(Z)-6-[(5-Chloro-2-hydroxy­phenyl)­aminomethyl­ene]-2-ethoxy­cyclo­hexa-2,4-dienone

Özek, A.; Albayrak, Ç.; Büyükgüngör, O.

doi:10.1107/S1600536809031298

Volume 65
Part 9
Page o2153
September 2009

Received 4 August 2009
Accepted 7 August 2009
Online 15 August 2009

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.041
wR = 0.099
Data-to-parameter ratio = 11.3
Details

(Z)-6-[(5-Chloro-2-hydroxyphenyl)aminomethylene]-2-ethoxycyclohexa-2,4-dienone

Arzu Özek,^a ^* Çigdem Albayrak ^b and Orhan Büyükgüngör ^a

^aDepartment of Physics, Ondokuz Mayis University, TR-55139, Samsun, Turkey, and ^bFaculty of Education, Sinop University, Sinop, Turkey
Correspondence e-mail: arzuozek@omu.edu.tr

The title compound, C₁₅H₁₄ClNO₃, exists as the keto-amine form in the crystal and two intramolecular N-HO hydrogen bonds are observed. The aromatic rings are oriented at a dihedral angle of 5.85 (8)°. In the crystal structure, intermolecular O-HO and C-HO hydrogen bonds link the molecules into chains. A [pi] - [pi] contact between the benzene rings [centroid-centroid distance = 3.6623 (10) Å] further stabilizes the structure.

Related literature

For general background, see: Büyükgüngör et al. (2007); Ersanli et al. (2003); Tanak et al. (2008) For related structures, see: Özek et al. (2007, 2008).

Experimental

Crystal data

C₁₅H₁₄ClNO₃
M_r = 291.72
Monoclinic, P 2₁ /c
a = 15.4313 (7) Å
b = 7.1710 (2) Å
c = 12.6071 (6) Å
= 111.168 (4)°
V = 1300.94 (10) Å³
Z = 4
Mo K radiation
= 0.30 mm^-1
T = 296 K
0.52 × 0.29 × 0.09 mm

Data collection

STOE IPDS II diffractometer
Absorption correction: integration X-RED32 (Stoe & Cie, 2002) T_min = 0.616, T_max = 0.927
15989 measured reflections
2680 independent reflections
2084 reflections with I > 2(I)
R_int = 0.060

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.099
S = 1.05
2680 reflections
237 parameters
All H-atom parameters refined
_max = 0.15 e Å^-3
_min = -0.25 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O1	0.86 (2)	1.88 (2)	2.5957 (17)	140 (2)
N1-H1O3	0.86 (2)	2.29 (2)	2.640 (2)	104.3 (17)
O3-H3O1ⁱ	0.85 (2)	1.79 (2)	2.6258 (17)	165 (2)
C9-H9O3ⁱⁱ	0.96 (2)	2.594 (19)	3.419 (2)	143.8 (14)
Symmetry codes: (i) -x+1, -y, -z+1; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5027 ).

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayis University, Turkey, for the use of the Stoe IPDS II diffractometer (purchased under grant No. F.279 of the University Research Fund).

References

Büyükgüngör, O., Odabasoglu, M., Narayana, B., Vijesh, A. M. & Yathirajan, H. S. (2007). Acta Cryst. E63, o1996-o1998.
Ersanli, C. C., Albayrak, Ç., Odabasoglu, M. & Erdönmez, A. (2003). Acta Cryst. C59, o601-o602.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Özek, A., Albayrak, Ç., Odabasoglu, M. & Büyükgüngör, O. (2007). Acta Cryst. C63, o177-o180.
Özek, A., Büyükgüngör, O., Albayrak, Ç. & Odabasoglu, M. (2008). Acta Cryst. E64, o1613-o1614.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.
Tanak, H., Ersahin, F., Agar, E. & Büyükgüngör, O. (2008). Anal. Sci. 24, 237-238.

organic compounds