and the OH and CH3 substituents project to the same side of the ring. In the crystal, O-H...O hydrogen bonds link the molecules into [010] chains and C-H...O and C-H...[pi] interactions consolidate the packing.

Related literature

For the synthesis of the title compound, see: Wada et al. (2007[Wada, Y., Kaga, H., Uchiito, S., Kumazawa, E., Tomiki, M., Onozaki, Y., Kurono, N., Tokuda, M., Ohkuma, T. & Orit, K. (2007). J. Org. Chem. 72, 7301-7306.]). For the biological activity of allocryptopine derivatives, see: Morteza et al. (2003[Morteza, K., Amin, G., Shidfar, M. R., Hadizadeh, H. & Shafiee, A. (2003). Fitoterapia, 74, 493-496.]); Yan et al. (2009[Yan, M., Sun, J. H., Lu, Z. Q., Chen, G. T., Guan, S. H., Liu, X., Jiang, B. H., Ye, M. & Guo, D. A. (2009). J. Chromatogr. A, 1216, 2045-2062.]); Capasso et al. (1997[Capasso, A., Piacente, S. & Pizza, C. (1997). Planta Med. 63, 326-328.]); Jeong et al. (2009[Jeong, E. J., Ma, C. J., Lee, K. Y., Kim, S. H., Sung, S. H. & Kim, Y. C. (2009). J. Ethnopharmacol. 121, 98-105.]); Zhao et al. (2008[Zhao, G., Jiang, Z. H., Zheng, X. W., Zang, S. Y. & Guo, L. H. (2008). Pharmacol. Biochem. Behav. 90, 363-371.]). For a related structure, see: Valpuesta et al. (2006[Valpuesta, M., Diaz, A., Suau, R. & Torres, G. (2006). Eur. J. Org. Chem. pp. 964-971.]).

[Scheme 1]

Experimental

Crystal data
  • C21H25NO5

  • Mr = 371.42

  • Monoclinic, P 21 /c

  • a = 14.2557 (19) Å

  • b = 9.3705 (13) Å

  • c = 15.278 (2) Å

  • [beta] = 106.601 (2)°

  • V = 1955.8 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 296 K

  • 0.45 × 0.24 × 0.21 mm

Data collection
  • Bruker SMART APEX II CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.961, Tmax = 0.981

  • 14189 measured reflections

  • 3646 independent reflections

  • 2766 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.110

  • S = 1.02

  • 3646 reflections

  • 248 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1-C6 benzene ring.

D-H...A D-H H...A D...A D-H...A
O3-H3...O5i 0.82 2.03 2.8380 (16) 168
C7-H7A...O4ii 0.97 2.57 3.405 (3) 144
C18-H18...O3iii 0.93 2.53 3.229 (2) 132
C7-H7B...Cg2iv 0.97 2.57 3.464 (3) 153
Symmetry codes: (i) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) x+1, y, z; (iii) -x, -y, -z; (iv) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). 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: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6507 ).


Acknowledgements

This work was supported by the National Natural Science Foundation of China (NNSF; No. 31172365; 31101469).

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Capasso, A., Piacente, S. & Pizza, C. (1997). Planta Med. 63, 326-328.  [CrossRef] [ChemPort] [PubMed] [ISI]
Jeong, E. J., Ma, C. J., Lee, K. Y., Kim, S. H., Sung, S. H. & Kim, Y. C. (2009). J. Ethnopharmacol. 121, 98-105.  [ISI] [CrossRef] [PubMed]
Morteza, K., Amin, G., Shidfar, M. R., Hadizadeh, H. & Shafiee, A. (2003). Fitoterapia, 74, 493-496.  [PubMed]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Valpuesta, M., Diaz, A., Suau, R. & Torres, G. (2006). Eur. J. Org. Chem. pp. 964-971.  [CrossRef]
Wada, Y., Kaga, H., Uchiito, S., Kumazawa, E., Tomiki, M., Onozaki, Y., Kurono, N., Tokuda, M., Ohkuma, T. & Orit, K. (2007). J. Org. Chem. 72, 7301-7306.  [CrossRef] [PubMed] [ChemPort]
Yan, M., Sun, J. H., Lu, Z. Q., Chen, G. T., Guan, S. H., Liu, X., Jiang, B. H., Ye, M. & Guo, D. A. (2009). J. Chromatogr. A, 1216, 2045-2062.  [ISI] [PubMed]
Zhao, G., Jiang, Z. H., Zheng, X. W., Zang, S. Y. & Guo, L. H. (2008). Pharmacol. Biochem. Behav. 90, 363-371.  [ISI] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2012). E68, o69  [ doi:10.1107/S1600536811052172 ]

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