cis-Bis[(4-nitro­phen­yl)cyanamido-κN1]bis­(1,10-phenanthroline-κ2N,N′)nickel(II) methanol monosolvate

Chiniforoshan, H.; Jazestani, M.; Notash, B.

doi:10.1107/S1600536812009890

Volume 68
Part 4
Pages m417-m418
April 2012

Received 5 February 2012
Accepted 6 March 2012
Online 14 March 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.005 Å
R = 0.061
wR = 0.139
Data-to-parameter ratio = 19.0
Details

cis-Bis[(4-nitrophenyl)cyanamido-N¹]bis(1,10-phenanthroline-²N,N')nickel(II) methanol monosolvate

Hossein Chiniforoshan,^a ^* Mehdi Jazestani ^a and Behrouz Notash ^b

^aDepartment of Chemistry, Isfahan University of Technology, Isfahan 84456-38111, Iran, and ^bDepartment of Chemistry, Shahid Beheshti University, G. C., Evin, Tehran 1983963113, Iran
Correspondence e-mail: chinif@cc.iut.ac.ir

In the title compound, [Ni(C₇H₄N₃O₂)₂(C₁₂H₈N₂)₂]·CH₃OH, the Ni^II atom is six-coordinated in a distorted N₆ octahedral geometry and is chelated by two phenanthroline ligands and two phenylcyanamide groups which occupy cis positions. The (4-nitrophenyl)cyanamide anions act as monodentate ligands. There is one classical intermolecular O-HN hydrogen bond and several C-HO hydrogen bonds are also observed.

Related literature

For background to phenylcyanamide ligands and their complexes, see: Crutchley (2001). For mononuclear complexes of phenylcyanamide complexes, see: Letcher et al. (1993); Kim et al. (2002); Shen et al. (1999). For polynuclear complexes of phenylcyanamide ligands, see: Ainscough et al. (1991); Chiniforoshan et al. (2009, 2010, 2012); Escuer et al. (2004). For related structures, see: Wu et al. (2004); Cheng et al. (2002); Shen et al. (1999). For the preparation of 4-nitro-phenylcyanamide used in the synthesis of the title compound, see: Crutchley & Naklicki (1989).

Experimental

Crystal data

[Ni(C₇H₄N₃O₂)₂(C₁₂H₈N₂)₂]·CH₄O
M_r = 775.40
Triclinic, $[P \overline 1]$
a = 10.019 (2) Å
b = 11.307 (2) Å
c = 16.403 (3) Å
= 103.54 (3)°
= 92.96 (3)°
= 99.77 (3)°
V = 1772.3 (7) Å³
Z = 2
Mo K radiation
= 0.61 mm^-1
T = 298 K
0.25 × 0.20 × 0.10 mm

Data collection

Stoe IPDS II diffractometer
Absorption correction: numerical (X-RED and X-SHAPE; Stoe & Cie, 2005) T_min = 0.862, T_max = 0.938
19823 measured reflections
9512 independent reflections
6693 reflections with I > 2(I)
R_int = 0.053

Refinement

R[F² > 2(F²)] = 0.061
wR(F²) = 0.139
S = 1.06
9512 reflections
501 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.65 e Å^-3
_min = -0.31 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O5-H5AN9ⁱ	0.91 (3)	1.98 (4)	2.883 (4)	174 (5)
C39-H39BO4ⁱⁱ	0.96	2.55	3.435 (7)	153
C22-H22O1ⁱⁱⁱ	0.93	2.57	3.469 (6)	162
C16-H16O2^iv	0.93	2.45	3.312 (6)	154
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y, -z+1; (iii) -x+2, -y+1, -z+2; (iv) x-1, y-1, z.

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); 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: BT5812 ).

Acknowledgements

The authors acknowledge financial support from Isfahan University of Technology.

References

Ainscough, E. W., Baker, E. N., Brader, M. L. & Brodie, A. M. (1991). J. Chem. Soc. Dalton Trans. pp. 1243-1249.
Cheng, Y.-Q., Liu, A.-L., Hu, M.-L. & Ng, S. W. (2002). Acta Cryst. E58, m545-m547.
Chiniforoshan, H., Jalilpour, S., Shirinfar, B. & Khavasi, H. R. (2009). Acta Cryst. E65, m386.
Chiniforoshan, H., Jazestani, M. & Notash, B. (2012). Acta Cryst. E68, m232.
Chiniforoshan, H., Shirinfar, B., Jalilpour, S. & Khavasi, H. R. (2010). Acta Cryst. E66, m331.
Crutchley, R. J. (2001). Coord. Chem. Rev. 219, 125-155.
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Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Kim, Y.-J., Joo, Y.-S., Han, J.-T. & Han, W. S. (2002). J. Chem. Soc. Dalton Trans. pp. 3611-3618.
Letcher, R. J., Zhang, W., Bensimon, C. & Crutchley, R. J. (1993). Inorg. Chim. Acta, 210, 183-191.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shen, X., Shan, J., Sun, H.-B. & Kang, B.-S. (1999). J. Chin. Chem. Soc. 46, 179-183.
Stoe & Cie (2005). X-AREA, X-RED and X-SHAPE. Stoe & Cie, Darmstadt, Germany.
Wu, A.-Q., Zheng, F.-K., Guo, G.-C. & Huang, J.-S. (2004). Acta Cryst. E60, m373-m375.

metal-organic compounds

cis-Bis[(4-nitrophenyl)cyanamido-N1]bis(1,10-phenanthroline-2N,N')nickel(II) methanol monosolvate