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Volume 69 
Part 8 
Pages o1247-o1248  
August 2013  

Received 13 April 2013
Accepted 8 July 2013
Online 13 July 2013

Key indicators
Single-crystal X-ray study
T = 291 K
Mean [sigma](C-C) = 0.007 Å
Disorder in solvent or counterion
R = 0.060
wR = 0.123
Data-to-parameter ratio = 13.9
Details
Open access

7-Benzyl-3-methyl-6-phenylimidazo[2,1-b][1,3]thiazol-7-ium chloride 0.75-hydrate

aSchool of Chemistry and Chemical Engineering, Yunnan Normal University, Knuming 650050, People's Republic of China
Correspondence e-mail: hgli2005@126.com

Theasymmetric unit of the title salt, C19H17N2S+·Cl-·0.75H2O, contains two symmetrically independent formula units of the carbenium salt along with three water molecules. The water molecules are only 50% occupated, and one of them is positioned in a hydrophobic pocket not forming any hydrogen bonds. The conformation of the independent cations is very similar, with dihedral angles of 61.0 (2) and 61.5 (3)° between the benzene rings. They form quasi-centrosymmetric couples via [pi]-[pi] stacking interactions between the benzene and imidazo[2,1-b]thiazole rings [centroid-centroid distances = 3.718 (3) and 3.663 (3) Å]. In the crystal, O-H...Cl hydrogen bonds lead to the formation of a helical anion-water chain along the c-axis direction. The cations connect to the anion-water chain through C-H...Cl interactions, generating a three-dimensional supramolecular network. O-H...S hydrogen bonds and C-H...O interactions also occur.

Related literature

For applications in catalysis of abnormal N-heterocyclic carbenes, see: Mattson et al. (2006[Mattson, A. E., Zuhl, A. M., Reynolds, T. E. & Scheidt, K. A. (2006). J. Am. Chem. Soc. 128, 4932-4933.]); Liu et al. (2008[Liu, Q., Perreault, S. & Rovis, R. (2008). J. Am. Chem. Soc. 130, 14066-14067.]); Padmanaban et al. (2011[Padmanaban, M., Biju, A. T. & Glorius, F. (2011). Org. Lett. 13, 98-101.]). For related structures, see: Huang et al. (2011[Huang, G. L., Sun, H. S., Qiu, X. J., Jin, C., Lin, C., Shen, Y. Z., Jiang, J. L. & Wang, L. Y. (2011). Org. Lett. 13, 5224-5227.]); Akkurt et al. (2011[Akkurt, M., Güzeldemirci, N. U., Karaman, B. & Büyükgüngör, O. (2011). Acta Cryst. E67, o184-o185.], 2007[Akkurt, M., Yalçin, S. P., Gürsoy, E., Güzeldemirci, N. U. & Büyükgüngör, O. (2007). Acta Cryst. E63, o3103.]); Song et al. (2008[Song, G. Y., Zhang, Y. & Li, X. W. (2008). Organometallics, 13, 1936-1943.]).

[Scheme 1]

Experimental

Crystal data
  • C19H17N2S+·Cl-·0.75H2O

  • Mr = 354.37

  • Trigonal, P 32

  • a = 13.211 (1) Å

  • c = 19.555 (3) Å

  • V = 2955.7 (6) Å3

  • Z = 6

  • Mo K[alpha] radiation

  • [mu] = 0.31 mm-1

  • T = 291 K

  • 0.28 × 0.24 × 0.22 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.919, Tmax = 0.936

  • 16250 measured reflections

  • 6594 independent reflections

  • 4827 reflections with I > 2[sigma](I)

  • Rint = 0.053

Refinement
  • R[F2 > 2[sigma](F2)] = 0.060

  • wR(F2) = 0.123

  • S = 1.00

  • 6594 reflections

  • 476 parameters

  • 15 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.])

  • Flack parameter: 0.04 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1W-H1WA...Cl1i 0.94 2.75 3.208 (6) 111
O1W-H1WA...S2ii 0.94 2.88 3.819 (6) 174
O1W-H1WB...Cl2 0.86 2.61 3.240 (7) 132
O3W-H3WA...Cl2iii 0.85 2.68 3.275 (10) 129
O3W-H3WB...Cl1i 0.85 2.60 3.301 (10) 141
C8-H8...Cl1 0.93 2.78 3.664 (5) 159
C10-H10...Cl1iv 0.93 2.72 3.390 (5) 130
C18-H18...O3Wv 0.93 2.52 3.320 (9) 144
C27-H27...Cl1 0.93 2.72 3.642 (5) 175
Symmetry codes: (i) x, y+1, z; (ii) [-x+y, -x+1, z+{\script{1\over 3}}]; (iii) [-y+1, x-y+1, z-{\script{1\over 3}}]; (iv) [-x+y+1, -x+1, z+{\script{1\over 3}}]; (v) x+1, y, z.

Data collection: SMART (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. 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: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LD2101 ).


Acknowledgements

The authors thank the Scientific Researching Fund Projects of Yunnan Educational Department (grant No. 22012Z017) and the Youth Scientific Fund Projects of Yunnan Normal University for financial support.

References

Akkurt, M., Güzeldemirci, N. U., Karaman, B. & Büyükgüngör, O. (2011). Acta Cryst. E67, o184-o185.  [CrossRef] [ChemPort] [IUCr Journals]
Akkurt, M., Yalçin, S. P., Gürsoy, E., Güzeldemirci, N. U. & Büyükgüngör, O. (2007). Acta Cryst. E63, o3103.  [CSD] [CrossRef] [IUCr Journals]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [IUCr Journals]
Huang, G. L., Sun, H. S., Qiu, X. J., Jin, C., Lin, C., Shen, Y. Z., Jiang, J. L. & Wang, L. Y. (2011). Org. Lett. 13, 5224-5227.  [Web of Science] [CSD] [CrossRef] [ChemPort] [PubMed]
Liu, Q., Perreault, S. & Rovis, R. (2008). J. Am. Chem. Soc. 130, 14066-14067.  [Web of Science] [CSD] [CrossRef] [PubMed] [ChemPort]
Mattson, A. E., Zuhl, A. M., Reynolds, T. E. & Scheidt, K. A. (2006). J. Am. Chem. Soc. 128, 4932-4933.  [Web of Science] [CSD] [CrossRef] [PubMed] [ChemPort]
Padmanaban, M., Biju, A. T. & Glorius, F. (2011). Org. Lett. 13, 98-101.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Song, G. Y., Zhang, Y. & Li, X. W. (2008). Organometallics, 13, 1936-1943.  [CSD] [CrossRef]


Acta Cryst (2013). E69, o1247-o1248   [ doi:10.1107/S1600536813018795 ]

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