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Volume 69 
Part 7 
Page o1048  
July 2013  

Received 26 May 2013
Accepted 4 June 2013
Online 8 June 2013

Key indicators
Single-crystal X-ray study
T = 90 K
Mean [sigma](C-C) = 0.002 Å
R = 0.045
wR = 0.109
Data-to-parameter ratio = 16.5
Details
Open access

5,15-Bis(4-pentyloxyphenyl)porphyrin

aSchool of Chemistry, SFI Tetrapyrrole Laboratory, Trinity Biomedical Sciences Institute, 152-160 Pearse Street, Trinity College Dublin, Dublin 2, Ireland
Correspondence e-mail: sengem@tcd.ie

In the title compound, C42H42N4O2, the complete molecule is generated by a crystallographic inversion centre. The porphyrin system exhibits a near planar macrocycle conformation with an average deviation from the least-squares plane of the 24 macrocycle atoms of 0.037 (5) Å. The phenyl ipso C atoms are positioned above and below the porphyrin plane by 0.35 (1) Å and the macrocycle shows evidence of in-plane rectangular elongation with N...N separations of 3.032 (5) and 2.803 (5) Å. Two intramolecular N-H...N hydrogen bonds occur.

Related literature

For the conformation of porphyrins, see: Scheidt & Lee (1987[Scheidt, W. R. & Lee, Y. J. (1987). Struct. Bond. 64, 1-70.]); Senge et al. (1997[Senge, M. O., Medforth, C. J., Forsyth, T. P., Lee, D. A., Olmstead, M. M., Jentzen, W., Pandey, R. K., Shelnutt, J. A. & Smith, K. M. (1997). Inorg. Chem. 36, 1149-1163.]); Senge (2006[Senge, M. O. (2006). Chem. Commun. pp. 243-256.]). For the synthesis of such compounds, see: Wiehe et al. (2005[Wiehe, A., Shaker, Y. M., Brandt, J. C., Mebs, S. & Senge, M. O. (2005). Tetrahedron, 61, 5535-5564.]).

[Scheme 1]

Experimental

Crystal data
  • C42H42N4O2

  • Mr = 634.80

  • Triclinic, [P \overline 1]

  • a = 9.5222 (6) Å

  • b = 9.5799 (6) Å

  • c = 10.2195 (6) Å

  • [alpha] = 67.777 (1)°

  • [beta] = 88.063 (1)°

  • [gamma] = 72.464 (1)°

  • V = 819.49 (9) Å3

  • Z = 1

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 90 K

  • 0.30 × 0.10 × 0.08 mm

Data collection
  • Bruker SMART APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.97, Tmax = 0.99

  • 9093 measured reflections

  • 3606 independent reflections

  • 2489 reflections with I > 2[sigma](I)

  • Rint = 0.039

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.109

  • S = 1.04

  • 3606 reflections

  • 219 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N21-H21...N24 0.88 2.50 3.033 (2) 119
N21-H21...N24i 0.88 2.22 2.804 (2) 123
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). SMART, SAINT 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: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: XP in SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2552 ).


Acknowledgements

This work was supported by a grant from Science Foundation Ireland (SFI P.I. 09/IN.1/B2650).

References

Bruker (2005). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Scheidt, W. R. & Lee, Y. J. (1987). Struct. Bond. 64, 1-70.  [CrossRef] [ChemPort]
Senge, M. O. (2006). Chem. Commun. pp. 243-256.  [CrossRef]
Senge, M. O., Medforth, C. J., Forsyth, T. P., Lee, D. A., Olmstead, M. M., Jentzen, W., Pandey, R. K., Shelnutt, J. A. & Smith, K. M. (1997). Inorg. Chem. 36, 1149-1163.  [CrossRef] [PubMed] [ChemPort] [Web of Science]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Wiehe, A., Shaker, Y. M., Brandt, J. C., Mebs, S. & Senge, M. O. (2005). Tetrahedron, 61, 5535-5564.  [Web of Science] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1048  [ doi:10.1107/S160053681301550X ]

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