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Volume 68 
Part 11 
Pages o3247-o3248  
November 2012  

Received 2 October 2012
Accepted 22 October 2012
Online 31 October 2012

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.053
wR = 0.163
Data-to-parameter ratio = 9.8
Details
Open access

3,5-Bis(benzyloxy)benzoic acid

aDepartamento de Química, Facultad de Ciencias, Universidad del Valle, Apartado 25360, Santiago de Cali, Colombia,bPrograma de Ingenieria Agroindustrial, Universidad San Buenaventura, AA 7154, Santiago de Cali, Colombia,cCase Western Reserve University, Department of Macromolecular Science and Engineering, 2100 Adelbert Road, Kent Hale Smith Bldg, Cleveland, Ohio 44106, USA, and dInstituto de Física de São Carlos, IFSC, Universidade de São Paulo, USP, São Carlos, SP, Brazil
Correspondence e-mail: rodimo26@yahoo.es

In the title compound, C21H18O4, the outer benzyl rings are disordered over two resolved positions in a 0.50 ratio. The O-CH2 groups form dihedral angles of 4.1 (2) and 10.9 (4)° with the central benzene ring, adopting a syn-anti conformation with respect to this ring. In the crystal, the molecules are linked by O-H...O hydrogen bonds and weak C-H...O interactions, forming chains along [010].

Related literature

For properties of dendrimer chemistry, see: Fréchet (2002[Fréchet, J. M. J. (2002). PNAS, 99, 4782-4787.]). For the diverse applications of 3,5-bis(benzyloxy)benzoic acid and its benzoate derivatives, see: Sivakumar et al. (2010[Sivakumar, S., Reddy, M. L., Cowley, A. H. & Vasudevan, K. V. (2010). Dalton Trans. 39, 776-786.]); Remya et al. (2008[Remya, P. N., Biju, S., Reddy, M. L., Cowley, A. H. & Findlater, M. (2008). Inorg. Chem. 47, 7396-7404.]); Hawker & Fréchet (1992[Hawker, C. & Fréchet, J. M. J. (1992). J. Chem. Soc. Perkin Trans. 1, pp. 2459-2469.]). For magnetic and luminiscent properties of lanthanide benzoates, see: Busskamp et al. (2007[Busskamp, H., Deacon, G. B., Hilder, M., Junk, P. C., Kynast, U. H., Lee, W. W. & Turner, D. R. (2007). CrystEngComm, 9, 394-411.]). For the conformation of O-CH2 groups, see: Xiao et al. (2007[Xiao, Z.-P., Fang, R.-Q., Shi, L., Ding, H., Xu, C. & Zhu, H.-L. (2007). Can. J. Chem. 85, 951-957.]). For related structures, see: Gainsford et al. (2009[Gainsford, G. J., Bhuiyan, M. D. H. & Kay, A. J. (2009). Acta Cryst. E65, o3261-o3262.]); Zhu et al. (2009[Zhu, P., Zhao, Y., Chen, H., Cui, Q. & Wei, Q. (2009). Acta Cryst. E65, o823.]). For graph-set motifs, see: Etter (1990[Etter, M. (1990). Acc. Chem. Res. 23, 120-126.]). For hydrogen bonding, see: Nardelli (1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]); Desiraju & Steiner (1999[Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology, pp. 350-362. New York: Oxford University Press Inc.]).

[Scheme 1]

Experimental

Crystal data
  • C21H18O4

  • Mr = 334.37

  • Triclinic, [P \overline 1]

  • a = 5.2801 (2) Å

  • b = 11.6830 (5) Å

  • c = 14.4803 (7) Å

  • [alpha] = 83.303 (2)°

  • [beta] = 80.775 (2)°

  • [gamma] = 79.031 (1)°

  • V = 862.17 (6) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 295 K

  • 0.43 × 0.11 × 0.10 mm

Data collection
  • Nonius KappaCCD diffractometer

  • 5626 measured reflections

  • 3084 independent reflections

  • 1801 reflections with I > 2[sigma](I)

  • Rint = 0.036

Refinement
  • R[F2 > 2[sigma](F2)] = 0.053

  • wR(F2) = 0.163

  • S = 1.03

  • 3084 reflections

  • 316 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.15 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2...O1i 0.82 1.82 2.6333 (18) 175
C20-H20...O1ii 0.93 2.66 3.507 (13) 153
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+2, -y, -z+1.

Data collection: COLLECT (Nonius, 2000[Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and SCALEPACK; 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: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) 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: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5257 ).


Acknowledgements

RMF is grateful to the Spanish Research Council (CSIC) for the use of a free-of-charge licence to the Cambridge Structural Database. RMF also thanks the Universidad del Valle, Colombia, and CG thanks the Universidad San Buenaventura, Cali, Colombia, for partial financial support.

References

Busskamp, H., Deacon, G. B., Hilder, M., Junk, P. C., Kynast, U. H., Lee, W. W. & Turner, D. R. (2007). CrystEngComm, 9, 394-411.  [ChemPort]
Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology, pp. 350-362. New York: Oxford University Press Inc.
Etter, M. (1990). Acc. Chem. Res. 23, 120-126.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Fréchet, J. M. J. (2002). PNAS, 99, 4782-4787.  [PubMed]
Gainsford, G. J., Bhuiyan, M. D. H. & Kay, A. J. (2009). Acta Cryst. E65, o3261-o3262.  [CrossRef] [details]
Hawker, C. & Fréchet, J. M. J. (1992). J. Chem. Soc. Perkin Trans. 1, pp. 2459-2469.  [CrossRef]
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]
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [details]
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Remya, P. N., Biju, S., Reddy, M. L., Cowley, A. H. & Findlater, M. (2008). Inorg. Chem. 47, 7396-7404.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sivakumar, S., Reddy, M. L., Cowley, A. H. & Vasudevan, K. V. (2010). Dalton Trans. 39, 776-786.  [CrossRef] [ChemPort] [PubMed]
Xiao, Z.-P., Fang, R.-Q., Shi, L., Ding, H., Xu, C. & Zhu, H.-L. (2007). Can. J. Chem. 85, 951-957.  [ISI] [CSD] [CrossRef] [ChemPort]
Zhu, P., Zhao, Y., Chen, H., Cui, Q. & Wei, Q. (2009). Acta Cryst. E65, o823.  [CrossRef] [details]


Acta Cryst (2012). E68, o3247-o3248   [ doi:10.1107/S1600536812043796 ]

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