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

Miroslaw, B.; Koziol, A.E.; Pakosinska-Parys, M.; Struga, M.

doi:10.1107/S1600536812045151

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 (C-C) = 0.002 Å
R = 0.036
wR = 0.096
Data-to-parameter ratio = 12.7
Details

17-Hydroxy-1,8-dimethyl-17-azapentacyclo[6.6.5.0^2,7.0^9,14.0^15,19]nonadeca-2,4,6,9(14),10,12-hexaene-16,18-dione

Barbara Miroslaw,^a ^* Anna E. Koziol,^a Magdalena Pakosinska-Parys ^b and Marta Struga ^b

^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-HO hydrogen bonds, forming chains along [010]. C-HO 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). For the biological activity of related compounds, see: Bova et al. (2009). For related structures, see: Atherton & Jones (2002); Smet et al. (2000); Su et al. (2011), Guo et al. (2010); Adams et al. (2006); He & Ng (2007); Weber et al. (1991, 1994); Yang & Swager (1998). The rigid ethanoanthracenedicarboximide moiety of the title compound shows the typical roof-shaped geometry (Weber et al., 1991; Csöregh et al., 2003). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental

Crystal data

C₂₀H₁₇NO₃
M_r = 319.36
Monoclinic, P 2₁ /n
a = 13.904 (1) Å
b = 8.104 (1) Å
c = 13.946 (1) Å
= 97.39 (1)°
V = 1558.4 (3) Å³
Z = 4
Mo K radiation
= 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(I)
R_int = 0.023

Refinement

R[F² > 2(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
_max = 0.30 e Å^-3
_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-HA	D-H	HA	DA	D-HA
O3-H3AO1ⁱ	0.96 (2)	1.69 (2)	2.630 (1)	167 (2)
C8-H8O1ⁱⁱ	0.95	2.54	3.408 (2)	152
C15-H15O3ⁱⁱⁱ	0.95	2.46	3.273 (2)	143
C17-H17O2^iv	0.95	2.54	3.457 (2)	163
C4-H4Cg1^v	1.00	2.66	3.518 (3)	144
C10-H10Cg2^vi	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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); 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

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