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Volume 69 
Part 4 
Page o536  
April 2013  

Received 4 February 2013
Accepted 7 March 2013
Online 16 March 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.002 Å
R = 0.038
wR = 0.106
Data-to-parameter ratio = 12.1
Details
Open access

2-Hydroxy-7-nitrocyclohepta-2,4,6-trien-1-one

aInstitute of Nuclear Chemistry and Technology, Dorodna 16, 03-195 Warsaw, Poland
Correspondence e-mail: k.lyczko@ichtj.waw.pl

The title compound, also known as 7-nitrotropolone, C7H5NO4, exists in the crystalline state as the 2-hydroxy-7-nitrocyclohepta-2,4,6-trien-1-one tautomer and not as 2-hydroxy-3-nitrocyclohepta-2,4,6-trien-1-one. The dihedral angle between the ring and the nitro group is 70.3 (2)°. In the crystal, neighbouring molecules are linked into dimers by a pair of O-H...O hydrogen bonds. In addition, the crystal is stabilized by O...[pi] [3.4039 (14) Å] and O...O [3.073 (2) Å] interactions.

Related literature

For the structure of tropolone and 5-nitrotropolone, see: Shimanouchi & Sasada (1973[Shimanouchi, H. & Sasada, Y. (1973). Acta Cryst. B29, 81-90.]); Kubo et al. (2001[Kubo, K., Yamamoto, E. & Mori, A. (2001). Acta Cryst. C57, 611-613.]), respectively. Structural data on other mono-substituted tropolones were reported by Derry & Hamor (1972[Derry, J. E. & Hamor, T. A. (1972). J. Chem. Soc. Perkin Trans. 2, pp. 694-697.]); Berg et al. (1976[Berg, J.-E., Karlsson, B., Pilotti, A.-M. & Wiehager, A.-C. (1976). Acta Cryst. B32, 3121-3123.]); Tsuji et al. (1991[Tsuji, T., Sekiya, H., Nishimura, Y., Mori, A., Takeshita, H. & Nishiyama, N. (1991). Acta Cryst. C47, 2428-2430.]); Kubo et al. (2001[Kubo, K., Yamamoto, E. & Mori, A. (2001). Acta Cryst. C57, 611-613.], 2006a[Kubo, K., Yamamoto, E. & Mori, A. (2006a). Acta Cryst. E62, o2988-o2990.],b[Kubo, K., Yamamoto, E. & Mori, A. (2006b). Acta Cryst. E62, o4325-o4326.], 2007a[Kubo, K., Matsumoto, T. & Mori, A. (2007a). Acta Cryst. E63, o941-o943.],b[Kubo, K., Matsumoto, T. & Mori, A. (2007b). Acta Cryst. E63, o1063-o1064.],c[Kubo, K., Matsumoto, T. & Mori, A. (2007c). Acta Cryst. E63, o1297-o1299.],d[Kubo, K., Matsumoto, T., Kuribayashi, D. & Mori, A. (2007d). Acta Cryst. E63, o1570-o1572.]). For the synthesis of nitrotropolone, see Cook et al. (1954[Cook, J. W., Loudon, J. D. & Steel, D. K. V. (1954). J. Chem. Soc. pp. 530-535.]).

[Scheme 1]

Experimental

Crystal data
  • C7H5NO4

  • Mr = 167.12

  • Monoclinic, P 21 /c

  • a = 9.6167 (2) Å

  • b = 6.4772 (1) Å

  • c = 11.7326 (4) Å

  • [beta] = 96.162 (2)°

  • V = 726.59 (3) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 1.11 mm-1

  • T = 295 K

  • 0.45 × 0.35 × 0.15 mm

Data collection
  • Agilent SuperNova (Dual, Eos) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.]) Tmin = 0.541, Tmax = 1.000

  • 8694 measured reflections

  • 1364 independent reflections

  • 1314 reflections with I > 2[sigma](I)

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.106

  • S = 1.07

  • 1364 reflections

  • 113 parameters

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

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2...O1 0.84 (3) 2.05 (3) 2.5796 (14) 120 (2)
O2-H2...O1i 0.84 (3) 2.04 (3) 2.7349 (15) 139 (3)
Symmetry code: (i) -x, -y, -z.

Data collection: CrysAlis PRO (Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, 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: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and 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.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KJ2222 ).


Acknowledgements

The authors thank the Institute of Nuclear Chemistry and Technology for financial support.

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.
Berg, J.-E., Karlsson, B., Pilotti, A.-M. & Wiehager, A.-C. (1976). Acta Cryst. B32, 3121-3123.  [CrossRef] [details] [ISI]
Cook, J. W., Loudon, J. D. & Steel, D. K. V. (1954). J. Chem. Soc. pp. 530-535.  [CrossRef]
Derry, J. E. & Hamor, T. A. (1972). J. Chem. Soc. Perkin Trans. 2, pp. 694-697.
Kubo, K., Matsumoto, T., Kuribayashi, D. & Mori, A. (2007d). Acta Cryst. E63, o1570-o1572.  [CSD] [CrossRef] [details]
Kubo, K., Matsumoto, T. & Mori, A. (2007a). Acta Cryst. E63, o941-o943.  [CSD] [CrossRef] [details]
Kubo, K., Matsumoto, T. & Mori, A. (2007b). Acta Cryst. E63, o1063-o1064.  [CSD] [CrossRef] [details]
Kubo, K., Matsumoto, T. & Mori, A. (2007c). Acta Cryst. E63, o1297-o1299.  [CSD] [CrossRef] [details]
Kubo, K., Yamamoto, E. & Mori, A. (2001). Acta Cryst. C57, 611-613.  [CSD] [CrossRef] [ChemPort] [details]
Kubo, K., Yamamoto, E. & Mori, A. (2006a). Acta Cryst. E62, o2988-o2990.  [CSD] [CrossRef] [details]
Kubo, K., Yamamoto, E. & Mori, A. (2006b). Acta Cryst. E62, o4325-o4326.  [CSD] [CrossRef] [details]
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.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Shimanouchi, H. & Sasada, Y. (1973). Acta Cryst. B29, 81-90.  [CrossRef] [ChemPort] [details] [ISI]
Tsuji, T., Sekiya, H., Nishimura, Y., Mori, A., Takeshita, H. & Nishiyama, N. (1991). Acta Cryst. C47, 2428-2430.  [CrossRef] [details]


Acta Cryst (2013). E69, o536  [ doi:10.1107/S1600536813006594 ]

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