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Volume 68 
Part 1 
Page o241  
January 2012  

Received 17 December 2011
Accepted 18 December 2011
Online 23 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.046
wR = 0.137
Data-to-parameter ratio = 20.1
Details
Open access

3-{2-[(3-{(E)-2-[4-(Dimethylamino)phenyl]ethenyl}quinoxalin-2-yl)oxy]ethyl}-1,3-oxazolidin-2-one monohydrate

aLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco,bCNRST Division UATRS, Angle Allal Fassi/FAR, BP 8027 Hay Riad, Rabat, Morocco,cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and dChemistry Department, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
Correspondence e-mail: seikweng@um.edu.my

In the title compound, C23H24N4O3·H2O, the 1,3-oxazoline ring is nearly planar [maximum deviation = 0.059 (2) Å] and its mean plane is twisted by 30.12 (8)° with respect to the quinoxaline fused-ring system; the benzene ring is nearly coplanar with the quinoxaline fused-ring system [dihedral angle = 2.52 (2)°]. The water molecule of crystallization is hydrogen-bond donor to an N atom of the quinoxaline ring system as well as an O atom of the oxazolinone unit, the two hydrogen bonds generating a chain running along the c axis.

Related literature

For general background, see: Noolvi et al. (2011[Noolvi, M., Patel, H. M., Bhardwaj, V. & Chauhan, A. (2011). Eur. J. Med. Chem. 46, 2327-2346.]).

[Scheme 1]

Experimental

Crystal data
  • C23H24N4O3·H2O

  • Mr = 422.48

  • Monoclinic, P 21 /c

  • a = 7.20980 (1) Å

  • b = 23.3271 (4) Å

  • c = 12.3994 (2) Å

  • [beta] = 98.119 (1)°

  • V = 2064.47 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 293 K

  • 0.21 × 0.20 × 0.15 mm

Data collection
  • Bruker APEX DUO diffractometer

  • 28134 measured reflections

  • 5836 independent reflections

  • 4141 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.137

  • S = 1.03

  • 5836 reflections

  • 290 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.48 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1w-H11...N1 0.87 (1) 2.18 (1) 3.039 (2) 170 (2)
O1w-H12...O3i 0.86 (1) 1.96 (1) 2.820 (2) 176 (3)
Symmetry code: (i) x, y, z-1.

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). APEX2 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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5414 ).


Acknowledgements

We thank Université Mohammed V-Agdal and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.  [CrossRef] [ChemPort]
Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Noolvi, M., Patel, H. M., Bhardwaj, V. & Chauhan, A. (2011). Eur. J. Med. Chem. 46, 2327-2346.  [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2012). E68, o241  [ doi:10.1107/S1600536811054481 ]

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