Bis(6-meth­oxy-1-methyl-2,3,4,9-tetra­hydro-1H-β-carbolin-2-ium) tetra­chloridozincate(II) dihydrate

Goh, T.B.; Mordi, M.N.; Mansor, S.M.; Rosli, M.M.; Fun, H.-K.

doi:10.1107/S1600536812011130

Volume 68
Part 4
Pages m464-m465
April 2012

Received 29 February 2012
Accepted 14 March 2012
Online 24 March 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R = 0.043
wR = 0.098
Data-to-parameter ratio = 24.6
Details

Bis(6-methoxy-1-methyl-2,3,4,9-tetrahydro-1H--carbolin-2-ium) tetrachloridozincate(II) dihydrate

Teik Beng Goh,^a Mohd Nizam Mordi,^a Sharif Mahsufi Mansor,^a Mohd Mustaqim Rosli ^b and Hoong-Kun Fun ^b ^*

^aCentre for Drug Research, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: hkfun@usm.my

The asymmetric unit of the title compound, (C₁₃H₁₇N₂O)₂[ZnCl₄]·2H₂O, contains two tetrahydroharmine cations, one tetrachlorozincate(II) anion and two water molecules. In the cations, the two 1H-indole ring systems are essentially planar, with maximum deviations of 0.016 (2) and 0.018 (2) Å, and both tetrahydropyridinium rings show a half-chair conformation. The Zn^II complex anion has a distorted tetrahedral geometry. In the crystal, intermolecular N-HO, N-HCl, O-HO, O-HCl and C-HO hydrogen bonds link the components into a three-dimensional network. A [pi] - [pi] interaction with a centroid-centroid distance of 3.542 (14) Å is also observed.

Related literature

For the biological activity of metal complexes with 6-methoxy-1-methyl-4,9-dihydro-3H-pyrido[3,4-b]indole, see: Al-Allaf et al. (1990); Herraiz et al. (2003). For structures of [beta] -carboline and related compounds, see: Anlong et al. (2007); Larghi et al. (2005); Reimers et al. (1984); Wouters (1997); Ferretti et al. (2004). For a related tetrachloridozincate structure, see: Ma et al. (2009). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental

Crystal data

(C₁₃H₁₇N₂O)₂[ZnCl₄]·2H₂O
M_r = 677.77
Monoclinic, P 2₁ /c
a = 7.3319 (1) Å
b = 18.5135 (3) Å
c = 22.0578 (3) Å
= 91.516 (1)°
V = 2993.06 (8) Å³
Z = 4
Mo K radiation
= 1.22 mm^-1
T = 100 K
0.39 × 0.17 × 0.11 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.648, T_max = 0.876
33557 measured reflections
8753 independent reflections
6404 reflections with I > 2(I)
R_int = 0.060

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.098
S = 1.03
8753 reflections
356 parameters
H-atom parameters constrained
_max = 0.70 e Å^-3
_min = -0.42 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1A-H1NACl3ⁱ	0.90	2.49	3.271 (2)	146
N2A-H2NACl4ⁱⁱ	0.80	2.43	3.208 (2)	164
N2A-H3NAO1WBⁱⁱⁱ	0.89	1.92	2.790 (3)	166
N1B-H1NBO1WB	0.92	1.99	2.872 (3)	159
N2B-H2NBCl1ⁱⁱⁱ	0.86	2.28	3.141 (2)	176
N2B-H3NBCl3ⁱⁱ	0.92	2.32	3.231 (2)	171
O1WA-H1WACl4^iv	0.92	2.42	3.204 (2)	143
O1WA-H2WAO1A^v	0.91	1.89	2.799 (3)	173
O1WB-H1WBO1WA^iv	0.90	1.78	2.672 (3)	175
O1WB-H2WBCl2	0.91	2.33	3.231 (2)	169
C12B-H12EO1WA^vi	0.98	2.58	3.487 (3)	153
C3B-H3BAO1B^vii	0.95	2.56	3.373 (3)	143
Symmetry codes: (i) x, y-1, z; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) -x+1, -y+1, -z+1; (v) x+1, y, z; (vi) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (vii) -x+1, -y+2, -z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5085 ).

Acknowledgements

This work was supported by USM Research University Grant No. 1001/CDADAH/815020 and the R&D Initiative Fund, Ministry of Science, Technology and Innovation, Malaysia (MOSTI). HKF also thanks Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160.

References

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Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Ferretti, V., Gilli, P. & Borea, P. A. (2004). Acta Cryst. B60, 481-489.
Herraiz, T., Galisteo, J. & Chamorro, C. (2003). J. Agric. Food Chem. 51, 2168-2173.
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