[Journal logo]

Volume 69 
Part 7 
Pages m354-m355  
July 2013  

Received 19 May 2013
Accepted 30 May 2013
Online 8 June 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
R = 0.028
wR = 0.074
Data-to-parameter ratio = 16.2
Details
Open access

Aqua(5,10,15,20-tetraphenylporphyrinato-[kappa]4N)cadmium(II)-18-crown-6 (1/1)

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

The title compound, [Cd(C44H28N4)(H2O)]·(C12H24O6), was made by the reaction of the [Cd(TPP)] with an excess of 18-crown-6 in chlorobenzene (where TPP is tetraphenylporphyrinate). The CdII cation is chelated by a TPP anion and coordinated by a water molecule in a distorted N4O square-pyramidal geometry, the CdII cation being displaced by 0.7533 (9) Å from the mean plane of four N atoms of TPP anion. The porphyrin core presents a significant distortion, the maximum atomic deviation from the 24-atom mean plane is 0.1517 (2) Å. The 18-crown-6 molecule is linked with the CdII complex via classical O-H...O hydrogen bonds. In the crystal, weak C-H...[pi] interactions link the complex and 18-crown-6 molecules into a three-dimensional supramolecular architecture.

Related literature

For the synthesis, see: Rodesiler et al. (1985b[Rodesiler, P. F., Griffith, E. A. H., Charles, N. G., Lebioda, L. & Amma, E. L. (1985b). Inorg. Chem. 24, 4595-4600.]). For related structures, see: Byrn et al. (1991[Byrn, M. P., Curtis, C. J., Goldberg, I., Hsiou, Y., Khan, S. I., Sawin, P. A., Tendick, S. K. & Strouse, C. E. (1991). J. Am. Chem. Soc. 113, 6549-6557.]); Ezzayani et al. (2013[Ezzayani, K., Nasri, S., Belkhiria, M. S., Daran, J.-C. & Nasri, H. (2013). Acta Cryst. E69, m114-m115.]); Rodesiler et al. (1985a[Rodesiler, P. F., Griffith, E. A. H., Charles, N. G. & Amma, E. L. (1985a). Acta Cryst. C41, 673-678.]); Mansour et al. (2010[Mansour, A., Belkhiria, M. S., Daran, J.-C. & Nasri, H. (2010). Acta Cryst. E66, m509-m510.]); Yang et al. (2003[Yang, F.-A., Chen, J.-H., Hsieh, H.-Y., Elango, S. & Hwang, L.-P. (2003). Inorg. Chem. 42, 4603-4609.]); Maldonado et al. (2009[Maldonado, C. R., Quiros, M. & Salas, J. M. (2009). Polyhedron, 28, 911-916.]). For bond lengths in CdII complexes, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]). For further details of geometric distortions in related compounds, see: Scheidt & Lee (1987[Scheidt, W. R. & Lee, Y. (1987). Struct. Bonding (Berlin), 64, 1-7.]); Jentzen et al. (1997[Jentzen, W., Song, X. & Shelnutt, J. A. (1997). J. Phys. Chem. B, 101, 1684-1699.]).

[Scheme 1]

Experimental

Crystal data
  • [Cd(C44H28N4)(H2O)]·C12H24O6

  • Mr = 1007.42

  • Monoclinic, P 21 /n

  • a = 17.1956 (2) Å

  • b = 17.0918 (2) Å

  • c = 17.3903 (2) Å

  • [beta] = 106.416 (1)°

  • V = 4902.72 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.50 mm-1

  • T = 173 K

  • 0.48 × 0.40 × 0.30 mm

Data collection
  • Agilent Xcalibur (Eos, Gemini ultra) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]) Tmin = 0.959, Tmax = 1.000

  • 53048 measured reflections

  • 10009 independent reflections

  • 8403 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.028

  • wR(F2) = 0.074

  • S = 1.04

  • 10009 reflections

  • 619 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.64 e Å-3

  • [Delta][rho]min = -0.53 e Å-3

Table 1
Selected bond lengths (Å)

Cd-N1 2.2296 (15)
Cd-N2 2.2296 (15)
Cd-N3 2.2322 (16)
Cd-N4 2.2265 (15)
Cd-O1 2.2368 (18)

Table 2
Hydrogen-bond geometry (Å, °)

Cg2, Cg3, Cg4 and Cg11 are the centroids of the N2/C6-C9, N3/C11-C14, N4/C16-C19 and C33-C38 rings, respectively.

D-H...A D-H H...A D...A D-H...A
O1-H1O1...O4 1.01 (2) 2.06 (2) 3.057 (2) 176
O1-H2O1...O6 1.00 (2) 2.04 (2) 3.013 (2) 165
C31-H31...Cg3i 0.95 2.93 3.651 (2) 133
C41-H41...Cg11ii 0.95 2.91 3.794 (2) 154
C44-H44...Cg2iii 0.95 2.95 3.648 (2) 131
C47-H47A...Cg2 0.99 2.91 3.898 (3) 173
C54-H54B...Cg4 0.99 2.98 3.971 (3) 176
Symmetry codes: (i) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) -x, -y+1, -z; (iii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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, Tennesse, 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: XU5709 ).


Acknowledgements

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

References

Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.
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, Tennesse, USA.
Byrn, M. P., Curtis, C. J., Goldberg, I., Hsiou, Y., Khan, S. I., Sawin, P. A., Tendick, S. K. & Strouse, C. E. (1991). J. Am. Chem. Soc. 113, 6549-6557.  [CrossRef] [ChemPort] [Web of Science]
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]
Jentzen, W., Song, X. & Shelnutt, J. A. (1997). J. Phys. Chem. B, 101, 1684-1699.  [CrossRef] [ChemPort]
Maldonado, C. R., Quiros, M. & Salas, J. M. (2009). Polyhedron, 28, 911-916.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Mansour, A., Belkhiria, M. S., Daran, J.-C. & Nasri, H. (2010). Acta Cryst. E66, m509-m510.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Rodesiler, P. F., Griffith, E. A. H., Charles, N. G. & Amma, E. L. (1985a). Acta Cryst. C41, 673-678.  [CrossRef] [IUCr Journals]
Rodesiler, P. F., Griffith, E. A. H., Charles, N. G., Lebioda, L. & Amma, E. L. (1985b). Inorg. Chem. 24, 4595-4600.  [CrossRef] [ChemPort] [Web of Science]
Scheidt, W. R. & Lee, Y. (1987). Struct. Bonding (Berlin), 64, 1-7.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Yang, F.-A., Chen, J.-H., Hsieh, H.-Y., Elango, S. & Hwang, L.-P. (2003). Inorg. Chem. 42, 4603-4609.  [Web of Science] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, m354-m355   [ doi:10.1107/S160053681301489X ]

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.