(3S)-2-Benzyl-3-carb­oxy-1,2,3,4-tetra­hydro­isoquinolinium chloride monohydrate

Naicker, T.; Govender, T.; Kruger, H.G.; Maguire, G.E.M.

doi:10.1107/S1600536810053122

Volume 67
Part 1
Page o228
January 2011

Received 22 November 2010
Accepted 17 December 2010
Online 24 December 2010

Key indicators
Single-crystal X-ray study
T = 193 K
Mean (C-C) = 0.003 Å
R = 0.036
wR = 0.082
Data-to-parameter ratio = 19.5
Details

(3S)-2-Benzyl-3-carboxy-1,2,3,4-tetrahydroisoquinolinium chloride monohydrate

Tricia Naicker,^a Thavendran Govender,^a Hendrik G. Kruger ^b and Glenn E. M. Maguire ^b ^*

^aSchool of Pharmacy and Pharmacology, University of KwaZulu Natal, Durban 4000, South Africa, and ^bSchool of Chemistry, University of KwaZulu Natal, Durban 4000, South Africa
Correspondence e-mail: maguireg@ukzn.ac.za

In the title compound, C₁₇H₁₈NO₂⁺·Cl^-·H₂O, a precursor to novel asymmetric catalysts, the N-containing six-membered ring of the tetrahydroquinolinium unit assumes a half-boat conformation. In the crystal, intermolecular O-HO, O-HCl, N-HCl and C-HO hydrogen bonds and C-H [pi] interactions link the molecules into a three-dimensional network.

Related literature

For related structures of tetrahydroisoquinoline derivatives, see: Naicker, Petzold et al. (2010); Naicker, Govender et al. (2010, 2011); Peters et al. (2010). For related structures with the same chiral centre and conformation of the six-membered ring, see: Naicker et al. (2009); Chakka et al. (2010).

Experimental

Crystal data

C₁₇H₁₈NO₂⁺·Cl^-·H₂O
M_r = 321.79
Monoclinic, P 2₁
a = 8.6159 (8) Å
b = 10.0670 (9) Å
c = 10.1392 (9) Å
= 108.686 (2)°
V = 833.08 (13) Å³
Z = 2
Mo K radiation
= 0.24 mm^-1
T = 193 K
0.30 × 0.11 × 0.02 mm

Data collection

Bruker Kappa DUO APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a) T_min = 0.931, T_max = 0.995
9083 measured reflections
4158 independent reflections
3414 reflections with I > 2(I)
R_int = 0.024

Refinement

R[F² > 2(F²)] = 0.036
wR(F²) = 0.082
S = 1.04
4158 reflections
213 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.19 e Å^-3
_min = -0.16 e Å^-3
Absolute structure: Flack (1983), 1961 Friedel pairs
Flack parameter: -0.01 (5)

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C12-C17 ring.

D-HA	D-H	HA	DA	D-HA
N1-H1Cl1ⁱ	0.97 (2)	2.09 (2)	3.0521 (15)	176 (1)
O2-H2O3ⁱⁱ	0.96 (2)	1.59 (2)	2.533 (2)	167 (3)
O3-H3ACl1ⁱ	0.96 (2)	2.21 (2)	3.1615 (15)	172 (2)
O3-H3BCl1	0.96 (2)	2.20 (2)	3.1434 (16)	165 (2)
C9-H9O1ⁱⁱⁱ	1.00	2.30	3.169 (2)	145
C15-H15Cgⁱⁱⁱ	0.95	2.78	3.386 (3)	122
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+1]$ ; (ii) x, y, z-1; (iii) $[-x+1, y+{\script{1\over 2}}, -z]$ .

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2635 ).

Acknowledgements

The authors wish to thank Dr Hong Su of the Chemistry Department of the University of Cape Town for her assistance with the crystallographic data collection.

References

Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chakka, S. K., Govender, T., Kruger, H. G. & Maguire, G. E. M. (2010). Acta Cryst. E66, o1818.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Naicker, T., Govender, T., Kruger, H. G. & Maguire, G. E. M. (2010). Acta Cryst. E66, o3105.
Naicker, T., Govender, T., Kruger, H. G. & Maguire, G. E. M. (2011). Acta Cryst. E67, o67.
Naicker, T., McKay, M., Govender, T., Kruger, H. G. & Maguire, G. E. M. (2009). Acta Cryst. E65, o3278.
Naicker, T., Petzold, K., Singh, T., Arvidsson, P. I., Kruger, H. G., Maguire, G. E. M. & Govender, T. (2010). Tetrahedron Asymmetry. In the press. doi:10.1016/j.tetasy.2010.11.010.
Peters, B. K., Chakka, S. K., Naicker, T., Maguire, G. E. M., Kruger, H. G., Andersson, P. G. & Govender, T. (2010). Tetrahedron Asymmetry, 21, 679-687.
Sheldrick, G. M. (2008a). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.

organic compounds