4-(2-Bromo­phen­yl)-2-phenyl­pyrano[3,2-c]chromen-5(4H)-one

Gohain, M.; Loganathan, N.; Bezuidenhoudt, B.C.B.; Roodt, A.

doi:10.1107/S1600536812044510

Volume 68
Part 12
Pages o3279-o3280
December 2012

Received 5 October 2012
Accepted 26 October 2012
Online 3 November 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.027
wR = 0.068
Data-to-parameter ratio = 17.6
Details

4-(2-Bromophenyl)-2-phenylpyrano[3,2-c]chromen-5(4H)-one

Mukut Gohain,^a Nagarajan Loganathan,^a ^* Barend C. B. Bezuidenhoudt ^a and Andreas Roodt ^a

^aDepartment of Chemistry, University of the Free State, PO Box 339, Bloemfontein 9300, South Africa
Correspondence e-mail: nagagold@gmail.com

In the title compound, C₂₄H₁₅BrO₃, the pyranochromenone ring is essentially planar, while the 2-bromophenyl group is almost perpendicular to it [85.58 (6)°]. In the crystal, inversion dimers linked by pairs of weak C-H [pi] bonds occur; there is also a short interatomic contact found between the Br and carbonyl O atoms [3.016 (1) Å].

Related literature

For coumarin chemistry and applications, see: Hinman et al. (1956); Soine (1964); Murray et al. (1982); Patil et al. (1993); Verotta et al. (2004); Heide (2009); Magolan et al. (2012). For related structures, see: Shi et al. (2004, 2005); Lakshmi et al. (2006). For related synthesis and structures, see: Naveen et al. (2007); Shaabani et al. (2008); Sarma et al. (2010); He et al. (2010).

Experimental

Crystal data

C₂₄H₁₅BrO₃
M_r = 431.27
Monoclinic, P 2₁ /c
a = 11.5959 (2) Å
b = 17.7890 (4) Å
c = 8.7610 (2) Å
= 97.060 (1)°
V = 1793.53 (7) Å³
Z = 4
Mo K radiation
= 2.32 mm^-1
T = 100 K
0.52 × 0.40 × 0.23 mm

Data collection

Bruker X8 APEXII KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008) T_min = 0.380, T_max = 0.618
41256 measured reflections
4464 independent reflections
4019 reflections with I > 2(I)
R_int = 0.045

Refinement

R[F² > 2(F²)] = 0.027
wR(F²) = 0.068
S = 1.05
4464 reflections
253 parameters
H-atom parameters constrained
_max = 0.51 e Å^-3
_min = -0.34 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C12-C17 ring.

D-HA	D-H	HA	DA	D-HA
C3-H3Cg4ⁱ	1.00	2.80	3.4956 (18)	127
Symmetry code: (i) -x+1, -y+2, -z.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT-Plus (Bruker, 2008); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008) and WinGX (Farrugia,1999); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BV2211 ).

Acknowledgements

The University of the Free State and Sasol Ltd are gratefully acknowledged for financial support.

References

Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2008). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
He, Z., Lin, X., Zhu, Y. & Wang, Y. (2010). Heterocycles, 81, 965-976.
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