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Volume 69 
Part 2 
Pages m92-m93  
February 2013  

Received 19 December 2012
Accepted 21 December 2012
Online 9 January 2013

Key indicators
Single-crystal X-ray study
T = 294 K
Mean [sigma](C-C) = 0.005 Å
R = 0.044
wR = 0.124
Data-to-parameter ratio = 15.6
Details
Open access

rac-Dichlorido[3-ethoxy-3-(1-ethyl-1H-benzimidazol-2-yl)-2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazole]copper(II)

aDepartment of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, 610 Taylor Road, Piscataway, New Jersey 08854, USA
Correspondence e-mail: DZSquared@aol.com

The title complex, [CuCl2(C21H22N4O)], contains a bis(benzimidazole) unit with a chiral bridgehead C atom that forms part of a tetrahydropyrrole ring fused to one of the benzimidazoles. The chelate angle is 90.45 (9)° and the dihedral angle between the essentially planar benzimidazole fragments is 26.68 (9)°. The CuII coordination geometry lies approximately midway between tetrahedral and square planar. Overall, each chiral molecule contains six fused rings, and a racemic mixture is formed with symmetry-related enantiomers. In the crystal, C-H...[pi] and C-H...Cl interactions link molecules into a supramolecular chain along the a-axis direction.

Related literature

For 19F NMR studies of related compounds, see: Stibrany (2003[Stibrany, R. T. (2003). Copper-Based Olefin Polymerization Catalysts: High-Pressure 19F NMR Catalyst Probe, ACS Symp. Ser. 857, Beyond Metallocenes, edited by G. G. Hlatky & A. O. Patil, pp. 210-221. Washington, DC: ACS Press.]). For polymerization studies, see: Stibrany et al. (2003[Stibrany, R. T., Schulz, D. N., Kacker, S., Patil, A. O., Baugh, L. S., Rucker, S. P., Zushma, S., Berluche, E. & Sissano, J. A. (2003). Macromolecules, 36, 8584-8586.]). For their use as agents to study electron transfer, see: Knapp et al. (1990[Knapp, S., Keenan, T. P., Zhang, X., Fikar, R., Potenza, J. A. & Schugar, H. J. (1990). J. Am. Chem. Soc. 112, 3452-3464.]). For related structures, see: Baugh et al. (2006[Baugh, L. S., Sissano, J. A., Kacker, S., Berluche, E., Stibrany, R. T., Schulz, D. N. & Rucker, S. P. (2006). J. Polymer Sci. Part A: Polymer Chem. 44, 1817-1840.]); Stibrany (2009[Stibrany, R. T. (2009). J. Chem. Crystallogr. 39, 719-722.]); Stibrany et al. (2002[Stibrany, R. T., Schugar, H. J. & Potenza, J. A. (2002). Acta Cryst. E58, o1142-o1144.], 2004[Stibrany, R. T., Lobanov, M. V., Schugar, H. J. & Potenza, J. A. (2004). Inorg. Chem. 43, 1472-1480.]); Stibrany & Potenza (2006[Stibrany, R. T. & Potenza, J. A. (2006). Private communication (refcode TEVJAG). CCDC, Cambridge, England.], 2008[Stibrany, R. T. & Potenza, J. A. (2008). Acta Cryst. C64, m213-m216.]). For calculation of the four-coordination geometry, see: Yang et al. (2007[Yang, L., Powell, D. R. & Houser, R. P. (2007). Dalton Trans. pp. 955-964.]).

[Scheme 1]

Experimental

Crystal data
  • [CuCl2(C21H22N4O)]

  • Mr = 480.87

  • Triclinic, [P \overline 1]

  • a = 8.9409 (17) Å

  • b = 9.5209 (18) Å

  • c = 14.323 (3) Å

  • [alpha] = 106.973 (4)°

  • [beta] = 92.373 (4)°

  • [gamma] = 113.778 (4)°

  • V = 1049.3 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 1.32 mm-1

  • T = 294 K

  • 0.43 × 0.23 × 0.06 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000;[Bruker (2000). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.] Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) Tmin = 0.771, Tmax = 1.00

  • 10062 measured reflections

  • 4126 independent reflections

  • 3380 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.124

  • S = 1.00

  • 4126 reflections

  • 264 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.90 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Selected geometric parameters (Å, °)

Cu-N23 1.993 (2)
Cu-N13 2.005 (2)
Cu-Cl1 2.2169 (9)
Cu-Cl2 2.2198 (9)
N23-Cu-N13 90.45 (9)
N23-Cu-Cl1 141.12 (8)
N13-Cu-Cl1 94.14 (7)
N23-Cu-Cl2 100.17 (7)
N13-Cu-Cl2 143.67 (8)
Cl1-Cu-Cl2 98.64 (4)

Table 2
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C11/C13-C17 phenyl ring.

D-H...A D-H H...A D...A D-H...A
C4-H4B...Cg1i 0.96 2.99 3.910 (5) 160
C17-H17...Cl1ii 0.93 2.78 3.694 (4) 169
Symmetry codes: (i) -x, -y+2, -z; (ii) x+1, y, z.

Data collection: SMART (Bruker, 2000[Bruker (2000). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SAINT, SMART and SADABS. Bruker 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: ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.]), ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5184 ).


References

Baugh, L. S., Sissano, J. A., Kacker, S., Berluche, E., Stibrany, R. T., Schulz, D. N. & Rucker, S. P. (2006). J. Polymer Sci. Part A: Polymer Chem. 44, 1817-1840.
Blessing, R. H. (1995). Acta Cryst. A51, 33-38.  [CrossRef] [details]
Bruker (2000). SAINT, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Knapp, S., Keenan, T. P., Zhang, X., Fikar, R., Potenza, J. A. & Schugar, H. J. (1990). J. Am. Chem. Soc. 112, 3452-3464.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Stibrany, R. T. (2003). Copper-Based Olefin Polymerization Catalysts: High-Pressure 19F NMR Catalyst Probe, ACS Symp. Ser. 857, Beyond Metallocenes, edited by G. G. Hlatky & A. O. Patil, pp. 210-221. Washington, DC: ACS Press.
Stibrany, R. T. (2009). J. Chem. Crystallogr. 39, 719-722.  [ISI] [CSD] [CrossRef] [ChemPort]
Stibrany, R. T., Lobanov, M. V., Schugar, H. J. & Potenza, J. A. (2004). Inorg. Chem. 43, 1472-1480.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Stibrany, R. T. & Potenza, J. A. (2006). Private communication (refcode TEVJAG). CCDC, Cambridge, England.
Stibrany, R. T. & Potenza, J. A. (2008). Acta Cryst. C64, m213-m216.  [CSD] [CrossRef] [details]
Stibrany, R. T., Schugar, H. J. & Potenza, J. A. (2002). Acta Cryst. E58, o1142-o1144.  [CSD] [CrossRef] [details]
Stibrany, R. T., Schulz, D. N., Kacker, S., Patil, A. O., Baugh, L. S., Rucker, S. P., Zushma, S., Berluche, E. & Sissano, J. A. (2003). Macromolecules, 36, 8584-8586.  [ISI] [CSD] [CrossRef] [ChemPort]
Yang, L., Powell, D. R. & Houser, R. P. (2007). Dalton Trans. pp. 955-964.  [CSD] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, m92-m93   [ doi:10.1107/S1600536812051641 ]

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