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Volume 65 
Part 2 
Pages o314-o315  
February 2009  

Received 6 November 2008
Accepted 8 January 2009
Online 14 January 2009

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.055
wR = 0.140
Data-to-parameter ratio = 16.3
Details
Open access

Dimethyl 2,2'-[(4-oxo-2-phenyl-4H-chromene-5,7-diyl)dioxy]diacetate: a less densely packed polymorph

aDepartment of Chemistry, National Institute of Technology, Tiruchirappalli 620 015, India,bDepartment of Inorganic and Physical Chemistry, Indian Institute of Science, Bangalore 560 012, India,cDepartment of Chemistry, Urumu Dhanalakshmi College, Tiruchirappalli 620 019, India, and dDepartment of Chemistry, Government Arts College, Karur 639 005, India
Correspondence e-mail: vembu57@yahoo.com

The title molecule, C21H18O8, crystallizes in two crystal polymorphs, see also Nallasivam, Nethaji, Vembu & Jaswant [Acta Cryst. (2009), E65, o312-o313]. The main difference between the two polymorphs is in the conformation of the oxomethylacetate groups with regard to the almost planar [total puckering amplitude 0.047 (2) Å] chromene ring. In the title compound, the best planes of the oxomethylacetate groups through the non-H atoms are almost perpendicular to the chromene ring [making dihedral angles of 89.61 (6) and 80.59 (5)°], while in the second polymorph the molecules are close to planar. Both crystal structures are stabilized by C-H...O.

Related literature

For the second polymorph, see: Nallasivam et al. (2009[Nallasivam, A., Nethaji, M., Vembu, N., Jaswant, B. & Sulochana, N. (2009). Acta Cryst. E65, o312-o313.]). For the biological and pharmacological properties of benzopyrans and their derivatives, see: Brooks (1998[Brooks, G. T. (1998). Pestic. Sci. 22, 41-50.]); Hatakeyama et al. (1988[Hatakeyama, S., Ochi, N., Numata, H. & Takano, S. (1988). J. Chem. Soc. Chem. Commun. pp. 1022-1024.]); 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 the importance of 4H-chromenes, see Liu et al. (2007[Liu, C.-B., Chen, Y.-H., Zhou, X.-Y., Ding, L. & Wen, H.-L. (2007). Acta Cryst. E63, o90-o91.]); Wang, Fang et al. (2003[Wang, J.-F., Fang, M.-J., Huang, H.-Q., Li, G.-L., Su, W.-J. & Zhao, Y.-F. (2003). Acta Cryst. E59, o1517-o1518.]); Wand, Zheng et al. (2003[Wang, J.-F., Zhang, Y.-J., Fang, M.-J., Huang, Y.-J., Wei, Z.-B., Zheng, Z.-H., Su, W.-J. & Zhao, Y.-F. (2003). Acta Cryst. E59, o1244-o1245.]).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.]); Desiraju & Steiner (1999[Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology, pp. 11-40. New York: Oxford University Press.]); Etter (1990[Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.]).

[Scheme 1]

Experimental

Crystal data
  • C21H18O8

  • Mr = 398.35

  • Triclinic, [P \overline 1]

  • a = 9.4024 (16) Å

  • b = 9.8506 (17) Å

  • c = 11.1570 (18) Å

  • [alpha] = 67.817 (3)°

  • [beta] = 80.300 (3)°

  • [gamma] = 89.683 (3)°

  • V = 941.3 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 293 (2) K

  • 0.42 × 0.35 × 0.29 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1998[Sheldrick, G. M. (1998). SADABS. University of Gottingen, Germany.]) Tmin = 0.955, Tmax = 0.969

  • 8351 measured reflections

  • 4316 independent reflections

  • 2424 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.055

  • wR(F2) = 0.140

  • S = 0.98

  • 4316 reflections

  • 264 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C19-H19A...O17i 0.97 2.54 3.214 (3) 127
C19-H19A...O18i 0.97 2.58 3.366 (2) 138
Symmetry codes: (i) -x+1, -y+1, -z.

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). 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, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FB2124 ).


Acknowledgements

AN thanks Dr Naresh Kumar and Dr G. Vengatachalam, School of Chemistry, Bharathidasan University, Tiruchirappalli, and Organica Aromatics Pvt Ltd Bangalore, India, for providing laboratory facilities.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Brooks, G. T. (1998). Pestic. Sci. 22, 41-50.  [CrossRef]
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology, pp. 11-40. New York: Oxford University Press.
Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.  [CrossRef] [ChemPort] [ISI]
Hatakeyama, S., Ochi, N., Numata, H. & Takano, S. (1988). J. Chem. Soc. Chem. Commun. pp. 1022-1024.
Hyana, T. & Saimoto, H. (1987). Jpn Patent JP 621 812 768.
Liu, C.-B., Chen, Y.-H., Zhou, X.-Y., Ding, L. & Wen, H.-L. (2007). Acta Cryst. E63, o90-o91.  [CSD] [CrossRef] [details]
Nallasivam, A., Nethaji, M., Vembu, N., Jaswant, B. & Sulochana, N. (2009). Acta Cryst. E65, o312-o313.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (1998). SADABS. University of Gottingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.  [ISI] [CrossRef] [ChemPort] [details]
Tang, Q.-G., Wu, W.-Y., He, W., Sun, H.-S. & Guo, C. (2007). Acta Cryst. E63, o1437-o1438.  [CSD] [CrossRef] [details]
Wang, J.-F., Fang, M.-J., Huang, H.-Q., Li, G.-L., Su, W.-J. & Zhao, Y.-F. (2003). Acta Cryst. E59, o1517-o1518.  [CSD] [CrossRef] [details]
Wang, J.-F., Zhang, Y.-J., Fang, M.-J., Huang, Y.-J., Wei, Z.-B., Zheng, Z.-H., Su, W.-J. & Zhao, Y.-F. (2003). Acta Cryst. E59, o1244-o1245.  [CSD] [CrossRef] [details]


Acta Cryst (2009). E65, o314-o315   [ doi:10.1107/S1600536809001019 ]

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