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Volume 69 
Part 1 
Pages m22-m23  
January 2013  

Received 19 November 2012
Accepted 3 December 2012
Online 8 December 2012

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Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.005 Å
R = 0.021
wR = 0.053
Data-to-parameter ratio = 13.1
Details
Open access

Poly[([mu]6-4-amino-3,5,6-trichloropyridine-2-carboxylato)aquacaesium]

Graham Smitha*

aScience and Engineering Faculty, Queensland University of Technology, GPO Box 2434, Brisbane, Queensland 4001, Australia
Correspondence e-mail: g.smith@qut.edu.au

In the structure of the title complex, [Cs(C6H2Cl3N2O2)(H2O)]n, the caesium salt of the commercial herbicide picloram, the Cs+ cation lies on a crystallographic mirror plane, which also contains the coordinating water molecule and all non-H atoms of the 4-amino-3,5,6-trichloropicolinate anion except the carboxylate O-atom donors. The irregular CsCl4O5 coordination polyhedron comprises chlorine donors from the ortho-related ring substituents of the picloramate ligand in a bidentate chelate mode, with a third chlorine bridging [Cs-Cl range 3.6052 (11)-3.7151 (11) Å] as well as a bidentate chelate carboxylate group giving sheets extending parallel to (010). A three-dimensional coordination polymer structure is generated through the carboxylate group, which also bridges the sheets down [010]. Within the structure, there are intra-unit water O-H...Ocarboxylate and amine N-H...Npyridine hydrogen-bonding interactions.

Related literature

For background information on picloram, see: Mullinson (1985[Mullinson, W. R. (1985). Proc. West. Soc. Weed Sci. 38, 21-92.]); O'Neil (2001[O'Neil, M. J. (2001). Editor. The Merck Index, 13th ed., pp. 1325-1326. Whitehouse Station, NJ, USA: Merck & Co. Inc.]). For examples of structures of metal complexes with picloram, see: Smith et al. (1981a[Smith, G., O'Reilly, E. J. & Kennard, C. H. L. (1981a). Aust. J. Chem. 34, 891-896.],b[Smith, G., O'Reilly, E. J. & Kennard, C. H. L. (1981b). Cryst. Struct. Commun. 10, 1277-1282.]); O'Reilly et al. (1983[O'Reilly, E. J., Smith, G., Kennard, C. H. L. & White, A. H. (1983). Aust. J. Chem. 36, 183-190.]). For another structure with caesium cations involving coordinating carbon-bound Cl, see: Levitskaia et al. (2000[Levitskaia, T. G., Bryan, J. C., Sachleben, R. A., Lamb, J. D. & Moyer, B. A. (2000). J. Am. Chem. Soc. 122, 554-562.]). For a caesium complex with dipicolinic acid, see: Santra et al. (2011[Santra, S., Das, B. & Baruah, J. B. (2011). J. Chem. Crystallogr. 41, 1981-1987.]).

[Scheme 1]

Experimental

Crystal data

  • [Cs(C6H2Cl3N2O2)(H2O)]

  • Mr = 391.37

  • Monoclinic, P 21 /m

  • a = 7.0816 (3) Å

  • b = 6.6863 (2) Å

  • c = 11.7382 (5) Å

  • [beta] = 101.005 (4)°

  • V = 545.58 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 4.11 mm-1

  • T = 200 K

  • 0.25 × 0.20 × 0.08 mm
Data collection

  • Oxford Diffraction Gemini-S CCD detector diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]) Tmin = 0.67, Tmax = 0.98

  • 3773 measured reflections

  • 1164 independent reflections

  • 1118 reflections with I > 2[sigma](I)

  • Rint = 0.026
Refinement

  • R[F2 > 2[sigma](F2)] = 0.021

  • wR(F2) = 0.053

  • S = 0.98

  • 1164 reflections

  • 89 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.55 e Å-3

  • [Delta][rho]min = -0.56 e Å-3

Table 1
Selected bond lengths (Å)

Cs1-Cl5 3.7151 (11)
Cs1-Cl6 3.6052 (11)
Cs1-O1W 3.129 (3)
Cs1-O21i 3.116 (2)
Cs1-O21ii 3.116 (2)
Cs1-O21iii 3.150 (2)
Cs1-O21iv 3.150 (2)
Cs1-Cl3v 3.7127 (4)
Cs1-Cl3vi 3.7127 (4)
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+1]; (ii) -x+1, -y, -z+1; (iii) [x, -y+{\script{1\over 2}}, z+1]; (iv) x, y, z+1; (v) [-x, y-{\script{1\over 2}}, -z+1]; (vi) [-x, y+{\script{1\over 2}}, -z+1].

Table 2
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1W-H11W...O21vii 0.92 2.00 2.905 (3) 168
N4-H42...N1viii 0.79 2.44 2.985 (5) 127
Symmetry codes: (vii) -x, -y, -z+1; (viii) x-1, y, z.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) within WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WM2705 ).

Acknowledgements

The author acknowledges financial support from the Science and Engineering Faculty and the University Library, Queensland University of Technology.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.
Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.  [CrossRef] [ISI] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Levitskaia, T. G., Bryan, J. C., Sachleben, R. A., Lamb, J. D. & Moyer, B. A. (2000). J. Am. Chem. Soc. 122, 554-562.  [ISI] [CSD] [CrossRef] [ChemPort]
Mullinson, W. R. (1985). Proc. West. Soc. Weed Sci. 38, 21-92.
O'Neil, M. J. (2001). Editor. The Merck Index, 13th ed., pp. 1325-1326. Whitehouse Station, NJ, USA: Merck & Co. Inc.
O'Reilly, E. J., Smith, G., Kennard, C. H. L. & White, A. H. (1983). Aust. J. Chem. 36, 183-190.  [ChemPort]
Santra, S., Das, B. & Baruah, J. B. (2011). J. Chem. Crystallogr. 41, 1981-1987.  [ISI] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Smith, G., O'Reilly, E. J. & Kennard, C. H. L. (1981a). Aust. J. Chem. 34, 891-896.  [CrossRef] [ChemPort]
Smith, G., O'Reilly, E. J. & Kennard, C. H. L. (1981b). Cryst. Struct. Commun. 10, 1277-1282.  [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]

Acta Cryst (2013). E69, m22-m23   [ doi:10.1107/S1600536812049562 ]

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