[Journal logo]

Volume 68 
Part 11 
Pages m1335-m1336  
November 2012  

Received 27 August 2012
Accepted 28 September 2012
Online 6 October 2012

Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.003 Å
R = 0.050
wR = 0.117
Data-to-parameter ratio = 22.4
Details
Open access

Bis[2,3,4-trimethyl-5-[(3,4,5-trimethyl-2H-pyrrol-2-ylidene-[kappa]N)methyl]-1H-pyrrolato-[kappa]N]copper(II)1

aDepartment of Chemistry, Louisiana State University, Baton Rouge LA 70803-1804 USA
Correspondence e-mail: ffroncz@lsu.edu

In the title complex, [Cu(C15H19N2)2] or [Cu(L2)] (HL is 3,3',4,4',5,5'-hexamethylpyrromethene), the CuII atom is coordinated by four N atoms [Cu-N 1.939 (2)-1.976 (2) Å] from two L ligands in a distorted tetrahedral geometry. The mean planes of the CuN2C3 metallocyclic rings form a dihedral angle of 72.73 (6)°. In the L ligands, the pyrrole rings are inclined to each other at dihedral angles of 3.03 (7) and 9.83 (7)°. The crystal packing exhibits weak intermolecular C-H...[pi] interactions, which form chains in [100].

Related literature

For the structure of the neutral ligand, see: Mroginski et al. (2005[Mroginski, M.-A., Nemeth, K., Bauschlicher, T., Klotzbucher, W., Goddard, R., Heinemann, O., Hildebrandt, P. & Mark, F. (2005). J. Phys. Chem. A, 109, 2139-2150.]). For the structures of related organometallic complexes, see: Elder & Penfold (1969[Elder, M. & Penfold, B. R. (1969). J. Chem. Soc. A, pp. 2556-2559.]); Cotton et al. (1970[Cotton, F. A., DeBoer, B. G. & Pipal, J. R. (1970). Inorg. Chem. 9, 783-788.]); Fergusson et al. (1971[Fergusson, J. E., March, F. C., Couch, D. A., Emerson, K. & Robinson, W. T. (1971). J. Chem. Soc. A, pp. 440-448.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]). For transition metal complexes of dipyrromethenes, see: Bruckner et al. (1997[Bruckner, C., Zhang, Y., Rettig, S. J. & Dolphin, D. (1997). Inorg. Chim. Acta, 263, 279-286.]); Zhang et al. (1998[Zhang, Y., Thompson, A., Retting, S. J. & Dolphin, D. (1998). J. Am. Chem. Soc. 120, 13537-13538.]). For the chemistry and applications of pyrrole derivatives, see: Dolphin (1979[Dolphin, D. (1979). The porphyrins, New York: Academic Press.]); Falk (1989[Falk, H. (1989). The Chemistry of Linear Oligopyrroles and Bile Pigments, Vienna: Springer-Verlag.]). For the synthesis of the title compound, see: Murakami & Sakata (1968[Murakami, Y. & Sakata, K. (1968). Inorg. Chim. Acta, 2, 273-279.]). For IDEAL software, see: Gould et al. (1988[Gould, R. O., Moulden, N. & Taylor, P. (1988). IDEAL. Department of Chemistry, University of Edinburgh, Scotland.]).

[Scheme 1]

Experimental

Crystal data
  • [Cu(C15H19N2)2]

  • Mr = 518.18

  • Triclinic, [P \overline 1]

  • a = 7.9737 (1) Å

  • b = 12.0896 (3) Å

  • c = 13.9411 (4) Å

  • [alpha] = 92.8065 (8)°

  • [beta] = 105.4205 (8)°

  • [gamma] = 91.9772 (18)°

  • V = 1292.39 (5) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.87 mm-1

  • T = 120 K

  • 0.18 × 0.10 × 0.02 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (HKL SCALEPACK; Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) Tmin = 0.859, Tmax = 0.983

  • 20968 measured reflections

  • 7342 independent reflections

  • 5581 reflections with I > 2[sigma](I)

  • Rint = 0.052

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.117

  • S = 1.02

  • 7342 reflections

  • 328 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.49 e Å-3

  • [Delta][rho]min = -0.48 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the N3/C16-C19 pyrrole ring.

D-H...A D-H H...A D...A D-H...A
C29-H29C...Cgi 0.98 2.78 3.551 (3) 136
Symmetry code: (i) x-1, y, z.

Data collection: COLLECT (Nonius, 2000[Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR2002 (Burla et al., 2003[Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.]); 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, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5335 ).


Acknowledgements

Purchase of the diffractometer was made possible by grant No. LEQSF(1999-2000)-ENH-TR-13, administered by the Louisiana Board of Regents.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [ISI] [CrossRef] [details]
Bruckner, C., Zhang, Y., Rettig, S. J. & Dolphin, D. (1997). Inorg. Chim. Acta, 263, 279-286.  [ChemPort]
Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.  [CrossRef] [details]
Cotton, F. A., DeBoer, B. G. & Pipal, J. R. (1970). Inorg. Chem. 9, 783-788.  [CrossRef] [ChemPort] [ISI]
Dolphin, D. (1979). The porphyrins, New York: Academic Press.
Elder, M. & Penfold, B. R. (1969). J. Chem. Soc. A, pp. 2556-2559.
Falk, H. (1989). The Chemistry of Linear Oligopyrroles and Bile Pigments, Vienna: Springer-Verlag.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Fergusson, J. E., March, F. C., Couch, D. A., Emerson, K. & Robinson, W. T. (1971). J. Chem. Soc. A, pp. 440-448.
Gould, R. O., Moulden, N. & Taylor, P. (1988). IDEAL. Department of Chemistry, University of Edinburgh, Scotland.
Mroginski, M.-A., Nemeth, K., Bauschlicher, T., Klotzbucher, W., Goddard, R., Heinemann, O., Hildebrandt, P. & Mark, F. (2005). J. Phys. Chem. A, 109, 2139-2150.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Murakami, Y. & Sakata, K. (1968). Inorg. Chim. Acta, 2, 273-279.  [CrossRef] [ChemPort]
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Zhang, Y., Thompson, A., Retting, S. J. & Dolphin, D. (1998). J. Am. Chem. Soc. 120, 13537-13538.  [ISI] [CSD] [CrossRef] [ChemPort]


Acta Cryst (2012). E68, m1335-m1336   [ doi:10.1107/S1600536812040998 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.