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Volume 69 
Part 8 
Page o1310  
August 2013  

Received 11 July 2013
Accepted 16 July 2013
Online 24 July 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.041
wR = 0.108
Data-to-parameter ratio = 15.5
Details
Open access

Methyl 2-(2,2-dimethyl-3a,6a-dihydrofuro[3,2-d][1,3]dioxol-5-yl)-4-oxo-4H-chromene-3-carboxylate

aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
Correspondence e-mail: shirai2011@gmail.com

In the title molecule, C18H16O7, the dioxolane ring adopts an envelope conformation with the dimethyl-substituted C atom as the flap. The furan ring is almost coplanar with the pyran ring, with a dihedral angle of 1.04 (10)° between the planes, and it makes a dihedral angle of 67.97 (11)° with the mean plane of the dioxolane ring. The latter makes a dihedral angle of 67.15 (10)° with the pyran ring. The O atom attached to the pyran ring deviates by -0.009 (1) Å. The crystal packing features C-H...O hydrogen bonds, forming a three-dimensional structure. The methoxycarbonyl atoms are disordered over two positions, with a refined occupancy ratio of 0.508 (18):0.492 (18).

Related literature

For the biological importance of 4H-chromene derivatives, see: Cai (2007[Cai, S. X. (2007). Recent Patents Anticancer Drug Discov. 2, 79-101.], 2008[Cai, S. X. (2008). Bioorg. Med. Chem. Lett. 18, 603-607.]); Cai et al. (2006[Cai, S. X., Drewe, J. & Kasibhatla, S. (2006). Curr. Med. Chem. 13, 2627-2644.]); Caine (1993[Caine, B. (1993). Science, 260, 1814-1816.]); Gabor (1988[Gabor, M. (1988). The Pharmacology of Benzopyrone Derivatives and Related Compounds, pp. 91-126. Budapest: Akademiai Kiado.]); Brooks (1998[Brooks, G. T. (1998). Pestic. Sci. 22, 41-50.]); Valenti et al. (1993[Valenti, P., Da Re, P., Rampa, A., Montanari, P., Carrara, M. & Cima, L. (1993). Anticancer Drug. Des. 8, 349-360.]); Hyana & Saimoto (1987[Hyana, T. & Saimoto, H. (1987). Jpn Patent JP 621 812 768.]); Tang et al. (2007[Tang, Q.-G., Wu, W.-Y., He, W., Sun, H.-S. & Guo, C. (2007). Acta Cryst. E63, o1437-o1438.]). For conformational analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C18H16O7

  • Mr = 344.31

  • Orthorhombic, P 21 21 21

  • a = 6.8875 (3) Å

  • b = 15.4958 (6) Å

  • c = 15.9035 (6) Å

  • V = 1697.34 (12) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 293 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker SMART APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.969, Tmax = 0.979

  • 9565 measured reflections

  • 4131 independent reflections

  • 2983 reflections with I > 2[sigma](I)

  • Rint = 0.021

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

  • wR(F2) = 0.108

  • S = 1.03

  • 4131 reflections

  • 267 parameters

  • 99 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C6-H6...O7i 0.93 2.59 3.296 (2) 133
C13-H13...O3ii 0.93 2.59 3.230 (10) 127
C14-H14...O1ii 0.98 2.50 3.429 (2) 159
C18-H18C...O1iii 0.96 2.55 3.460 (3) 159
Symmetry codes: (i) [-x+{\script{3\over 2}}, -y+1, z+{\script{1\over 2}}]; (ii) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) 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: SU2622 ).


Acknowledgements

ZF,TS and DV thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for data collection and UGC (SAP-CAS) is acknowleged for the departmental facilties. ZF also thanks the UGC for a meritorious fellowship and TS thanks DST Inspire for a fellowship.

References

Brooks, G. T. (1998). Pestic. Sci. 22, 41-50.  [CrossRef]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cai, S. X. (2007). Recent Patents Anticancer Drug Discov. 2, 79-101.
Cai, S. X. (2008). Bioorg. Med. Chem. Lett. 18, 603-607.  [PubMed]
Cai, S. X., Drewe, J. & Kasibhatla, S. (2006). Curr. Med. Chem. 13, 2627-2644.  [Web of Science] [PubMed] [ChemPort]
Caine, B. (1993). Science, 260, 1814-1816.  [CrossRef] [ChemPort] [PubMed] [Web of Science]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Gabor, M. (1988). The Pharmacology of Benzopyrone Derivatives and Related Compounds, pp. 91-126. Budapest: Akademiai Kiado.
Hyana, T. & Saimoto, H. (1987). Jpn Patent JP 621 812 768.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Tang, Q.-G., Wu, W.-Y., He, W., Sun, H.-S. & Guo, C. (2007). Acta Cryst. E63, o1437-o1438.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Valenti, P., Da Re, P., Rampa, A., Montanari, P., Carrara, M. & Cima, L. (1993). Anticancer Drug. Des. 8, 349-360.  [ChemPort] [PubMed]


Acta Cryst (2013). E69, o1310  [ doi:10.1107/S1600536813019648 ]

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