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Volume 69 
Part 5 
Pages o810-o811  
May 2013  

Received 22 April 2013
Accepted 23 April 2013
Online 30 April 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
R = 0.043
wR = 0.117
Data-to-parameter ratio = 15.0
Details
Open access

3,4,5-Trimethoxy-4'-methylbiphenyl

aUniversity of Jyväskylä, Department of Chemistry, PO Box 35, FI-40014 JY, Finland,bVTT Technical Research Centre of Finland, Tampere, FIN-33101, Finland, and cMolecular Materials, Department of Applied Physics, School of Science, Aalto University, PO Box 15100, FI-00076 Aalto, Finland
Correspondence e-mail: sami.nummelin@aalto.fi

In the title compound, C16H18O3, the dihedral angle between the benzene rings is 33.4 (2)°. In the crystal, molecules are packed in a zigzag arrangement along the b-axis and are interconnected via weak C-H...O hydrogen bonds, and C-H...[pi] interactions involving the methoxy groups and the benzene rings of neighbouring molecules.

Related literature

For related single-crystal structures based on AB2- and AB3-branched biphenyls, see: Lahtinen et al. (2013a[Lahtinen, M., Nättinen, K. & Nummelin, S. (2013a). Acta Cryst. E69, o383.],b[Lahtinen, M., Nättinen, K. & Nummelin, S. (2013b). Acta Cryst. E69, o460.],c[Lahtinen, M., Nättinen, K. & Nummelin, S. (2013c). Acta Cryst. E69, o510-o511.]); Lahtinen & Nummelin (2013[Lahtinen, M. & Nummelin, S. (2013). Acta Cryst. E69, o681.]). For synthesis of the title compound, see: Percec et al. (2006[Percec, V., Holerca, M. N., Nummelin, S., Morrison, J. J., Glodde, M., Smidrkal, J., Peterca, M., Uchida, S., Balagurusamy, V. S. K., Sienkowska, M. J. & Heiney, P. A. (2006). Chem. Eur. J. 12, 6216-6241.], 2007[Percec, V., Smidrkal, J., Peterca, M., Mitchell, C. M., Nummelin, S., Dulcey, A. E., Sienkowska, M. J. & Heiney, P. A. (2007). Chem. Eur. J. 13, 3989-4007.]). For crystal structures of dendrimers, see: Mekelburger et al. (1993[Mekelburger, H.-B., Rissanen, K. & Vögtle, F. (1993). Chem. Ber. 126, 1161-1169.]); Nättinen & Rissanen (2003[Nättinen, K. & Rissanen, K. (2003). Cryst. Growth Des. 3, 339-353.]); Ropponen et al. (2004a[Ropponen, J., Nättinen, K., Lahtinen, M. & Rissanen, K. (2004a). CrystEngComm, 6, 559-566.]). For related Percec-type self-assembling supramolecular dendrimers, see: Percec et al. (2006[Percec, V., Holerca, M. N., Nummelin, S., Morrison, J. J., Glodde, M., Smidrkal, J., Peterca, M., Uchida, S., Balagurusamy, V. S. K., Sienkowska, M. J. & Heiney, P. A. (2006). Chem. Eur. J. 12, 6216-6241.], 2007[Percec, V., Smidrkal, J., Peterca, M., Mitchell, C. M., Nummelin, S., Dulcey, A. E., Sienkowska, M. J. & Heiney, P. A. (2007). Chem. Eur. J. 13, 3989-4007.], 2008[Percec, V., Peterca, M., Dulcey, A. E., Imam, M. R., Hudson, S. D., Nummelin, S., Adelman, P. & Heiney, P. A. (2008). J. Am. Chem. Soc. 130, 13079-13094.]); Roche & Percec (2013[Roche, C. & Percec, V. (2013). Isr. J. Chem. 53, 30-44.]). For dendrimersomes, see: Percec et al. (2010[Percec, V., Wilson, D. A., Leowanawat, P., Wilson, C. J., Hughes, A. D., Kaucher, M. S., Hammer, D. A., Levine, D. H., Kim, A. J., Bates, F. S., Davis, K. P., Lodge, T. P., Klein, M. L., DeVane, R. H., Aqad, E., Rosen, B. R., Argintaru, A. O., Sienkowska, M. J., Rissanen, K., Nummelin, S. & Ropponen, J. (2010). Science, 328, 1009-1014.]). For aliphatic and aromatic polyester building blocks for dendrimersomes, see: Ropponen et al. (2004b[Ropponen, J., Nummelin, S. & Rissanen, K. (2004b). Org. Lett. 6, 2495-2497.],c[Ropponen, J., Tuuttila, T., Lahtinen, M., Nummelin, S. & Rissanen, K. (2004c). J. Polym. Sci. Part A Polym. Chem. 42, 5574-5586.]); Nummelin et al. (2000[Nummelin, S., Skrifvars, M. & Rissanen, K. (2000). Top. Curr. Chem. 210, 1-67.]).

[Scheme 1]

Experimental

Crystal data
  • C16H18O3

  • Mr = 258.30

  • Orthorhombic, P b c a

  • a = 8.4669 (2) Å

  • b = 15.0636 (3) Å

  • c = 21.4516 (4) Å

  • V = 2735.98 (10) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 173 K

  • 0.3 × 0.25 × 0.2 mm

Data collection
  • Bruker-Nonius KappaCCD diffractometer equipped with an APEXII detector

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.975, Tmax = 0.983

  • 17856 measured reflections

  • 2589 independent reflections

  • 1984 reflections with I > 2[sigma](I)

  • Rint = 0.052

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.117

  • S = 1.03

  • 2589 reflections

  • 173 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2-C7 and C8-C10/C13/C16/C19 aromatic rings, respectively.

D-H...A D-H H...A D...A D-H...A
C4-H4...O11i 0.95 2.57 3.382 (2) 144
C12-H12B...O14i 0.98 2.56 3.465 (2) 154
C18-H18C...O17ii 0.98 2.63 3.488 (2) 146
C15-H15A...Cg1iii 0.98 2.84 3.692 (2) 139
C12-H12A...Cg2iv 0.98 3.19 4.061 (2) 132
C18-H18B...Cg1v 0.98 3.01 3.976 (2) 149
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]; (ii) [x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]; (iii) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]; (iv) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]; (v) [-x+{\script{3\over 2}}, -y+1, z-{\script{1\over 2}}].

Data collection: COLLECT (Nonius, 1998[Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and SCALEPACK; 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: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GO2088 ).


Acknowledgements

SN acknowledges the Academy of Finland for financial support (No. 138850).

References

Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [ISI] [CrossRef] [ChemPort] [details]
Lahtinen, M., Nättinen, K. & Nummelin, S. (2013a). Acta Cryst. E69, o383.  [CrossRef] [details]
Lahtinen, M., Nättinen, K. & Nummelin, S. (2013b). Acta Cryst. E69, o460.  [CrossRef] [details]
Lahtinen, M., Nättinen, K. & Nummelin, S. (2013c). Acta Cryst. E69, o510-o511.  [CrossRef] [ChemPort] [details]
Lahtinen, M. & Nummelin, S. (2013). Acta Cryst. E69, o681.  [CrossRef] [details]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Mekelburger, H.-B., Rissanen, K. & Vögtle, F. (1993). Chem. Ber. 126, 1161-1169.  [CrossRef] [ChemPort]
Nättinen, K. & Rissanen, K. (2003). Cryst. Growth Des. 3, 339-353.
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Nummelin, S., Skrifvars, M. & Rissanen, K. (2000). Top. Curr. Chem. 210, 1-67.  [CrossRef] [ChemPort]
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Percec, V., Holerca, M. N., Nummelin, S., Morrison, J. J., Glodde, M., Smidrkal, J., Peterca, M., Uchida, S., Balagurusamy, V. S. K., Sienkowska, M. J. & Heiney, P. A. (2006). Chem. Eur. J. 12, 6216-6241.  [CrossRef] [PubMed] [ChemPort]
Percec, V., Peterca, M., Dulcey, A. E., Imam, M. R., Hudson, S. D., Nummelin, S., Adelman, P. & Heiney, P. A. (2008). J. Am. Chem. Soc. 130, 13079-13094.  [ISI] [CrossRef] [PubMed] [ChemPort]
Percec, V., Smidrkal, J., Peterca, M., Mitchell, C. M., Nummelin, S., Dulcey, A. E., Sienkowska, M. J. & Heiney, P. A. (2007). Chem. Eur. J. 13, 3989-4007.  [CrossRef] [PubMed] [ChemPort]
Percec, V., Wilson, D. A., Leowanawat, P., Wilson, C. J., Hughes, A. D., Kaucher, M. S., Hammer, D. A., Levine, D. H., Kim, A. J., Bates, F. S., Davis, K. P., Lodge, T. P., Klein, M. L., DeVane, R. H., Aqad, E., Rosen, B. R., Argintaru, A. O., Sienkowska, M. J., Rissanen, K., Nummelin, S. & Ropponen, J. (2010). Science, 328, 1009-1014.  [CrossRef] [ChemPort] [PubMed]
Roche, C. & Percec, V. (2013). Isr. J. Chem. 53, 30-44.  [CrossRef] [ChemPort]
Ropponen, J., Nättinen, K., Lahtinen, M. & Rissanen, K. (2004a). CrystEngComm, 6, 559-566.  [CrossRef] [ChemPort]
Ropponen, J., Nummelin, S. & Rissanen, K. (2004b). Org. Lett. 6, 2495-2497.  [CrossRef] [PubMed] [ChemPort]
Ropponen, J., Tuuttila, T., Lahtinen, M., Nummelin, S. & Rissanen, K. (2004c). J. Polym. Sci. Part A Polym. Chem. 42, 5574-5586.  [CrossRef] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o810-o811   [ doi:10.1107/S1600536813010969 ]

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