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Volume 69 
Part 6 
Page o888  
June 2013  

Received 7 May 2013
Accepted 9 May 2013
Online 15 May 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.053
wR = 0.141
Data-to-parameter ratio = 12.1
Details
Open access

2-(1-Amino-4-tert-butylcyclohexyl)acetic acid (tBu-[beta]3,3-Ac6c) hemihydrate1

aMedicinal Chemistry Division, Indian Institute of Integrative Medicine, Canal Road, Jammu Tawi 180 001, India, and bX-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India
Correspondence e-mail: saravinda@iiim.ac.in,raj@iiim.ac.in

The title compound, C12H23NO2·0.5H2O, crystallized with two 2-(1-amino-4-tert-butylcyclohexyl)acetic acid molecules, which are present as zwitterions, and one water molecule in the asymmetric unit. The molecular structure of each zwitterion is stabilized by an intramolecular six-membered (C6 ) N-H...O hydrogen bond. In the crystal, the two independent zwitterions are linked head-to-head by N-H...O hydrogen bonds. Further O-H...O and N-H...O hydrogen bonds link the zwitterions and the water molecules, forming sandwich-like layers, with a hydrophilic filling and a hydrophobic exterior, lying parallel to the ab plane.

Related literature

For the importance of [beta]-amino acids, see: Politi et al. (2009[Politi, A., Durdagi, S., Moutevelis-Minakakis, P., Kokotos, G., Papadopoulos, M. G. & Mavromoustakos, T. (2009). Eur. J. Med. Chem. 44, 3703-3711.]); Jiang & Yu (2007[Jiang, Z. X. & Yu, Y. B. (2007). J. Org. Chem. 72, 1464-1467.]); Hansen et al. (2011[Hansen, T., Ausbacher, D., Flaten, G. E., Havelkova, M. & Stro/m, M. B. (2011). J. Med. Chem. 54, 858-868.]). For related structures, see: Seebach et al. (1998[Seebach, D., Abele, S., Sifferlen, T., Hänggi, T., Gruner, M. S. & Seiler, P. (1998). Helv. Chim. Acta, 81, 2218-2243.]); Vasudev et al. (2008[Vasudev, P. G., Rai, R., Shamala, N. & Balaram, P. (2008). Biopolymers (Peptide Sci.), 90, 138-150.], 2009[Vasudev, P. G., Aravinda, S., Ananda, K., Shettykere, D. V., Nagarajan, K., Shamala, N. & Balaram, P. (2009). Chem. Biol. Drug. Des. 73, 83-96.]).

[Scheme 1]

Experimental

Crystal data
  • C12H23NO2·0.5H2O

  • Mr = 222.32

  • Triclinic, [P \overline 1]

  • a = 6.4164 (2) Å

  • b = 10.8091 (3) Å

  • c = 19.1335 (6) Å

  • [alpha] = 96.843 (3)°

  • [beta] = 92.018 (3)°

  • [gamma] = 93.901 (3)°

  • V = 1313.25 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 293 K

  • 0.3 × 0.08 × 0.08 mm

Data collection
  • Oxford Diffraction Xcalibur Sapphire3 diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.830, Tmax = 1.000

  • 22269 measured reflections

  • 5701 independent reflections

  • 3628 reflections with I > 2[sigma](I)

  • Rint = 0.048

Refinement
  • R[F2 > 2[sigma](F2)] = 0.053

  • wR(F2) = 0.141

  • S = 1.02

  • 5701 reflections

  • 472 parameters

  • All H-atom parameters refined

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N...O2 1.00 (2) 2.12 (2) 2.792 (2) 123.5 (15)
N1-H1N...O1Wi 1.00 (2) 2.11 (2) 2.919 (2) 137.8 (17)
O1W-H1W...O1 0.89 (3) 2.03 (3) 2.903 (2) 166 (3)
N1-H2N...O4ii 0.96 (2) 1.81 (2) 2.747 (2) 166.0 (17)
O1W-H2W...O3iii 0.90 (4) 2.04 (4) 2.929 (2) 169 (3)
N1-H3N...O3 0.97 (2) 1.86 (2) 2.7903 (19) 160.7 (17)
N2-H4N...O2i 1.00 (2) 1.73 (2) 2.729 (2) 170.5 (19)
N2-H5N...O1iii 0.99 (2) 1.818 (19) 2.779 (2) 163.1 (18)
N2-H6N...O3 0.93 (2) 2.10 (2) 2.836 (2) 135.4 (17)
Symmetry codes: (i) -x, -y, -z; (ii) -x, -y-1, -z; (iii) -x+1, -y, -z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: QM2098 ).


Acknowledgements

RR acknowledges the Council of Scientific and Industrial Research (CSIR), India, for financial assistance under MLP5009. RK wishes to acknowledge the Department of Science and Technology, India, for sanctioning the single-crystal X-ray diffractometer as a National Facility under project No. SR/S2 /CMP/47.

References

Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Hansen, T., Ausbacher, D., Flaten, G. E., Havelkova, M. & Stro/m, M. B. (2011). J. Med. Chem. 54, 858-868.
Jiang, Z. X. & Yu, Y. B. (2007). J. Org. Chem. 72, 1464-1467.  [CrossRef] [PubMed] [ChemPort]
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Politi, A., Durdagi, S., Moutevelis-Minakakis, P., Kokotos, G., Papadopoulos, M. G. & Mavromoustakos, T. (2009). Eur. J. Med. Chem. 44, 3703-3711.  [ISI] [CrossRef] [PubMed] [ChemPort]
Seebach, D., Abele, S., Sifferlen, T., Hänggi, T., Gruner, M. S. & Seiler, P. (1998). Helv. Chim. Acta, 81, 2218-2243.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Vasudev, P. G., Aravinda, S., Ananda, K., Shettykere, D. V., Nagarajan, K., Shamala, N. & Balaram, P. (2009). Chem. Biol. Drug. Des. 73, 83-96.  [CSD] [CrossRef] [PubMed] [ChemPort]
Vasudev, P. G., Rai, R., Shamala, N. & Balaram, P. (2008). Biopolymers (Peptide Sci.), 90, 138-150.  [CSD] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o888  [ doi:10.1107/S1600536813012725 ]

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