{4,4′,5,5′-Tetra­methyl-2,2′-[1,1′-(ethane-1,2-diyldinitrilo)diethyl­idyne]diphenolato}nickel(II)–methanol–chloro­form (1/1/1)

Fun, H.-K.; Kia, R.

doi:10.1107/S1600536808024306

Volume 64
Part 9
Pages m1116-m1117
September 2008

Received 10 July 2008
Accepted 30 July 2008
Online 6 August 2008

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R = 0.041
wR = 0.104
Data-to-parameter ratio = 24.1
Details

{4,4',5,5'-Tetramethyl-2,2'-[1,1'-(ethane-1,2-diyldinitrilo)diethylidyne]diphenolato}nickel(II)-methanol-chloroform (1/1/1)

Hoong-Kun Fun ^a ^* and Reza Kia ^a ⁺

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: hkfun@usm.my

In the title compound, [Ni(C₂₂H₂₆N₂O₂)]·CH₃OH·CHCl₃, the Ni^II ion is in a slightly distorted square-planar geometry involving an N₂O₂ atom set of the tetradentate Schiff base ligand. The asymmetric unit contains one molecule of the complex and one molecule each of chloroform and methanol. The methanol molecule is hydrogen bonded to the phenolate O atoms. In the crystal structure, short intermolecular distances between the centroids of six-membered chelate rings [3.7002 (9) Å] indicate the presence of [pi] - [pi] interactions, which link the molecules into stacks along the a axis. In addition, there are NiNi distances which are shorter than the sum of the van der Waals radii of two Ni atoms. The crystal structure is further stabilized by intermolecular O-HO and C-HO hydrogen bonds, and weak intermolecular C-H [pi] interactions linking molecules into extended one-dimensional chains along the c axis.

Related literature

For bond-length data, see Allen et al. (1987). For related structures see, for example: Clark et al. (1968, 1969, 1970). For applications and bioactivities see, for example: Elmali et al. (2000); Blower (1998); Granovski et al. (1993); Li & Chang (1991); Shahrokhian et al. (2000).

Experimental

Crystal data

[Ni(C₂₂H₂₆N₂O₂)]·CH₄O·CHCl₃
M_r = 560.59
Triclinic, $[P \overline 1]$
a = 7.5473 (1) Å
b = 12.3899 (2) Å
c = 14.2481 (2) Å
= 75.949 (1)°
= 83.761 (1)°
= 74.693 (1)°
V = 1245.21 (3) Å³
Z = 2
Mo K radiation
= 1.13 mm^-1
T = 100.0 (1) K
0.36 × 0.17 × 0.11 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.684, T_max = 0.882
29477 measured reflections
7348 independent reflections
5851 reflections with I > 2(I)
R_int = 0.038

Refinement

R[F² > 2(F²)] = 0.040
wR(F²) = 0.103
S = 1.04
7348 reflections
305 parameters
H-atom parameters constrained
_max = 0.71 e Å^-3
_min = -0.80 e Å^-3

Table 1
Selected geometric parameters (Å, °)

Ni1-O2	1.8276 (13)
Ni1-O1	1.8298 (13)
Ni1-N1	1.8534 (15)
Ni1-N2	1.8592 (16)

Ni1Ni1ⁱ	4.1276 (3)
Ni1Ni1ⁱⁱ	4.5626 (3)

O2-Ni1-O1	82.98 (6)
O2-Ni1-N1	177.05 (6)
O1-Ni1-N1	94.26 (6)
O2-Ni1-N2	93.94 (6)
O1-Ni1-N2	176.90 (6)
N1-Ni1-N2	88.82 (7)
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+2, -y, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O3-H1O3O1	0.89	2.23	2.980 (2)	142
O3-H1O3O2	0.89	2.10	2.901 (2)	149
C23-H23AO3	0.98	2.10	2.974 (3)	148
C9-H9ACg1ⁱⁱ	0.97	2.47	3.404 (2)	162
C20-H20ACg2ⁱⁱ	0.96	2.94	3.801 (2)	150
C21-H21BCg3ⁱⁱⁱ	0.96	2.82	3.691 (2)	152
Symmetry codes: (ii) -x+2, -y, -z+1; (iii) -x+2, -y, -z. Cg1, Cg2 and Cg3 are the centroids of the Ni1/O1/C1/C6/C7/N1, C1-C6, and C11-C16 rings, respectively.

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2659 ).

Acknowledgements

HKF and RK thank the Malaysian Government and Universiti sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. RK thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-S19.
Blower, P. J. (1998). Transition Met. Chem. 23, 109-112.
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Clark, G. R., Hall, D. & Waters, T. N. (1968). J. Chem. Soc. A, 223-226.
Clark, G. R., Hall, D. & Waters, T. N. (1969). J. Chem. Soc. A, 823-829.
Clark, G. R., Hall, D. & Waters, T. N. (1970). J. Chem. Soc. A, 396-399.
Elmali, A., Elerman, Y. & Svoboda, I. (2000). Acta Cryst. C56, 423-424.
Granovski, A. D., Nivorozhkin, A. L. & Minkin, V. I. (1993). Coord. Chem. Rev. 126, 1-69.
Li, C. H. & Chang, T. C. (1991). Eur. Polym. J. 27, 35-39.
Shahrokhian, S., Amini, M. K., Kia, R. & Tangestaninejad, S. (2000). Anal. Chem. 72, 956-962.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.

metal-organic compounds