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Volume 69 
Part 1 
Pages o85-o86  
January 2013  

Received 3 December 2012
Accepted 9 December 2012
Online 15 December 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.028
wR = 0.077
Data-to-parameter ratio = 16.9
Details
Open access

9-(3-Bromo-5-chloro-2-hydroxyphenyl)-10-(2-hydroxyethyl)-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione

aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England,bChemistry Department, Faculty of Science, Minia University, El-Minia, Egypt,cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,dSchool of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, England, and eDepartment of Chemistry, Sohag University, 82524 Sohag, Egypt
Correspondence e-mail: akkurt@erciyes.edu.tr

In the title compound, C21H21BrClNO4, the dihydropyridine ring adopts a flattened boat conformation. The 3-bromo-5-chloro-2-hydroxyphenyl ring forms a dihedral angles of 84.44 (7)° with the dihydropyridine mean plane. The molecular conformation is stabilized by an intramolecular O-H...O hydrogen bond, with an S(8) ring motif. In the crystal, O-H...O and C-H...O hydrogen bonds link the molecules, forming a three-dimensional network.

Related literature

For the synthesis and bioactivity of acridines, see, for example: Karolak-Wojciechowska et al. (1996[Karolak-Wojciechowska, J., Mrozek, A., Amiel, P., Brouant, P. & Barbe, J. (1996). Acta Cryst. C52, 2939-2941.]). For related structures, see: Abdelhamid et al. (2011a[Abdelhamid, A. A., Mohamed, S. K., Khalilov, A. N., Gurbanov, A. V. & Ng, S. W. (2011a). Acta Cryst. E67, o744.],b[Abdelhamid, A. A., Mohamed, S. K., Allahverdiyev, M. A., Gurbanov, A. V. & Ng, S. W. (2011b). Acta Cryst. E67, o785.]); Mohamed et al. (2012[Mohamed, S. K., Abdelhamid, A. A., Maharramov, A. M., Khalilov, A. N., Gurbanov, A. V. & Allahverdiyev, M. A. (2012). J. Chem. Pharm. Res. 4, 955-965.]); Guo et al. (2004[Guo, C., Tu, S., Li, T. & Zhu, S. (2004). Acta Cryst. E60, o2035-o2037.]); Sughanya & Sureshbabu (2012[Sughanya, V. & Sureshbabu, N. (2012). Acta Cryst. E68, o2755.]); Yogavel et al. (2005[Yogavel, M., Velmurugan, D., Murugan, P., Shanmuga Sundara Raj, S. & Fun, H.-K. (2005). Acta Cryst. E61, o2761-o2763.]). For ring puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). 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.]).

[Scheme 1]

Experimental

Crystal data
  • C21H21BrClNO4

  • Mr = 466.74

  • Monoclinic, P 21 /n

  • a = 8.810 (2) Å

  • b = 13.809 (3) Å

  • c = 15.797 (4) Å

  • [beta] = 100.026 (4)°

  • V = 1892.5 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 2.34 mm-1

  • T = 100 K

  • 0.22 × 0.14 × 0.03 mm

Data collection
  • Rigaku AFC12 (Right) diffractometer

  • Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2012[Rigaku (2012). CrystalClear-SM Expert. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.627, Tmax = 0.933

  • 14959 measured reflections

  • 4299 independent reflections

  • 4126 reflections with I > 2[sigma](i)

  • Rint = 0.024

Refinement
  • R[F2 > 2[sigma](F2)] = 0.028

  • wR(F2) = 0.077

  • S = 1.03

  • 4299 reflections

  • 255 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.86 e Å-3

  • [Delta][rho]min = -0.38 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1A...O2 0.84 1.88 2.6749 (19) 158
O4-H4...O2i 0.84 1.94 2.782 (2) 176
C6-H6B...O3ii 0.99 2.33 3.051 (2) 129
C20-H20A...O3ii 0.99 2.53 3.486 (2) 163
C20-H20B...O1i 0.99 2.57 3.492 (2) 154
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (ii) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: CrystalClear-SM Expert (Rigaku, 2012[Rigaku (2012). CrystalClear-SM Expert. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert Expert; 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.]) 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: HG5278 ).


Acknowledgements

The EPSRC National Crystallography Service is gratefully acknowledged for the data collection. The authors are thankful to Manchester Metropolitan University, Sohag University and Erciyes University for supporting this study.

References

Abdelhamid, A. A., Mohamed, S. K., Allahverdiyev, M. A., Gurbanov, A. V. & Ng, S. W. (2011b). Acta Cryst. E67, o785.  [CSD] [CrossRef] [details]
Abdelhamid, A. A., Mohamed, S. K., Khalilov, A. N., Gurbanov, A. V. & Ng, S. W. (2011a). Acta Cryst. E67, o744.  [CSD] [CrossRef] [details]
Bernstein, J., Davis, 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]
Guo, C., Tu, S., Li, T. & Zhu, S. (2004). Acta Cryst. E60, o2035-o2037.  [CSD] [CrossRef] [details]
Karolak-Wojciechowska, J., Mrozek, A., Amiel, P., Brouant, P. & Barbe, J. (1996). Acta Cryst. C52, 2939-2941.  [CSD] [CrossRef] [details]
Mohamed, S. K., Abdelhamid, A. A., Maharramov, A. M., Khalilov, A. N., Gurbanov, A. V. & Allahverdiyev, M. A. (2012). J. Chem. Pharm. Res. 4, 955-965.  [ChemPort]
Rigaku (2012). CrystalClear-SM Expert. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Sughanya, V. & Sureshbabu, N. (2012). Acta Cryst. E68, o2755.  [CSD] [CrossRef] [details]
Yogavel, M., Velmurugan, D., Murugan, P., Shanmuga Sundara Raj, S. & Fun, H.-K. (2005). Acta Cryst. E61, o2761-o2763.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o85-o86   [ doi:10.1107/S1600536812050222 ]

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