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Volume 69 
Part 1 
Pages m34-m35  
January 2013  

Received 30 November 2012
Accepted 3 December 2012
Online 8 December 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.006 Å
R = 0.038
wR = 0.086
Data-to-parameter ratio = 14.7
Details
Open access

Chlorido[1H-1,2,4-triazole-5(4H)-thione-[kappa]S]bis(triphenylphosphane-[kappa]P)copper(I) acetronitrile monosolvate

aDepartment of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Prince of Songkla University, Hat Yai, Songkhla 90112, Thailand
Correspondence e-mail: saowanit.sa@psu.ac.th

In the title solvate, [CuCl(C2H3N3S)(C18H15P)2]·CH3CN, the CuI ion is bonded to two triphenylphosphane ligands, one 1H-1,2,4-triazole-5(4H)-thione ligand via its S atom and one chloride ion in a distorted CuP2SCl tetrahedron. An intramolecular N-H...Cl hydrogen bond, which closes an S(6) ring, helps to establish the conformation of the complex. In the crystal, N-H...Cl hydrogen bonds and C-H...[pi] interactions link the components, generating (110) layers.

Related literature

For the properties of mixed-ligand copper(I) complexes, see: Oshio et al. (1996[Oshio, H., Watanabe, T., Ohto, A., Ito, T. & Masuda, H. (1996). Inorg. Chem. 35, 472-479.]); Henary et al. (1997[Henary, M., Wootton, J. L., Khan, S. I. & Zink, J. I. (1997). Inorg. Chem. 36, 796-801.]); Vitale & Ford (2001[Vitale, M. & Ford, P. C. (2001). Coord. Chem. Rev. 219-221, 3-16.]); Zhang & Chen (2003[Zhang, X.-M. & Chen, X.-M. (2003). Eur. J. Inorg. Chem. pp. 413-417.]). For structurally related mixed-ligand complexes of triphenylphosphane and thione ligands, see: Skoulika et al. (1991[Skoulika, S., Aubry, A., Karagiannidis, P., Aslanidis, P. & Papastefanou, S. (1991). Inorg. Chim. Acta, 183, 207-211.]); Aslanidis et al. (1998[Aslanidis, P., Hadjikakou, S. K., Karagiannidis, P. & Cox, P. J. (1998). Inorg. Chim. Acta, 271, 243-247.]); Chen et al. (2001[Chen, Z.-F., Li, B.-Q., Xie, Y.-R., Xiong, R.-G., You, X.-Z. & Feng, X.-L. (2001). Inorg. Chem. Commun. 4, 346-349.]); Li et al. (2004[Li, D., Shi, W.-J., Wu, T. & Ng, S. W. (2004). Acta Cryst. E60, m776-m777.]); Lobana et al. (2008[Lobana, T. S., Sultana, R. & Hundal, G. (2008). Polyhedron, 27, 1008-1016.]); La-o et al. (2009[La-o, L., Pakawatchai, C., Saithong, S. & Skelton, B. W. (2009). Acta Cryst. E65, m926.]). For complexes of 1,2,4-triazole-2-thione and its derivatives, see: Sen et al. (1996[Sen, A. K., Dubey, S. N. & Squattrito, P. J. (1996). Acta Cryst. C52, 865-868.]); Zhang et al. (2008[Zhang, R.-B., Li, Z.-J., Cheng, J.-K., Qin, Y.-Y., Zhang, J. & Yao, Y.-G. (2008). Cryst. Growth Des. 8, 2562-2573.]).

[Scheme 1]

Experimental

Crystal data
  • [CuCl(C2H3N3S)(C18H15P)2]·C2H3N

  • Mr = 765.72

  • Orthorhombic, P 21 21 21

  • a = 10.2348 (4) Å

  • b = 16.4046 (7) Å

  • c = 22.3632 (9) Å

  • V = 3754.7 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.83 mm-1

  • T = 293 K

  • 0.27 × 0.18 × 0.09 mm

Data collection
  • Bruker APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2003[Bruker (2003). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.840, Tmax = 0.928

  • 30968 measured reflections

  • 6602 independent reflections

  • 6040 reflections with I > 2[sigma](I)

  • Rint = 0.044

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.086

  • S = 1.11

  • 6602 reflections

  • 449 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.52 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2890 Friedel pairs

  • Flack parameter: -0.001 (11)

Table 1
Selected bond lengths (Å)

Cu1-P1 2.2802 (9)
Cu1-P2 2.2824 (9)
Cu1-S1 2.3582 (9)
Cu1-Cl1 2.4035 (9)

Table 2
Hydrogen-bond geometry (Å, °)

Cg7 is the centroid of the C31-C36 ring.

D-H...A D-H H...A D...A D-H...A
N3-H3A...Cl1 0.84 (2) 2.41 (3) 3.183 (3) 155 (5)
N1-H1A...Cl1i 0.84 (2) 2.34 (2) 3.154 (3) 163 (5)
C15-H15...Cg7ii 0.93 2.88 3.749 (4) 155
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+2]; (ii) [-x-1, y+{\script{5\over 2}}, -z+{\script{5\over 2}}].

Data collection: SMART (Bruker, 2003[Bruker (2003). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2003[Bruker (2003). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT (Bruker, 2003[Bruker (2003). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7008 ).


Acknowledgements

Financial support from the Center of Excellence for Innovation in Chemistry (PERCH-CIC), the Office of the Higher Education Commission, the Ministry of Education and the Graduate School, Prince of Songkla University, are gratefully acknowledged.

References

Aslanidis, P., Hadjikakou, S. K., Karagiannidis, P. & Cox, P. J. (1998). Inorg. Chim. Acta, 271, 243-247.  [ISI] [CrossRef] [ChemPort]
Bruker (2003). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chen, Z.-F., Li, B.-Q., Xie, Y.-R., Xiong, R.-G., You, X.-Z. & Feng, X.-L. (2001). Inorg. Chem. Commun. 4, 346-349.  [ISI] [CrossRef] [ChemPort]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Henary, M., Wootton, J. L., Khan, S. I. & Zink, J. I. (1997). Inorg. Chem. 36, 796-801.  [CrossRef] [ChemPort] [ISI]
La-o, L., Pakawatchai, C., Saithong, S. & Skelton, B. W. (2009). Acta Cryst. E65, m926.  [CSD] [CrossRef] [details]
Li, D., Shi, W.-J., Wu, T. & Ng, S. W. (2004). Acta Cryst. E60, m776-m777.  [CSD] [CrossRef] [details]
Lobana, T. S., Sultana, R. & Hundal, G. (2008). Polyhedron, 27, 1008-1016.  [ISI] [CSD] [CrossRef] [ChemPort]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Oshio, H., Watanabe, T., Ohto, A., Ito, T. & Masuda, H. (1996). Inorg. Chem. 35, 472-479.  [CrossRef] [PubMed] [ChemPort] [ISI]
Sen, A. K., Dubey, S. N. & Squattrito, P. J. (1996). Acta Cryst. C52, 865-868.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Skoulika, S., Aubry, A., Karagiannidis, P., Aslanidis, P. & Papastefanou, S. (1991). Inorg. Chim. Acta, 183, 207-211.  [CrossRef] [ChemPort] [ISI]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Vitale, M. & Ford, P. C. (2001). Coord. Chem. Rev. 219-221, 3-16.  [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Zhang, X.-M. & Chen, X.-M. (2003). Eur. J. Inorg. Chem. pp. 413-417.  [CSD] [CrossRef]
Zhang, R.-B., Li, Z.-J., Cheng, J.-K., Qin, Y.-Y., Zhang, J. & Yao, Y.-G. (2008). Cryst. Growth Des. 8, 2562-2573.  [CSD] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, m34-m35   [ doi:10.1107/S1600536812049537 ]

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