Methyl 3-[(1-adamantylcarbon­yloxy)amino­carbon­yl]propanoate

Joe Liu; Jack K Clegg; Rachel Codd

doi:10.1107/S1600536809024210

. 2009 Jul 4;65(Pt 8):o1742–o1743. doi: 10.1107/S1600536809024210

Methyl 3-[(1-adamantylcarbonyloxy)aminocarbonyl]propanoate

Joe Liu ^a, Jack K Clegg ^b, Rachel Codd ^a,^*

PMCID: PMC2977356 PMID: 21583454

Abstract

In the title compound, C₁₆H₂₃NO₅, the H—N—O—C torsion angle is 98.6 (1)°, which is of a similar magnitude to other N,O-diacylhydroxylamines. The N—O distance is 1.4029 (14) Å, which is similar to the N—O distance in other N,O-diacylhydroxylamines. In the crystal, intermolecular N—H⋯O hydrogen bonds generate chains of molecules.

Related literature

For the biological activity of compounds related to N,O-diacylhydroxylamines, see: Pelto & Pratt (2008 ▶). For linear N,O-diacylhydroxylamines, see: Göttlicher & Ochsenreiter (1974 ▶); Schraml et al. (2004 ▶); Baert et al. (1984 ▶); Masui et al. (1983 ▶); Grassi et al. (2002 ▶); Buscemi et al. (2006 ▶). For cyclic N,O-diacylhydroxylamines, see: Kongprakaiwoot et al. (2008 ▶). For a precursor of the title compound, see: Liu et al. (2009 ▶).

Experimental

Crystal data

C₁₆H₂₃NO₅
M _r = 309.35
Orthorhombic,
a = 15.7837 (5) Å
b = 21.0715 (7) Å
c = 9.5341 (3) Å
V = 3170.91 (18) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 150 K
0.30 × 0.20 × 0.15 mm

Data collection

Bruker APEXII-FR591 diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T _min = 0.851, T _max = 0.981
22952 measured reflections
4586 independent reflections
2890 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.132
S = 1.04
4586 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: APEX2 (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT and XPREP (Bruker, 2003 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶), WinGX32 (Farrugia, 1999 ▶), POV-RAY (Cason, 2002 ▶) and WebLab ViewerPro (Molecular Simulations, 2000 ▶); software used to prepare material for publication: enCIFer (Allen et al., 2004 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809024210/bg2266sup1.cif

e-65-o1742-sup1.cif^{(20.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024210/bg2266Isup2.hkl

e-65-o1742-Isup2.hkl^{(224.8KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3ⁱ	0.88	1.87	2.7250 (19)	165

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Symmetry code: (i) Inline graphic .

Acknowledgments

Support from the NHMRC-Project Grant 570844 (RC) and from the University of Sydney (2009 Bridging Support Grant (RC), co-funded postgraduate scholarship from the Faculty of Medicine (JL)) is gratefully acknowledged.

supplementary crystallographic information

Comment

O-Adamantanecarboxoyl-N-4-methoxy-4-oxobutanoyl-hydroxylamine (I) (Fig 1.) was prepared in our laboratory as part of our program in understanding resonance and tautomerism in biologically relevant molecules such as N,O-diacylhydroxylamines and hydroxamic acids. The torsion angle defined by H—N—O—C in each of N,O-diacetylhydroxylamine (-99.0 (1) °), N-acetyl-O-benzoylhydroxylamine (-101.3 (1) °), and N-benzoyl-O-acetylhydroxylamine (-94.1 (1) °) is negative, which is distinct from the analogous angle in N,O-dibenzoylhydroxylamine determined by the same group, which is positive (99.7 (1) °) (Schraml et al., 2004). The positive torsion angle defined by H1—N1—O4—C6 in I is 98.6 (1) °, which is akin to N,O-dibenzoylhydroxylamine. The N—O distance in I (N1—O4 = 1.4029 (14) Å) is similar to the N—O distance in other N,O-diacylhydroxylamines as cited above. Intermolecular hydrogen bonds exist in I between respective amide groups, with H1···O3 = 1.87 Å (Table 1) forming an infinite one-dimensional polymer extending along the c-axis (Fig 2.).

Experimental

O-Adamantanecarboxoyl-N-4-methoxy-4-oxobutanoyl-hydroxylamine (I) was isolated from a methanol solution (14 ml) containing adamantane-1-carboxylate-2,5-pyrrolidinedione (0.25 g, 0.89 mmol) (Liu, et al., 2009) and NaOH (0.018 g, 0.45 mmol). The product was dried in vacuo; colourless crystals of I appeared after approximately 1 month from a 4.5 mg mL^-1 solution of I in ethanol:water (7:3).