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Volume 69 
Part 10 
Page o1588  
October 2013  

Received 7 September 2013
Accepted 19 September 2013
Online 25 September 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.004 Å
R = 0.059
wR = 0.171
Data-to-parameter ratio = 13.5
Details
Open access

6-[(4'-Ethoxycarbonyl-[1,1'-biphenyl]-4-yl)oxy]hexanoic acid

aFacultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla, Puebla, Pue, Mexico, and bCentro de Química, ICUAP, Benemérita Universidad Autónoma de Puebla, Puebla, Pue, Mexico
Correspondence e-mail: angel.mendoza@correo.buap.mx

In the title compound, C21H24O5, the dihedral angle between the benzene rings is 19.57 (15)°. In the crystal, the molecular arrangement makes up head-to-head centrosymmetric dimers assembled by pairs of O-H...O bonds; this arrangement builds a graph-set ring motif of R22(8). The dimers are linked into a tape running along the b-axis direction through C-H...O interactions. The packing is further consolidated by C-H...[pi] interactions, forming layers parallel to (10-2).

Related literature

For hydrogen-bonding assemblies, see: Braga et al. (2004[Braga, D., Grepioni, F., Hardie, M. J., Hubberstey, P., Maini, L., Poloto, M., Suksangpanya, U. & Vilar, R. (2004). Structure and Bonding, Vol. 111, edited by D. M. P. Mingos. Berlin: Springer.]). For hydrogen-bonding packing modes and applications of hydrogen bonds, see: Jeong et al. (2006[Jeong, K. U., Knapp, B. S., Ge, J. J., Jin, S., Graham, M. J., Harris, F. W. & Cheng, S. Z. D. (2006). Chem. Mater. 18, 680-690.]); Leiserowitz (1976[Leiserowitz, L. (1976). Acta Cryst. B32, 775-802.]). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]); Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C21H24O5

  • Mr = 356.4

  • Monoclinic, P 21 /c

  • a = 9.111 (2) Å

  • b = 14.753 (3) Å

  • c = 14.427 (2) Å

  • [beta] = 100.785 (14)°

  • V = 1904.9 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 298 K

  • 0.5 × 0.5 × 0.4 mm

Data collection
  • Siemens P4 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 = 0.891, Tmax = 0.911

  • 4265 measured reflections

  • 3217 independent reflections

  • 1628 reflections with I > 2[sigma](I)

  • Rint = 0.031

  • 3 standard reflections every 97 reflections intensity decay: 6%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.059

  • wR(F2) = 0.171

  • S = 1.06

  • 3217 reflections

  • 238 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C13-C18 ring.

D-H...A D-H H...A D...A D-H...A
O1-H1...O2i 0.82 1.80 2.612 (3) 170
C18-H18...O1ii 0.93 2.54 3.460 (4) 173
C6-H6A...Cg1iii 0.97 2.78 3.668 (4) 152
Symmetry codes: (i) -x+2, -y-2, -z+1; (ii) x, y+1, z; (iii) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: XSCANS (Siemens, 1994[Siemens (1994). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5302 ).


Acknowledgements

The authors acknowledge financial support from the VIEP-BUAP Project (LOVD-NAT12-1), PIFI-2012, Programa Anual de Cooperación Académica BUAP-UNAM 2012 and thank A. R. Hernández-Sosa for the crystal preparation.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Braga, D., Grepioni, F., Hardie, M. J., Hubberstey, P., Maini, L., Poloto, M., Suksangpanya, U. & Vilar, R. (2004). Structure and Bonding, Vol. 111, edited by D. M. P. Mingos. Berlin: Springer.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [Web of Science] [IUCr Journals]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Jeong, K. U., Knapp, B. S., Ge, J. J., Jin, S., Graham, M. J., Harris, F. W. & Cheng, S. Z. D. (2006). Chem. Mater. 18, 680-690.  [Web of Science] [CrossRef] [ChemPort]
Leiserowitz, L. (1976). Acta Cryst. B32, 775-802.  [CrossRef] [IUCr Journals]
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]
Siemens (1994). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.


Acta Cryst (2013). E69, o1588  [ doi:10.1107/S1600536813025877 ]

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