[Journal logo]

Volume 69 
Part 6 
Page o883  
June 2013  

Received 22 March 2013
Accepted 7 May 2013
Online 15 May 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.055
wR = 0.142
Data-to-parameter ratio = 13.5
Details
Open access

8-{(E)-[(4-Chlorophenyl)imino]methyl}-1,1,7,7-tetramethyl-1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinolin-9-ol

aDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayis University, TR-55139 Samsun, Turkey,bYesilyurt Demir Celik Vocational School, Ondokuz Mayis University, TR-55139 Samsun, Turkey,cDepartment of Chemistry, Amasya Faculty of Arts and Sciences, Ondokuz Mayis University, 05000 Amasya, Turkey,dDepartment of Chemistry, Faculty of Arts and Sciences, Ondokuz Mayis University, Kurupelit, 55139 Samsun, Turkey, and eDepartment of Physics, Faculty of Arts and Sciences, Giresun University, Giresun, Turkey
Correspondence e-mail: esen.nur@oposta.omu.edu.tr

The title Schiff base, C23H27ClN2O adopts the phenol-imine tautomeric form, with an intramolecular O-H...N hydrogen bond, which generates an S(6) ring motif. Three C atoms of the heterocyclic moiety of the hexahydropyridoquinoline unit, as well as the two methyl groups bonded to one of these C atoms, are disordered over two set of sites, with anoccupancy ratio of 0.740 (4):0.260 (4).

Related literature

For a related structure, see: Kantar et al. (2012[Kantar, E. N., Köysal, Y., Gümüs, S., Agar, E. & Soylu, M. S. (2012). Acta Cryst. E68, o1587.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davies, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For ring conformational parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.])

[Scheme 1]

Experimental

Crystal data
  • C23H27ClN2O

  • Mr = 382.92

  • Triclinic, [P \overline 1]

  • a = 6.4716 (3) Å

  • b = 9.8468 (6) Å

  • c = 16.9206 (7) Å

  • [alpha] = 75.438 (4)°

  • [beta] = 80.307 (4)°

  • [gamma] = 75.863 (4)°

  • V = 1005.42 (9) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.21 mm-1

  • T = 293 K

  • 0.30 × 0.10 × 0.10 mm

Data collection
  • Oxford Diffraction SuperNova (Dual, Cu at zero, Eos) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.947, Tmax = 0.975

  • 5887 measured reflections

  • 3651 independent reflections

  • 2959 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.055

  • wR(F2) = 0.142

  • S = 1.08

  • 3651 reflections

  • 270 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.51 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
O13-H13...N8 0.98 1.65 2.563 (2) 155

Data collection: CrysAlis PRO (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: LR2103 ).


Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Giresun University, Turkey, for the use of the diffractometer

References

Bernstein, J., Davies, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Kantar, E. N., Köysal, Y., Gümüs, S., Agar, E. & Soylu, M. S. (2012). Acta Cryst. E68, o1587.  [CSD] [CrossRef] [details]
Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o883  [ doi:10.1107/S1600536813012579 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.