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Volume 68 
Part 12 
Page o3296  
December 2012  

Received 31 August 2012
Accepted 1 November 2012
Online 7 November 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.006 Å
R = 0.069
wR = 0.216
Data-to-parameter ratio = 13.2
Details
Open access

2-[(Adamantan-1-yl)aminomethyl]-4-chlorophenol hemihydrate

aCollege of Chemistry, Liaoning University, Shenyang 110036, People's Republic of China
Correspondence e-mail: jinxudong@yahoo.com

In the title compound, C17H22ClNO·0.5H2O, the water molecule O atom resides on a twofold rotation axis. In the organic molecule, the phenol group forms an intramolecular O-H...N hydrogen bond. In the crystal, pairs of organic molecules are hydrogen bonded through bridging solvent water molecules, forming chains along the b-axis direction.

Related literature

For the synthesis and crystal structure of 2-[(adamantan-1-ylamino)methyl]phenol, see: Wang & Tao (2012[Wang, Y.-C. & Tao, R. (2012). Acta Cryst. E68, o293.]). For the synthesis and applications of amantadine derivatives, see: Camps et al. (2008[Camps, P., Duque, M. D., Vazquez, S., Naesens, L., De-Clercq, E., Sureda, F. X., Lopez-Querol, M., Camins, A., Pallas, M., Prathalingam, S. R., Kelly, J. M., Romero, V., Ivorra, D. & Cortes, D. (2008). Bioorg. Med. Chem. 16, 9925-9936.]).

[Scheme 1]

Experimental

Crystal data
  • C17H22ClNO·0.5H2O

  • Mr = 300.82

  • Monoclinic, C 2/c

  • a = 25.469 (16) Å

  • b = 6.365 (4) Å

  • c = 18.306 (11) Å

  • [beta] = 91.815 (12)°

  • V = 2966 (3) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.26 mm-1

  • T = 296 K

  • 0.35 × 0.30 × 0.16 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.915, Tmax = 0.960

  • 6372 measured reflections

  • 2606 independent reflections

  • 1798 reflections with I > 2[sigma](I)

  • Rint = 0.098

Refinement
  • R[F2 > 2[sigma](F2)] = 0.069

  • wR(F2) = 0.216

  • S = 1.08

  • 2606 reflections

  • 198 parameters

  • 3 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.39 e Å-3

  • [Delta][rho]min = -0.40 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...N1 0.83 (6) 2.07 (9) 2.611 (5) 122 (7)
O1W-H1W...O1i 0.84 (4) 1.99 (4) 2.768 (5) 153 (5)
N1-H1A...O1W 0.90 (4) 2.20 (4) 3.012 (5) 150 (4)
Symmetry code: (i) [-x+1, y+1, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LD2073 ).


Acknowledgements

This work was supported financially by the Foundation of Liaoning Educational Department (No. 2008T073&LT2012001), the Science and Technology Foundation of Liaoning Province (No. 20071027), the Liaoning University Foundation of 211 Project for Innovative Talents Training and the Technology Major Projects Research Foundation (No. 2011ZX09102-007-02), China.

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Camps, P., Duque, M. D., Vazquez, S., Naesens, L., De-Clercq, E., Sureda, F. X., Lopez-Querol, M., Camins, A., Pallas, M., Prathalingam, S. R., Kelly, J. M., Romero, V., Ivorra, D. & Cortes, D. (2008). Bioorg. Med. Chem. 16, 9925-9936.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wang, Y.-C. & Tao, R. (2012). Acta Cryst. E68, o293.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o3296  [ doi:10.1107/S1600536812045175 ]

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