4,4′-Dichloro-2,2′-(piperazine-1,4-diyldimethyl­ene)diphenol

Kubono, K.; Tsuno, Y.; Tani, K.; Yokoi, K.

doi:10.1107/S1600536808035769

Volume 64
Part 12
Page o2309
December 2008

Received 15 October 2008
Accepted 31 October 2008
Online 13 November 2008

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.004 Å
R = 0.039
wR = 0.105
Data-to-parameter ratio = 11.6
Details

4,4'-Dichloro-2,2'-(piperazine-1,4-diyldimethylene)diphenol

Koji Kubono,^a ^* Yuki Tsuno,^a Keita Tani ^a and Kunihiko Yokoi ^a

^aDivision of Natural Sciences, Osaka Kyoiku University, Kashiwara, Osaka 582-8582, Japan
Correspondence e-mail: kubono@cc.osaka-kyoiku.ac.jp

In the titile compound, C₁₈H₂₀Cl₂N₂O₂, the piperazine ring adopts a chair conformation. The molecule has a non-crystallographic inversion centre in the middle of the piperazine ring at approximate position (3/4, 1/8, 3/8). There are intramolecular O-HN hydrogen bonds forming S(6) ring motifs. Intermolecular C-HO hydrogen bonds generate antiparallel C(5) chain motifs propagating along the b axis, forming sheets parallel to the bc plane with a first-level graph-set S(6)C(5)R₆⁶(26).

Related literature

For graph-set notations for hydrogen bonds, see: Bernstein et al. (1995). For the synthesis of a ligand with two piperazine arms, see: Bharathi et al. (2006). For the use of piperazine derivatives as buffers, see: Good et al. (1966). For the monoclinic and orthorhombic polymorphs of a tetrachloro-2,2'-(piperazine-1,4-diyldimethylene)diphenol, see: Kubono & Yokoi (2007). For the structure of 1,4-bis(2-hydroxy-5-methylbenzyl)piperazine, see: Kuppayee et al. (1999).

Experimental

Crystal data

C₁₈H₂₀Cl₂N₂O₂
M_r = 367.26
Orthorhombic, P b c a
a = 14.055 (4) Å
b = 21.214 (11) Å
c = 11.873 (3) Å
V = 3540 (2) Å³
Z = 8
Mo K radiation
= 0.38 mm^-1
T = 298.1 K
0.18 × 0.13 × 0.13 mm

Data collection

Rigaku AFC-7R diffractometer
Absorption correction: none
5928 measured reflections
4066 independent reflections
2735 reflections with F² > 2(F²)
R_int = 0.039
3 standard reflections every 150 reflections intensity decay: 0.7%

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.105
S = 1.00
2739 reflections
237 parameters
All H-atom parameters refined
_max = 0.33 e Å^-3
_min = -0.45 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1N1	0.85	1.88	2.649 (3)	150
O2-H20N2	0.85	1.87	2.647 (3)	151
C7-H6O2ⁱ	0.95	2.59	3.230 (3)	125
C12-H15O1ⁱⁱ	0.95	2.56	3.300 (3)	134
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, -y, z+{\script{1\over 2}}]$ .

Data collection: WinAFC (Rigaku/MSC, 2006); cell refinement: WinAFC; data reduction: CrystalStructure (Rigaku/MSC, 2006); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: CrystalStructure.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SI2120 ).

Acknowledgements

This study was supported financially in part by Grants-in-Aid (Nos. 19550040 and 20550075) from the Ministry of Education, Culture, Sports, Science, and Technology, Japan.

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.
Bharathi, K. S., Rahiman, A. K., Rajesh, K., Sreedaran, S., Aravindan, P. G., Velmurugan, D. & Narayanan, V. (2006). Polyhedron, 25, 2859-2868.
Good, N. E., Winget, G. D., Winter, W., Connolly, T. N., Izawa, S. & Singh, R. M. (1966). Biochemistry, 5, 467-477.
Kubono, K. & Yokoi, K. (2007). Acta Cryst. C63, o535-o537.
Kuppayee, M., Kumaran, D., Ponnuswamy, M. N., Kandaswamy, M., Violet, M. J., Chinnakali, K. & Fun, H.-K. (1999). Acta Cryst. C55, 2147-2149.
Rigaku/MSC (2006). WinAFC and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.

organic compounds