(3β,18β,20β)-N-Eth­oxy­carbonyl­methyl-3-nitrato-11-oxoolean-12-ene-29-carboxamide methanol monosolvate

Czollner, L.; Jordis, U.; Mereiter, K.

doi:10.1107/S1600536812012561

Volume 68
Part 4
Pages o1229-o1230
April 2012

Received 16 March 2012
Accepted 22 March 2012
Online 31 March 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R = 0.044
wR = 0.122
Data-to-parameter ratio = 13.4
Details

(3,18,20)-N-Ethoxycarbonylmethyl-3-nitrato-11-oxoolean-12-ene-29-carboxamide methanol monosolvate

Laszlo Czollner,^a Ulrich Jordis ^a and Kurt Mereiter ^b ^*

^aInstitute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9/163, A-1060 Vienna, Austria, and ^bInstitute of Chemical Technologies and Analytics, Vienna University of Technology, Getreidemarkt 9/164SC, A-1060 Vienna, Austria
Correspondence e-mail: kurt.mereiter@tuwien.ac.at

The title compound, C₃₄H₅₂N₂O₇·CH₄O, is the methanol solvate of a difunctionalized derivative of the therapeutic agent 18 [beta] -glycyrrhetinic acid, a pentacyclic triterpene. The five six-membered rings of the glycyrrhetinic acid moiety show normal geometries, with four rings in chair conformations and the unsaturated ring in a half-chair conformation. This moiety is substituted by a nitrate ester group and an O-ethylglycine group. In the crystal, the nonsolvent molecules are packed parallel to (010) in a herringbone fashion with the nitrato, ethylglycine and methanol-O atom being proximate. The methanol solvent molecule is anchored via a donated O-HO_acyl and an accepted N-HO hydrogen bond, giving rise to infinite zigzag chains of hydrogen bonds parallel to [100]. Two weak intermolecular C-HO interactions to the methanol and to an acyl oxygen establish links along [100] and [010], respectively.

Related literature

For overviews on the therapeutic aspects of glycyrrhetinic acid, see: Baran et al. (1974); Asl & Hosseinzadeh (2008). For the synthesis of new derivatives of 18 [beta] -glycyrrhetinic acid and their effect on 11 [beta] -hydroxysteroid dehydrogenase, see: Su et al. (2004); Beseda et al. (2010); Amer et al. (2010). For the crystal structure of 18 [beta] -glycyrrhetinic acid, see: Campsteyn et al. (1977); Alvarez-Larena et al. (2007). For the crystal structures of derivatives of 18 [beta] -glycyrrhetinic acid, see: Beseda et al. (2010); Amer et al. (2010); Czollner et al. (2011).

Experimental

Crystal data

C₃₄H₅₂N₂O₇·CH₄O
M_r = 632.82
Orthorhombic, P 2₁ 2₁ 2₁
a = 10.1598 (8) Å
b = 11.1275 (9) Å
c = 30.387 (2) Å
V = 3435.3 (5) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 100 K
0.55 × 0.53 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008) T_min = 0.88, T_max = 1.00
49017 measured reflections
5565 independent reflections
5044 reflections with I > 2(I)
R_int = 0.036

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.122
S = 1.10
5565 reflections
416 parameters
H-atom parameters constrained
_max = 0.68 e Å^-3
_min = -0.38 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2NO8ⁱ	0.88	2.04	2.806 (3)	144
O8-H8O5	0.84	1.89	2.728 (2)	177
C1-H1AO4	0.99	2.34	2.968 (2)	120
C19-H19BO8ⁱ	0.99	2.40	3.359 (3)	163
C25-H25AO4	0.98	2.41	3.058 (3)	123
C34-H34BO5ⁱⁱ	0.98	2.58	3.515 (4)	160
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ .

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT, SADABS and XPREP (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5490 ).

Acknowledgements

The work was supported by the ZIT Zentrum für Innovation und Technologie GmbH (Vienna Spot of Excellence, 182081).

References

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