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Volume 69 
Part 7 
Pages m412-m413  
July 2013  

Received 2 April 2013
Accepted 17 June 2013
Online 26 June 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.030
wR = 0.096
Data-to-parameter ratio = 17.8
Details
Open access

Bis{2-[(5-hydroxypentyl)iminomethyl]phenolato-[kappa]2N,O1}copper(II)

aDepartment of Chemistry, University of Calcutta, 92 A.P.C. Road, Kolkata 700 009, USA
Correspondence e-mail: sgchem@caluniv.ac.in

In the title compound, [Cu(C12H16NO2)2], the CuII ion, located on a center of inversion, is coordinated by two singly deprotonated Schiff base ligands derived from condensation of salicyldehyde and 1-aminopentan-5-ol. The imino N and phenol O atoms from both ligands offer a square-planar arrangement around the metal ion. The Cu-N and Cu-O bond lengths are 2.0146 (15) and 1.8870 (12) Å, respectively. Since the Cu-O and Cu-N bond lengths are different, it can be concluded that the resulting geometry of the complex is distorted. The aliphatic -OH group of the ligand is not coordinated and points away from the metal coordination zone and actively participates in hydrogen bonding connecting two other units and thus stabilizing the crystal lattice. This results in a two-dimensional extended array parallel to (201).

Related literature

For the participation of the copper ion in the active sites of a large number of metalloproteins involved in important biological electron-transfer reactions, see: Reedijk & Bouwman (1999[Reedijk, J. & Bouwman, E. (1999). In Bioinorganic Catalysis, 2nd ed. New York: Marcel Dekker.]); Solomon et al. (2001[Solomon, E. I., Chen, P., Metz, M., Lee, S.-K. & Palmer, A. E. (2001). Angew. Chem. Int. Ed. 40, 4570-4590.]); Hatcher & Karlin (2004[Hatcher, L. Q. & Karlin, K. D. (2004). J. Biol. Inorg. Chem. 9, 669-683.]); Kaim & Rall (1996[Kaim, W. & Rall, J. (1996). Angew. Chem. Int. Ed. 35, 43-60.]). For references regarding the t4 value, see: Yang et al. (2007[Yang, L., Powell, D. R. & Houser, R. P. (2007). Dalton Trans. pp. 955-964.]). For similar Cu-N and Cu-O bond lengths, see: Maeda et al. (2003[Maeda, H., Osuka, A., Ishikawa, Y., Aritome, I., Hisaeda, Y. & Furuta, H. (2003). Org. Lett. 5, 1293-1296.]); Akimova et al. (2001[Akimova, E. V. R., Nazarenko, A. Y., Chen, L., Krieger, P. W., Herrera, A. M., Tarasov, V. V. & Robinson, P. D. (2001). Inorg. Chim. Acta, 324, 1-15.]); Pawlicki et al. (2007[Pawlicki, M., Kanska, I. & Latos-Grazynski, L. (2007). Inorg. Chem. 46, 6575-6584.]); Verma et al. (2011[Verma, P., Weir, J., Mirica, L., Stack, T. & Daniel, P. (2011). Inorg. Chem. 50, 9816-9825.]); Khandar & Nejati (2000[Khandar, A. A. & Nejati, M. (2000). Polyhedron, 19, 607-613.]); Sundaravel et al. (2009[Sundaravel, K., Suresh, E. & Palaniandavar, M. (2009). Inorg. Chim. Acta, 362, 199-207.]).

[Scheme 1]

Experimental

Crystal data
  • [Cu(C12H16NO2)2]

  • Mr = 476.07

  • Monoclinic, P 21 /c

  • a = 11.8815 (8) Å

  • b = 5.2219 (3) Å

  • c = 18.9588 (12) Å

  • [beta] = 102.876 (2)°

  • V = 1146.70 (12) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.99 mm-1

  • T = 296 K

  • 0.8 × 0.6 × 0.4 mm

Data collection
  • Bruker APEXII SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.497, Tmax = 0.674

  • 13343 measured reflections

  • 2549 independent reflections

  • 2174 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.030

  • wR(F2) = 0.096

  • S = 0.95

  • 2549 reflections

  • 143 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O1i 0.82 2.07 2.864 (2) 163
C1-H1B...O2ii 0.97 2.34 2.771 (2) 106
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) -x+2, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker-Nonius AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker-Nonius 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BV2221 ).


Acknowledgements

Financial support from the University Grants Commission for a junior research fellowship to SM [Sanction No. UGC/749/Jr. Fellow(Sc.)] and an RFSMS fellowship (Sanction No. UGC/740/RFSMS) to RM is gratefully acknowledged. We thank the DST for a junior research fellowship to YS (Sanction No. SERB/F/1585/2012-13). DST-FIST is acknowledged for providing the X-ray diffraction facility at the Department of Chemistry, University of Calcutta.

References

Akimova, E. V. R., Nazarenko, A. Y., Chen, L., Krieger, P. W., Herrera, A. M., Tarasov, V. V. & Robinson, P. D. (2001). Inorg. Chim. Acta, 324, 1-15.
Bruker (2004). APEX2 and SAINT. Bruker-Nonius AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Hatcher, L. Q. & Karlin, K. D. (2004). J. Biol. Inorg. Chem. 9, 669-683.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Kaim, W. & Rall, J. (1996). Angew. Chem. Int. Ed. 35, 43-60.  [ChemPort]
Khandar, A. A. & Nejati, M. (2000). Polyhedron, 19, 607-613.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Maeda, H., Osuka, A., Ishikawa, Y., Aritome, I., Hisaeda, Y. & Furuta, H. (2003). Org. Lett. 5, 1293-1296.  [Web of Science] [CSD] [CrossRef] [PubMed] [ChemPort]
Pawlicki, M., Kanska, I. & Latos-Grazynski, L. (2007). Inorg. Chem. 46, 6575-6584.  [Web of Science] [CSD] [CrossRef] [PubMed] [ChemPort]
Reedijk, J. & Bouwman, E. (1999). In Bioinorganic Catalysis, 2nd ed. New York: Marcel Dekker.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Solomon, E. I., Chen, P., Metz, M., Lee, S.-K. & Palmer, A. E. (2001). Angew. Chem. Int. Ed. 40, 4570-4590.  [CrossRef] [ChemPort]
Sundaravel, K., Suresh, E. & Palaniandavar, M. (2009). Inorg. Chim. Acta, 362, 199-207.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Verma, P., Weir, J., Mirica, L., Stack, T. & Daniel, P. (2011). Inorg. Chem. 50, 9816-9825.  [Web of Science] [CSD] [CrossRef] [ChemPort] [PubMed]
Yang, L., Powell, D. R. & Houser, R. P. (2007). Dalton Trans. pp. 955-964.  [CSD] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, m412-m413   [ doi:10.1107/S1600536813016802 ]

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