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

Mohamed, S.K.; Akkurt, M.; Horton, P.N.; Abdelhamid, A.A.; Remaily, M.A.A.E.

doi:10.1107/S1600536812050222

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 (C-C) = 0.002 Å
R = 0.028
wR = 0.077
Data-to-parameter ratio = 16.9
Details

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

Shaaban K. Mohamed,^a,^b Mehmet Akkurt,^c ^* Peter N. Horton,^d Antar A. Abdelhamid ^e and Mahmoud A. A. El Remaily ^e

^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-HO hydrogen bond, with an S(8) ring motif. In the crystal, O-HO and C-HO 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). For related structures, see: Abdelhamid et al. (2011a,b); Mohamed et al. (2012); Guo et al. (2004); Sughanya & Sureshbabu (2012); Yogavel et al. (2005). For ring puckering parameters, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₂₁H₂₁BrClNO₄
M_r = 466.74
Monoclinic, P 2₁ /n
a = 8.810 (2) Å
b = 13.809 (3) Å
c = 15.797 (4) Å
= 100.026 (4)°
V = 1892.5 (8) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.627, T_max = 0.933
14959 measured reflections
4299 independent reflections
4126 reflections with I > 2(i)
R_int = 0.024

Refinement

R[F² > 2(F²)] = 0.028
wR(F²) = 0.077
S = 1.03
4299 reflections
255 parameters
H-atom parameters constrained
_max = 0.86 e Å^-3
_min = -0.38 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1AO2	0.84	1.88	2.6749 (19)	158
O4-H4O2ⁱ	0.84	1.94	2.782 (2)	176
C6-H6BO3ⁱⁱ	0.99	2.33	3.051 (2)	129
C20-H20AO3ⁱⁱ	0.99	2.53	3.486 (2)	163
C20-H20BO1ⁱ	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); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert Expert; 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, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

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

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