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Volume 69 
Part 5 
Pages m244-m245  
May 2013  

Received 21 March 2013
Accepted 28 March 2013
Online 5 April 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
Disorder in solvent or counterion
R = 0.047
wR = 0.110
Data-to-parameter ratio = 20.1
Details
Open access

(anti-Chloridothiosemicabazide-[kappa]S)bis(triphenylphosphane-[kappa]P)copper(I) 0.48-hydrate

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

In the mononuclear title complex, [CuCl(CH5N3S)(C18H15P)2]·0.48H2O, the CuI ion is in a slightly distorted tetrahedral coordination geometry formed by two P atoms from two triphenylphosphane ligands, one S atom from a thiosemicarbazide ligand and one chloride anion. An intramolecular N-H...N hydrogen bond [graph-set motif S(5)] stabilizes the thiosemicarbazide ligand in its anti conformation, and an intramolecular N-H...Cl hydrogen bond between the hydrazine N-H group and the chloride anion influences the arrangement and orientation of the ligands around the metal center. A weak intramolecular C-H...Cl hydrogen bond is also present. In the crystal, complex molecules are connected through N-H...Cl hydrogen bonds originating from the amide -NH2 group, and through O-H...S and O-H...Cl hydrogen bonds involving the solvent water molecule. Both the direct N-H...Cl hydrogen bonds as well as the bridging hydrogen bonds mediated by the water molecule connect the complex molecules into zigzag chains that propagate along [010]. The solvent water molecule is partially occupied, with a refined occupancy of 0.479 (7).

Related literature

For the coordination of thiosemicarbazide and thiosemicarbazones with metal complexes, see: Andreetti et al. (1970[Andreetti, G. D., Domiano, P., Gasparri, G. F., Nardelli, M. & Sgarabotto, P. (1970). Acta Cryst. B26, 1005-1009.]); Chattopadhyay et al. (1991[Chattopadhyay, D., Majumdar, S. K., Lowe, P., Schwalbe, C. H., Chattopadhyay, S. K. & Ghosh, S. (1991). J. Chem. Soc. Dalton Trans. pp. 2121-2124.]); Jia et al. (2008a[Jia, L., Ma, S. & Li, D. (2008a). Acta Cryst. E64, m796.],b[Jia, L., Ma, S.-X. & Li, D.-C. (2008b). Acta Cryst. E64, m820.]); Villa et al. (1972a[Villa, A. C., Manfredotti, A. G. & Guastini, C. (1972a). Cryst. Struct. Commun. 1, 125.],b[Villa, A. C., Manfredotti, A. G. & Guastini, C. (1972b). Cryst. Struct. Commun. 1, 207.]); Qirong et al. (1987[Qirong, C., Cun, L., Jingyu, Z., Xiaozeng, Y., Jinshun, H., Manfang, W. & Tongbao, K. (1987). Chin. Sci. Bull. 32, 321-330.]). For potential applications of related complexes, see: Alagarsamy & Parthiban (2011[Alagarsamy, V. & Parthiban, P. (2011). Rasayan. J. Chem. 4, 736-743.]); Kowol et al. (2007[Kowol, C. R., Berger, R., Eichinger, R., Roller, A., Jakupec, M. A., Schmidt, P. P., Arion, V. B. & Keppler, B. K. (2007). J. Med. Chem. 50, 1254-1265.]); Pelosi (2010[Pelosi, G. (2010). The Open Crystallogr. J. 3, 16-28.]); Yu et al. (2009[Yu, Y., Kalinowski, D. S., Kovacevic, Z., Siafakas, A. R., Jansson, P. J., Stefani, C., Lovejoy, D. B., Sharpe, P. C. & Richardson, D. R. (2009). J. Med. Chem. 52, 5271-5294.]); Wattanakanjana et al. (2012[Wattanakanjana, Y., Pakawatchai, C., Saithong, S., Piboonphon, P. & Nimthong, R. (2012). Acta Cryst. E68, m1417-m1418.]). For hydrogen-bond graph-set motifs, see: Bernstein, et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For a description of the Cambridge Structural Database (CSD), see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data
  • [CuCl(CH5N3S)(C18H15P)2]·0.48H2O

  • Mr = 723.29

  • Monoclinic, P 21 /n

  • a = 14.8723 (7) Å

  • b = 12.4829 (6) Å

  • c = 19.2103 (9) Å

  • [beta] = 96.126 (1)°

  • V = 3546.0 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.87 mm-1

  • T = 293 K

  • 0.34 × 0.11 × 0.07 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2003)[Bruker (2003). SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.] Tmin = 0.880, Tmax = 1

  • 48021 measured reflections

  • 8591 independent reflections

  • 6691 reflections with I > 2[sigma](I)

  • Rint = 0.047

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.110

  • S = 1.06

  • 8591 reflections

  • 428 parameters

  • 4 restraints

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

  • [Delta][rho]max = 0.42 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1C...Cl1 0.82 (2) 2.37 (2) 3.186 (5) 179 (12)
O1-H1D...S1i 0.82 (2) 2.70 (10) 3.218 (5) 123 (9)
N1-H1B...Cl1ii 0.86 2.48 3.302 (3) 161
N1-H1A...N3 0.86 2.27 2.628 (5) 105
N2-H2...Cl1 0.86 2.35 3.202 (2) 170
C42-H42...Cl1 0.93 2.72 3.626 (3) 164
Symmetry codes: (i) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2003[Bruker (2003). 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: SHELXL2012 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and SHELXLE Rev609 (Hübschle et al., 2011[Hübschle, C. B., Sheldrick, G. M. & Dittrich, B. (2011). J. Appl. Cryst. 44, 1281-1284.]); 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: SHELXL97 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: LH5600 ).


Acknowledgements

Financial support from the Center of Excellence for Innovation in Chemistry (PERCH-CIC), the Office of the Higher Education Commission, Ministry of Education and Department of Chemistry, Prince of Songkla University, is gratefully acknowledged. RN would like to thank Dr Matthias Zeller for valuable suggestions and assistance with X-ray structure determination and use of structure refinement programs.

References

Alagarsamy, V. & Parthiban, P. (2011). Rasayan. J. Chem. 4, 736-743.  [ChemPort]
Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Andreetti, G. D., Domiano, P., Gasparri, G. F., Nardelli, M. & Sgarabotto, P. (1970). Acta Cryst. B26, 1005-1009.  [CrossRef] [ChemPort] [details] [ISI]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2003). SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chattopadhyay, D., Majumdar, S. K., Lowe, P., Schwalbe, C. H., Chattopadhyay, S. K. & Ghosh, S. (1991). J. Chem. Soc. Dalton Trans. pp. 2121-2124.  [CrossRef]
Hübschle, C. B., Sheldrick, G. M. & Dittrich, B. (2011). J. Appl. Cryst. 44, 1281-1284.  [ISI] [CrossRef] [details]
Jia, L., Ma, S. & Li, D. (2008a). Acta Cryst. E64, m796.  [CSD] [CrossRef] [details]
Jia, L., Ma, S.-X. & Li, D.-C. (2008b). Acta Cryst. E64, m820.  [CSD] [CrossRef] [details]
Kowol, C. R., Berger, R., Eichinger, R., Roller, A., Jakupec, M. A., Schmidt, P. P., Arion, V. B. & Keppler, B. K. (2007). J. Med. Chem. 50, 1254-1265.  [ISI] [CSD] [CrossRef] [PubMed] [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]
Pelosi, G. (2010). The Open Crystallogr. J. 3, 16-28.  [CrossRef] [ChemPort]
Qirong, C., Cun, L., Jingyu, Z., Xiaozeng, Y., Jinshun, H., Manfang, W. & Tongbao, K. (1987). Chin. Sci. Bull. 32, 321-330.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Villa, A. C., Manfredotti, A. G. & Guastini, C. (1972a). Cryst. Struct. Commun. 1, 125.
Villa, A. C., Manfredotti, A. G. & Guastini, C. (1972b). Cryst. Struct. Commun. 1, 207.
Wattanakanjana, Y., Pakawatchai, C., Saithong, S., Piboonphon, P. & Nimthong, R. (2012). Acta Cryst. E68, m1417-m1418.  [CSD] [CrossRef] [ChemPort] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Yu, Y., Kalinowski, D. S., Kovacevic, Z., Siafakas, A. R., Jansson, P. J., Stefani, C., Lovejoy, D. B., Sharpe, P. C. & Richardson, D. R. (2009). J. Med. Chem. 52, 5271-5294.  [ISI] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, m244-m245   [ doi:10.1107/S1600536813008556 ]

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