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Volume 69 
Part 7 
Page o1044  
July 2013  

Received 20 May 2013
Accepted 3 June 2013
Online 8 June 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.037
wR = 0.111
Data-to-parameter ratio = 14.0
Details
Open access

4-Nitrophenol-piperazine (2/1)

aDepartment of Physics, Anna University, Chennai 600 025, India, and bCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India
Correspondence e-mail: shirai2011@gmail.com

In the title adduct, C6H5NO3·0.5C4H10N2, the piperazine ring possesses inversion symmetry and has a chair conformation. Its mean plane makes a dihedral angle of 65.45 (7)° with the 4-nitrophenol ring. In the crystal, the piperazine ring is linked to two 4-nitrophenol molecules via O-H...N hydrogen bonds. The molecules are also linked via bifurcated N-H...(O,O) hydrogen bonds involving the NO2 O atoms, forming a two-dimensional network lying parallel to (102). The networks are linked via C-H...O hydrogen bonds, forming a three-dimensional structure.

Related literature

For the biological properties of piperazine compounds, see: Foroumadi et al. (2007[Foroumadi, A., Emami, S., Mansouri, S., Javidnia, A., Saeid-Adeli, N., Shirazi, F. H. & Shafiee, A. (2007). Eur. J. Med. Chem. 42, 985-992.]); Upadhayaya et al. (2004[Upadhayaya, R. S., Sinha, N., Jain, S., Kishore, N., Chandra, R. & Arora, S. K. (2004). Bioorg. Med. Chem. 12, 2225-2238.]); Chen et al. (2006[Chen, J. J., Lu, M., Jing, Y. K. & Dong, J. H. (2006). Bioorg. Med. Chem. 14, 6539-6547.]); Cunico et al. (2009[Cunico, W., Gomes, C. R. B., Moreth, M., Manhanini, D. P., Figueiredo, I. H., Penido, C., Henriques, M. G. M. O., Varotti, F. P. & Krettli, A. U. (2009). Eur. J. Med. Chem. 44, 1363-1368.]); Smits et al. (2008[Smits, R. A., Lim, H. D., Hanzer, A., Zuiderveld, O. P., Guaita, E., Adami, M., Coruzzi, G., Leurs, R. & Esch, I. J. P. (2008). J. Med. Chem. 51, 2457-2467.]); Becker et al. (2006[Becker, O. M., Dhanoa, D. S., Marantz, Y., Chen, D., Shacham, S., Cheruku, S., Heifetz, A., Mohanty, P., Fichman, M., Sharadendu, A., Nudelman, R., Kauffman, M. & Noiman, S. (2006). J. Med. Chem. 49, 3116-3135.]).

[Scheme 1]

Experimental

Crystal data
  • C6H5NO3·0.5C4H10N2

  • Mr = 182.18

  • Monoclinic, P 21 /c

  • a = 6.1879 (2) Å

  • b = 19.9274 (7) Å

  • c = 6.9846 (2) Å

  • [beta] = 91.199 (1)°

  • V = 861.07 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 293 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker SMART APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, U. S. A.]) Tmin = 0.968, Tmax = 0.979

  • 12570 measured reflections

  • 1763 independent reflections

  • 1437 reflections with I > 2[sigma](I)

  • Rint = 0.024

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.111

  • S = 1.04

  • 1763 reflections

  • 126 parameters

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

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H3A...N2i 0.82 1.82 2.6210 (16) 167
N2-H2A...O1 0.796 (19) 2.58 (2) 3.2437 (17) 141.4 (17)
N2-H2A...O2 0.796 (19) 2.557 (19) 3.2273 (17) 142.8 (19)
C2-H2...O1i 0.93 2.51 3.3428 (17) 149
C6-H6...O3ii 0.93 2.57 3.5035 (17) 179
Symmetry codes: (i) [x-1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, U. S. A.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, U. S. A.]); data reduction: SAINT; 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2605 ).


Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. TS and DV thank the UGC (SAP-CAS) for the departmental facilities. TS also thanks DST Inspire for a fellowship.

References

Becker, O. M., Dhanoa, D. S., Marantz, Y., Chen, D., Shacham, S., Cheruku, S., Heifetz, A., Mohanty, P., Fichman, M., Sharadendu, A., Nudelman, R., Kauffman, M. & Noiman, S. (2006). J. Med. Chem. 49, 3116-3135.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, U. S. A.
Chen, J. J., Lu, M., Jing, Y. K. & Dong, J. H. (2006). Bioorg. Med. Chem. 14, 6539-6547.  [CrossRef] [PubMed] [ChemPort]
Cunico, W., Gomes, C. R. B., Moreth, M., Manhanini, D. P., Figueiredo, I. H., Penido, C., Henriques, M. G. M. O., Varotti, F. P. & Krettli, A. U. (2009). Eur. J. Med. Chem. 44, 1363-1368.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Foroumadi, A., Emami, S., Mansouri, S., Javidnia, A., Saeid-Adeli, N., Shirazi, F. H. & Shafiee, A. (2007). Eur. J. Med. Chem. 42, 985-992.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Smits, R. A., Lim, H. D., Hanzer, A., Zuiderveld, O. P., Guaita, E., Adami, M., Coruzzi, G., Leurs, R. & Esch, I. J. P. (2008). J. Med. Chem. 51, 2457-2467.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Upadhayaya, R. S., Sinha, N., Jain, S., Kishore, N., Chandra, R. & Arora, S. K. (2004). Bioorg. Med. Chem. 12, 2225-2238.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o1044  [ doi:10.1107/S1600536813015328 ]

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