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Volume 69 
Part 9 
Pages m479-m480  
September 2013  

Received 24 July 2013
Accepted 1 August 2013
Online 7 August 2013

Key indicators
Single-crystal X-ray study
T = 98 K
Mean [sigma](C-C) = 0.003 Å
R = 0.040
wR = 0.100
Data-to-parameter ratio = 20.0
Details
Open access

{[Ethyl(pyridin-4-ylmethyl)carbamothioyl]sulfanido-[kappa]2S,S'}(1,4,7,10,13,16-hexaoxacyclooctadecane-[kappa]6O)potassium

aDepartment of Chemistry, The University of Texas at San Antonio, One UTSA Circle, San Antonio, Texas 78249-0698, USA,bChemical Abstracts Service, 2540 Olentangy River Rd, Columbus, Ohio 43202, USA, and cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: edward.tiekink@gmail.com

The asymmetric unit of title salt co-crystal, [K(C9H11N2S2)(C12H24O6)], comprises a K+ cation, an -S2CN(Et)py anion and a 18-crown-6 molecule. Substantial delocalization of [pi]-electron density is evident in the dithiocarbamate anion, as indicated by the equivalent C-S bond lengths. The K+ cation sits within an O6S2 donor set lying 0.7506 (6) Å out of the least-squares plane through the six O atoms (r.m.s. deviation = 0.1766 Å) of the 18-crown-6 molecule with the two S atoms being on one side of this plane. Supramolecular layers in the bc plane, sustained by C-H...O and C-H...[pi] interactions, feature in the crystal packing.

Related literature

For the relevance of functionalized dithiocarbamate ligands, see: Tan et al. (2013[Tan, Y. S., Sudlow, A. L., Molloy, K. C., Morishima, Y., Fujisawa, K., Jackson, W. J., Henderson, W., Halim, S. N., Bt, A., Ng, S. W. & Tiekink, E. R. T. (2013). Cryst. Growth Des. 13, 3046-3056.]). For Cu, Hg and Sn structures of -S2CN(Et)py, see: Barba et al. (2012[Barba, V., Arenaza, B., Guerrero, J. & Reyes, R. (2012). Heteroat. Chem. 23, 422-428.]); Singh et al. (2011[Singh, V., Kumar, A., Prasad, R., Rajput, G., Drew, M. G. B. & Singh, N. (2011). CrystEngComm, 13, 6817-6826.]); Rajput et al. (2012[Rajput, G., Singh, V., Singh, S. K., Prasad, L. B., Drew, M. G. B. & Singh, N. (2012). Eur. J. Inorg. Chem. pp. 3885-3891.]). For a structure featuring a similar coordination geometry for K+, see: Harrington et al. (2004[Harrington, J. M., Jones, S. B., White, P. H. & Hancock, R. D. (2004). Inorg. Chem. 43, 4456-4463.]).

[Scheme 1]

Experimental

Crystal data
  • [K(C9H11N2S2)(C12H24O6)]

  • Mr = 514.73

  • Monoclinic, P 21 /c

  • a = 17.077 (3) Å

  • b = 17.816 (3) Å

  • c = 8.5107 (17) Å

  • [beta] = 96.010 (3)°

  • V = 2575.1 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.41 mm-1

  • T = 98 K

  • 0.50 × 0.40 × 0.08 mm

Data collection
  • Rigaku AFC12/SATURN724 diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.634, Tmax = 1.000

  • 13965 measured reflections

  • 5807 independent reflections

  • 5310 reflections with I > 2[sigma](I)

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.100

  • S = 1.09

  • 5807 reflections

  • 290 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.54 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Selected bond lengths (Å)

K1-O1 2.7710 (12)
K1-O2 2.9414 (13)
K1-O3 2.8203 (13)
K1-O4 2.9712 (13)
K1-O5 2.8098 (13)
K1-O6 2.9788 (13)
K1-S1 3.1804 (7)
K1-S2 3.2393 (6)
S1-C1 1.7174 (17)
S2-C1 1.7103 (16)
N1-C1 1.362 (2)

Table 2
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N3,C3-C7 ring.

D-H...A D-H H...A D...A D-H...A
C6-H6...O1i 0.95 2.51 3.311 (2) 143
C2-H2B...Cg1ii 0.99 2.87 3.4275 (18) 116
C12-H12B...Cg1iii 0.99 2.95 3.820 (2) 148
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) [x, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]; (iii) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2005[Molecular Structure Corporation & Rigaku (2005). CrystalClear. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: ORTEPII (Johnson, 1976[Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: 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: LH5639 ).


Acknowledgements

We gratefully thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/03).

References

Barba, V., Arenaza, B., Guerrero, J. & Reyes, R. (2012). Heteroat. Chem. 23, 422-428.  [ISI] [CSD] [CrossRef] [ChemPort]
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Harrington, J. M., Jones, S. B., White, P. H. & Hancock, R. D. (2004). Inorg. Chem. 43, 4456-4463.  [ISI] [CrossRef] [PubMed] [ChemPort]
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.
Molecular Structure Corporation & Rigaku (2005). CrystalClear. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.
Rajput, G., Singh, V., Singh, S. K., Prasad, L. B., Drew, M. G. B. & Singh, N. (2012). Eur. J. Inorg. Chem. pp. 3885-3891.  [ISI] [CSD] [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Singh, V., Kumar, A., Prasad, R., Rajput, G., Drew, M. G. B. & Singh, N. (2011). CrystEngComm, 13, 6817-6826.  [ISI] [CSD] [CrossRef] [ChemPort]
Tan, Y. S., Sudlow, A. L., Molloy, K. C., Morishima, Y., Fujisawa, K., Jackson, W. J., Henderson, W., Halim, S. N., Bt, A., Ng, S. W. & Tiekink, E. R. T. (2013). Cryst. Growth Des. 13, 3046-3056.  [CrossRef] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, m479-m480   [ doi:10.1107/S1600536813021569 ]

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