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Volume 69 
Part 5 
Page o732  
May 2013  

Received 12 December 2012
Accepted 9 April 2013
Online 13 April 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
Disorder in main residue
R = 0.078
wR = 0.233
Data-to-parameter ratio = 11.6
Details
Open access

1-(3-Chlorophenyl)-5-(2,4-dihydroxybenzoyl)pyridin-2(1H)-one

aThe First Affiliated Hospital of Xinxiang Medical University, Weihui 453100, Henan Province, People's Republic of China
Correspondence e-mail: RenFang788@163.com

The chlorophenyl group of the title compound, C18H12ClNO4, is disordered over two orientations with occupancies of 0.331 (8) and 0.669 (8). An intramolecular hydrogen bond is formed between a hydroxy group and the acyclic carbonyl group. In the crystal, molecules are linked into chains along [110] by O-H...O and C-H...O hydrogen bonds, forming a ladder motif.

Related literature

For similar structures, see: Ravinder et al. (2012[Ravinder, M., Mahendar, B., Mattapally, S., Hamsini, K. V., Reddy, T. N., Rohit, C., Srinivas, K., Banerjee, S. K. & Rao, V. J. (2012). Bioorg. Med. Chem. Lett. 22, 6010-6015.]); Sengupta et al. (2012[Sengupta, T., Gayen, K. S., Pandit, P. & Maiti, D. K. (2012). Chem. Eur. J. 18, 1905-1909.]). For the synthesis, see: Chen et al. (2011[Chen, H., Xie, F., Gong, J. & Hu, Y. (2011). J. Org. Chem. 70, 8495-8500.]); Kim & Hong (2011[Kim, D. & Hong, S. (2011). Org. Lett. 13, 4466-4469.]). For the biological activity of similar structures, see: Kim et al. (2010[Kim, K. H., Kim, N. D. & Seong, B. L. (2010). Molecules, 15, 5878-5908.]).

[Scheme 1]

Experimental

Crystal data
  • C18H12ClNO4

  • Mr = 341.74

  • Triclinic, [P \overline 1]

  • a = 6.689 (3) Å

  • b = 9.009 (4) Å

  • c = 13.257 (6) Å

  • [alpha] = 87.193 (5)°

  • [beta] = 87.719 (5)°

  • [gamma] = 82.674 (5)°

  • V = 791.0 (6) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.26 mm-1

  • T = 293 K

  • 0.15 × 0.12 × 0.05 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2002[Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.962, Tmax = 0.987

  • 3286 measured reflections

  • 2726 independent reflections

  • 1929 reflections with I > 2[sigma](I)

  • Rint = 0.049

Refinement
  • R[F2 > 2[sigma](F2)] = 0.078

  • wR(F2) = 0.233

  • S = 1.00

  • 2726 reflections

  • 236 parameters

  • 48 restraints

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

  • [Delta][rho]max = 0.36 e Å-3

  • [Delta][rho]min = -0.43 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2...O3 0.91 (4) 1.75 (4) 2.587 (3) 152 (3)
O1-H1...O4i 0.87 (5) 1.79 (5) 2.655 (3) 175 (4)
C3-H3...O4i 0.93 2.50 3.165 (3) 129
C15-H15...O1ii 0.93 2.71 3.37 (2) 129
Symmetry codes: (i) x-1, y-1, z; (ii) -x+1, -y, -z+1.

Data collection: SMART (Bruker, 2002[Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FY2085 ).


Acknowledgements

We are grateful to Attending Physician Tongqin Hao (The First Affiliated Hospital of Xinxiang Medical University, Henan, China) for the assistance with the antitumor assay.

References

Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chen, H., Xie, F., Gong, J. & Hu, Y. (2011). J. Org. Chem. 70, 8495-8500.  [CrossRef]
Kim, D. & Hong, S. (2011). Org. Lett. 13, 4466-4469.  [ISI] [CrossRef] [ChemPort] [PubMed]
Kim, K. H., Kim, N. D. & Seong, B. L. (2010). Molecules, 15, 5878-5908.  [CrossRef] [ChemPort] [PubMed]
Ravinder, M., Mahendar, B., Mattapally, S., Hamsini, K. V., Reddy, T. N., Rohit, C., Srinivas, K., Banerjee, S. K. & Rao, V. J. (2012). Bioorg. Med. Chem. Lett. 22, 6010-6015.  [CrossRef] [ChemPort] [PubMed]
Sengupta, T., Gayen, K. S., Pandit, P. & Maiti, D. K. (2012). Chem. Eur. J. 18, 1905-1909.  [CSD] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o732  [ doi:10.1107/S1600536813009689 ]

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