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Volume 69 
Part 11 
Pages o1687-o1688  
November 2013  

Received 16 October 2013
Accepted 16 October 2013
Online 23 October 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
R = 0.041
wR = 0.119
Data-to-parameter ratio = 14.8
Details
Open access

4-Methyl-N-(4-nitro­benzyl­idene)piperazin-1-amine

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, C12H16N4O2, the piperazine ring is in a slightly distorted chair conformation. In the mol­ecule, the mean plane of the nitro group is twisted by 8.0 (3)° from that of the benzene ring. Also, the mean plane of the 2-nitro­benzyl ring is twisted slightly from that of the piperazine ring, with an N-N=C-C torsion angle of -176.24 (11)°. In the crystal, pairs of weak C-H...O inter­actions link the mol­ecules into dimers approximately along [010].

Related literature

For the biological activity of Schiff base piperzine derivatives, see: Kharb et al. (2012[Kharb, R., Bansal, K. & Sharma, A. K. (2012). Pharma Chem. 4, 2470-2488.]); Savaliya et al. (2010[Savaliya, M. D., Dobaria, J. G. & Purohit, D. M. (2010). An Indian J. 6, 267-271.]); Xu et al. (2009[Xu, R.-B., Xu, X.-Y., Wang, D.-Q., Yang, X.-J. & Li, S. (2009). Acta Cryst. E65, o2997.]); Zhou et al. (2011[Zhou, L.-N., Yan, L., Zhou, H.-L., Yang, Q.-F. & Hu, Q.-L. (2011). Acta Cryst. E67, o100.]). For therapeutic areas related to piperazines as drug mol­ecules, see: 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.]); 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.]); Cai et al. (2009[Cai, J.-L., Lu, Y.-H., Gan, L.-L. & Zhou, C.-H. (2009). Chin. J. Antibiot. 34, 454-462.]); Choudhary et al. (2006[Choudhary, P., Kumar, R. & Verma, K. (2006). Bioorg. Med. Chem. 14, 1819-1826.]); Upadhayaya et al. (2004[Upadhayaya, P. S., Sinha, N. & Jain, S. (2004). Bioorg. Med. Chem. 12, 2225-2238.]). For a review of current pharmacological and toxicological information for piperazine derivatives, see: Elliott (2011[Elliott, S. (2011). Drug Test Anal. 3, 430-438]). For the synthesis of related piperazine compounds and their medicinal and pharmaceutical activity, see: Capuano et al. (2002[Capuano, B., Crosby, I. T., Lloyd, E. J. & Taylor, D. A. (2002). Aust. J. Chem. 55, 565-576.]); Contreras et al. (2001[Contreras, J. M., Parrot, I., Sippl, W., Rival, Y. M. & Wermuth, C. G. (2001). J. Med. Chem. 44, 2707-2718.]). For related structures, see: Guo (2007[Guo, M.-L. (2007). Acta Cryst. E63, o1788-o1789.]); Ming-Lin et al. (2007[Ming-Lin, G. & You-Nong, Q. (2007). Acta Cryst. E63, o4641.]); Xu et al. (2012[Xu, R.-B., Zhang, N., Zhou, H.-Y., Yang, S. P., Li, Y.-Y., Shi, D.-H., Ma, W.-X. & Xu, X.-Y. (2012). J. Chem. Crystallogr. 42, 928-932.]); Zhou et al. (2011[Zhou, L.-N., Yan, L., Zhou, H.-L., Yang, Q.-F. & Hu, Q.-L. (2011). Acta Cryst. E67, o100.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C12H16N4O2

  • Mr = 248.29

  • Monoclinic, C 2/c

  • a = 27.9353 (14) Å

  • b = 5.9247 (3) Å

  • c = 18.7763 (7) Å

  • [beta] = 126.527 (3)°

  • V = 2497.2 (2) Å3

  • Z = 8

  • Cu K[alpha] radiation

  • [mu] = 0.77 mm-1

  • T = 173 K

  • 0.38 × 0.32 × 0.22 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 = 0.868, Tmax = 1.000

  • 7200 measured reflections

  • 2439 independent reflections

  • 2022 reflections with I > 2[sigma](I)

  • Rint = 0.031

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

  • wR(F2) = 0.119

  • S = 1.02

  • 2439 reflections

  • 165 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2B...O1i 0.99 2.47 3.4052 (19) 158
Symmetry code: (i) [-x+{\script{3\over 2}}, -y+{\script{5\over 2}}, -z+2].

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: ZL2568 ).


Acknowledgements

CNK thanks University of Mysore for research facilities and is also grateful to the Principal, Maharani's Science College for Women, Mysore, for giving permission to undertake 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.
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
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]
Cai, J.-L., Lu, Y.-H., Gan, L.-L. & Zhou, C.-H. (2009). Chin. J. Antibiot. 34, 454-462.  [ChemPort]
Capuano, B., Crosby, I. T., Lloyd, E. J. & Taylor, D. A. (2002). Aust. J. Chem. 55, 565-576.  [Web of Science] [CrossRef] [ChemPort]
Choudhary, P., Kumar, R. & Verma, K. (2006). Bioorg. Med. Chem. 14, 1819-1826.  [CrossRef] [PubMed]
Contreras, J. M., Parrot, I., Sippl, W., Rival, Y. M. & Wermuth, C. G. (2001). J. Med. Chem. 44, 2707-2718.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
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]
Guo, M.-L. (2007). Acta Cryst. E63, o1788-o1789.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Kharb, R., Bansal, K. & Sharma, A. K. (2012). Pharma Chem. 4, 2470-2488.  [ChemPort]
Ming-Lin, G. & You-Nong, Q. (2007). Acta Cryst. E63, o4641.  [CSD] [CrossRef] [IUCr Journals]
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Savaliya, M. D., Dobaria, J. G. & Purohit, D. M. (2010). An Indian J. 6, 267-271.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Upadhayaya, P. S., Sinha, N. & Jain, S. (2004). Bioorg. Med. Chem. 12, 2225-2238.  [CrossRef] [PubMed] [ChemPort]
Xu, R.-B., Xu, X.-Y., Wang, D.-Q., Yang, X.-J. & Li, S. (2009). Acta Cryst. E65, o2997.  [CSD] [CrossRef] [IUCr Journals]
Xu, R.-B., Zhang, N., Zhou, H.-Y., Yang, S. P., Li, Y.-Y., Shi, D.-H., Ma, W.-X. & Xu, X.-Y. (2012). J. Chem. Crystallogr. 42, 928-932.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Zhou, L.-N., Yan, L., Zhou, H.-L., Yang, Q.-F. & Hu, Q.-L. (2011). Acta Cryst. E67, o100.  [CrossRef] [IUCr Journals]


Acta Cryst (2013). E69, o1687-o1688   [ doi:10.1107/S1600536813028493 ]

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