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

Lin, H.; Zhang, Y.-P.

doi:10.1107/S1600536812049550

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 (C-C) = 0.002 Å
R = 0.046
wR = 0.132
Data-to-parameter ratio = 17.4
Details

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

Hong Lin ^a ^* and Yi-Ping Zhang ^b

^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-HN 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).

Experimental

Crystal data

C₁₉H₁₆N₂O₄
M_r = 336.34
Monoclinic, P 2₁ /c
a = 11.1523 (6) Å
b = 11.2120 (6) Å
c = 13.9255 (7) Å
= 102.827 (3)°
V = 1697.79 (15) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.965, T_max = 0.980
25948 measured reflections
3936 independent reflections
2980 reflections with I > 2(I)
R_int = 0.025

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.132
S = 1.04
3936 reflections
226 parameters
1 restraint
H-atom parameters constrained
_max = 0.26 e Å^-3
_min = -0.25 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H1AN2ⁱ	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); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.
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.

organic compounds