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Volume 69 
Part 4 
Pages o510-o511  
April 2013  

Received 27 February 2013
Accepted 3 March 2013
Online 9 March 2013

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.003 Å
R = 0.039
wR = 0.094
Data-to-parameter ratio = 12.5
Details
Open access

3,5-Dimethoxy-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

The title compound, C15H16O2, crystallizes with three independent molecules in the asymmetric unit. The intramolecular torsion angle between the aromatic rings of each molecule are -36.4 (3), 41.3 (3) and -37.8 (3)°. In the crystal, the complicated packing of the molecules forms wave-like layers along the b and c axes. The molecules are connected via extensive methoxy-phenyl C-H...[pi] interactions. A weak C-H...O hydrogen-bonding network also exists between methoxy O atoms and aromatic or methoxy H atoms.

Related literature

For discussion of hydrogen bonding, see: Steiner (2002[Steiner, T. (2002). Angew. Chem. Int. Ed. 41, 48-76.]). For similar structures, see: Nakagawa et al. (1984[Nakagawa, F., Takahashi, S., Naito, A., Sato, S., Iwabuchi, S. & Tamura, C. (1984). J. Antibiot. 37, 10-12.]); Pandi et al. (2000[Pandi, A. S., Velmurugan, D., Kumar, V. R., Ramakrishnan, V. T., Sundararaj, S. S. & Fun, H.-K. (2000). Cryst. Res. Technol. 35, 1373-1381.]); 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.]). For details of the synthesis, see: Dol et al. (1998[Dol, G. C., Kamer, P. C. J. & van Leeuwen, P. W. N. M. (1998). Eur. J. Org. Chem. pp. 359-364.]); 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.]). The Suzuki-Miyaura cross-coupling reaction (Miyaura & Suzuki, 1995[Miyaura, N. & Suzuki, A. (1995). Chem. Rev. 95, 2457-2483.]) is widely used for the synthesis of biphenyls and related biaryl structures in organic, polymer, and supramolecular chemistry. Such structures are frequently used as building blocks for e.g. precursors to liquid crystals (Solladié & Zimmermann 1984[Solladié, G. & Zimmermann, R. G. (1984). Angew. Chem. Int. Ed. Engl. 23, 348-362.]), supramolecular polymers (Brunsveld et al. 2001[Brunsveld, L., Folmer, B. J. B., Meijer, E. W. & Sijbesma, R. P. (2001). Chem. Rev. 101, 4071-4098.]), dendritic molecules (Nummelin et al. 2000[Nummelin, S., Skrifvars, M. & Rissanen, K. (2000). Top. Curr. Chem. 210, 1-67.]) as well as Percec-type self-assembling biphenyl dendrons (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.]; Rosen et al., 2009[Rosen, B. M., Wilson, D. A., Wilson, C. J., Peterca, M., Won, B. C., Huang, C., Lipski, L. R., Zeng, X., Ungar, G., Heiney, P. A. & Percec, V. (2009). J. Am. Chem. Soc. 131, 17500-17521.], 2010[Rosen, B. M., Peterca, M., Huang, C. H., Zeng, X. B., Ungar, G. & Percec, V. (2010). Angew. Chem. Int. Ed. 49, 7002-7005.]).

[Scheme 1]

Experimental

Crystal data
  • C15H16O2

  • Mr = 228.28

  • Orthorhombic, P 21 21 21

  • a = 7.16505 (18) Å

  • b = 15.3511 (4) Å

  • c = 33.3834 (8) Å

  • V = 3671.88 (16) Å3

  • Z = 12

  • Cu K[alpha] radiation

  • [mu] = 0.64 mm-1

  • T = 123 K

  • 0.31 × 0.07 × 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 = 0.900, Tmax = 0.979

  • 8494 measured reflections

  • 5862 independent reflections

  • 5181 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.094

  • S = 1.04

  • 5862 reflections

  • 470 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2062 Friedel pairs

  • Flack parameter: 0.09 (19)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1-Cg6 are the centroids of C26-C31, C2-C7, C33-C38, C20-C25, C8-C13 and C26-C31 aromatic rings, respectively.

D-H...A D-H H...A D...A D-H...A
C29-H29...O15i 0.95 2.40 3.321 (2) 164
C25-H25...O51ii 0.95 2.84 3.459 (3) 124
C24-H24...O17iii 0.95 2.91 3.703 (3) 141
C16-H16A...O34iv 0.98 2.68 3.521 (3) 143
C52-H52A...O17v 0.98 2.63 3.398 (3) 136
C18-H18A...Cg1iii 0.98 2.89 3.686 (3) 142
C16-H16C...Cg2iv 0.98 2.62 3.366 (3) 139
C33-H33B...Cg3iii 0.98 3.05 3.476 (3) 115
C52-H52B...Cg4v 0.98 2.77 3.424 (3) 134
C35-H35C...Cg5iii 0.98 2.77 3.639 (3) 146
C35-H35B...Cg5 0.98 2.78 3.563 (3) 143
C18-H18C...Cg6vi 0.98 2.75 3.663 (3) 148
Symmetry codes: (i) [-x-2, y+{\script{1\over 2}}, -z-{\script{1\over 2}}]; (ii) x+1, y-1, z; (iii) x+1, y, z; (iv) [-x-2, y-{\script{1\over 2}}, -z-{\script{1\over 2}}]; (v) x, y+1, z; (vi) x-1, y, z.

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: FJ2619 ).


Acknowledgements

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

References

Agilent (2010). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.
Brunsveld, L., Folmer, B. J. B., Meijer, E. W. & Sijbesma, R. P. (2001). Chem. Rev. 101, 4071-4098.  [ISI] [CrossRef] [PubMed] [ChemPort]
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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]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [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]
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]
Nakagawa, F., Takahashi, S., Naito, A., Sato, S., Iwabuchi, S. & Tamura, C. (1984). J. Antibiot. 37, 10-12.  [CrossRef] [ChemPort] [PubMed]
Nummelin, S., Skrifvars, M. & Rissanen, K. (2000). Top. Curr. Chem. 210, 1-67.  [CrossRef] [ChemPort]
Pandi, A. S., Velmurugan, D., Kumar, V. R., Ramakrishnan, V. T., Sundararaj, S. S. & Fun, H.-K. (2000). Cryst. Res. Technol. 35, 1373-1381.  [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., 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]
Rosen, B. M., Peterca, M., Huang, C. H., Zeng, X. B., Ungar, G. & Percec, V. (2010). Angew. Chem. Int. Ed. 49, 7002-7005.  [ISI] [CrossRef] [ChemPort]
Rosen, B. M., Wilson, D. A., Wilson, C. J., Peterca, M., Won, B. C., Huang, C., Lipski, L. R., Zeng, X., Ungar, G., Heiney, P. A. & Percec, V. (2009). J. Am. Chem. Soc. 131, 17500-17521.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Solladié, G. & Zimmermann, R. G. (1984). Angew. Chem. Int. Ed. Engl. 23, 348-362.
Steiner, T. (2002). Angew. Chem. Int. Ed. 41, 48-76.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o510-o511   [ doi:10.1107/S1600536813006053 ]

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