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Volume 66 
Part 8 
Page m877  
August 2010  

Received 14 June 2010
Accepted 29 June 2010
Online 3 July 2010

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Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.026
wR = 0.064
Data-to-parameter ratio = 12.7
Details
Open access

Bis[N-(4-chlorophenyl)pyridine-3-carboxamide]silver(I) nitrate

Chun-Yue Shi,a,b Chun-Hua Gec and Qi-Tao Liua,c*

aDepartment of Chemistry, Northeast Normal University, Changchun 130024, People's Republic of China,bApplied Chemistry Department, Shenyang University of Chemical Technology, Shenyang 110142, People's Republic of China, and cCollege of Chemistry, Liaoning University, Shenyang 110036, People's Republic of China
Correspondence e-mail: qtliu@yahoo.com.cn

In the title compound, [Ag(C12H9ClN2O)2]NO3, two N atoms from two pyridine rings of two N-(4-chlorophenyl)pyridine-3-carboxamide ligands coordinate to the AgI atom, forming a nearly linear geometry with an N-Ag-N angle of 173.41 (7)°. The crystal structure is stabilized by N-H...O, C-H...O and C-H...Cl hydrogen bonds and [pi]-[pi] stacking interactions [centroid-centroid distance = 3.5469 (16) Å] between the pyridyl and benzene rings. The shortest Ag...Ag distance is 3.2574 (5) Å.

Related literature

For general background to metal-organic complexes with pyridyl carboxamide ligands, see: Noveron et al. (2002[Noveron, J. C., Lah, M. S., Del Sesto, R. E., Arif, A. M., Miller, J. S. & Stang, P. J. (2002). J. Am. Chem. Soc. 124, 6613-6625.]); Zhang et al. (2002[Zhang, J., Liu, Q., Duan, C., Shao, Y., Ding, J., Miao, J., You, X. & Guo, Z. (2002). J. Chem. Soc. Dalton Trans. pp. 591-597.]); Mondal et al. (2004[Mondal, A., Li, Y., Khan, M. A., Ross, J. H. & Houser, R. P. (2004). Inorg. Chem. 43, 7075-7082.]); Jacob & Mukherjee (2006[Jacob, W. & Mukherjee, R. (2006). Inorg. Chim. Acta, 359, 4565-4573.]). For related structures and the synthesis of the title ligand, see: Shi et al. (2007[Shi, C.-Y., Ge, C.-H., Song, X.-M. & Liu, Q.-T. (2007). Acta Cryst. E63, m2104-m2105.], 2008[Shi, C. Y., Ge, C. H., Gao, E. J., Yin, H. X. & Liu, Q. T. (2008). Inorg. Chem. Commun. 11, 703-706.]).

[Scheme 1]

Experimental

Crystal data

  • [Ag(C12H9ClN2O)2]NO3

  • Mr = 635.20

  • Triclinic, [P \overline 1]

  • a = 10.0745 (10) Å

  • b = 10.1425 (10) Å

  • c = 13.473 (2) Å

  • [alpha] = 107.515 (2)°

  • [beta] = 102.602 (2)°

  • [gamma] = 103.706 (1)°

  • V = 1211.6 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 1.10 mm-1

  • T = 296 K

  • 0.24 × 0.23 × 0.18 mm
Data collection

  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.776, Tmax = 0.820

  • 6194 measured reflections

  • 4232 independent reflections

  • 3848 reflections with I > 2[sigma](I)

  • Rint = 0.014
Refinement

  • R[F2 > 2[sigma](F2)] = 0.026

  • wR(F2) = 0.064

  • S = 1.05

  • 4232 reflections

  • 334 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.39 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H1...O4 0.86 2.10 2.953 (3) 169
N4-H2...O1i 0.86 2.10 2.931 (3) 162
C2-H3...O5 0.93 2.51 3.210 (3) 133
C3-H4...O3ii 0.93 2.57 3.300 (3) 136
C4-H5...Cl2iii 0.93 2.83 3.516 (3) 132
C5-H6...O1iv 0.93 2.55 3.376 (3) 148
C8-H7...O1 0.93 2.27 2.841 (3) 119
C11-H9...O2v 0.93 2.49 3.194 (4) 132
C16-H13...O5vi 0.93 2.48 3.370 (4) 160
C20-H15...O2 0.93 2.46 2.906 (3) 109
Symmetry codes: (i) x+1, y+1, z+1; (ii) -x+2, -y+1, -z+1; (iii) -x+2, -y+1, -z+2; (iv) -x+1, -y, -z; (v) x, y, z-1; (vi) -x+2, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. 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: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2286 ).

Acknowledgements

This project was supported by the Innovation Team Foundation of the Education Bureau of Liaoning Province (2007 T052) and by the Key Laboratory Foundation of the Education Bureau of Liaoning Province (2008 S104).

References

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Jacob, W. & Mukherjee, R. (2006). Inorg. Chim. Acta, 359, 4565-4573.  [ISI] [CSD] [CrossRef] [ChemPort]
Mondal, A., Li, Y., Khan, M. A., Ross, J. H. & Houser, R. P. (2004). Inorg. Chem. 43, 7075-7082.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Noveron, J. C., Lah, M. S., Del Sesto, R. E., Arif, A. M., Miller, J. S. & Stang, P. J. (2002). J. Am. Chem. Soc. 124, 6613-6625.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Shi, C. Y., Ge, C. H., Gao, E. J., Yin, H. X. & Liu, Q. T. (2008). Inorg. Chem. Commun. 11, 703-706.  [ISI] [CSD] [CrossRef] [ChemPort]
Shi, C.-Y., Ge, C.-H., Song, X.-M. & Liu, Q.-T. (2007). Acta Cryst. E63, m2104-m2105.  [CSD] [CrossRef] [details]
Zhang, J., Liu, Q., Duan, C., Shao, Y., Ding, J., Miao, J., You, X. & Guo, Z. (2002). J. Chem. Soc. Dalton Trans. pp. 591-597.  [CSD] [CrossRef] [ChemPort]

Acta Cryst (2010). E66, m877  [ doi:10.1107/S1600536810025511 ]

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