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Volume 69 
Part 3 
Pages m137-m138  
March 2013  

Received 6 November 2012
Accepted 30 January 2013
Online 6 February 2013

Key indicators
Single-crystal X-ray study
T = 90 K
Mean [sigma](C-C) = 0.005 Å
R = 0.042
wR = 0.103
Data-to-parameter ratio = 27.4
Details
Open access

Chlorido{4-ethyl-1-[1-(pyrazin-2-yl)ethylidene]thiosemicabazidato-[kappa]S}bis(triphenylphosphane-[kappa]P)silver(I)

aDepartment of Chemistry and Biochemistry, Jackson State University, Jackson, MS 39217-0510, USA,bDepartment of Civil and Env. Engineering, Jackson State University, Jackson, MS 39217-0510, USA, and cDepartment of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USA
Correspondence e-mail: ramaiyer.venkatraman@jsums.edu

The title compound, [Ag(C9H13N5S)Cl(C18H15P)2], crystallizes with four independent molecules in the asymmetric unit, in each of which the Ag atom is in a distorted tetrahedral coordination, defined by the chloride ligand, the S atom of the neutral ligand and two P atoms derived from the triphenyl phosphine ligands. The thiosemicarbazone acts as a monodentate ligand through its thione S atom. An intramolecular N-H...Cl hydrogen bond occurs in two of the independent molecules. In the crystal, the molecules are assembled through N-H...Cl hydrogen bonds, forming chains along [101].

Related literature

For general background to thiosemicarbazones, see: Akinchan et al. (2002[Akinchan, N. T., Drozdzewski, P. M. & Holzer, W. J. (2002). J. Mol. Struct. 641, 17-22.]); Ali & Livingstone (1974[Ali, M. & Livingstone, S. F. (1974). Coord. Chem. Rev. 13, 101-132.]); Bermejo et al. (2003[Bermejo, E., Castineiras, A., Garcia, I. & West, D. X. (2003). Polyhedron, 22, 1147-1154.]); Blanz & French (1968[Blanz, E. J. Jr & French, F. A. (1968). Cancer Res. 28, 2419-2422.]); Campbell (1975[Campbell, M. J. M. (1975). Coord. Chem. Rev. 15, 279-319.]); Casas et al. (2000[Casas, J. S., Garcia-Tasende, M. S. & Sordo, J. (2000). Coord. Chem. Rev. 209, 197-261.]); Grecu & Neamtu (1967[Grecu, I. & Neamtu, M. (1967). Rev. Chim. (Euchavest), 12, 1115-1121.]); Hossain et al. (2002[Hossain, M. A., Llinares, J. M., Powell, D. & Bowman-James, K. (2002). Supramol. Chem. 2, 143-1151.]); Huheey et al. (1993[Huheey, J. E., Keiter, E. A. & Keiter, R. L. (1993). Inorganic Chemistry: Principles and Structure and Reactivity, 4th ed. New York: Harper Collins.]); Lobana et al. (1998[Lobana, T. S., Sanchez, A., Casas, J. S., Castineiras, A., Sordo, J. & Garcia-Tasende, M. S. (1998). Polyhedron, 21, 3701-3709.], 2008[Lobana, T. S., Khanna, S., Sharma, R., Hundal, G., Sultana, R., Chaudhary, M., Butcher, R. J. & Castineiras, A. (2008). Cryst. Growth Des. 8, 1203-1212.]); Pellerito & Negy (2002[Pellerito, L. & Negy, L. (2002). Coord. Chem. Rev. 224, 111-150.]); Raper (1985[Raper, E. S. (1985). Coord. Chem. Rev. 61, 115-184.]); Venkatraman et al. (2009[Venkatraman, R., Ameera, H., Sitole, L., Ellis, E., Fronczek, F. R. & Valente, E. J. (2009). J. Chem. Crystallogr. 30, 711-718.]); Zhou et al. (2008[Zhou, J., Wang, Y.-X., Chen, C.-L. & Li, M.-X. (2008). Acta Cryst. E64, o94.]).

[Scheme 1]

Experimental

Crystal data
  • [Ag(C9H13N5S)Cl(C18H15P)2]

  • Mr = 891.17

  • Monoclinic, P 21

  • a = 12.0640 (5) Å

  • b = 31.810 (2) Å

  • c = 21.9207 (15) Å

  • [beta] = 98.029 (5)°

  • V = 8329.7 (9) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.71 mm-1

  • T = 90 K

  • 0.27 × 0.22 × 0.20 mm

Data collection
  • Nonius KappaCCD diffractometer with Oxford Cryostream system

  • Absorption correction: multi-scan (DENZO and SCALEPACK; Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) Tmin = 0.831, Tmax = 0.870

  • 138032 measured reflections

  • 54942 independent reflections

  • 44399 reflections with I > 2[sigma](I)

  • Rint = 0.055

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.103

  • S = 1.03

  • 54942 reflections

  • 2007 parameters

  • 9 restraints

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

  • [Delta][rho]max = 1.03 e Å-3

  • [Delta][rho]min = -0.85 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 25,519 Friedel pairs

  • Flack parameter: 0.382 (11)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N...Cl1 0.88 (2) 2.54 (2) 3.381 (3) 163 (3)
N3-H3N...Cl3 0.87 (2) 2.68 (3) 3.406 (3) 142 (3)
N6-H6N...Cl2 0.88 (2) 2.53 (2) 3.370 (3) 162 (3)
N8-H8N...Cl4 0.86 (2) 2.68 (3) 3.411 (3) 143 (3)
N11-H11N...Cl3 0.88 (2) 2.52 (2) 3.363 (3) 161 (3)
N13-H13N...Cl2 0.88 (2) 2.65 (2) 3.423 (3) 147 (3)
N16-H16N...Cl4 0.86 (2) 2.50 (2) 3.338 (3) 164 (3)
N18-H18N...Cl1i 0.86 (2) 2.70 (3) 3.425 (3) 143 (3)
Symmetry code: (i) x-1, y, z-1.

Data collection: COLLECT (Nonius, 2000[Nonius (2000). COLLECT. Nonius BV. Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXH (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXH.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2386 ).


Acknowledgements

The National Science Foundation is acknowledged for a CAREER award (CHE-1056927) to MAH. Purchase of the diffractometer was made possible by grant No. LEQSF (1999-2000)-ENH-TR-13, administered by the Louisiana Board of Regents.

References

Akinchan, N. T., Drozdzewski, P. M. & Holzer, W. J. (2002). J. Mol. Struct. 641, 17-22.  [ISI] [CrossRef] [ChemPort]
Ali, M. & Livingstone, S. F. (1974). Coord. Chem. Rev. 13, 101-132.  [ChemPort]
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [ISI] [CrossRef] [ChemPort] [details]
Bermejo, E., Castineiras, A., Garcia, I. & West, D. X. (2003). Polyhedron, 22, 1147-1154.  [ISI] [CSD] [CrossRef] [ChemPort]
Blanz, E. J. Jr & French, F. A. (1968). Cancer Res. 28, 2419-2422.  [ChemPort] [PubMed] [ISI]
Campbell, M. J. M. (1975). Coord. Chem. Rev. 15, 279-319.  [CrossRef] [ChemPort] [ISI]
Casas, J. S., Garcia-Tasende, M. S. & Sordo, J. (2000). Coord. Chem. Rev. 209, 197-261.  [ISI] [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Grecu, I. & Neamtu, M. (1967). Rev. Chim. (Euchavest), 12, 1115-1121.  [ChemPort]
Hossain, M. A., Llinares, J. M., Powell, D. & Bowman-James, K. (2002). Supramol. Chem. 2, 143-1151.  [ChemPort]
Huheey, J. E., Keiter, E. A. & Keiter, R. L. (1993). Inorganic Chemistry: Principles and Structure and Reactivity, 4th ed. New York: Harper Collins.
Lobana, T. S., Khanna, S., Sharma, R., Hundal, G., Sultana, R., Chaudhary, M., Butcher, R. J. & Castineiras, A. (2008). Cryst. Growth Des. 8, 1203-1212.  [CSD] [CrossRef] [ChemPort]
Lobana, T. S., Sanchez, A., Casas, J. S., Castineiras, A., Sordo, J. & Garcia-Tasende, M. S. (1998). Polyhedron, 21, 3701-3709.  [ISI] [CrossRef]
Nonius (2000). COLLECT. Nonius BV. Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Pellerito, L. & Negy, L. (2002). Coord. Chem. Rev. 224, 111-150.  [ISI] [CrossRef] [ChemPort]
Raper, E. S. (1985). Coord. Chem. Rev. 61, 115-184.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Venkatraman, R., Ameera, H., Sitole, L., Ellis, E., Fronczek, F. R. & Valente, E. J. (2009). J. Chem. Crystallogr. 30, 711-718.  [ISI] [CSD] [CrossRef]
Zhou, J., Wang, Y.-X., Chen, C.-L. & Li, M.-X. (2008). Acta Cryst. E64, o94.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, m137-m138   [ doi:10.1107/S1600536813003152 ]

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