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Volume 69 
Part 4 
Page o541  
April 2013  

Received 4 March 2013
Accepted 8 March 2013
Online 16 March 2013

Key indicators
Single-crystal X-ray study
T = 294 K
Mean [sigma](C-C) = 0.004 Å
Disorder in main residue
R = 0.050
wR = 0.136
Data-to-parameter ratio = 18.8
Details
Open access

Ethyl 4-(5-bromo-2-hydroxyphenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate

aDepartment of Organic Chemistry, Baku State University, Baku, Azerbaijan,bDepartment of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran, and cStructural Dynamics of (Bio)Chemical Systems, Max Planck Institute for Biophysical Chemistry, Am Fassberg 11, 37077 Göttingen, Germany
Correspondence e-mail: organik10@hotmail.com

In the title compound, C21H24BrNO4, the dihedral angle between the heterocyclic ring and the pendant aromatic ring is 80.20 (13)°. The hexahydroquinone [i.e. the one with the C=O group] ring adopts a sofa conformation. An intramolecular O-H...O hydrogen bond generates an S(6) ring motif. The ethyl group is disordered over two sets of sites with a refined site occupancy ratio of 0.633 (10):0.366 (10). In the crystal, molecules are linked by N-H...O interactions, forming chains parallel to [101]. There are no significant C-H...[pi] or [pi]-[pi] interactions in the crystal structure.

Related literature

For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For background to hexahydroquinoline compounds and their applications, see: Sausins & Duburs (1988[Sausins, A. & Duburs, G. (1988). Heterocycles, 27, 269-289.]); Nakayama & Kasoaka (1996[Nakayama, H. & Kasoaka, Y. (1996). Heterocycles, 42, 901-909.]); Klusa (1995[Klusa, V. (1995). Drugs Future, 20, 135-138.]). For the synthesis of related compounds, see: Kumar et al. (2008[Kumar, S., Sharma, P., Kapoor, K. K. & Hundal, M. S. (2008). Tetrahedron, 64, 536-542.]); Song et al. (2012[Song, S. J., Shan, Z. X. & Jin, J. (2012). Synth. Commun. 40, 3067-3077.]).

[Scheme 1]

Experimental

Crystal data
  • C21H24BrNO4

  • Mr = 434.32

  • Monoclinic, P 21 /n

  • a = 9.5969 (3) Å

  • b = 19.0805 (5) Å

  • c = 11.0678 (3) Å

  • [beta] = 97.387 (1)°

  • V = 2009.84 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 2.07 mm-1

  • T = 294 K

  • 0.24 × 0.22 × 0.18 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.636, Tmax = 0.707

  • 23241 measured reflections

  • 5008 independent reflections

  • 3604 reflections with I > 2[sigma](I)

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.136

  • S = 1.05

  • 5008 reflections

  • 266 parameters

  • 3 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 1.10 e Å-3

  • [Delta][rho]min = -1.02 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O4-H4...O1 0.88 1.75 2.625 (3) 171
N1-H1...O2i 0.86 2.05 2.866 (3) 158
Symmetry code: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ5051 ).


Acknowledgements

The authors thank the Chemistry Department, Baku State University, for providing the X-ray diffraction facility.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Klusa, V. (1995). Drugs Future, 20, 135-138.
Kumar, S., Sharma, P., Kapoor, K. K. & Hundal, M. S. (2008). Tetrahedron, 64, 536-542.  [ISI] [CSD] [CrossRef] [ChemPort]
Nakayama, H. & Kasoaka, Y. (1996). Heterocycles, 42, 901-909.  [CrossRef] [ChemPort]
Sausins, A. & Duburs, G. (1988). Heterocycles, 27, 269-289.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Song, S. J., Shan, Z. X. & Jin, J. (2012). Synth. Commun. 40, 3067-3077.  [ISI] [CSD] [CrossRef]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o541  [ doi:10.1107/S1600536813006739 ]

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