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Volume 68 
Part 12 
Pages o3293-o3294  
December 2012  

Received 27 July 2012
Accepted 31 October 2012
Online 7 November 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.036
wR = 0.096
Data-to-parameter ratio = 12.7
Details
Open access

17-Hydroxy-1,8-dimethyl-17-azapentacyclo[6.6.5.02,7.09,14.015,19]nonadeca-2,4,6,9(14),10,12-hexaene-16,18-dione

aFaculty of Chemistry, Maria Curie-Sklodowska University, pl. M. Curie-Sklodowskiej 3, 20-031 Lublin, Poland, and bDepartment of Medical Chemistry, The Medical University, 02-007 Warsaw, Poland
Correspondence e-mail: barbara.miroslaw@poczta.umcs.lublin.pl

In the title compound, C20H17NO3 (alternative name: N-hydroxy-9,10-dimethyl-9,10-ethanoanthracene-11,12-dicarboximide), the rigid ethanoanthracene-dicarboximide moiety has a roof-shaped geometry, the interplanar angle between the two terminal phenyl rings being 124.9 (6)°. In the crystal, molecules are linked via O-H...O hydrogen bonds, forming chains along [010]. C-H...O and C-H...[pi] interactions link adjacent chains, leading to the formation of a three-dimensional structure.

Related literature

For the synthesis of the title compound, see: Kossakowski & Jarocka (2000[Kossakowski, J. & Jarocka, M. (2000). Acta Pol. Pharm. 57, 60-62.]). For the biological activity of related compounds, see: Bova et al. (2009[Bova, S., Saponara, S., Rampa, A., Gobbi, S., Cima, L., Fusi, F., Sgaragli, G., Cavalli, M., de los Rios, C., Striessnig, J. & Bisi, A. (2009). J. Med. Chem. 52, 1259-1262.]). For related structures, see: Atherton & Jones (2002[Atherton, J. C. C. & Jones, S. (2002). J. Chem. Soc. Perkin Trans. 1, pp. 2166-2173.]); Smet et al. (2000[Smet, M., Corens, D., Van Meervelt, L. & Dehaen, W. (2000). Molecules, 5, 179-188.]); Su et al. (2011[Su, Y.-S., Liu, J.-W., Jiang, Y. & Chen, C.-F. (2011). Chem. Eur. J. 17, 2435-2441.]), Guo et al. (2010[Guo, J.-B., Xiang, J.-F. & Chen, C.-F. (2010). Eur. J. Org. Chem. pp. 5056-5062.]); Adams et al. (2006[Adams, H., Bawa, R. A. & Jones, S. (2006). Org. Biomol. Chem. 4, 4206-4213.]); He & Ng (2007[He, L. & Ng, S. W. (2007). Acta Cryst. E63, o602-o603.]); Weber et al. (1991[Weber, E., Finge, S. & Csöregh, I. (1991). J. Org. Chem. 56, 7281-7288.], 1994[Weber, E., Reutel, C., Foces-Foces, C. & Llamas-Saiz, A. L. (1994). J. Chem. Soc. Perkin Trans. 2, pp. 1455-1461.]); Yang & Swager (1998[Yang, J.-S. & Swager, T. M. (1998). J. Am. Chem. Soc. 120, 11864-11873.]). The rigid ethanoanthracenedicarboximide moiety of the title compound shows the typical roof-shaped geometry (Weber et al., 1991[Weber, E., Finge, S. & Csöregh, I. (1991). J. Org. Chem. 56, 7281-7288.]; Csöregh et al., 2003[Csöregh, I., Finge, S. & Weber, E. (2003). Struct. Chem. 14, 241-246.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data
  • C20H17NO3

  • Mr = 319.36

  • Monoclinic, P 21 /n

  • a = 13.904 (1) Å

  • b = 8.104 (1) Å

  • c = 13.946 (1) Å

  • [beta] = 97.39 (1)°

  • V = 1558.4 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 100 K

  • 0.40 × 0.40 × 0.30 mm

Data collection
  • Oxford Diffraction Xcalibur (Sapphire2) diffractometer

  • 5321 measured reflections

  • 2827 independent reflections

  • 2467 reflections with I > 2[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.096

  • S = 1.04

  • 2827 reflections

  • 223 parameters

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

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C6-C11 ring. Cg2 refers to the mid-point of the C15-C16 bond.

D-H...A D-H H...A D...A D-H...A
O3-H3A...O1i 0.96 (2) 1.69 (2) 2.630 (1) 167 (2)
C8-H8...O1ii 0.95 2.54 3.408 (2) 152
C15-H15...O3iii 0.95 2.46 3.273 (2) 143
C17-H17...O2iv 0.95 2.54 3.457 (2) 163
C4-H4...Cg1v 1.00 2.66 3.518 (3) 144
C10-H10...Cg2vi 0.95 2.77 3.668 (3) 158
Symmetry codes: (i) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (iii) -x+1, -y+1, -z+1; (iv) x, y+1, z; (v) -x, -y+1, -z+1; (vi) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: publCIF.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2475 ).


References

Adams, H., Bawa, R. A. & Jones, S. (2006). Org. Biomol. Chem. 4, 4206-4213.  [CSD] [CrossRef] [PubMed] [ChemPort]
Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Atherton, J. C. C. & Jones, S. (2002). J. Chem. Soc. Perkin Trans. 1, pp. 2166-2173.
Bova, S., Saponara, S., Rampa, A., Gobbi, S., Cima, L., Fusi, F., Sgaragli, G., Cavalli, M., de los Rios, C., Striessnig, J. & Bisi, A. (2009). J. Med. Chem. 52, 1259-1262.  [ISI] [CrossRef] [PubMed] [ChemPort]
Csöregh, I., Finge, S. & Weber, E. (2003). Struct. Chem. 14, 241-246.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Guo, J.-B., Xiang, J.-F. & Chen, C.-F. (2010). Eur. J. Org. Chem. pp. 5056-5062.  [CSD] [CrossRef]
He, L. & Ng, S. W. (2007). Acta Cryst. E63, o602-o603.  [CSD] [CrossRef] [details]
Kossakowski, J. & Jarocka, M. (2000). Acta Pol. Pharm. 57, 60-62.  [PubMed] [ChemPort]
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Smet, M., Corens, D., Van Meervelt, L. & Dehaen, W. (2000). Molecules, 5, 179-188.  [CrossRef] [ChemPort]
Su, Y.-S., Liu, J.-W., Jiang, Y. & Chen, C.-F. (2011). Chem. Eur. J. 17, 2435-2441.  [ChemPort] [PubMed]
Weber, E., Finge, S. & Csöregh, I. (1991). J. Org. Chem. 56, 7281-7288.  [CrossRef] [ChemPort]
Weber, E., Reutel, C., Foces-Foces, C. & Llamas-Saiz, A. L. (1994). J. Chem. Soc. Perkin Trans. 2, pp. 1455-1461.
Yang, J.-S. & Swager, T. M. (1998). J. Am. Chem. Soc. 120, 11864-11873.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o3293-o3294   [ doi:10.1107/S1600536812045151 ]

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