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Volume 69 
Part 6 
Page o871  
June 2013  

Received 2 May 2013
Accepted 5 May 2013
Online 11 May 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.043
wR = 0.123
Data-to-parameter ratio = 10.6
Details
Open access

6-[(2,4-Dimethylanilino)methylidene]-2-hydroxycyclohexa-2,4-dienone

aDepartment of Chemistry, Kohat University of Science & Technology, Kohat 26000, Kohat, Pakistan,bDepartment of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan,cDepartment of Physics, University of Sargodha, Sargodha, Pakistan, and dCrystal Structure Center, Chemical Physics, Zernike Institute for Advanced Materials, University of Groningen, Nijenborgh 4, NL-9747 AG Groningen, The Netherlands
Correspondence e-mail: shaukat.shujah@yahoo.com

In the title compound, C15H15NO2, the dihedral angle between the aromatic rings is 5.86 (6)°, and an intramolecular N-H...O hydrogen bond generates an S(6) motif, which helps to stabilize the enamine-keto tautomer. An intramolecular O-H...O hydrogen bond also occurs. In the crystal, inversion dimers linked by pairs of O-H...O hydrogen bonds generate R22(10) loops. A C-H...O interaction links the dimers into [010] chains and aromatic [pi]-[pi] stacking [centroid-centroid separation = 3.6131 (9) Å] also occurs.

Related literature

For a related structure and background to Schiff bases, see: Shuja et al. (2007[Shuja, S., Ali, S., Khalid, N. & Meetsma, A. (2007). Acta Cryst. E63, o3162-o3164.]). For further structural aspects, see: Blagus & Kaitner (2011[Blagus, A. & Kaitner, B. (2011). Acta Cryst. E67, o2958-o2959.]).

[Scheme 1]

Experimental

Crystal data
  • C15H15NO2

  • Mr = 241.28

  • Triclinic, [P \overline 1]

  • a = 7.6731 (8) Å

  • b = 8.4348 (9) Å

  • c = 10.5806 (12) Å

  • [alpha] = 80.6107 (18)°

  • [beta] = 75.8216 (19)°

  • [gamma] = 63.3573 (16)°

  • V = 592.31 (11) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 100 K

  • 0.53 × 0.48 × 0.29 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2006[Bruker (2006). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.943, Tmax = 0.974

  • 4681 measured reflections

  • 2363 independent reflections

  • 2148 reflections with I > 2[sigma](I)

  • Rint = 0.009

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.123

  • S = 1.09

  • 2363 reflections

  • 223 parameters

  • All H-atom parameters refined

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H21...O2 0.85 (2) 2.340 (17) 2.7674 (12) 111.3 (12)
O1-H21...O2i 0.85 (2) 2.00 (2) 2.7320 (13) 143.4 (15)
N1-H31...O2 1.00 (2) 1.72 (2) 2.5873 (12) 142.7 (18)
C13-H13...O1ii 0.980 (14) 2.557 (14) 3.3069 (14) 133.3 (13)
Symmetry codes: (i) -x, -y+2, -z+1; (ii) x, y-1, z.

Data collection: SMART (Bruker, 2006[Bruker (2006). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2006[Bruker (2006). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SIR2004 (Burla et al., 2005[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLUTO (Meetsma, 2006[Meetsma, A. (2006). Extended version of the program PLUTO. University of Groningen, The Netherlands. Unpublished.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: PLATON.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7078 ).


Acknowledgements

SS thanks the HEC (Higher Education Commission), Islamabad, for a fellowship (PIN No. 042-111889-PS2-104).

References

Blagus, A. & Kaitner, B. (2011). Acta Cryst. E67, o2958-o2959.  [CSD] [CrossRef] [ChemPort] [details]
Bruker (2006). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.  [ISI] [CrossRef] [ChemPort] [details]
Meetsma, A. (2006). Extended version of the program PLUTO. University of Groningen, The Netherlands. Unpublished.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Shuja, S., Ali, S., Khalid, N. & Meetsma, A. (2007). Acta Cryst. E63, o3162-o3164.  [CSD] [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o871  [ doi:10.1107/S1600536813012233 ]

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