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Volume 69 
Part 11 
Page o1671  
November 2013  

Received 9 October 2013
Accepted 12 October 2013
Online 19 October 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
R = 0.041
wR = 0.113
Data-to-parameter ratio = 14.5
Details
Open access

1-[4-(4-Hy­droxy­phen­yl)piperazin-1-yl]ethanone

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, C12H16N2O2, the piperazine ring has a chair conformation. The dihedral angle between the mean planes of the benzene ring and the acetyl group is 48.7 (1)°. In the crystal, mol­ecules are linked via O-H...O hydrogen bonds, forming chains propagating along [010].

Related literature

For the biological activity of piperazine derivatives, 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.]); Elliott (2011[Elliott, S. (2011). Drug Test Anal. 3, 430-438.]); Kharb et al. (2012[Kharb, R., Bansal, K. & Sharma, A. K. (2012). Pharma Chem. 4, 2470-2488.]). For the crystal structures of related compounds, see: Dayananda et al. (2012[Dayananda, A. S., Yathirajan, H. S., Keeley, A. C. & Jasinski, J. P. (2012). Acta Cryst. E68, o2237.]); Kavitha et al. (2013a[Kavitha, C. N., Butcher, R. J., Jasinski, J. P., Yathirajan, H. S. & Dayananda, A. S. (2013a). Acta Cryst. E69, o485-o486.],b[Kavitha, C. N., Jasinski, J. P., Matar, S. M., Yathirajan, H. S. & Ramesha, A. R. (2013b). Acta Cryst. E69, o1344.]); Peeters et al. (1979[Peeters, O. M., Blaton, N. M. & De Ranter, C. J. (1979). Acta Cryst. B35, 2461-2464.], 2004[Peeters, O. M., Blaton, N. M., Gerber, J. G. & Gal, J. (2004). Acta Cryst. E60, o367-o369.]). 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
  • C12H16N2O2

  • Mr = 220.27

  • Monoclinic, P 21 /c

  • a = 6.13183 (19) Å

  • b = 12.0106 (4) Å

  • c = 14.8704 (5) Å

  • [beta] = 94.025 (3)°

  • V = 1092.46 (6) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.75 mm-1

  • T = 173 K

  • 0.48 × 0.46 × 0.32 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 = 0.833, Tmax = 1.000

  • 6224 measured reflections

  • 2134 independent reflections

  • 1944 reflections with I > 2[sigma](I)

  • Rint = 0.025

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

  • wR(F2) = 0.113

  • S = 1.07

  • 2134 reflections

  • 147 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
O2-H2...O1i 0.82 1.88 2.6953 (14) 170
Symmetry code: (i) x, y+1, z.

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: SU2656 ).


Acknowledgements

CNK thanks the University of Mysore for research facilities and is also grateful to the Principal, Maharani's Science College for Women, Mysore, for permission to carry out 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]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Dayananda, A. S., Yathirajan, H. S., Keeley, A. C. & Jasinski, J. P. (2012). Acta Cryst. E68, o2237.  [CSD] [CrossRef] [IUCr Journals]
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]
Kavitha, C. N., Butcher, R. J., Jasinski, J. P., Yathirajan, H. S. & Dayananda, A. S. (2013a). Acta Cryst. E69, o485-o486.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Kavitha, C. N., Jasinski, J. P., Matar, S. M., Yathirajan, H. S. & Ramesha, A. R. (2013b). Acta Cryst. E69, o1344.  [CSD] [CrossRef] [IUCr Journals]
Kharb, R., Bansal, K. & Sharma, A. K. (2012). Pharma Chem. 4, 2470-2488.  [ChemPort]
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Peeters, O. M., Blaton, N. M. & De Ranter, C. J. (1979). Acta Cryst. B35, 2461-2464.  [CSD] [CrossRef] [IUCr Journals]
Peeters, O. M., Blaton, N. M., Gerber, J. G. & Gal, J. (2004). Acta Cryst. E60, o367-o369.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1671  [ doi:10.1107/S1600536813028031 ]

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