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Volume 69 
Part 7 
Page o1140  
July 2013  

Received 17 June 2013
Accepted 18 June 2013
Online 22 June 2013

Key indicators
Single-crystal X-ray study
T = 291 K
Mean [sigma](C-C) = 0.002 Å
R = 0.039
wR = 0.112
Data-to-parameter ratio = 13.2
Details
Open access

2-{4-[(1,3-Benzodioxol-5-yl)methyl]piperazin-1-yl}pyrimidine

aSchool of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou 450001, People's Republic of China
Correspondence e-mail: wcllaoshi@yahoo.com.cn

In the title compound, C16H18N4O2, known also as peribedil, the dihedral angle between the mean planes of the pyrimidine and benzene rings is 56.5 (8)°. The 1,3-dioxole fragment adopts an envelope conformation with the methylene C atom forming the flap; this atom deviates by 0.232 (3) Å from the plane defined by the remaining atoms of the 1,3-benzodioxole unit. In the crystal, C-H...[pi] interactions between c-glide-related molecules arrange them into columns extending along the c-axis direction. The columns related by a unit translation along the b axis are packed into (100) layers via another C-H...[pi] interaction involving the pyrimidine ring as an acceptor.

Related literature

For details of the synthesis of piribedil, see: Duncton et al. (2006[Duncton, M. A. J., Roffey, J. R. A., Hamlyn, R. J. & Adams, D. R. (2006). Tetrahedron Lett. 47, 2549-2552.]); Conroy & Denton (1953[Conroy, E. A. & Denton, J. J. (1953). J. Org. Chem. 18, 1489-1491.]); Hamid et al. (2007[Hamid, M. H. A. & Williams, J. M. J. (2007). Tetrahedron Lett., 48, 8263-8265.]). For the pharmacological activity of the title compound, see: Rondot et al. (1992[Rondot, P. & Ziegler, M. (1992). J. Neurol. pp. S28-S34.]).

[Scheme 1]

Experimental

Crystal data
  • C16H18N4O2

  • Mr = 298.34

  • Orthorhombic, P c c n

  • a = 21.3085 (6) Å

  • b = 18.6249 (4) Å

  • c = 7.48851 (19) Å

  • V = 2971.95 (12) Å3

  • Z = 8

  • Cu K[alpha] radiation

  • [mu] = 0.74 mm-1

  • T = 291 K

  • 0.25 × 0.2 × 0.2 mm

Data collection
  • Agilent Xcalibur (Eos, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.])' Tmin = 0.910, Tmax = 1.000

  • 6334 measured reflections

  • 2635 independent reflections

  • 2186 reflections with I > 2[sigma](I)

  • Rint = 0.019

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.112

  • S = 1.03

  • 2635 reflections

  • 200 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.13 e Å-3

  • [Delta][rho]min = -0.14 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the pyrimidine ring and Cg2 is the centroid of the benzene ring.

D-H...A D-H H...A D...A D-H...A
C2-H2...Cg1i 0.93 2.83 3.6771 (17) 152
C9-H9B...Cg1ii 0.97 2.92 3.8090 (18) 152
C16-H16A...Cg2iii 0.97 2.80 3.689 (2) 153
Symmetry codes: (i) [x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) x, y, z-1; (iii) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2582 ).


Acknowledgements

We thank Hongmin Liu (Zhengzhou University) for the analysis of the single-crystal data.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Conroy, E. A. & Denton, J. J. (1953). J. Org. Chem. 18, 1489-1491.  [CrossRef] [ChemPort]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Duncton, M. A. J., Roffey, J. R. A., Hamlyn, R. J. & Adams, D. R. (2006). Tetrahedron Lett. 47, 2549-2552.  [Web of Science] [CrossRef] [ChemPort]
Hamid, M. H. A. & Williams, J. M. J. (2007). Tetrahedron Lett., 48, 8263-8265.  [Web of Science] [CrossRef] [ChemPort]
Rondot, P. & Ziegler, M. (1992). J. Neurol. pp. S28-S34.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1140  [ doi:10.1107/S1600536813016851 ]

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