3,5-Bis(benz­yloxy)benzoic acid

Moreno-Fuquen, R.; Grande, C.; Advincula, R.C.; Tenorio, J.C.; Ellena, J.

doi:10.1107/S1600536812043796

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 (C-C) = 0.003 Å
Disorder in main residue
R = 0.053
wR = 0.163
Data-to-parameter ratio = 9.8
Details

3,5-Bis(benzyloxy)benzoic acid

Rodolfo Moreno-Fuquen,^a ^* Carlos Grande,^b Rigoberto C. Advincula,^c Juan C. Tenorio ^d and Javier Ellena ^d

^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-HO hydrogen bonds and weak C-HO interactions, forming chains along [010].

Related literature

For properties of dendrimer chemistry, see: Fréchet (2002). For the diverse applications of 3,5-bis(benzyloxy)benzoic acid and its benzoate derivatives, see: Sivakumar et al. (2010); Remya et al. (2008); Hawker & Fréchet (1992). For magnetic and luminiscent properties of lanthanide benzoates, see: Busskamp et al. (2007). For the conformation of O-CH₂ groups, see: Xiao et al. (2007). For related structures, see: Gainsford et al. (2009); Zhu et al. (2009). For graph-set motifs, see: Etter (1990). For hydrogen bonding, see: Nardelli (1995); Desiraju & Steiner (1999).

Experimental

Crystal data

C₂₁H₁₈O₄
M_r = 334.37
Triclinic, $[P \overline 1]$
a = 5.2801 (2) Å
b = 11.6830 (5) Å
c = 14.4803 (7) Å
= 83.303 (2)°
= 80.775 (2)°
= 79.031 (1)°
V = 862.17 (6) Å³
Z = 2
Mo K radiation
= 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(I)
R_int = 0.036

Refinement

R[F² > 2(F²)] = 0.053
wR(F²) = 0.163
S = 1.03
3084 reflections
316 parameters
H-atom parameters constrained
_max = 0.15 e Å^-3
_min = -0.15 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2O1ⁱ	0.82	1.82	2.6333 (18)	175
C20-H20O1ⁱⁱ	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); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).

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

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organic compounds