cis-3-(tert-Butoxy­carbonyl­amino)cyclo­hexa­necarboxylic acid

Yu Hu; XiaoXia Sun; Ying Guo; Hua Yao

doi:10.1107/S1600536808027098

. 2008 Aug 30;64(Pt 9):o1847. doi: 10.1107/S1600536808027098

cis-3-(tert-Butoxycarbonylamino)cyclohexanecarboxylic acid

Yu Hu ^a,^*, XiaoXia Sun ^b, Ying Guo ^a, Hua Yao ^a

PMCID: PMC2960558 PMID: 21201818

Abstract

The title compound, C₁₂H₂₁NO₄, a γ-aminobutyric acid derivative, crystallizes with two molecules in the asymmetric unit. The crystal structure is stabilized by intermolecular N—H⋯O and O—H⋯O hydrogen bonds, forming a strand. An intramolecular N—H⋯O hydrogen bond is also observed.

Related literature

For related literature, see: Allan et al. (1981 ▶); Amorin et al. (2003 ▶); Hu et al. (2006 ▶); Roberts et al. (1976 ▶); Schousboe (2000 ▶).

Experimental

Crystal data

C₁₂H₂₁NO₄
M _r = 243.30
Triclinic,
a = 5.854 (1) Å
b = 10.000 (2) Å
c = 23.014 (5) Å
α = 85.64 (2)°
β = 88.68 (2)°
γ = 88.51 (2)°
V = 1342.6 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 (2) K
0.56 × 0.46 × 0.20 mm

Data collection

Bruker SMART 1K area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.767, T _max = 0.921 (expected range = 0.818–0.982)
5514 measured reflections
4822 independent reflections
2483 reflections with I > 2σ(I)
R _int = 0.017

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.109
S = 0.81
4822 reflections
324 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 1999 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808027098/bt2775sup1.cif

e-64-o1847-sup1.cif^{(25.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808027098/bt2775Isup2.hkl

e-64-o1847-Isup2.hkl^{(236.2KB, 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—H1A⋯O6	0.856 (9)	2.163 (10)	3.009 (2)	169 (2)
N2—H2A⋯O2ⁱ	0.854 (9)	2.180 (11)	3.013 (2)	164.9 (19)
O3—H3⋯O4ⁱⁱ	0.82	1.86	2.672 (2)	172
O7—H7⋯O8ⁱⁱⁱ	0.82	1.84	2.656 (2)	171

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

Acknowledgments

This work was supported by the Science Fund of the Education Office of Jiangxi, China ([2007]279).

supplementary crystallographic information

Comment

γ aminobutyric acid (GABA) and its derivatives have an extensive appliction in medicine. For instance, GABA is an important inhibitory neurotransmitter in certain neurological and psychiatric disorders (Schousboe, 2000; Roberts et al., 1976). As the analogue of GABA, cis-3-aminocyclohexanecarboxylic acid is an inhibitor of GABA uptake (Allan et al., 1981). cis-3-aminocyclohexanecarboxylic acid is incorporated in cyclic peptides and organic nanotubes (Amorin et al., 2003). The title compound is a key intermediate for the synthesis of cis-3- aminocyclohexanecarboxylic acid (Hu et al., 2006). The synthesis and crystal structure of the title compound are described in this paper.

Interolecular O-H···O hydrogen bonds result in eight-membered rings that can be described in terms of graph-set notation as R₂²(8) (Figure 2).

One-dimensional strands are formed along the crystallographic b axis by N-H···O hydrogen bonds (Figure 2 and Table 2).

Experimental

cis-3-tert-butoxycarbonylamino-cyclohexanecarboxylic acid was synthesized from 3-aminobenzoic acid (Amorin et al., 2003). The compound identity was conformed by the NMR spectra and IR. Crystal were obtained from ethyl acetate by solvent evaporation. ¹H NMR in CDCl₃ (300 MHz): 9.20–10.4 (br, 1H,), 5.72 (s, 1H), 4.82 (s, H), 3.67–3.74 (m, 1H), 1.43 (s, 9H), 1.05–2.40 (m, 8H).