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Volume 68 
Part 12 
Pages o3421-o3422  
December 2012  

Received 26 October 2012
Accepted 20 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.004 Å
Disorder in main residue
R = 0.046
wR = 0.136
Data-to-parameter ratio = 9.5
Details
Open access

(1R,3R,4R,6S)-4-(7-Methoxy-2-oxo-2H-chromen-6-yl)-1-methyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl acetate

aNatural Products Research Laboratory, School of Science, Mae Fah Luang, University, Tasud, Muang, Chiang Rai 57100, Thailand,bDepartment of Chemistry, University of Hull, Cottingham Road, Hull HU6 7RX, England, and cDepartment of Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai 50200, Thailand
Correspondence e-mail: apinpus@gmail.com

In the title compound, C17H16O7, which was isolated from the leaves of Micromelum integerrimum, the furan ring adopts an envelope conformation with the O atom as the flap. An intramolecular C-H...O hydrogen bond occurs. The carbonyl O atom is disordered in a 0.57 (8):0.43 (8) ratio. In the crystal, molecules are linked by weak C-H...O hydrogen bonds into a C(10) chain along [010].

Related literature

Micromelum integerrimum is a shrub in the Rutacae family containing the coumarin molecule, micromelin, as the major chemical constituent (Cassady et al., 1979[Cassady, J. M., Ojima, N., Chang, C. J. & McLaughlin, J. L. (1979). J. Nat. Prod. 42, 274-278.]). Many coumarins including micromelin have been extracted from Rutacae plants, and for some their cytotoxicity has been investigated (Sripisut et al., 2012[Sripisut, T., Cheenpracha, S., Ritthiwigrom, T., Prawat, U. & Laphookhieo, S. (2012). Rec. Nat. Prod. 6, 386-389.]; He et al., 2001[He, H. P., Zou, Y., Shen, Y. M., Hao, X. Y., Zuo, G. Y. & Hao, X. J. (2001). Chin. Chem. Lett. 12, 603-606.]). For previous reports on the isolation of micromelin (micromelumin) from a Northern Queensland collection, an Assamese collection, and a Northeast Thailand collection, see: Lamberton et al. (1967[Lamberton, J. A., Price, J. R. & Redcliffe, A. H. (1967). Aust. J. Chem. 20, 973-979.]); Das et al. (1984[Das, S., Baruah, R. H., Sharma, R. P., Barua, J. N., Kulanthaivel, P. & Herz, W. (1984). Phytochemistry, 23, 2317-2321.]); Siridechakorn et al. (2012[Siridechakorn, I., Ritthiwigrom, T. & Laphookhieo, S. (2012). Biochem. Syst. Ecol. 40, 69-70.]). For detailed H1 NMR spectroscopic data, see: Das et al. (1984[Das, S., Baruah, R. H., Sharma, R. P., Barua, J. N., Kulanthaivel, P. & Herz, W. (1984). Phytochemistry, 23, 2317-2321.]); Siridechakorn et al. (2012[Siridechakorn, I., Ritthiwigrom, T. & Laphookhieo, S. (2012). Biochem. Syst. Ecol. 40, 69-70.]). For a phytochemical investigation, see: Siridechakorn et al. (2012[Siridechakorn, I., Ritthiwigrom, T. & Laphookhieo, S. (2012). Biochem. Syst. Ecol. 40, 69-70.]). For a closely related micromelin structure, C15H12O6, see: Fun et al. (2011[Fun, H.-K., Siridechakorn, I., Laphookhieo, S. & Chantrapromma, S. (2011). Acta Cryst. E67, o1706-o1707.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C17H16O7

  • Mr = 332.31

  • Monoclinic, P 21

  • a = 10.4825 (16) Å

  • b = 6.9213 (9) Å

  • c = 11.0212 (18) Å

  • [beta] = 95.970 (7)°

  • V = 795.3 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 298 K

  • 0.64 × 0.32 × 0.24 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1997[Bruker (1997). SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.653, Tmax = 0.746

  • 4381 measured reflections

  • 2123 independent reflections

  • 1692 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.136

  • S = 1.06

  • 2123 reflections

  • 223 parameters

  • 2 restraints

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

  • [Delta][rho]max = 0.47 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C4-H4...O19Ai 1.07 (3) 2.46 (2) 3.064 (8) 114 (1)
C5-H5...O13 1.01 (3) 2.58 (3) 3.403 (3) 139 (1)
C12-H12...O2ii 0.98 2.35 3.282 (5) 158
C16-H16B...O2iii 0.96 2.54 3.419 (4) 153
Symmetry codes: (i) [-x, y+{\script{1\over 2}}, -z]; (ii) [-x, y+{\script{1\over 2}}, -z+1]; (iii) x+1, y, z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SAINT and SADABS. 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: DIAMOND (Brandenburg, 2007[Brandenburg, K. (2007). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BX2427 ).


Acknowledgements

The Thailand Research Fund is acknowledged for a research grant.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Brandenburg, K. (2007). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (1997). SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2008). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Cassady, J. M., Ojima, N., Chang, C. J. & McLaughlin, J. L. (1979). J. Nat. Prod. 42, 274-278.  [CrossRef] [ChemPort] [PubMed] [ISI]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Das, S., Baruah, R. H., Sharma, R. P., Barua, J. N., Kulanthaivel, P. & Herz, W. (1984). Phytochemistry, 23, 2317-2321.  [CrossRef] [ChemPort] [ISI]
Fun, H.-K., Siridechakorn, I., Laphookhieo, S. & Chantrapromma, S. (2011). Acta Cryst. E67, o1706-o1707.  [CSD] [CrossRef] [details]
He, H. P., Zou, Y., Shen, Y. M., Hao, X. Y., Zuo, G. Y. & Hao, X. J. (2001). Chin. Chem. Lett. 12, 603-606.  [ChemPort]
Lamberton, J. A., Price, J. R. & Redcliffe, A. H. (1967). Aust. J. Chem. 20, 973-979.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Siridechakorn, I., Ritthiwigrom, T. & Laphookhieo, S. (2012). Biochem. Syst. Ecol. 40, 69-70.  [ISI] [CrossRef] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Sripisut, T., Cheenpracha, S., Ritthiwigrom, T., Prawat, U. & Laphookhieo, S. (2012). Rec. Nat. Prod. 6, 386-389.  [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2012). E68, o3421-o3422   [ doi:10.1107/S1600536812047617 ]

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