[Journal logo]

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 [sigma](C-C) = 0.002 Å
R = 0.027
wR = 0.068
Data-to-parameter ratio = 17.6
Details
Open access

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

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[Hinman, W., Hoeksema, H., Caron, E. L. & Jackson, W. G. (1956). J. Am. Chem. Soc. 78, 1072-1074.]); Soine (1964[Soine, T. O. (1964). J. Pharm. Sci. 53, 231-264.]); Murray et al. (1982[Murray, R. D. H., Mendez, J. & Brown, S. A. (1982). In The Natural Coumarins: Occurrence, Chemistry and Biochemistry. UK: Wiley-VCH.]); Patil et al. (1993[Patil, A. D., Freyer, A. J., Eggleston, D. S., Haltiwanger, R. C., Bean, M. F., Taylor, P. B., Caranfa, M. J., Breen, A. L., Bartus, H. R., Johnson, R. K., Hertzberg, R. P. & Westley, J. W. (1993). J. Med. Chem. 36, 4131-4138.]); Verotta et al. (2004[Verotta, L., Lovaglio, E., Vidari, G., Finzi, P. V., Neri, M. G., Raimondi, A., Parapini, S., Taramelli, D., Riva, A. & Bombardelli, E. (2004). Phytochemistry, 65, 2867-2989.]); Heide (2009[Heide, L. (2009). Methods in Enzymology, Vol. 459, Aminocoumarins Mutasynthesis, Chemoenzymatic Synthesis, and Metabolic Engineering, pp. 437-455. New York: Academic Press.]); Magolan et al. (2012[Magolan, J., Adams, N. B. P., Onozuka, H., Hungerford, N. L., Esumi, H. & Coster, M. J. (2012). ChemMedChem, 7, 766-770.]). For related structures, see: Shi et al. (2004[Shi, D., Wu, N., Zhuang, Q. & Zhang, Y. (2004). Acta Cryst. E60, o2339-o2341.], 2005[Shi, D.-Q., Wu, N., Zhuang, Q.-Y. & Zhang, Y. (2005). Acta Cryst. E61, o87-o89.]); Lakshmi et al. (2006[Lakshmi, S., Manvar, D., Parecha, A., Shah, A., Sridhar, M. A. & Shashidhara Prasad, J. (2006). Acta Cryst. E62, o2163-o2165.]). For related synthesis and structures, see: Naveen et al. (2007[Naveen, S., Lakshmi, S., Manvar, D., Parecha, A., Shah, A., Sridhar, M. A. & Prasad, J. S. (2007). J. Chem. Crystallogr. 37, 733-738.]); Shaabani et al. (2008[Shaabani, A., Rezayan, A. H., Sarvary, A., Rahmati, A. & Khavasi, H. R. (2008). Catal. Commun. 9, 1082-1086.]); Sarma et al. (2010[Sarma, R., Sarmah, M. M., Lekhok, K. C. & Prajapati, D. (2010). Synlett, 19, 2847-2852.]); He et al. (2010[He, Z., Lin, X., Zhu, Y. & Wang, Y. (2010). Heterocycles, 81, 965-976.]).

[Scheme 1]

Experimental

Crystal data
  • C24H15BrO3

  • Mr = 431.27

  • Monoclinic, P 21 /c

  • a = 11.5959 (2) Å

  • b = 17.7890 (4) Å

  • c = 8.7610 (2) Å

  • [beta] = 97.060 (1)°

  • V = 1793.53 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2008). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.380, Tmax = 0.618

  • 41256 measured reflections

  • 4464 independent reflections

  • 4019 reflections with I > 2[sigma](I)

  • Rint = 0.045

Refinement
  • R[F2 > 2[sigma](F2)] = 0.027

  • wR(F2) = 0.068

  • S = 1.05

  • 4464 reflections

  • 253 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.51 e Å-3

  • [Delta][rho]min = -0.34 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C12-C17 ring.

D-H...A D-H H...A D...A D-H...A
C3-H3...Cg4i 1.00 2.80 3.4956 (18) 127
Symmetry code: (i) -x+1, -y+2, -z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2008[Bruker (2008). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and WinGX (Farrugia,1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg & Putz, 2005[Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); 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.  [CrossRef] [ChemPort] [details]
He, Z., Lin, X., Zhu, Y. & Wang, Y. (2010). Heterocycles, 81, 965-976.  [ChemPort]
Heide, L. (2009). Methods in Enzymology, Vol. 459, Aminocoumarins Mutasynthesis, Chemoenzymatic Synthesis, and Metabolic Engineering, pp. 437-455. New York: Academic Press.
Hinman, W., Hoeksema, H., Caron, E. L. & Jackson, W. G. (1956). J. Am. Chem. Soc. 78, 1072-1074.  [CrossRef] [ChemPort] [ISI]
Lakshmi, S., Manvar, D., Parecha, A., Shah, A., Sridhar, M. A. & Shashidhara Prasad, J. (2006). Acta Cryst. E62, o2163-o2165.  [CSD] [CrossRef] [details]
Magolan, J., Adams, N. B. P., Onozuka, H., Hungerford, N. L., Esumi, H. & Coster, M. J. (2012). ChemMedChem, 7, 766-770.  [CrossRef] [ChemPort] [PubMed]
Murray, R. D. H., Mendez, J. & Brown, S. A. (1982). In The Natural Coumarins: Occurrence, Chemistry and Biochemistry. UK: Wiley-VCH.
Naveen, S., Lakshmi, S., Manvar, D., Parecha, A., Shah, A., Sridhar, M. A. & Prasad, J. S. (2007). J. Chem. Crystallogr. 37, 733-738.  [ISI] [CSD] [CrossRef] [ChemPort]
Patil, A. D., Freyer, A. J., Eggleston, D. S., Haltiwanger, R. C., Bean, M. F., Taylor, P. B., Caranfa, M. J., Breen, A. L., Bartus, H. R., Johnson, R. K., Hertzberg, R. P. & Westley, J. W. (1993). J. Med. Chem. 36, 4131-4138.  [CrossRef] [ChemPort] [PubMed] [ISI]
Sarma, R., Sarmah, M. M., Lekhok, K. C. & Prajapati, D. (2010). Synlett, 19, 2847-2852.
Shaabani, A., Rezayan, A. H., Sarvary, A., Rahmati, A. & Khavasi, H. R. (2008). Catal. Commun. 9, 1082-1086.  [ISI] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Shi, D., Wu, N., Zhuang, Q. & Zhang, Y. (2004). Acta Cryst. E60, o2339-o2341.  [CSD] [CrossRef] [details]
Shi, D.-Q., Wu, N., Zhuang, Q.-Y. & Zhang, Y. (2005). Acta Cryst. E61, o87-o89.  [CSD] [CrossRef] [details]
Soine, T. O. (1964). J. Pharm. Sci. 53, 231-264.  [CrossRef] [PubMed] [ChemPort] [ISI]
Verotta, L., Lovaglio, E., Vidari, G., Finzi, P. V., Neri, M. G., Raimondi, A., Parapini, S., Taramelli, D., Riva, A. & Bombardelli, E. (2004). Phytochemistry, 65, 2867-2989.  [ISI] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2012). E68, o3279-o3280   [ doi:10.1107/S1600536812044510 ]

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.