3-(4-Chloro­benzo­yl)-4-(4-chloro­phen­yl)-1-phenethyl­piperidin-4-ol

Aydın, A.; Akkurt, M.; Mete, E.; Sahin, E.; Gul, H.I.

doi:10.1107/S1600536811018034

Volume 67
Part 6
Pages o1447-o1448
June 2011

Received 22 April 2011
Accepted 12 May 2011
Online 20 May 2011

Key indicators
Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.008 Å
R = 0.097
wR = 0.148
Data-to-parameter ratio = 17.1
Details

3-(4-Chlorobenzoyl)-4-(4-chlorophenyl)-1-phenethylpiperidin-4-ol

Abdullah Aydin,^a ^* Mehmet Akkurt,^b Ebru Mete,^c Ertan Sahin ^c and Halise Inci Gul ^d

^aDepartment of Science Education, Faculty of Education, Kastamonu University, 37200 Kastamonu, Turkey,^bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,^cDepartment of Chemistry, Faculty of Sciences, Ataturk University, 25240 Erzurum, Turkey, and ^dDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Ataturk University, 25240 Erzurum, Turkey
Correspondence e-mail: aaydin@kastamonu.edu.tr

In the title compound, C₂₆H₂₅Cl₂NO₂, the piperidine ring adopts a chair conformation with a cis configuration of the carbonyl and hydroxy substituents. The dihedral angle between the aromatic rings of the chlorobenzene groups is 24.3 (2)°. The phenyl ring forms dihedral angles of 59.4 (3) and 44.1 (3)° with the benzene rings. In the crystal, molecules are linked by intermolecular O-HN and C-HO hydrogen bonds and C-H [pi] interactions into layers parallel to the bc plane.

Related literature

For the synthesis and biological activity of Mannich bases, see: Dimmock et al. (1991); Dimmock & Kumar (1997); Gul et al. (2001, 2004, 2005); Atwal et al. (1969); Gul (2005); Erciyas et al. (1994); Porretta et al. (1995); Piscopo et al. (1986); Manavathu et al. (1998); Vashishtha et al. (1998); Canturk et al. (2008); Suleyman et al. (2007); Yogeeswari et al. (2005); Mete et al. (2010a,b) For MOPAC AM1 theoretical full-geometry optimization, see: Dewar et al. (1985); Stewart (1993). For bond-length data, see: Allen et al. (1987). For puckering parameters, see: Cremer & Pople (1975).

Experimental

Crystal data

C₂₆H₂₅Cl₂NO₂
M_r = 454.37
Monoclinic, P 2₁ /c
a = 16.950 (4) Å
b = 12.863 (3) Å
c = 10.792 (2) Å
= 97.779 (13)°
V = 2331.3 (9) Å³
Z = 4
Mo K radiation
= 0.30 mm^-1
T = 294 K
0.23 × 0.14 × 0.12 mm

Data collection

Rigaku R-AXIS RAPID-S diffractometer
Absorption correction: multi-scan [XABS2 (Parkin et al., 1995); cubic fit to sin()/, 24 parameters] T_min = 0.934, T_max = 0.965
4830 measured reflections
4830 independent reflections
1939 reflections with I > 2(I)

Refinement

R[F² > 2(F²)] = 0.097
wR(F²) = 0.148
S = 1.07
4830 reflections
282 parameters
H-atom parameters constrained
_max = 0.18 e Å^-3
_min = -0.13 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C15-C20 and C21-C26 benzene rings, respectively.

D-HA	D-H	HA	DA	D-HA
O1-H1AN1ⁱ	0.82	2.11	2.879 (5)	155
C13-H13BO2ⁱⁱ	0.97	2.54	3.372 (5)	144
C2-H2Cg2ⁱⁱⁱ	0.93	2.85	3.739 (9)	159
C16-H16Cg3^iv	0.93	2.85	3.646 (5)	144
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x, -y+1, -z; (iii) $[-x, y-{\script{1\over 2}}, -z-{\script{1\over 2}}]$ ; (iv) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2590 ).

Acknowledgements

The authors are indebted to the Department of Chemistry, Ataturk University, Erzurum, Turkey, for use of the X-ray diffractometer purchased under grant No. 2003/219 of the University Research Fund. In addition, this work was partly supported by a grant from the Ataturk University Research Fund (project No. 2006/96).

References

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organic compounds