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

Barbara Miroslaw; Anna E Koziol; Magdalena Pakosinska-Parys; Marta Struga

doi:10.1107/S1600536812045151

. 2012 Nov 7;68(Pt 12):o3293–o3294. doi: 10.1107/S1600536812045151

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, Marta Struga ^b

PMCID: PMC3588838 PMID: 23468803

Abstract

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⋯π 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,
a = 13.904 (1) Å
b = 8.104 (1) Å
c = 13.946 (1) Å
β = 97.39 (1)°
V = 1558.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 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 > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.096
S = 1.04
2827 reflections
223 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); 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 Material

Click here for additional data file.^{(17.6KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812045151/bg2475sup1.cif

e-68-o3293-sup1.cif^{(17.6KB, cif)}

Click here for additional data file.^{(4.2KB, mol)}

Supplementary material file. DOI: 10.1107/S1600536812045151/bg2475Isup2.mol

Click here for additional data file.^{(136KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812045151/bg2475Isup3.hkl

e-68-o3293-Isup3.hkl^{(136KB, hkl)}

Click here for additional data file.^{(6.5KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812045151/bg2475Isup4.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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⋯O2^iv	0.95	2.54	3.457 (2)	163
C4—H4⋯Cg1^v	1.00	2.66	3.518 (3)	144
C10—H10⋯Cg2^vi	0.95	2.77	3.668 (3)	158

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .

supplementary crystallographic information

Comment

Roof-shaped aromatic hydrocarbon derivatives have been used for inclusion of neutral compounds (Weber et al., 1991; 1994) and as porous polymer films and sensors for dinitrotoluene with possible application as a land mine detectors (Yang & Swager, 1998). The N-substitution is the most common way of modification of these molecules (Weber et al., 1994; Smet et al., 2000). Some experiments were also conducted on the substitution in the aryl moiety (Atherton & Jones, 2002; Adams et al., 2006; He & Ng, 2007). The search of the CSD (CSD v5.33 and updates; Allen, 2002) revealed 67 crystal structures of compounds with the rigid pentacyclic 9,10-ethanoanthracenedicarboximide skeleton. However, none of these derivatives has N-hydroxy substituent and only two molecules are symmetrically substituted at bridgehead C atoms (here C5, C12; see Fig. 1). In these crystals the polycyclic skeletons are combined with voluminous macrocyclic fragments. (Su et al., 2011; Guo et al., 2010). The rigid ethanoanthracenedicarboximide moiety of the title compound (Fig. 1) shows the typical roof-shaped geometry (Weber et al., 1991; Csöregh et al., 2003); the interplanar angle between the two terminal phenyl rings is 124.9 °. The hydroxyl O atom interacts through the O3–H···O1 hydrogen bond (Fig. 2). Molecules form chains along the 2₁ screw axis. Between adjacent chains many C–H···O and C–H···π interactions are observed (Figs. 2–4, Table 1).

Experimental

The title compound, UPAC name: 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, was synthesized in the search of compounds with potential anxiolytic activity, as described previously (Kossakowski & Jarocka, 2000).