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Volume 69 
Part 11 
Page o1706  
November 2013  

Received 16 October 2013
Accepted 17 October 2013
Online 26 October 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.004 Å
R = 0.058
wR = 0.163
Data-to-parameter ratio = 23.4
Details
Open access

N-(1H-Indol-3-yl­methyl­idene)-4-methyl­piperazin-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, C14H18N4, the piperazine ring is in a slightly distorted chair conformation. The indole ring system is twisted from the piperazine ring, making a dihedral angle of 7.27 (11)°. In the crystal, N-H...N hydrogen bonds link mol­ecules into chains along [10-1].

Related literature

For a review of the current pharmacological and toxicological information for piperazine, see: Elliott (2011[Elliott, S. (2011). Drug Test Anal. 3, 430-438.]). For the biological activity of Schiff base ligands, 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. (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.]). 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. (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 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
  • C14H18N4

  • Mr = 242.32

  • Monoclinic, P n

  • a = 7.5630 (5) Å

  • b = 6.5593 (4) Å

  • c = 13.2319 (9) Å

  • [beta] = 100.072 (6)°

  • V = 646.29 (7) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 173 K

  • 0.48 × 0.33 × 0.18 mm

Data collection
  • Agilent Gemini Eos 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

  • 7074 measured reflections

  • 3857 independent reflections

  • 3214 reflections with I > 2[sigma](I)

  • Rint = 0.050

Refinement
  • R[F2 > 2[sigma](F2)] = 0.058

  • wR(F2) = 0.163

  • S = 1.06

  • 3857 reflections

  • 165 parameters

  • 2 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.35 e Å-3

  • [Delta][rho]min = -0.31 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N4-H4...N1i 0.88 2.29 2.947 (3) 131
Symmetry code: (i) [x-{\script{1\over 2}}, -y+1, z+{\script{1\over 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: HG5354 ).


Acknowledgements

CNK thanks University of Mysore for research facilities and 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.
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]
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, o1706  [ doi:10.1107/S1600536813028523 ]

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