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Volume 69 
Part 3 
Page o340  
March 2013  

Received 28 January 2013
Accepted 29 January 2013
Online 2 February 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.002 Å
R = 0.044
wR = 0.125
Data-to-parameter ratio = 19.1
Details
Open access

6-Hydroxy-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one

aDepartment of Chemistry, Moscow State University, Moscow 119992, Russian Federation,bSTC "Institute for Single Crystals", National Academy of Sciences of Ukraine, 60 Lenina ave., Kharkiv 61001, Ukraine, and cNational University of Pharmacy, 4 Blyukhera St., Kharkiv 61002, Ukraine
Correspondence e-mail: rybakov20021@yandex.ru

The molecule of the title compound, C11H9NO2, is essentially planar [r.m.s. deviation of the non-H atoms = 0.056 (1) Å]. In the crystal, strong O-H...O hydrogen bonds form zigzag chains along the b axis. The molecules form stacks along the a axis due to [pi]-[pi] interactions, the shortest distance between the centroids of the benzene and pyridinone rings being 3.6146 (7) Å.

Related literature

For condensation of secondary anilines with triethyl methanetricarboxylate, see: Kutyrev & Kappe (1997[Kutyrev, A. & Kappe, T. (1997). J. Heterocycl. Chem. 34, 969-972.]); Jönsson et al. (2004[Jönsson, S., Andersson, G., Fex, T., Fristedt, T., Hedlund, G., Jansson, K., Abramo, L., Fritzson, I., Pekarski, O., Runstrom, A., Sandin, H., Thuvesson, I. & Björk, A. (2004). J. Med. Chem. 47, 2075-2088.]); Ukrainets et al. (2006[Ukrainets, I. V., Sidorenko, L. V., Gorokhova, O. V., Mospanova, E. V. & Shishkin, O. V. (2006). Chem. Heterocycl. Compd, 42, 631-635.], 2010[Ukrainets, I. V., Golik, N. Yu., Andreeva, X. V. & Gorokhova, O. V. (2010). Chem. Heterocycl. Compd, 46, 1459-1466.], 2011[Ukrainets, I. V., Golik, N. Yu., Shemchuk, A. L., Naboka, O. I., Voronina, Yu. V. & Turov, A. V. (2011). Chem. Heterocycl. Compd, 47, 826-832.]). 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.]). For a related structure, see: Baumer et al. (2004[Baumer, V. N., Shishkin, O. V., Ukrainets, I. V., Sidorenko, L. V. & Kayal, S. A. E. (2004). Acta Cryst. E60, o2356-o2358.]).

[Scheme 1]

Experimental

Crystal data
  • C11H9NO2

  • Mr = 187.19

  • Monoclinic, P 21 /c

  • a = 7.9987 (3) Å

  • b = 7.6297 (2) Å

  • c = 14.3500 (4) Å

  • [beta] = 101.386 (3)°

  • V = 858.51 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 295 K

  • 0.20 × 0.10 × 0.10 mm

Data collection
  • Agilent Xcalibur Sapphire3 CCD diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Agilent, 2011[Agilent (2011). CrysAlis CCD and CrysAlis RED, Agilent Technologies, Yarnton, England.]) Tmin = 0.983, Tmax = 1.000

  • 7610 measured reflections

  • 2501 independent reflections

  • 1806 reflections with I > 2[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.125

  • S = 1.07

  • 2501 reflections

  • 131 parameters

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

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2...O1i 1.09 (2) 1.51 (2) 2.5922 (13) 172 (2)
Symmetry code: (i) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrysAlis CCD (Agilent, 2011[Agilent (2011). CrysAlis CCD and CrysAlis RED, Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Agilent, 2011[Agilent (2011). CrysAlis CCD and CrysAlis RED, Agilent Technologies, Yarnton, England.]); 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.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: YK2087 ).


References

Agilent (2011). CrysAlis CCD 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.
Baumer, V. N., Shishkin, O. V., Ukrainets, I. V., Sidorenko, L. V. & Kayal, S. A. E. (2004). Acta Cryst. E60, o2356-o2358.  [CSD] [CrossRef] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Jönsson, S., Andersson, G., Fex, T., Fristedt, T., Hedlund, G., Jansson, K., Abramo, L., Fritzson, I., Pekarski, O., Runstrom, A., Sandin, H., Thuvesson, I. & Björk, A. (2004). J. Med. Chem. 47, 2075-2088.  [ISI] [PubMed]
Kutyrev, A. & Kappe, T. (1997). J. Heterocycl. Chem. 34, 969-972.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Ukrainets, I. V., Golik, N. Yu., Andreeva, X. V. & Gorokhova, O. V. (2010). Chem. Heterocycl. Compd, 46, 1459-1466.  [CrossRef]
Ukrainets, I. V., Golik, N. Yu., Shemchuk, A. L., Naboka, O. I., Voronina, Yu. V. & Turov, A. V. (2011). Chem. Heterocycl. Compd, 47, 826-832.  [CrossRef] [ChemPort]
Ukrainets, I. V., Sidorenko, L. V., Gorokhova, O. V., Mospanova, E. V. & Shishkin, O. V. (2006). Chem. Heterocycl. Compd, 42, 631-635.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o340  [ doi:10.1107/S1600536813003000 ]

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