5,10,15,20-Tetra­kis(4-acetyl­oxyphen­yl)porphyrin including an unknown solvate

Miranda, M.D.; Ramos Silva, M.; Maria, T.M.R.; Balakrishna, A.; Sobral, A.J.F.N.

doi:10.1107/S1600536812047332

Volume 68
Part 12
Pages o3462-o3463
December 2012

Received 6 November 2012
Accepted 17 November 2012
Online 28 November 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R = 0.080
wR = 0.248
Data-to-parameter ratio = 15.7
Details

5,10,15,20-Tetrakis(4-acetyloxyphenyl)porphyrin including an unknown solvate

Micael D. Miranda,^a Manuela Ramos Silva,^a ^* Teresa M. R. Maria,^b Avula Balakrishna ^b and Abilio J. F. N. Sobral ^b ⁺

^aCEMDRX, Physics Department, University of Coimbra, P-3004-516 Coimbra, Portugal, and ^bChemistry Department, University of Coimbra, P-3004 Coimbra, Portugal
Correspondence e-mail: manuela@pollux.fis.uc.pt

Molecules of the title compound, C₅₂H₃₈N₄O₈, are located on an inversion center so that the asymmetric cell contains one half of the molecule. The macrocycle exhibits a ruffled conformation with a maximum deviation of 0.16 Å for the 24 macrocycle atoms: the dihedral angle between adjacent five-membered rings is 5.13 (19)°. The benzene rings are rotated by 70.25 (19)° with respect to their adjacent protonated five-membered rings, and by 65.56 (19)° with respect to the unprotonated rings. The porphyrin conformation is supported by bifurcated N-H(N,N) hydrogen bonds. The structure contained poorly resolved solvent molecules in voids of volume 217 Å³ per unit cell. The latter were treated using the SQUEEZE routine in PLATON [Spek (2009). Acta Cryst. D65, 148-155]. As the solvent could not be identified exactly, it was not included in the calculation of the overall formula weight, density and absorption coefficient.

Related literature

For general background on porphyrin and porphyrin precursors synthesized in our group, see Paixão, Matos Beja et al. (2002); Paixão, Ramos Silva et al. (2002); Paixão et al. (2003); Ramos Silva et al. (2002a,b); Sobral et al. (2001a,b). For the applications of porphyrins, see: Zhang et al. (2010); Eichhorn (2000).

Experimental

Crystal data

C₅₂H₃₈N₄O₈
M_r = 846.86
Triclinic, $[P \overline 1]$
a = 6.6203 (2) Å
b = 14.1043 (3) Å
c = 14.4936 (3) Å
= 113.862 (1)°
= 97.771 (2)°
= 98.060 (2)°
V = 1197.58 (5) Å³
Z = 1
Mo K radiation
= 0.08 mm^-1
T = 293 K
0.30 × 0.12 × 0.04 mm

Data collection

Bruker APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2000) T_min = 0.790, T_max = 0.999
24062 measured reflections
4566 independent reflections
2956 reflections with I > 2(I)
R_int = 0.031

Refinement

R[F² > 2(F²)] = 0.080
wR(F²) = 0.248
S = 1.14
4566 reflections
291 parameters
H-atom parameters constrained
_max = 0.98 e Å^-3
_min = -0.51 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1N2	0.86	2.35	2.885 (3)	121
N1-H1N2ⁱ	0.86	2.42	2.944 (3)	120
Symmetry code: (i) -x+2, -y+2, -z+1.

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6985 ).

Acknowledgements

This work was supported by Fundo Europeu de Desenvolvimento Regional-QREN-COMPETE through project PEst-C/FIS/UI0036/2011, PTDC/AAC-CLI/098308/2008 and PTDC/AAC-CLI/118092/2010 - Fundação para a Ciência e a Tecnologia (FCT).

References

Bruker (2003). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Eichhorn, H. (2000). J. Porphyrins Phthalocyanines, 4, 88-102.
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.
Paixão, J. A., Matos Beja, A., Ramos Silva, M., Alte da Veiga, L., Sobral, A. J. F. N., Lopes, S. H. & Rocha Gonsalves, A. M. (2002). Z. Kristallogr. New Cryst. Struct. 217, 430-432.
Paixão, J. A., Ramos Silva, M., Matos Beja, A., Sobral, A. J. F. N., Lopes, S. H. & Rocha Gonsalves, A. M. d'A. (2002). Acta Cryst. C58, o721-o723.
Paixão, J. A., Ramos Silva, M., Matos Beja, A., Sobral, A. J. F. N., Lopes, S. H. & Rocha Gonsalves, A. M. d'A. (2003). Acta Cryst. E59, o94-o96.
Ramos Silva, M., Matos Beja, A., Paixão, J. A., Sobral, A. J. F. N., Lopes, S. H. & Rocha Gonsalves, A. M. d'A. (2002a). Acta Cryst. C58, o572-o574.
Ramos Silva, M., Matos Beja, A., Paixão, J. A., Sobral, A. J. F. N., Lopes, S. H. & Rocha Gonsalves, A. M. d'A. (2002b). Acta Cryst. C58, o685-o687.
Sheldrick, G. M. (2000). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sobral, A. J. F. N., Gonsalves, A. M. & dA, R. (2001a). J. Porphyrins Phthalocyanines, 5, 428-430.
Sobral, A. J. F. N., Gonsalves, A. M. & dA, R. (2001b). J. Porphyrins Phthalocyanines, 5, 861-866.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Zhang, D., Zhang, L. F., Chen, Y., Wang, H., Ni, Z. H., Wernsdorfer, W. & Jiang, J. (2010). Chem. Commun. 46, 3550-3552.

organic compounds