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Volume 69 
Part 10 
Page o1562  
October 2013  

Received 10 September 2013
Accepted 13 September 2013
Online 18 September 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.045
wR = 0.138
Data-to-parameter ratio = 13.5
Details
Open access

Methyl 4-(benzyloxy)-3-methoxybenzoate

aHigh Technology Research Institute of Nanjing University, Changzhou 213162, Jiangsu, People's Republic of China, and bSchool of Petrochemical Engineering, Changzhou University & High Technology Research Institute of Nanjing University, Changzhou 213164, Jiangsu, People's Republic of China
Correspondence e-mail: wkcoool@163.com

In the title compound, C16H16O4, the aromatic rings are almost normal to one another, making a dihedral angle of 85.81 (10)°. In the crystal, molecules are linked by C-H...O hydrogen bonds, forming chains propagating along the b-axis direction. There are also C-H...[pi] interactions present which link the chains, forming two-dimensional networks lying parallel to (102).

Related literature

For details of the anticancer properties of the drug Cediranib {systematic name: 4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxy-7-[3-(pyrrolidin-1-yl)propoxy]quinazoline}, for which the title compound is an important intermediate in the synthesis, see: Folkman (1996[Folkman, J. (1996). Sci. Am. 275, 150-154.]). For the synthetic procedure, see: Li & Zhang (2012[Li, H.-S. & Zhang, S.-X. (2012). Patent No. CN 102603718A.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C16H16O4

  • Mr = 272.29

  • Monoclinic, P 21 /c

  • a = 5.2466 (7) Å

  • b = 17.973 (2) Å

  • c = 14.8785 (18) Å

  • [beta] = 94.018 (3)°

  • V = 1399.6 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.12 × 0.12 × 0.10 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.989, Tmax = 0.991

  • 7732 measured reflections

  • 2454 independent reflections

  • 1666 reflections with I > 2[sigma](I)

  • Rint = 0.029

  • 3 standard reflections every 120 min intensity decay: 1%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.138

  • S = 0.91

  • 2454 reflections

  • 182 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1-C6 ring

D-H...A D-H H...A D...A D-H...A
C14-H14B...O3i 0.96 2.53 3.379 (3) 147
C14-H14A...Cgii 0.96 2.75 3.519 (2) 137
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [x-1, -y-{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: CAD-4 Software (Enraf-Nonius, 1985)[Enraf-Nonius (1985). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]; cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2645 ).


Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University for the data collection.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Enraf-Nonius (1985). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Folkman, J. (1996). Sci. Am. 275, 150-154.  [CrossRef] [ChemPort] [PubMed]
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Li, H.-S. & Zhang, S.-X. (2012). Patent No. CN 102603718A.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1562  [ doi:10.1107/S1600536813025415 ]

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