[Journal logo]

Volume 69 
Part 3 
Page o460  
March 2013  

Received 12 February 2013
Accepted 24 February 2013
Online 28 February 2013

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.002 Å
R = 0.040
wR = 0.111
Data-to-parameter ratio = 13.0
Details
Open access

Methyl 3',5'-dimethoxybiphenyl-4-carboxylate

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, C16H16O4, the dihedral angle between the benzene rings is 28.9 (2)°. In the crystal, molecules are packed in layers parallel to the b axis in which they are connected via weak intermolecular C-H...O contacts. Face-to-face [pi]-[pi] interactions also exist between the benzene rings of adjacent molecules, with centroid-centroid and plane-to-plane shift distances of 3.8597 (14) and 1.843 (2) Å, respectively.

Related literature

For related structures, see: Lahtinen et al. (2013[Lahtinen, M., Nättinen, K. & Nummelin, S. (2013). Acta Cryst. E69, o383.]); Van Eerdenbrugh et al. (2010[Van Eerdenbrugh, B., Fanwick, P. E. & Taylor, L. S. (2010). Acta Cryst. E66, o2609.]). For the nature of hydrogen bonding, see: Steiner (2002[Steiner, T. (2002). Angew. Chem. Int. Ed. 41, 48-76.]). For synthesis details and related supramolecular structures based on 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 related synthetic biphenyl structures, see: Rosen et al. (2008[Rosen, B. M., Huang, C. & Percec, V. (2008). Org. Lett. 12, 2597-2600.]); 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 polyester functionalized dendrons and dendrimers, see: Nummelin et al. (2000[Nummelin, S., Skrifvars, M. & Rissanen, K. (2000). Top. Curr. Chem. 210, 1-67.]). For a general review on self-assembling dendrons and dendrimers, see: Rosen et al. (2009[Rosen, B. M., Wilson, C. J., Wilson, D. A., Peterca, M., Imam, M. R. & Percec, V. (2009). Chem. Rev. 109, 6275-6540.]).

[Scheme 1]

Experimental

Crystal data
  • C16H16O4

  • Mr = 272.29

  • Triclinic, [P \overline 1]

  • a = 6.0990 (9) Å

  • b = 7.1622 (16) Å

  • c = 16.2408 (18) Å

  • [alpha] = 96.589 (14)°

  • [beta] = 91.472 (11)°

  • [gamma] = 112.493 (18)°

  • V = 649.27 (19) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 0.82 mm-1

  • T = 123 K

  • 0.29 × 0.19 × 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 = 0.924, Tmax = 0.983

  • 3989 measured reflections

  • 2395 independent reflections

  • 2025 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.111

  • S = 1.05

  • 2395 reflections

  • 184 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C6-H6...O2i 0.95 2.89 3.7702 (19) 154
C7-H7...O4ii 0.95 2.85 3.4607 (19) 123
C12-H12...O4ii 0.95 2.71 3.644 (2) 170
C16-H16...O14iii 0.95 2.65 3.514 (2) 151
C1-H1A...O4iv 0.98 2.73 3.665 (2) 159
C19-H19A...O18v 0.98 2.65 3.538 (2) 151
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y+2, -z+2; (iii) -x, -y+1, -z+1; (iv) x+1, y, z; (v) -x+1, -y, -z+1.

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: SUPERFLIP (Palatinus & Chapuis, 2007[Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.]); 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: FJ2616 ).


Acknowledgements

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

References

Agilent (2010). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.
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. (2013). Acta Cryst. E69, o383.  [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]
Nummelin, S., Skrifvars, M. & Rissanen, K. (2000). Top. Curr. Chem. 210, 1-67.  [CrossRef] [ChemPort]
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.  [ISI] [CrossRef] [ChemPort] [details]
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., 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., Huang, C. & Percec, V. (2008). Org. Lett. 12, 2597-2600.  [CrossRef]
Rosen, B. M., Wilson, C. J., Wilson, D. A., Peterca, M., Imam, M. R. & Percec, V. (2009). Chem. Rev. 109, 6275-6540.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Steiner, T. (2002). Angew. Chem. Int. Ed. 41, 48-76.  [ISI] [CrossRef] [ChemPort]
Van Eerdenbrugh, B., Fanwick, P. E. & Taylor, L. S. (2010). Acta Cryst. E66, o2609.  [CrossRef] [details]
Wolfe, J. P., Singer, R. A., Yang, B. H. & Buchwald, S. L. (1999). J. Am. Chem. Soc. 121, 9550-9561.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o460  [ doi:10.1107/S1600536813005333 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.