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Volume 69 
Part 10 
Page o1580  
October 2013  

Received 8 August 2013
Accepted 13 September 2013
Online 21 September 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.002 Å
R = 0.043
wR = 0.119
Data-to-parameter ratio = 11.5
Details
Open access

3-(4-Hydroxyphenyl)-1,5-bis(pyridin-2-yl)pentane-1,5-dione

aState Key Laboratory of Non-Food Biomass and Enzyme Technology, National Engineering Research Center for Non-Food Biorefinery, Guangxi Key Laboratory of Biorefinery, Guangxi Academy of Sciences, Nanning, Guangxi 530007, People's Republic of China, and bSchool of Chemistry and Chemical Engeneering, Guangxi University, Nanning, Guangxi 530004, People's Republic of China
Correspondence e-mail: mzmz2009@sohu.com

In the title molecule, C21H18N2O3, the pyridine rings make a dihedral angle of 13.1 (1)°. The phenyl ring is approximately perpendicular to both of them, forming dihedral angles of 87.4 (1)and 81.9 (1)°. In the crystal, pairs of O-H...N hydrogen bonds link the molecules into centrosymmetric dimers. Additional C-H...O, [pi]-[pi] [centroid-centroid distance = 3.971 (2) Å] and C-H...[pi] interactions consolidate the dimers into a three-dimensional network.

Related literature

For the synthesis of the title compound, see: Constable et al. (1990[Constable, E. C., Lewis, J., Liptrot, M. C. & Raithby, P. R. (1990). Inorg. Chim. Acta, 178, 47-54.], 1998[Constable, E. C., Neuburger, M., Smith, D. R. & Zehnder, M. (1998). Inorg. Chim. Acta, 275, 359-365.]); He et al. (2006[He, G.-F., Huang, X.-Q., Dou, J.-M., Li, D.-C. & Wang, D.-Q. (2006). Acta Cryst. E62, o4689-o4690.]). For the syntheses of terpyridine compounds and their properties and applications, see: Ma et al. (2009[Ma, Z., Xing, Y., Yang, M., Hu, M., da Liu, B. G., Silva, M. F. C. & Pombeiro, A. J. L. (2009). Inorg. Chim. Acta, 362, 2921-2926.], 2010[Ma, Z., Cao, Y., Li, Q., da Guedes da Silva, M. F. C. F., Silva, J. J. R. & Pombeiro, A. J. L. (2010). J. Inorg. Biochem. 104, 704-711.], 2012[Ma, Z., Liang, B., Yang, M. & Lu, L. (2012). Acta Cryst. E68, m298-m299.], 2013[Ma, Z., Lu, W., Liang, B. & Pombeiro, A. J. L. (2013). New J. Chem. 37, 1529-1537.]). 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
  • C21H18N2O3

  • Mr = 346.37

  • Triclinic, [P \overline 1]

  • a = 8.4392 (6) Å

  • b = 10.6683 (7) Å

  • c = 11.0755 (8) Å

  • [alpha] = 100.623 (6)°

  • [beta] = 103.867 (6)°

  • [gamma] = 110.550 (6)°

  • V = 866.05 (10) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 298 K

  • 0.39 × 0.38 × 0.22 mm

Data collection
  • Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO, Agilent, 2012[Agilent (2012). CrysAlis PRO., Agilent Technologies, Yarnton, England.]) Tmin = 0.813, Tmax = 1.000

  • 6339 measured reflections

  • 3544 independent reflections

  • 2661 reflections with I > 2[sigma](I)

  • Rint = 0.017

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.119

  • S = 1.03

  • 3544 reflections

  • 308 parameters

  • All H-atom parameters refined

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.14 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C16-C21 ring.

D-H...A D-H H...A D...A D-H...A
O3-H03A...N2i 0.93 (2) 2.00 (2) 2.8940 (19) 160 (2)
C12-H12A...O2ii 0.96 (2) 2.48 (2) 3.312 (3) 145 (2)
C4a-H4a...Cg3iii 0.99 (2) 0.98 (2) 3.825 (2) 144 (2)
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+2, -y+2, -z+1; (iii) x, y-1, z.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO., Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); 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: LD2113 ).


Acknowledgements

The authors are grateful for financial support from the Opening Project of Guangxi Key Laboratory of Petrochemical Resource Processing and Process Intensification Technology (K008).

References

Agilent (2012). CrysAlis PRO., 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.
Constable, E. C., Lewis, J., Liptrot, M. C. & Raithby, P. R. (1990). Inorg. Chim. Acta, 178, 47-54.  [CSD] [CrossRef] [ChemPort] [Web of Science]
Constable, E. C., Neuburger, M., Smith, D. R. & Zehnder, M. (1998). Inorg. Chim. Acta, 275, 359-365.  [CSD] [CrossRef]
He, G.-F., Huang, X.-Q., Dou, J.-M., Li, D.-C. & Wang, D.-Q. (2006). Acta Cryst. E62, o4689-o4690.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Ma, Z., Cao, Y., Li, Q., da Guedes da Silva, M. F. C. F., Silva, J. J. R. & Pombeiro, A. J. L. (2010). J. Inorg. Biochem. 104, 704-711.  [Web of Science] [CSD] [CrossRef] [ChemPort] [PubMed]
Ma, Z., Liang, B., Yang, M. & Lu, L. (2012). Acta Cryst. E68, m298-m299.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Ma, Z., Lu, W., Liang, B. & Pombeiro, A. J. L. (2013). New J. Chem. 37, 1529-1537.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Ma, Z., Xing, Y., Yang, M., Hu, M., da Liu, B. G., Silva, M. F. C. & Pombeiro, A. J. L. (2009). Inorg. Chim. Acta, 362, 2921-2926.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1580  [ doi:10.1107/S1600536813025518 ]

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