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Volume 69 
Part 11 
Page o1669  
November 2013  

Received 10 October 2013
Accepted 13 October 2013
Online 19 October 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.004 Å
R = 0.041
wR = 0.108
Data-to-parameter ratio = 13.7
Details
Open access

Bis{4-[(1,3-benzodioxol-5-yl)meth­yl]piperazin-1-yl}methane

aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
Correspondence e-mail: jjasinski@keene.edu

In the title compound, C25H32N4O4, both piperazine rings adopt a chair conformation. One of dioxolane ring systems is essentially planar [dihedral angle = 0.9 (2)°] while the other adopts a slightly disordered envelope conformation, the mean plane of the dioxolane ring being twisted by 3.6 (2)° from that of the benzene ring. The dihedral angle between the benzene rings is 69.9 (5)°. No classical hydrogen bonds were observed.

Related literature

For the biological activity of piperazines, see: Choudhary et al. (2006[Choudhary, P., Kumar, R. & Verma, K. (2006). Bioorg. Med. Chem. 14, 1819-1826.]); Kharb et al. (2012[Kharb, R., Bansal, K. & Sharma, A. K. (2012). Pharma Chem. 4, 2470-2488.]); Millan et al. (2001[Millan, M. J., Cussac, D. & Milligan, G. (2001). J. Pharm. Exp. Ther. 297, 876-887.]); Brockunier et al. (2004[Brockunier, L. L., He, J., Colwell, L. F. Jr, Habulihaz, B., He, H., Leiting, B., Lyons, K. A., Marsilio, F., Patel, R. A., Teffera, Y., Wu, J. K., Thornberry, N. A., Weber, A. E. & Parmee, E. R. (2004). Bioorg. Med. Chem. Lett. 14, 4763-4766.]); Bogatcheva et al. (2006[Bogatcheva, E., Hanrahan, C., Nikonenko, B., Samala, R., Chen, P., Gearhart, J., Barbosa, F., Einck, L., Nacy, C. A. & Protopopova, M. (2006). J. Med. Chem. 49, 3045-3048.]); Elliott (2011[Elliott, S. (2011). Drug Test Anal. 3, 430-438.]). For related structures, see: Capuano et al. (2000[Capuano, B., Crosby, I. T., Gable, R. W. & Lloyd, E. J. (2000). Acta Cryst. C56, 339-340.]). For puckering parameters, see Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C25H32N4O4

  • Mr = 452.55

  • Orthorhombic, P n 21 a

  • a = 38.8025 (10) Å

  • b = 9.7675 (2) Å

  • c = 6.09571 (13) Å

  • V = 2310.29 (10) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.72 mm-1

  • T = 173 K

  • 0.38 × 0.21 × 0.11 mm

Data collection
  • Agilent Xcalibur (Eos, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]) Tmin = 0.836, Tmax = 1.000

  • 13559 measured reflections

  • 4199 independent reflections

  • 3869 reflections with I > 2[sigma](I)

  • Rint = 0.046

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.108

  • S = 1.02

  • 4199 reflections

  • 307 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

  • Absolute structure: Flack parameter determined using 1513 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack, 2004[Parsons, S. & Flack, H. (2004). Acta Cryst. A60, s61.])

  • Absolute structure parameter: -0.03 (15)

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007[Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.]); program(s) used to refine structure: SHELXL2012 (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: FJ2646 ).


Acknowledgements

CNK thanks the University of Mysore for research facilities and is also grateful to the Principal, Maharani's Science College for Women in Mysore, for giving permission to do research. JPJ acknowledges the NSF-MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

References

Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.
Bogatcheva, E., Hanrahan, C., Nikonenko, B., Samala, R., Chen, P., Gearhart, J., Barbosa, F., Einck, L., Nacy, C. A. & Protopopova, M. (2006). J. Med. Chem. 49, 3045-3048.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Brockunier, L. L., He, J., Colwell, L. F. Jr, Habulihaz, B., He, H., Leiting, B., Lyons, K. A., Marsilio, F., Patel, R. A., Teffera, Y., Wu, J. K., Thornberry, N. A., Weber, A. E. & Parmee, E. R. (2004). Bioorg. Med. Chem. Lett. 14, 4763-4766.  [CrossRef] [PubMed] [ChemPort]
Capuano, B., Crosby, I. T., Gable, R. W. & Lloyd, E. J. (2000). Acta Cryst. C56, 339-340.  [CSD] [CrossRef] [IUCr Journals]
Choudhary, P., Kumar, R. & Verma, K. (2006). Bioorg. Med. Chem. 14, 1819-1826.  [CrossRef] [PubMed]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
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]
Elliott, S. (2011). Drug Test Anal. 3, 430-438.  [CrossRef] [ChemPort] [PubMed]
Kharb, R., Bansal, K. & Sharma, A. K. (2012). Pharma Chem. 4, 2470-2488.  [ChemPort]
Millan, M. J., Cussac, D. & Milligan, G. (2001). J. Pharm. Exp. Ther. 297, 876-887.  [ChemPort]
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Parsons, S. & Flack, H. (2004). Acta Cryst. A60, s61.  [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1669  [ doi:10.1107/S1600536813028109 ]

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