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Volume 69 
Part 8 
Pages m444-m445  
August 2013  

Received 25 June 2013
Accepted 1 July 2013
Online 10 July 2013

Key indicators
Single-crystal X-ray study
T = 180 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.039
wR = 0.108
Data-to-parameter ratio = 14.5
Details
Open access

(5,10,15,20-Tetraphenylporphyrinato-[kappa]4N)zinc-18-crown-6 (1/1)

aLaboratoire de Physico-chimie des Matériaux, Université de Monastir, Faculté des Sciences de Monastir, Avenue de l'environnement, 5019 Monastir, Tunisia, and bLaboratoire de Chimie de Coordination, CNRS UPR 8241, 205 route de Norbonne, 31077 Toulouse, Cedex 04, France
Correspondence e-mail: hnasri1@gmail.com

In the title compound, [Zn(C44H28N4)]·C12H24O6, the ZnII ion lies on an inversion center and the asymmetric unit contains one half of a Zn(TPP) complex (TPP = 5,10,15,20-tetraphenylporphyrin dianion) and one half of a centrosymmetric 18-crown-6 molecule. The Zn(TPP) complex exhibits a nearly planar conformation of the porphyrin core [maximum deviation = 0.106 (2) Å] with an average Zn-N distance of 2.047 (2) Å. The title compound is considered as a one-dimensional polymer along [010], in which the Zn(TPP) moiety is linked to the closest O atoms of two symmetry-related 18-crown-6 molecules with a Zn-O distance of 2.582 (1) Å, completing a distorted octahedral coordination environment of the metal ion. The chains are mainly sustained by weak C-H...[pi] interactions. An ethylene group of the 18-crown-6 molecule is disordered over three sites with occupancies of 0.50, 0.25 and 0.25.

Related literature

For related structures, see: Cheng & Scheidt (1995[Cheng, B. & Scheidt, W. R. (1995). Inorg. Chim. Acta, 237, 5-11.]); Diskin-Posner et al. (1999[Diskin-Posner, Y., Kumar, R. K. & Goldberg, I. (1999). New J. Chem. 23, 885-890.]); Ezzayani et al. (2013[Ezzayani, K., Nasri, S., Belkhiria, M. S., Daran, J.-C. & Nasri, H. (2013). Acta Cryst. E69, m114-m115.]); Kojima et al. (2009[Kojima, T., Nakanishi, T., Honda, T., Harada, R., Shiro, M. & Fukuzumi, S. (2009). Eur. J. Inorg. Chem. pp. 727-734.]); Kumar et al. (1997[Kumar, R. K., Goldborth, A. & Goldberg, I. (1997). Z. Kristallogr. New Cryst. Struct. 212, 383-384.]); Mansour et al. (2010[Mansour, A., Belkhiria, M. S., Daran, J.-C. & Nasri, H. (2010). Acta Cryst. E66, m509-m510.]); Ricard et al. (2001[Ricard, D., Richard, P. & Boitrel, B. (2001). Acta Cryst. E57, m404-m406.]); Suijkerbuijk et al. (2007[Suijkerbuijk, B. M. J. M., Tooke, D. M., Spek, A. L., Van Koten, G. & Gebbink, R. J. M. K. (2007). Chem. Asian J. 2, 889-903.]); Toumi et al. (2013[Toumi, H., Belghith, Y., Daran, J.-C. & Nasri, H. (2013). Acta Cryst. E69, m354-m355.]). For the SIMU/ISOR restraints used in the refinement, see: McArdle (1995[McArdle, P. (1995). J. Appl. Cryst. 28, 65.]). For a description of the Cambridge Strcutural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]). For the synthesis, see: Oberda et al. (2011[Oberda, K., Deperasinska, I., Nizhnik, Y., Jerzykiewicz, L. & Szemik-Hojniak, A. (2011). Polyhedron, 30, 2391-2399.]).

[Scheme 1]

Experimental

Crystal data
  • [Zn(C44H28N4)]·C12H24O6

  • Mr = 942.39

  • Triclinic, [P \overline 1]

  • a = 10.2170 (3) Å

  • b = 11.1190 (4) Å

  • c = 11.8243 (3) Å

  • [alpha] = 104.384 (3)°

  • [beta] = 105.912 (3)°

  • [gamma] = 108.096 (3)°

  • V = 1143.23 (8) Å3

  • Z = 1

  • Mo K[alpha] radiation

  • [mu] = 0.60 mm-1

  • T = 180 K

  • 0.48 × 0.45 × 0.33 mm

Data collection
  • Oxford Diffraction Xcalibur diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrystAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.918, Tmax = 1.000

  • 22963 measured reflections

  • 4503 independent reflections

  • 3774 reflections with I > 2[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.108

  • S = 1.07

  • 4503 reflections

  • 310 parameters

  • 30 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.95 e Å-3

  • [Delta][rho]min = -0.67 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the N1/C1-C4, N2/C6-C9 and C11-C16 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C15-H15...Cg1i 0.93 2.98 3.824 (2) 152
C20-H20...Cg3ii 0.93 2.84 3.746 (2) 164
C24-H24A...Cg2 0.97 2.73 3.686 (3) 167
Symmetry codes: (i) -x+2, -y, -z+2; (ii) -x+3, -y, -z+2.

Data collection: CrysAlis CCD (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrystAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrystAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); data reduction: CrysAlis RED; program(s) used to solve structure: SIR2004 (Burla et al., 2005[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.]); 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.]) and ORTEP-3 for Windows (Farrugia, 2012)[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]; software used to prepare material for publication: WinGX (Farrugia, 2012)[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.].


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2633 ).


Acknowledgements

The authors gratefully acknowledge financial support from the Ministry of Higher Education and Scientific Research of Tunisia.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [Web of Science] [CrossRef] [IUCr Journals]
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
Cheng, B. & Scheidt, W. R. (1995). Inorg. Chim. Acta, 237, 5-11.  [CrossRef] [ChemPort] [Web of Science]
Diskin-Posner, Y., Kumar, R. K. & Goldberg, I. (1999). New J. Chem. 23, 885-890.  [ChemPort]
Ezzayani, K., Nasri, S., Belkhiria, M. S., Daran, J.-C. & Nasri, H. (2013). Acta Cryst. E69, m114-m115.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Kojima, T., Nakanishi, T., Honda, T., Harada, R., Shiro, M. & Fukuzumi, S. (2009). Eur. J. Inorg. Chem. pp. 727-734.  [Web of Science] [CSD] [CrossRef]
Kumar, R. K., Goldborth, A. & Goldberg, I. (1997). Z. Kristallogr. New Cryst. Struct. 212, 383-384.  [ChemPort]
Mansour, A., Belkhiria, M. S., Daran, J.-C. & Nasri, H. (2010). Acta Cryst. E66, m509-m510.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
McArdle, P. (1995). J. Appl. Cryst. 28, 65.  [CrossRef] [IUCr Journals]
Oberda, K., Deperasinska, I., Nizhnik, Y., Jerzykiewicz, L. & Szemik-Hojniak, A. (2011). Polyhedron, 30, 2391-2399.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Oxford Diffraction (2010). CrystAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Ricard, D., Richard, P. & Boitrel, B. (2001). Acta Cryst. E57, m404-m406.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Suijkerbuijk, B. M. J. M., Tooke, D. M., Spek, A. L., Van Koten, G. & Gebbink, R. J. M. K. (2007). Chem. Asian J. 2, 889-903.  [CSD] [CrossRef] [PubMed] [ChemPort]
Toumi, H., Belghith, Y., Daran, J.-C. & Nasri, H. (2013). Acta Cryst. E69, m354-m355.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, m444-m445   [ doi:10.1107/S1600536813018126 ]

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