2,2′-[4-Acetyl-1,3-phenyl­enebis(­oxy)]diacetic acid

Wang, J.-G.; Yan, P.; Zhong, C.; Yu, G.

doi:10.1107/S1600536812047897

Volume 68
Part 12
Page o3470
December 2012

Received 9 November 2012
Accepted 21 November 2012
Online 28 November 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.002 Å
R = 0.036
wR = 0.120
Data-to-parameter ratio = 11.6
Details

2,2'-[4-Acetyl-1,3-phenylenebis(oxy)]diacetic acid

Jian-Guo Wang,^a ^* Ping Yan,^a Chan-juan Zhong ^a and Guo-zhen Yu ^a

^aSchool of Chemistry & Environmental Engineering, Jiujiang University, Jiujiang 332005, People's Republic of China
Correspondence e-mail: jgwang117@163.com

In the title compound, C₁₂H₁₂O₇, the dihedral angles between the benzene ring and the mean planes of the 3-carboxymethoxy, 1-carboxymethoxy and acetyl substituents are 8.67 (7), 7.81 (6) and 10.3 (18)°, respectively. In the crystal, molecules are linked by typical carboxylic acid O-HO hydrogen bonds, forming a zigzag chain. C-HO interactions also occur.

Related literature

For a related structure, see: Zhang et al. (2007).

Experimental

Crystal data

C₁₂H₁₂O₇
M_r = 268.22
Triclinic, $[P \overline 1]$
a = 5.1351 (6) Å
b = 7.8346 (9) Å
c = 15.6157 (18) Å
= 86.217 (2)°
= 81.321 (1)°
= 72.101 (2)°
V = 590.86 (12) Å³
Z = 2
Mo K radiation
= 0.13 mm^-1
T = 298 K
0.12 × 0.10 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) T_min = 0.985, T_max = 0.987
3902 measured reflections
2049 independent reflections
1860 reflections with I > 2(I)
R_int = 0.016

Refinement

R[F² > 2(F²)] = 0.036
wR(F²) = 0.120
S = 1.05
2049 reflections
176 parameters
H-atom parameters constrained
_max = 0.24 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O2ⁱ	0.82	1.83	2.6530 (14)	180
O6-H6O5ⁱⁱ	0.82	1.83	2.6352 (15)	167
C2-H2O7ⁱⁱⁱ	0.93	2.44	3.3566 (17)	168
C4-H4O6^iv	0.93	2.52	3.4392 (19)	169
Symmetry codes: (i) -x+3, -y+2, -z; (ii) -x-1, -y+2, -z+1; (iii) x-1, y+1, z; (iv) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004; data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GO2075 ).

Acknowledgements

This study was funded by Jiangxi Provincial Department of Education (GJJ08433) and the Doctoral Research Initiating Project of Jiujiang University.

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Zhang, C., Li, H., Liu, D. & Liu, M. (2007). Acta Cryst. E63, o4210.

organic compounds