4-Hydr­oxy-2,2,6,6-tetra­methyl­piperidinium chloride–hydroxonium chloride (3/1)

Zhang, L.; Zhang, P.-W.; Wang, X.-H.; Chen, L.; Shen, Q.-F.

doi:10.1107/S1600536808002158

Volume 64
Part 2
Page o512
February 2008

Received 9 January 2008
Accepted 21 January 2008
Online 25 January 2008

Key indicators
Single-crystal X-ray study
T = 113 K
Mean (C-C) = 0.003 Å
Disorder in main residue
R = 0.051
wR = 0.130
Data-to-parameter ratio = 22.2
Details

4-Hydroxy-2,2,6,6-tetramethylpiperidinium chloride-hydroxonium chloride (3/1)

Li Zhang,^a ^* Peng-Wei Zhang,^a,^b Xiao-Hui Wang,^a Li Chen ^a and Qu-Fei Shen ^a

^aDepartment of Pharmaceutics, Medical College of the Chinese People's Armed Police Force, Tianjin 300162, People's Republic of China, and ^bSchool of Pharmaceutical Science & Technology, Tianjin University, Tianjin 300072, People's Republic of China
Correspondence e-mail: zpw0803@gmail.com

The crystal structure of the title compound, C₉H₂₀NO⁺·Cl^-·0.33(H₃O⁺·Cl^-), is composed of 4-hydroxy-2,2,6,6-tetramethylpiperidinium cations, hydroxonium cations and chloride anions, which are connected via O-HO, O-HCl and N-HCl hydrogen bonding. The 4-hydroxy-2,2,6,6-tetramethylpiperidinium cation and one of the two crystallographically independent chloride anions are located on a mirror plane. The hydroxonium cation is located on a threefold axis and the second crystallographically independent chloride anion is located on a sixfold rotoinversion axis. Due to symmetry, the hydroxonium cation is disordered over two positions.

Experimental

Crystal data

C₉H₂₀NO⁺·Cl^-·0.33(H₃O⁺·Cl^-)
M_r = 211.87
Hexagonal, P 6₃ /m
a = 13.4460 (19) Å
c = 11.528 (2) Å
V = 1804.9 (5) Å³
Z = 6
Mo K radiation
= 0.36 mm^-1
T = 113 (2) K
0.10 × 0.10 × 0.04 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) T_min = 0.968, T_max = 0.989
14051 measured reflections
1513 independent reflections
1424 reflections with I > 2(I)
R_int = 0.075

Refinement

R[F² > 2(F²)] = 0.051
wR(F²) = 0.130
S = 1.08
1513 reflections
68 parameters
H-atom parameters constrained
_max = 0.33 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1Cl2ⁱ	0.85	2.15	2.991 (2)	172
N1-H1BCl2ⁱⁱ	0.92	2.22	3.139 (2)	175
N1-H1CCl1ⁱⁱⁱ	0.92	2.25	3.166 (2)	176
O2-H2O1^iv	0.85	1.63	2.475 (2)	175
Symmetry codes: (i) -y, x-y, z; (ii) -x+y+1, -x+1, z; (iii) -x+1, -y+1, -z+1; (iv) x+1, y, z.

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2088 ).

References

Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds