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Volume 69 
Part 2 
Pages m114-m115  
February 2013  

Received 6 January 2013
Accepted 12 January 2013
Online 19 January 2013

Key indicators
Single-crystal X-ray study
T = 180 K
Mean [sigma](C-C) = 0.002 Å
Disorder in main residue
R = 0.044
wR = 0.118
Data-to-parameter ratio = 11.6
Details
Open access

Diaqua(5,10,15,20-tetraphenylporphyrinato-[kappa]4N)magnesium-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 Narbonne, 31077 Toulouse, Cedex 04, France
Correspondence e-mail: hnasri1@gmail.com

In the title compound, [Mg(C44H28N4)(H2O)2]·C12H24O6, the MgII cation lies on an inversion center and is octahedrally coordinated by the four N atoms of the deprotonated tetraphenylporphyrin (TPP) ligand and by two water molecules. The asymmetric unit contains one half of the [Mg(TPP)(H2O)2] complex and one half of an 18-crown-6 molecule. The average equatorial magnesium-pyrrole N atom distance (Mg-Np) is 2.071 (1) Å and the axial Mg-O(H2O) bond length is 2.213 (1) Å. The crystal packing is stabilized by two O-H...O hydrogen bonds between coordinating water molecules and adjacent 18-crown-6 molecules, and exhibits a one-dimensional supramolecular structure along the a axis. The supramolecular architecture is futher stabilized by weak C-H...[pi] interactions. The 18-crown-6 molecule is disordered over two sets of sites with an occupancy ratio of 0.8:0.2.

Related literature

For general background to magnesium porphyrin species and their applications, see: Ghosh et al. (2010[Ghosh, A., Mobin, S. M., Fröhlich, R., Butcher, R. J., Maity, D. K. & Ravikanth, M. (2010). Inorg. Chem. 49, 8287-8297.]). For related structures, see: Belghith et al. (2012[Belghith, Y., Daran, J.-C. & Nasri, H. (2012). Acta Cryst. E68, m1104-m1105.]); McArdle (1995[McArdle, P. (1995). J. Appl. Cryst. 28, 65.]); McKee et al. (1984[McKee, V., Choon, O. C. & Rodley, G. A. (1984). Inorg. Chem. 23, 4242-4248.]); Choon et al. (1986[Choon, O. C., McKee, V. & Rodley, G. A. (1986). Inorg. Chim. Acta, 11, 123-126.]); McKee & Rodley (1988[McKee, V. & Rodley, G. A. (1988). Inorg. Chim. Acta, 151, 233-236.]); Gryz et al. (2007[Gryz, M., Starosta, W. & Leciejewicz, J. (2007). J. Coord. Chem. 60, 539-546.]); Imaz et al. (2005[Imaz, I., Bravic, G. & Sutter, J.-P. (2005). Chem. Commun. pp. 993-995.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data
  • [Mg(C44H28N4)(H2O)2]·C12H24O6

  • Mr = 937.36

  • Triclinic, [P \overline 1]

  • a = 8.1440 (3) Å

  • b = 12.3080 (4) Å

  • c = 12.4170 (4) Å

  • [alpha] = 86.894 (3)°

  • [beta] = 75.163 (3)°

  • [gamma] = 79.529 (3)°

  • V = 1183.06 (7) Å3

  • Z = 1

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 180 K

  • 0.56 × 0.51 × 0.19 mm

Data collection
  • Oxford Diffraction Xcalibur (Sapphire1) diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrystAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.946, Tmax = 0.981

  • 23613 measured reflections

  • 4650 independent reflections

  • 4013 reflections with I > 2[sigma](I)

  • Rint = 0.031

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

  • wR(F2) = 0.118

  • S = 1.04

  • 4650 reflections

  • 400 parameters

  • 119 restraints

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

  • [Delta][rho]max = 0.46 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg4 are the centroids of the N2/C6-C9 and C17-C22 rings, respectively.

D-H...A D-H H...A D...A D-H...A
O1-H1O1...O2A 0.97 (2) 2.08 (2) 2.984 (2) 153 (2)
O1-H2O1...O2Ai 0.97 (2) 2.22 (2) 3.105 (2) 150 (2)
O1-H1O1...O2B 0.97 (2) 2.33 (2) 3.297 (10) 170 (2)
O1-H2O1...O2Bi 0.97 (2) 2.19 (2) 2.962 (8) 135 (1)
C15-H15...Cg4ii 0.93 2.96 3.730 (2) 141
C27A-H27A...Cg2iii 0.97 2.86 3.671 (5) 142
C26B-H26D...Cg2 0.97 2.89 3.678 (11) 139
C27B-H27D...Cg2iii 0.97 2.94 3.715 (17) 139
Symmetry codes: (i) -x+1, -y, -z+1; (ii) x, y-1, z; (iii) x+1, y, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrystAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). 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: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5669 ).


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.  [ISI] [CrossRef] [details]
Belghith, Y., Daran, J.-C. & Nasri, H. (2012). Acta Cryst. E68, m1104-m1105.  [CSD] [CrossRef] [details]
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.  [ISI] [CrossRef] [ChemPort] [details]
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
Choon, O. C., McKee, V. & Rodley, G. A. (1986). Inorg. Chim. Acta, 11, 123-126.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Ghosh, A., Mobin, S. M., Fröhlich, R., Butcher, R. J., Maity, D. K. & Ravikanth, M. (2010). Inorg. Chem. 49, 8287-8297.  [ISI] [CrossRef] [ChemPort] [PubMed]
Gryz, M., Starosta, W. & Leciejewicz, J. (2007). J. Coord. Chem. 60, 539-546.  [ISI] [CSD] [CrossRef] [ChemPort]
Imaz, I., Bravic, G. & Sutter, J.-P. (2005). Chem. Commun. pp. 993-995.  [CSD] [CrossRef]
McArdle, P. (1995). J. Appl. Cryst. 28, 65.  [CrossRef] [details]
McKee, V., Choon, O. C. & Rodley, G. A. (1984). Inorg. Chem. 23, 4242-4248.  [CrossRef] [ChemPort] [ISI]
McKee, V. & Rodley, G. A. (1988). Inorg. Chim. Acta, 151, 233-236.  [CrossRef] [ChemPort] [ISI]
Oxford Diffraction (2009). CrystAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, m114-m115   [ doi:10.1107/S1600536813001219 ]

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