5,7-Bis(benz­yloxy)-2-phenyl-4H-chromen-4-one

Nallasivam, A.; Nethaji, M.; Vembu, N.; Jaswant, B.; Sulochana, N.

doi:10.1107/S160053680803938X

Volume 64
Part 12
Pages o2490-o2491
December 2008

Received 6 November 2008
Accepted 23 November 2008
Online 29 November 2008

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.059
wR = 0.155
Data-to-parameter ratio = 17.8
Details

5,7-Bis(benzyloxy)-2-phenyl-4H-chromen-4-one

Angannan Nallasivam,^a Munirathinam Nethaji,^b Nagarajan Vembu,^c ^* Buckle Jaswant ^d and Nagarajan Sulochana ^a

^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

In the title compound, C₂₉H₂₂O₄, the chromene ring is almost planar with a small puckering [0.143 (2) Å]. The crystal structure is stabilized by C-HO and C-H [pi] interactions. Edge-to-face (centroid-centroid distances of 3.894 and 3.673 Å) and face-to-face (centroid-centroid distance of 3.460 Å) [pi] - [pi] -ring electron interactions are also observed.

Related literature

For the biological and pharmacological properties of benzopyrans and their derivatives, see: Brooks (1998); Hatakeyama et al. (1988); Hyana & Saimoto (1987); Tang et al. (2007). For the importance of 4H-chromenes, see Liu et al. (2007); Wang, Fang et al. (2003); Wang, Zhang et al. (2003). For hydrogen-bond motifs, see: Bernstein et al. (1995); Desiraju (1989); Desiraju & Steiner (1999); Etter (1990).

Experimental

Crystal data

C₂₉H₂₂O₄
M_r = 434.47
Triclinic, $[P \overline 1]$
a = 9.496 (3) Å
b = 11.572 (3) Å
c = 11.767 (3) Å
= 66.564 (4)°
= 79.668 (5)°
= 73.836 (5)°
V = 1136.1 (5) Å³
Z = 2
Mo K radiation
= 0.08 mm^-1
T = 293 (2) K
0.45 × 0.33 × 0.23 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1998) T_min = 0.963, T_max = 0.981
13435 measured reflections
5302 independent reflections
3534 reflections with I > 2(I)
R_int = 0.018

Refinement

R[F² > 2(F²)] = 0.059
wR(F²) = 0.155
S = 1.05
5302 reflections
298 parameters
H-atom parameters constrained
_max = 0.20 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C16-H16O17ⁱ	0.93	2.57	3.212 (3)	127
C30-H30Cg1ⁱⁱ	0.93	3.12	3.838	135
C8-H8Cg2ⁱⁱⁱ	0.93	3.29	4.066	142
C27-H27BCg2ⁱⁱⁱ	0.97	3.18	4.083	156
Symmetry codes: (i) -x+2, -y+1, -z; (ii) x, y, z+1; (iii) -x+2, -y+2, -z+1. Cg1 and Cg2 are the centroids of the C20-C25 and C28-C33 rings, respectively.

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FB2125 ).

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

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Desiraju, G. R. (1989). Crystal Engineering: The Design of Organic Solids, pp. 125-167. Amsterdam: Elsevier.
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.
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organic compounds