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Volume 69 
Part 5 
Page o764  
May 2013  

Received 25 March 2013
Accepted 4 April 2013
Online 20 April 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.045
wR = 0.117
Data-to-parameter ratio = 13.3
Details
Open access

2-[3-(2-Acetoxyphenyl)quinoxalin-2-yl]phenyl acetate

aState Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou, 310014, People's Republic of China
Correspondence e-mail: chrc@zjut.edu.cn

The title compound, C24H18N2O4, crystallizes as a syn-conformer, with dihedral angles between the quinoxaline moiety and the acetoxy-substituted benzene rings of 53.46 (3)° and 54.78 (3)°. In the crystal, the molecules form chains along [100] via C-H...O interactions.

Related literature

For general background to quinoxaline derivatives, see: Brasche & Buchwald (2008[Brasche, G. & Buchwald, S. L. (2008). Angew. Chem. Int. Ed. 47, 1932-1934.]); Do & Daugulis (2008[Do, H.-Q. & Daugulis, O. (2008). J. Am. Chem. Soc. 130, 1128-1129.]); He et al. (2003[He, W., Meyers, M. R., Hanney, B., Sapada, A., Blider, G., Galzeinski, H., Amin, D., Needle, S., Page, K., Jayyosi, Z. & Perrone, H. (2003). Bioorg. Med. Chem. Lett. 13, 3097-3100.]); Kim et al. (2004[Kim, Y. B., Kim, Y. H., Park, J. Y. & Kim, S. K. (2004). Bioorg. Med. Chem. Lett. 14, 541-544.]); Lyons & Sanford (2010[Lyons, T. W. & Sanford, M. S. (2010). Chem. Rev. 110, 1147-1169.]). For quinoxaline-directed C-H activation, see: Reddy et al. (2011[Reddy, B. V. S., Ramesh, K. & Yadav, J. S. (2011). Synlett, 2, 169-172.]). For a related structure, see: Rajnikant et al. (2006[Rajnikant, Dinesh,, Deshmukh, M. B., Jadhav, S. & Kanwal, P. (2006). Acta Cryst. E62, o2356-o2357.]).

[Scheme 1]

Experimental

Crystal data
  • C24H18N2O4

  • Mr = 398.40

  • Monoclinic, P 21 /c

  • a = 9.5723 (5) Å

  • b = 16.7309 (8) Å

  • c = 13.0555 (6) Å

  • [beta] = 92.929 (2)°

  • V = 2088.15 (18) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 296 K

  • 0.48 × 0.46 × 0.20 mm

Data collection
  • Rigaku R-AXIS RAPID/ZJUG diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.959, Tmax = 0.983

  • 15632 measured reflections

  • 3646 independent reflections

  • 2553 reflections with I > 2[sigma](I)

  • Rint = 0.043

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.117

  • S = 1.00

  • 3646 reflections

  • 274 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C13-H13...O4i 0.93 2.43 3.329 (2) 164
Symmetry code: (i) x-1, y, z.

Data collection: PROCESS-AUTO (Rigaku, 2006[Rigaku (2006). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2007[Rigaku (2007). CrystalStructure. Rigaku Americas Corporation, The Woodlands, Texas, USA.]); 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LD2099 ).


Acknowledgements

We thank Professor Jian-Ming Gu of Zhejiang University for his help.

References

Brasche, G. & Buchwald, S. L. (2008). Angew. Chem. Int. Ed. 47, 1932-1934.  [ISI] [CrossRef] [ChemPort]
Do, H.-Q. & Daugulis, O. (2008). J. Am. Chem. Soc. 130, 1128-1129.  [ISI] [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
He, W., Meyers, M. R., Hanney, B., Sapada, A., Blider, G., Galzeinski, H., Amin, D., Needle, S., Page, K., Jayyosi, Z. & Perrone, H. (2003). Bioorg. Med. Chem. Lett. 13, 3097-3100.  [CrossRef] [PubMed] [ChemPort]
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Kim, Y. B., Kim, Y. H., Park, J. Y. & Kim, S. K. (2004). Bioorg. Med. Chem. Lett. 14, 541-544.  [CrossRef] [PubMed] [ChemPort]
Lyons, T. W. & Sanford, M. S. (2010). Chem. Rev. 110, 1147-1169.  [ISI] [CrossRef] [ChemPort] [PubMed]
Rajnikant, Dinesh,, Deshmukh, M. B., Jadhav, S. & Kanwal, P. (2006). Acta Cryst. E62, o2356-o2357.
Reddy, B. V. S., Ramesh, K. & Yadav, J. S. (2011). Synlett, 2, 169-172.  [ISI] [CrossRef]
Rigaku (2006). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku (2007). CrystalStructure. Rigaku Americas Corporation, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o764  [ doi:10.1107/S1600536813009161 ]

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