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Volume 69 
Part 3 
Page o383  
March 2013  

Received 22 January 2013
Accepted 11 February 2013
Online 16 February 2013

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.002 Å
R = 0.034
wR = 0.096
Data-to-parameter ratio = 13.4
Details
Open access

Methyl 3',4',5'-trimethoxybiphenyl-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, C17H18O5, the dihedral angle between the benzene rings is 31.23 (16)°. In the crystal, the molecules are packed in an antiparallel fashion in layers along the a axis. In each layer, very weak C-H...O hydrogen bonds occur between the methoxy and methyl ester groups. Weak C-H...[pi] interactions between the 4'- and 5'-methoxy groups and neighbouring benzene rings [methoxy-C-ring centroid distances = 4.075 and 3.486 Å, respectively] connect the layers.

Related literature

For a related structure, see: Li et al. (2012[Li, X.-M., Hou, Y.-J., Chu, W.-Y. & Sun, Z.-Z. (2012). Acta Cryst. E68, o1292.]). For the nature of hydrogen bonding, see Steiner (2002[Steiner, T. (2002). Angew. Chem. Int. Ed. 41, 48-76.]); For related biphenyl structures, see: Leowanawat et al. (2011[Leowanawat, P., Zhang, N., Resmerita, A.-M., Rosen, B. M. & Percec, V. (2011). J. Org. Chem. 76, 9946-9955.]); Wilson et al. (2008[Wilson, D. A., Wilson, C. J., Rosen, B. M. & Percec, V. (2008). Org. Lett. 10, 4879-4882.]); Percec et al. (2004[Percec, V., Golding, G. M., Smidrkal, J. & Weichold, O. (2004). J. Org. Chem. 69, 3447-3452.]); Suzuki (1999[Suzuki, A. (1999). Organomet. Chem. 576, 147-168.]). For details of the synthesis and amphiphilic supramolecular biphenyl 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.]). For general background to 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.]); For the use of aromatic and aliphatic ester derivatives in the synthesis of dendrimers and dendrons, see Nummelin et al. (2000[Nummelin, S., Skrifvars, M. & Rissanen, K. (2000). Top. Curr. Chem. 210, 1-67.]); Twibanire & Grindley (2012[Twibanire, J. K. & Grindley, T. B. (2012). Polymers, 4, 794-879.]).

[Scheme 1]

Experimental

Crystal data
  • C17H18O5

  • Mr = 302.31

  • Triclinic, [P \overline 1]

  • a = 7.9103 (5) Å

  • b = 8.6054 (7) Å

  • c = 11.8779 (7) Å

  • [alpha] = 92.834 (6)°

  • [beta] = 92.448 (5)°

  • [gamma] = 115.822 (7)°

  • V = 725.07 (9) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 0.84 mm-1

  • T = 123 K

  • 0.49 × 0.23 × 0.10 mm

Data collection
  • Agilent SuperNova (Dual source with Cu, Atlas) diffractometer

  • Absorption correction: analytical (CrysAlis PRO; Agilent, 2010)[Agilent (2010). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.] Tmin = 0.827, Tmax = 0.951

  • 4547 measured reflections

  • 2731 independent reflections

  • 2524 reflections with I > 2[sigma](I)

  • Rint = 0.016

Refinement
  • R[F2 > 2[sigma](F2)] = 0.034

  • wR(F2) = 0.096

  • S = 1.05

  • 2731 reflections

  • 204 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 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
C15-H15A...O2i 0.98 2.58 3.4933 (15) 156
C18-H18C...O14ii 0.98 2.50 3.4453 (16) 161
Symmetry codes: (i) -x+2, -y+1, -z; (ii) -x, -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: 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: FJ2614 ).


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]
Leowanawat, P., Zhang, N., Resmerita, A.-M., Rosen, B. M. & Percec, V. (2011). J. Org. Chem. 76, 9946-9955.  [CrossRef] [ChemPort] [PubMed]
Li, X.-M., Hou, Y.-J., Chu, W.-Y. & Sun, Z.-Z. (2012). Acta Cryst. E68, o1292.  [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]
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., 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]
Suzuki, A. (1999). Organomet. Chem. 576, 147-168.  [ChemPort]
Twibanire, J. K. & Grindley, T. B. (2012). Polymers, 4, 794-879.  [CrossRef]
Wilson, D. A., Wilson, C. J., Rosen, B. M. & Percec, V. (2008). Org. Lett. 10, 4879-4882.  [ISI] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o383  [ doi:10.1107/S1600536813004133 ]

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