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Volume 69 
Part 8 
Page o1296  
August 2013  

Received 25 June 2013
Accepted 12 July 2013
Online 24 July 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.058
wR = 0.194
Data-to-parameter ratio = 15.5
Details
Open access

3-[1-(2-Hydroxyanilino)ethylidene]-3H-chromen-2,4-dione

aUnité de Chimie des Matériaux et de l'Environnement, ISSBAT, Université de Tunis-ElManar, 9 Avenue Dr Zoheir SAFI, 1006 Tunis, Tunisia, and bINSAT, Université de Carthage, Centre Urbain Nord, BP 676, 1080 Tunis Cedex, Tunis, Tunisia
Correspondence e-mail: rached.benhassen@fss.rnu.tn

The title compound is a new aminocoumarin derivative, C17H13NO4, and was synthesized by the condensation of 2-aminophenol and 3-acetyl-4-hydroxycoumarin. An intramolecular N-H...O hydrogen bond generates an S(6) ring motif. In the crystal, the molecules are linked into chains extending in the [010] direction by O-H...O hydrogen bonds. There is also a [pi]-[pi] stacking interaction between the bicyclic coumarin fragment and the phenol ring [centroid-centroid distance = 3.7510 (14) Å], and these ring systems form between them a dihedral angle of 53.3 (2)°. Intermolecular hydrogen bond C-H...O hydrogen bonding is also observed in the interconnection of the crystal packing.

Related literature

For related structures, see: Traven et al. (2000[Traven, V. F., Manaev, A. V., Safronova, O. B., Chibisova, T. A., Lyssenko, K. A. & Antipin, M. Yu. (2000). Russ. J. Gen. Chem. 70, 798-808.]); Malecka et al. (2004[Malecka, M., Grabowski, S. J. & El_zbieta, B. (2004). Chem. Phys. 297, 235-244.]); Mechi et al. (2009[Mechi, L., Chtiba, S., Hamdi, N. & Ben Hassen, R. (2009). Acta Cryst. E65, o1652-o1653.]); Ghouili et al. (2011[Ghouili, A. & Ben Hassen, R. (2011). Acta Cryst. E67, o2209.]); Ketata et al. (2012[Ketata, I., Mechi, L., Ben Ayed, T., Dusek, M., Petricek, V. & Ben Hassen, R. (2012). Open J. Inorg. Chem. 2, 33-39.]). For the properties of coumarin derivatives, see: Bordin et al. (1995[Bordin, F., Chilin, A., Dall Acqua, F., Guiotto, A. & Manzini, P. (1995). Rod Il Farm. 50, 479-488.]); Hamdi et al. (2010[Hamdi, N., Bouabdallah, F., Romerosa, A. & Ben Hassen, R. (2010). C. R. Chim. 13, 1261-1268.]); Mahidol et al. (2004[Mahidol, C., Ploypradith, P., Sahakitpichan, P. & Wongbundit, S. (2004). Angew. Chem. Int. Ed. 43, 866-868.]).

[Scheme 1]

Experimental

Crystal data
  • C17H13NO4

  • Mr = 295.29

  • Monoclinic, P 21 /n

  • a = 12.5596 (4) Å

  • b = 7.5870 (3) Å

  • c = 14.3433 (6) Å

  • [beta] = 94.660 (2)°

  • V = 1362.25 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 293 K

  • 0.16 × 0.13 × 0.10 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • 11784 measured reflections

  • 3891 independent reflections

  • 1721 reflections with I > 2[sigma](I)

  • Rint = 0.053

Refinement
  • R[F2 > 2[sigma](F2)] = 0.058

  • wR(F2) = 0.194

  • S = 0.91

  • 3891 reflections

  • 251 parameters

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

  • [Delta][rho]max = 0.23 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
O4-H12...O2i 0.82 1.92 2.742 (2) 175
N1-H13...O3 0.88 (3) 1.75 (3) 2.537 (3) 148 (3)
C8-H4...O2i 0.93 2.59 3.274 (3) 131
Symmetry code: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SMART; data reduction: SAINT (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, 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: FF2111 ).


Acknowledgements

Professor A. Ben Salah is acknowledged for his contribution to the X-ray diffraction data collection at the Laboratory of Materials Science and the Environment, University of Sfax, Tunisia.

References

Bordin, F., Chilin, A., Dall Acqua, F., Guiotto, A. & Manzini, P. (1995). Rod Il Farm. 50, 479-488.
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Ghouili, A. & Ben Hassen, R. (2011). Acta Cryst. E67, o2209.  [CrossRef] [IUCr Journals]
Hamdi, N., Bouabdallah, F., Romerosa, A. & Ben Hassen, R. (2010). C. R. Chim. 13, 1261-1268.  [CrossRef] [ChemPort]
Ketata, I., Mechi, L., Ben Ayed, T., Dusek, M., Petricek, V. & Ben Hassen, R. (2012). Open J. Inorg. Chem. 2, 33-39.  [CrossRef] [ChemPort]
Mahidol, C., Ploypradith, P., Sahakitpichan, P. & Wongbundit, S. (2004). Angew. Chem. Int. Ed. 43, 866-868.
Malecka, M., Grabowski, S. J. & El_zbieta, B. (2004). Chem. Phys. 297, 235-244.
Mechi, L., Chtiba, S., Hamdi, N. & Ben Hassen, R. (2009). Acta Cryst. E65, o1652-o1653.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Traven, V. F., Manaev, A. V., Safronova, O. B., Chibisova, T. A., Lyssenko, K. A. & Antipin, M. Yu. (2000). Russ. J. Gen. Chem. 70, 798-808.  [ChemPort]


Acta Cryst (2013). E69, o1296  [ doi:10.1107/S160053681301934X ]

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