(IUCr) Dichlorido(5,5'-dimethyl-2,2'-bipyridine-[kappa]2N,N')zinc(II)

Volume 64
Part 9
Pages m1211-m1212
September 2008

Received 22 August 2008
Accepted 22 August 2008
Online 30 August 2008

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.013 Å
R = 0.066
wR = 0.150
Data-to-parameter ratio = 23.3
Details

Dichlorido(5,5'-dimethyl-2,2'-bipyridine-²N,N')zinc(II)

Aida Khalighi,^a Roya Ahmadi,^a Vahid Amani ^a ^* and Hamid Reza Khavasi ^b

^aIslamic Azad University, Shahr-e-Rey Branch, Tehran, Iran, and ^bDepartment of Chemistry, Shahid Beheshti University, Tehran 1983963113, Iran
Correspondence e-mail: v_amani2002@yahoo.com

The asymmetric unit of the title compound, [ZnCl₂(C₁₂H₁₂N₂)], contains two independent molecules. The Zn^II atoms are four-coordinated in distorted tetrahedral configurations by two N atoms from 5,5'-dimethyl-2,2'-bipyridine and two terminal Cl atoms. In the crystal structure, intermolecular C-HCl hydrogen bonds link the molecules. There are C-H [pi] contacts between the methyl groups and the pyridine and five-membered rings containing Zn^II atoms; [pi] - [pi] contacts also exist between the pyridine rings [centroid-centroid distances = 3.665 (5) and 3.674 (5) Å].

Related literature

For related literature, see: Gruia et al. (2007); Khan & Tuck (1984); Khavasi et al. (2008); Kozhevnikov et al. (2006); Liu et al. (2004); Lundberg (1966); Preston & Kennard (1969); Qin et al. (1999); Reimann et al. (1966); Steffen & Palenik (1976, 1977).

Experimental

Crystal data

[ZnCl₂(C₁₂H₁₂N₂)]
M_r = 320.53
Orthorhombic, P n a 2₁
a = 16.267 (2) Å
b = 11.1704 (16) Å
c = 14.9328 (14) Å
V = 2713.4 (6) Å³
Z = 8
Mo K radiation
= 2.18 mm^-1
T = 298 (2) K
0.28 × 0.20 × 0.07 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1998) T_min = 0.612, T_max = 0.860
14309 measured reflections
7167 independent reflections
4463 reflections with I > 2(I)
R_int = 0.066

Refinement

R[F² > 2(F²)] = 0.066
wR(F²) = 0.150
S = 1.07
7167 reflections
307 parameters
1 restraint
H-atom parameters constrained
_max = 0.29 e Å^-3
_min = -0.30 e Å^-3
Absolute structure: Flack (1983), 3320 Friedel pairs
Flack parameter: 0.07 (3)

Table 1
Selected geometric parameters (Å, °)

Zn1-Cl1	2.206 (2)
Zn1-Cl2	2.215 (2)
Zn2-Cl3	2.211 (2)
Zn2-Cl4	2.207 (3)
Zn1-N1	2.058 (6)
Zn1-N2	2.057 (6)
Zn2-N3	2.063 (6)
Zn2-N4	2.066 (6)

N1-Zn1-N2	80.5 (2)
N1-Zn1-Cl1	112.2 (2)
N1-Zn1-Cl2	117.23 (18)
N2-Zn1-Cl1	115.64 (18)
N2-Zn1-Cl2	111.4 (2)
Cl1-Zn1-Cl2	115.28 (10)
N3-Zn2-N4	79.7 (3)
N3-Zn2-Cl3	112.09 (18)
N3-Zn2-Cl4	114.47 (17)
N4-Zn2-Cl4	112.8 (2)
N4-Zn2-Cl3	115.01 (18)
Cl4-Zn2-Cl3	117.19 (9)

Table 2
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C1-H1Cl3ⁱ	0.93	2.82	3.516 (8)	132
C16-H16Cl3ⁱⁱ	0.93	2.83	3.638 (10)	146
C3-H3ACg5	0.96	3.10	3.719 (6)	124
C11-H11ACg2ⁱⁱⁱ	0.96	2.83	3.688 (5)	150
C15-H15CCg1^iv	0.96	2.84	3.704 (6)	150
C23-H23CCg4	0.96	3.11	3.690 (6)	120
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y-{\script{3\over 2}}, z]$ ; (ii) $[x+{\script{1\over 2}}, -y-{\script{5\over 2}}, z]$ ; (iii) x, y+1, z; (iv) x, y-1, z. Cg1, Cg2, Cg4 and Cg5 are the centroids of atoms Zn1/N1/C6/C7/N2, N1/C1/C2/C4-C6, Zn2/N3/C18/C19/N4 and N3/C13/C14/C16-C18, respectively.

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2517 ).

Acknowledgements

We are grateful to the Islamic Azad University, Shahr-e-Rey Branch, for financial support.

References

Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Gruia, L. M., Rochon, F. D. & Beauchamp, A. L. (2007). Inorg. Chim. Acta, 360, 1825-1840.
Khan, M. A. & Tuck, D. G. (1984). Acta Cryst. C40, 60-62.
Khavasi, H. R., Abedi, A., Amani, V., Notash, B. & Safari, N. (2008). Polyhedron, 27, 1848-1854.
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Preston, H. S. & Kennard, C. H. L. (1969). J. Chem. Soc. A, pp. 1965-1968.
Qin, J., Su, N., Dai, C., Yang, C., Liu, D., Day, M. W., Wu, B. & Chen, C. (1999). Polyhedron, 18, 3461-3464.
Reimann, C. W., Block, S. & Perloff, A. (1966). Inorg. Chem. 5, 1185-1189.
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Steffen, W. L. & Palenik, G. J. (1976). Acta Cryst. B32, 298-300.
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metal-organic compounds

Dichlorido(5,5'-dimethyl-2,2'-bipyridine-2N,N')zinc(II)