[Journal logo]

Volume 69 
Part 1 
Page o77  
January 2013  

Received 12 November 2012
Accepted 3 December 2012
Online 12 December 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.046
wR = 0.132
Data-to-parameter ratio = 17.4
Details
Open access

3,5-Bis[(pyridin-4-yl)methoxy]benzoic acid

aJinhua Professional Technical College, No. 1188 Wuzhou Street, Jinhua, Zhejiang 321017, People's Republic of China, and bZhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, Institute of Physical Chemistry, Zhejiang Normal University, Jinhua, Zhejiang 321004, People's Republic of China
Correspondence e-mail: jh_ll@126.com

Single crystals of the title compound, C19H16N2O4, were obtained under hydrothermal conditions by an unintended recrystallization of the employed microcrystalline starting material. The [(pyridin-4-yl)methoxy]benzoic acid unit is nearly planar, with a maximum deviation from the least-squares plane of 0.194 (2) Å. This plane is inclined by 35.82 (6)° to that defined by the second (pyridin-4-yl)methoxy group [in which the largest deviation from the least-squares plane is 0.013 (2) Å]. In the crystal, molecules are linked by O-H...N hydrogen bonds involving the acid hydroxy group and a pyridine N atom into chains parallel to [-201].

Related literature

For compounds with metal-organic framework structures derived from the title compound, see: Xu et al. (2009[Xu, G. J., Zhao, Y. H., Shao, K. Z., Lan, Y. Q., Wang, X. L., Su, Z. M. & Yan, L. K. (2009). CrystEngComm, 11, 1842-1847.]).

[Scheme 1]

Experimental

Crystal data
  • C19H16N2O4

  • Mr = 336.34

  • Monoclinic, P 21 /c

  • a = 11.1523 (6) Å

  • b = 11.2120 (6) Å

  • c = 13.9255 (7) Å

  • [beta] = 102.827 (3)°

  • V = 1697.79 (15) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 296 K

  • 0.38 × 0.33 × 0.21 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2006[Bruker (2006). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.965, Tmax = 0.980

  • 25948 measured reflections

  • 3936 independent reflections

  • 2980 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.132

  • S = 1.04

  • 3936 reflections

  • 226 parameters

  • 1 restraint

  • 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
O2-H1A...N2i 0.85 1.83 2.6736 (16) 171
Symmetry code: (i) [x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2006[Bruker (2006). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: 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: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WM2702 ).


References

Bruker (2006). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
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]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Xu, G. J., Zhao, Y. H., Shao, K. Z., Lan, Y. Q., Wang, X. L., Su, Z. M. & Yan, L. K. (2009). CrystEngComm, 11, 1842-1847.  [ISI] [CSD] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o77  [ doi:10.1107/S1600536812049550 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.