(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

Phakhodee, W.; Laphookhieo, S.; Prior, T.J.; Rujiwatra, A.

doi:10.1107/S1600536812047617

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 (C-C) = 0.004 Å
Disorder in main residue
R = 0.046
wR = 0.136
Data-to-parameter ratio = 9.5
Details

(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

Wong Phakhodee,^a Surat Laphookhieo,^a Timothy John Prior ^b and Apinpus Rujiwatra ^c ^*

^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-HO 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-HO 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). Many coumarins including micromelin have been extracted from Rutacae plants, and for some their cytotoxicity has been investigated (Sripisut et al., 2012; He et al., 2001). 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); Das et al. (1984); Siridechakorn et al. (2012). For detailed H¹ NMR spectroscopic data, see: Das et al. (1984); Siridechakorn et al. (2012). For a phytochemical investigation, see: Siridechakorn et al. (2012). For a closely related micromelin structure, C₁₅H₁₂O₆, see: Fun et al. (2011). For hydrogen-bond motifs, see: Bernstein et al. (1995). For puckering parameters, see: Cremer & Pople (1975).

Experimental

Crystal data

C₁₇H₁₆O₇
M_r = 332.31
Monoclinic, P 2₁
a = 10.4825 (16) Å
b = 6.9213 (9) Å
c = 11.0212 (18) Å
= 95.970 (7)°
V = 795.3 (2) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.653, T_max = 0.746
4381 measured reflections
2123 independent reflections
1692 reflections with I > 2(I)
R_int = 0.021

Refinement

R[F² > 2(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
_max = 0.47 e Å^-3
_min = -0.24 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C4-H4O19Aⁱ	1.07 (3)	2.46 (2)	3.064 (8)	114 (1)
C5-H5O13	1.01 (3)	2.58 (3)	3.403 (3)	139 (1)
C12-H12O2ⁱⁱ	0.98	2.35	3.282 (5)	158
C16-H16BO2ⁱⁱⁱ	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); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2007); software used to prepare material for publication: publCIF (Westrip, 2010) and PLATON (Spek, 2009).

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

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