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Volume 69 
Part 5 
Page o681  
May 2013  

Received 2 April 2013
Accepted 2 April 2013
Online 10 April 2013

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.002 Å
R = 0.052
wR = 0.143
Data-to-parameter ratio = 14.5
Details
Open access

3,4-Dimethoxy-4'-methylbiphenyl

aUniversity of Jyväskylä, Department of Chemistry, PO Box 35, FI-40014 JY, Finland, and bMolecular 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, C15H16O2, the dihedral angle between the planes of the aromatic rings is 30.5 (2)°. In the crystal, molecules are linked via C-H...O hydrogen bonds and C-H...[pi] interactions, forming a two-dimensional network lying parallel to (100).

Related literature

For structural studies of related biphenyl derivatives, 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.]); Li et al. (2012a[Li, X.-M., Hou, Y.-J., Mei, P., Chu, W.-Y. & Sun, Z.-Z. (2012a). Acta Cryst. E68, o1137.],b[Li, X.-M., Hou, Y.-J., Chu, W.-Y. & Sun, Z.-Z. (2012b). Acta Cryst. E68, o1292.]). For details of the synthesis, see: Percec et al. (2004[Percec, V., Golding, G. M., Smidrkal, J. & Weichold, O. (2004). J. Org. Chem. 69, 3447-3452.], 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.]); Wolfe et al. (1999[Wolfe, J. P., Singer, R. A., Yang, B. H. & Buchwald, S. L. (1999). J. Am. Chem. Soc. 121, 9550-9561.]). For details of various cross-coupling reactions, see: Corbet & Mignani (2006[Corbet, J.-P. & Mignani, G. (2006). Chem. Rev. 106, 2651-2710.]); Miyaura et al. (1981[Miyaura, N., Yanagi, T. & Suzuki, A. (1981). Synth. Commun. 11, 513-519.]); Miyaura & Suzuki (1995[Miyaura, N. & Suzuki, A. (1995). Chem. Rev. 95, 2457-2483.]); Percec et al. (2004[Percec, V., Golding, G. M., Smidrkal, J. & Weichold, O. (2004). J. Org. Chem. 69, 3447-3452.]); Wolfe et al. (1999[Wolfe, J. P., Singer, R. A., Yang, B. H. & Buchwald, S. L. (1999). J. Am. Chem. Soc. 121, 9550-9561.]). For self-assembling supramolecular dendrons based on 3,4-branched biphenyls, 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 hollow supramolecular dendrimers, see Peterca et al. (2006[Peterca, M., Percec, V., Dulcey, A. E., Nummelin, S., Korey, S., Ilies, M. & Heiney, P. A. (2006). J. Am. Chem. Soc. 128, 6713-6720.]); Percec et al. (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.]). For dendritic polyaryl esters, see Nummelin et al. (2000[Nummelin, S., Skrifvars, M. & Rissanen, K. (2000). Top. Curr. Chem. 210, 1-67.]).

[Scheme 1]

Experimental

Crystal data
  • C15H16O2

  • Mr = 228.28

  • Monoclinic, P 21 /c

  • a = 17.7430 (9) Å

  • b = 8.7581 (3) Å

  • c = 8.1135 (3) Å

  • [beta] = 101.795 (5)°

  • V = 1234.17 (9) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.64 mm-1

  • T = 123 K

  • 0.36 × 0.26 × 0.04 mm

Data collection
  • Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer

  • Absorption correction: analytical (CrysAlis PRO; Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]) Tmin = 0.880, Tmax = 0.977

  • 4273 measured reflections

  • 2282 independent reflections

  • 1844 reflections with I > 2[sigma](I)

  • Rint = 0.038

Refinement
  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.143

  • S = 1.07

  • 2282 reflections

  • 157 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.31 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C8-C13 ring.

D-H...A D-H H...A D...A D-H...A
C15-H15A...O16i 0.98 2.57 3.389 (2) 141
C15-H15C...O16ii 0.98 2.42 3.356 (2) 160
C4-H4...Cg2ii 0.95 2.96 3.7807 (18) 145
C17-H17B...Cg2iii 0.98 2.83 3.7119 (19) 150
Symmetry codes: (i) [-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (iii) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2010[Agilent (2010). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: FJ2625 ).


Acknowledgements

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

References

Agilent (2010). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.
Corbet, J.-P. & Mignani, G. (2006). Chem. Rev. 106, 2651-2710.  [ISI] [CrossRef] [PubMed] [ChemPort]
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]
Li, X.-M., Hou, Y.-J., Chu, W.-Y. & Sun, Z.-Z. (2012b). Acta Cryst. E68, o1292.  [CSD] [CrossRef] [details]
Li, X.-M., Hou, Y.-J., Mei, P., Chu, W.-Y. & Sun, Z.-Z. (2012a). Acta Cryst. E68, o1137.  [CSD] [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]
Miyaura, N. & Suzuki, A. (1995). Chem. Rev. 95, 2457-2483.  [ISI] [CrossRef] [ChemPort]
Miyaura, N., Yanagi, T. & Suzuki, A. (1981). Synth. Commun. 11, 513-519.  [CrossRef] [ChemPort] [ISI]
Nummelin, S., Skrifvars, M. & Rissanen, K. (2000). Top. Curr. Chem. 210, 1-67.  [CrossRef] [ChemPort]
Percec, V., Golding, G. M., Smidrkal, J. & Weichold, O. (2004). J. Org. Chem. 69, 3447-3452.  [CrossRef] [PubMed] [ChemPort]
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]
Peterca, M., Percec, V., Dulcey, A. E., Nummelin, S., Korey, S., Ilies, M. & Heiney, P. A. (2006). J. Am. Chem. Soc. 128, 6713-6720.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Wolfe, J. P., Singer, R. A., Yang, B. H. & Buchwald, S. L. (1999). J. Am. Chem. Soc. 121, 9550-9561.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o681  [ doi:10.1107/S1600536813008957 ]

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