Bis[2,3,4-trimethyl-5-[(3,4,5-trimethyl-2H-pyrrol-2-yl­idene-κN)meth­yl]-1H-pyrrolato-κN]copper(II)CAS 38504-29-9 and 21710-26-9.

Erdem, S.S.; Fronczek, F.R.; Watkins, S.F.

doi:10.1107/S1600536812040998

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 (C-C) = 0.003 Å
R = 0.050
wR = 0.117
Data-to-parameter ratio = 22.4
Details

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

Sultan S. Erdem,^a ⁺ Frank R. Fronczek ^a ^* and Steven F. Watkins ^a

^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 Cu^II 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). For the structures of related organometallic complexes, see: Elder & Penfold (1969); Cotton et al. (1970); Fergusson et al. (1971). For a description of the Cambridge Structural Database, see: Allen (2002). For transition metal complexes of dipyrromethenes, see: Bruckner et al. (1997); Zhang et al. (1998). For the chemistry and applications of pyrrole derivatives, see: Dolphin (1979); Falk (1989). For the synthesis of the title compound, see: Murakami & Sakata (1968). For IDEAL software, see: Gould et al. (1988).

Experimental

Crystal data

[Cu(C₁₅H₁₉N₂)₂]
M_r = 518.18
Triclinic, $[P \overline 1]$
a = 7.9737 (1) Å
b = 12.0896 (3) Å
c = 13.9411 (4) Å
= 92.8065 (8)°
= 105.4205 (8)°
= 91.9772 (18)°
V = 1292.39 (5) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.859, T_max = 0.983
20968 measured reflections
7342 independent reflections
5581 reflections with I > 2(I)
R_int = 0.052

Refinement

R[F² > 2(F²)] = 0.050
wR(F²) = 0.117
S = 1.02
7342 reflections
328 parameters
H-atom parameters constrained
_max = 0.49 e Å^-3
_min = -0.48 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

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

D-HA	D-H	HA	DA	D-HA
C29-H29CCgⁱ	0.98	2.78	3.551 (3)	136
Symmetry code: (i) x-1, y, z.

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR2002 (Burla et al., 2003); 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 publication routines (Farrugia, 1999).

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

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