[Journal logo]

Volume 68 
Part 12 
Page o3419  
December 2012  

Received 14 November 2012
Accepted 17 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.003 Å
R = 0.051
wR = 0.158
Data-to-parameter ratio = 17.8
Details
Open access

8-Methoxy-2H-chromene-3-carbaldehyde

aDepartment of Applied Chemistry, Dongduk Women's University, Seoul 136-714, Republic of Korea
Correspondence e-mail: dskoh@dongduk.ac.kr

In the title molecule, C11H10O3, the fused dihydropyran ring is in a half-chair conformation with the O atom and the methylene C atom positioned 0.1318 (13) and 0.143 (2) Å, respectively, on either side of the mean plane formed by the other four atoms. In the crystal, weak C-H...O hydrogen bonds link molecules along [001].

Related literature

For the synthesis and biological properties of chromene derivatives, see: Mun et al. (2012[Mun, J., Jabbar, A. A., Devi, N. S., Liu, Y., Meir, E. G. V. & Goodman, M. M. (2012). Bioorg. Med. Chem. Lett. 20, 4590-4597.]); Kallikat et al. (2011[Kallikat, A. J., Agnes, B., Nath, A. R. & Atta, R. (2011). Synlett, 15, 2223-2227.]); Zhang et al. (2009[Zhang, J.-M., Lou, C.-L., Hu, Z.-P. & Yan, M. (2009). ARKIVOC, 14, 362-375.]); Gebhardt et al. (2007[Gebhardt, P., Dornberger, K., Gollmick, F. A., Grafe, U., Hartl, A., Gorls, H., Schlegela, B. & Hertweck, C. (2007). Bioorg. Med. Chem. Lett. 17, 2558-2560.]); Yoon et al. (2012[Yoon, H., Ahn, S., Hwang, D., Jo, G., Kim, D., Kim, S. H., Koh, D. & Lim, Y. (2012). Magn. Reson. Chem. 50, 759-764.]). For the chromene group in natural products, see: Escandón-Rivera et al. (2012[Escandón-Rivera, S., González-Andrade, M., Bye, R., Linares, E., Navarrete, A. & Mata, R. (2012). J. Nat. Prod. 75, 968-974.]); Chen et al. (2008[Chen, J.-J., Wang, T.-Y. & Hwang, T.-L. (2008). J. Nat. Prod. 71, 212-217.]). For related structures, see: Yusufzai et al. (2012[Yusufzai, S. K., Osman, H., Rahim, A. S. A., Arshad, S. & Razak, I. A. (2012). Acta Cryst. E68, o2416-o2417.]); Betz et al. (2011[Betz, R., McCleland, C. & Marchand, H. (2011). Acta Cryst. E67, o1151.]); Bardajee et al. (2007[Bardajee, G. R., Winnik, M. A. & Lough, A. J. (2007). Acta Cryst. E63, o1269-o1270.]).

[Scheme 1]

Experimental

Crystal data
  • C11H10O3

  • Mr = 190.19

  • Orthorhombic, P b c a

  • a = 6.8940 (6) Å

  • b = 13.2079 (11) Å

  • c = 20.0964 (16) Å

  • V = 1829.9 (3) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 200 K

  • 0.23 × 0.21 × 0.19 mm

Data collection
  • Bruker SMART CCD diffractometer

  • 12690 measured reflections

  • 2276 independent reflections

  • 1194 reflections with I > 2[sigma](I)

  • Rint = 0.056

Refinement
  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.158

  • S = 0.92

  • 2276 reflections

  • 128 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C6-H6B...O1i 0.98 2.49 3.340 (3) 145
Symmetry code: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5559 ).


References

Bardajee, G. R., Winnik, M. A. & Lough, A. J. (2007). Acta Cryst. E63, o1269-o1270.  [CSD] [CrossRef] [details]
Betz, R., McCleland, C. & Marchand, H. (2011). Acta Cryst. E67, o1151.  [CSD] [CrossRef] [details]
Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chen, J.-J., Wang, T.-Y. & Hwang, T.-L. (2008). J. Nat. Prod. 71, 212-217.  [ISI] [CrossRef] [PubMed] [ChemPort]
Escandón-Rivera, S., González-Andrade, M., Bye, R., Linares, E., Navarrete, A. & Mata, R. (2012). J. Nat. Prod. 75, 968-974.  [ISI] [PubMed]
Gebhardt, P., Dornberger, K., Gollmick, F. A., Grafe, U., Hartl, A., Gorls, H., Schlegela, B. & Hertweck, C. (2007). Bioorg. Med. Chem. Lett. 17, 2558-2560.  [CSD] [CrossRef] [PubMed] [ChemPort]
Kallikat, A. J., Agnes, B., Nath, A. R. & Atta, R. (2011). Synlett, 15, 2223-2227.
Mun, J., Jabbar, A. A., Devi, N. S., Liu, Y., Meir, E. G. V. & Goodman, M. M. (2012). Bioorg. Med. Chem. Lett. 20, 4590-4597.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Yoon, H., Ahn, S., Hwang, D., Jo, G., Kim, D., Kim, S. H., Koh, D. & Lim, Y. (2012). Magn. Reson. Chem. 50, 759-764.  [ISI] [CrossRef] [ChemPort] [PubMed]
Yusufzai, S. K., Osman, H., Rahim, A. S. A., Arshad, S. & Razak, I. A. (2012). Acta Cryst. E68, o2416-o2417.  [CSD] [CrossRef] [details]
Zhang, J.-M., Lou, C.-L., Hu, Z.-P. & Yan, M. (2009). ARKIVOC, 14, 362-375.


Acta Cryst (2012). E68, o3419  [ doi:10.1107/S1600536812047319 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.