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Volume 68 
Part 3 
Pages o672-o673  
March 2012  

Received 31 October 2011
Accepted 31 January 2012
Online 10 February 2012

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Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.035
wR = 0.095
Data-to-parameter ratio = 8.1
Details
Open access

14-Angeloyloxycacalohastine from Psacalium peltatum

Nadia Rojano-Vilchis,a Simón Hernández-Ortega,a* Manuel Jimenez-Estradaa and Armando Torres Avileza

aInstituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, México, DF 04510, Mexico
Correspondence e-mail: simonho@unam.mx

The title compound [systematic name: (9-methoxy-3,5-dimethyl-5,6-dihydronaphtho[2,3-b]furan-4-yl)methyl 2-methylbut-2-enoate], C21H24O4, was isolated from matarique, or Psacalium peltatum (Kunth). The structure is almost planar. The angeloyloxy group makes an angle of 62.08 (2)° with the furanoeremophilane skeleton. The carbonyl O atom is disordered between two positions with a 76:24 ratio. The molecules in the crystal are joined by very weak C-H-O interactions in the ac plane.

Related literature

For fundamental background information, see: Romo de Vivar et al. (2007[Romo de Vivar, A., Pérez-Castorena, A. L., Arciniegas, A. & Villaseñor, J. L. (2007). J. Mex. Chem. Soc. 51, 160-172.]). For biological activity, see: Acevedo-Quiroz et al. (2008[Acevedo-Quiroz, N., Domínguez-Villegas, V. & Garduño-Ramírez, M. L. (2008). Nat. Prod. Commun. 3, 313-317.]); Alarcón-Aguilar et al. (2000[Alarcón-Aguilar, F. J., Jiménez-Estrada, M., Reyes-Chilpa, R., González-Paredes, B., Contreras-Weber, C. C. & Roman-Ramos, R. (2000). J. Ethnopharmacol. 69, 207-215.]); Bye et al. (1995[Bye, R., Linares, E. & Estrada, H. (1995). Phytochemistry of Medicinal Plants, pp. 65-82. New York: Plenum Press.]); Contreras-Weber et al. (2002[Contreras-Weber, C., Perez-Gutierrez, S., Alarcón-Aguilar, F. J. & Roman-Ramos, R. (2002). Proc. West. Pharmacol. Soc. 45, 134-136.]); Jimenez-Estrada et al. (2006[Jimenez-Estrada, M., Reyes, R., Ramirez, T., Lledias, F., Hansberg, W., Arrieta, D. & Alarcón-Aguilar, F. J. (2006). J. Ethnopharmacol. 105, 34-38.]). For compound isolation, see: Abdo et al. (1992[Abdo, S., Bernardi, M., Marinoni, G., Mellerio, G., Samaniego, S., Vidari, G. & Vita Finzi, P. (1992). Phytochemistry, 31, 3937-3941.]); Bohlmann et al. (1977[Bohlmann, F., Knoll, K. H., Zedro, C., Mahanta, P. K., Grenz, M., Suwita, A., Ehlers, D., Le Van, N., Abraham, W. R. & Natu, A. A. (1977). Phytochemistry, 16, 965-985.]). For bond-length data, see: Allen et al. (1987[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.]).

[Scheme 1]

Experimental

Crystal data

  • C21H24O4

  • Mr = 340.40

  • Orthorhombic, P 21 21 21

  • a = 7.1627 (17) Å

  • b = 10.276 (2) Å

  • c = 24.605 (6) Å

  • V = 1811.1 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 298 K

  • 0.40 × 0.40 × 0.40 mm
Data collection

  • Bruker SMART APEX CCD area-detector diffractometer

  • 20061 measured reflections

  • 1945 independent reflections

  • 1701 reflections with I > 2[sigma](I)

  • Rint = 0.037
Refinement

  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.095

  • S = 1.12

  • 1945 reflections

  • 241 parameters

  • 21 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.15 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C15-H15A...O2i 0.97 2.62 3.536 (3) 157
C6-H6B...O4ii 0.97 2.61 3.42 (2) 142
Symmetry codes: (i) x+1, y, z; (ii) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+2].

Data collection: SMART (Bruker, 1999[Bruker (1999). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1999[Bruker (1999). SMART 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: AA2037 ).

Acknowledgements

NRV acknowledges a scholarship and financial support provided by the Conseja Nacional de Ciencia y Tecnología (CONACyT: 101038) and the Programa en Ciencias Biologicas of the Universidad Nacional Autónoma de México (UNAM).

References

Abdo, S., Bernardi, M., Marinoni, G., Mellerio, G., Samaniego, S., Vidari, G. & Vita Finzi, P. (1992). Phytochemistry, 31, 3937-3941.  [CrossRef] [ChemPort] [ISI]
Acevedo-Quiroz, N., Domínguez-Villegas, V. & Garduño-Ramírez, M. L. (2008). Nat. Prod. Commun. 3, 313-317.  [ChemPort]
Alarcón-Aguilar, F. J., Jiménez-Estrada, M., Reyes-Chilpa, R., González-Paredes, B., Contreras-Weber, C. C. & Roman-Ramos, R. (2000). J. Ethnopharmacol. 69, 207-215.  [ISI] [PubMed]
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.
Bohlmann, F., Knoll, K. H., Zedro, C., Mahanta, P. K., Grenz, M., Suwita, A., Ehlers, D., Le Van, N., Abraham, W. R. & Natu, A. A. (1977). Phytochemistry, 16, 965-985.  [CrossRef] [ChemPort] [ISI]
Bruker (1999). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bye, R., Linares, E. & Estrada, H. (1995). Phytochemistry of Medicinal Plants, pp. 65-82. New York: Plenum Press.
Contreras-Weber, C., Perez-Gutierrez, S., Alarcón-Aguilar, F. J. & Roman-Ramos, R. (2002). Proc. West. Pharmacol. Soc. 45, 134-136.  [PubMed]
Jimenez-Estrada, M., Reyes, R., Ramirez, T., Lledias, F., Hansberg, W., Arrieta, D. & Alarcón-Aguilar, F. J. (2006). J. Ethnopharmacol. 105, 34-38.  [ISI] [PubMed] [ChemPort]
Romo de Vivar, A., Pérez-Castorena, A. L., Arciniegas, A. & Villaseñor, J. L. (2007). J. Mex. Chem. Soc. 51, 160-172.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]

Acta Cryst (2012). E68, o672-o673   [ doi:10.1107/S1600536812004199 ]

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