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

Rybakov, V.B.; Shishkina, S.V.; Ukrainets, I.V.; Gorokhova, O.V.; Andreeva, X.V.

doi:10.1107/S1600536813003000

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 (C-C) = 0.002 Å
R = 0.044
wR = 0.125
Data-to-parameter ratio = 19.1
Details

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

Victor B. Rybakov,^a ^* Svitlana V. Shishkina,^b Igor V. Ukrainets,^c Olga V. Gorokhova ^c and Xeniya V. Andreeva ^c

^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-HO 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); Jönsson et al. (2004); Ukrainets et al. (2006, 2010, 2011). For standard bond lengths, see: Allen et al. (1987). For a related structure, see: Baumer et al. (2004).

Experimental

Crystal data

C₁₁H₉NO₂
M_r = 187.19
Monoclinic, P 2₁ /c
a = 7.9987 (3) Å
b = 7.6297 (2) Å
c = 14.3500 (4) Å
= 101.386 (3)°
V = 858.51 (5) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.983, T_max = 1.000
7610 measured reflections
2501 independent reflections
1806 reflections with I > 2(I)
R_int = 0.023

Refinement

R[F² > 2(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
_max = 0.23 e Å^-3
_min = -0.15 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2O1ⁱ	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); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

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.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
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.
Kutyrev, A. & Kappe, T. (1997). J. Heterocycl. Chem. 34, 969-972.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Ukrainets, I. V., Golik, N. Yu., Andreeva, X. V. & Gorokhova, O. V. (2010). Chem. Heterocycl. Compd, 46, 1459-1466.
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.
Ukrainets, I. V., Sidorenko, L. V., Gorokhova, O. V., Mospanova, E. V. & Shishkin, O. V. (2006). Chem. Heterocycl. Compd, 42, 631-635.

organic compounds