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

Jin, X.-D.; Yin, X.-Y.; Xu, L.-S.; Ge, C.-H.; Chang, X.-H.

doi:10.1107/S1600536812045175

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 (C-C) = 0.006 Å
R = 0.069
wR = 0.216
Data-to-parameter ratio = 13.2
Details

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

Xu-Dong Jin,^a ^* Xue-Yue Yin,^a Lu-Sha Xu,^a Chun-Hua Ge ^a and Xiao-Hong Chang ^a

^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-HN 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). For the synthesis and applications of amantadine derivatives, see: Camps et al. (2008).

Experimental

Crystal data

C₁₇H₂₂ClNO·0.5H₂O
M_r = 300.82
Monoclinic, C 2/c
a = 25.469 (16) Å
b = 6.365 (4) Å
c = 18.306 (11) Å
= 91.815 (12)°
V = 2966 (3) Å³
Z = 8
Mo K radiation
= 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) T_min = 0.915, T_max = 0.960
6372 measured reflections
2606 independent reflections
1798 reflections with I > 2(I)
R_int = 0.098

Refinement

R[F² > 2(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
_max = 0.39 e Å^-3
_min = -0.40 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1N1	0.83 (6)	2.07 (9)	2.611 (5)	122 (7)
O1W-H1WO1ⁱ	0.84 (4)	1.99 (4)	2.768 (5)	153 (5)
N1-H1AO1W	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); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); 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.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wang, Y.-C. & Tao, R. (2012). Acta Cryst. E68, o293.

organic compounds