2-Hydr­oxy-3-methoxy­benzoic acid monohydrate

Zhan-Qiang Fang; Rong-Hua Zeng; Mei Yang; Hui Liu; Xiao-Lei Chen

doi:10.1107/S1600536808006065

. 2008 Mar 12;64(Pt 4):o691. doi: 10.1107/S1600536808006065

2-Hydroxy-3-methoxybenzoic acid monohydrate

Zhan-Qiang Fang ^a,^*, Rong-Hua Zeng ^a, Mei Yang ^a, Hui Liu ^a, Xiao-Lei Chen ^a

PMCID: PMC2960960 PMID: 21202083

Abstract

The asymmetric unit of the title compound, C₈H₈O₄·H₂O, contains two organic molecules which are connected by the two water molecules through O—H⋯O hydrogen bonds, forming an R ₄ ⁴(12) ring. Further O—H⋯O hydrogen bonds assemble these rings through R ₆ ⁶(18) rings, giving rise to infinite helical chains arranged around the b axis. These helical chains are assembled by offset π–π stacking interactions [centroid–centroid distance = 3.6432 (8) Å] between the aromatic rings of neigboring chains, forming a supramolecular network.

Related literature

For related literature, see: Kozlevcar et al. (2006 ▶); Moncol et al. (2006 ▶); Liu et al. (2007 ▶); Bernstein et al. (1995 ▶); Etter et al. (1990 ▶).

Experimental

Crystal data

C₈H₈O₄·H₂O
M _r = 186.16
Monoclinic,
a = 17.9642 (4) Å
b = 14.5225 (3) Å
c = 6.8864 (2) Å
β = 91.770 (1)°
V = 1795.70 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 296 (2) K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: none
17337 measured reflections
4111 independent reflections
2658 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.110
S = 1.04
4111 reflections
241 parameters
H-atom parameters constrained
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.17 e Å⁻³

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: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808006065/dn2309sup1.cif

e-64-0o691-sup1.cif^{(17.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808006065/dn2309Isup2.hkl

e-64-0o691-Isup2.hkl^{(201.5KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3	0.82	1.90	2.6142 (14)	144
O4—H4A⋯O2W	0.82	1.77	2.5634 (16)	164
O5—H5A⋯O1W	0.82	1.78	2.5763 (16)	165
O7—H7⋯O6	0.82	1.88	2.5946 (14)	145
O1W—H1W⋯O3	0.85	1.96	2.8082 (16)	171
O2W—H4W⋯O6	0.85	1.97	2.8071 (16)	170
O1W—H2W⋯O1ⁱ	0.84	2.11	2.8741 (17)	150
O1W—H2W⋯O2ⁱ	0.84	2.49	3.1930 (16)	141
O2W—H3W⋯O8ⁱⁱ	0.84	2.13	2.8866 (19)	149
O2W—H3W⋯O7ⁱⁱ	0.84	2.33	3.0331 (15)	141

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors acknowledge South China Normal University for supporting this work.

supplementary crystallographic information

Comment

Hydrogen-bonding interactions between ligands are specific and directional. In this sense, 2-hydroxy-3-methoxybenzoic acid is an excellent candidate for the construction of supramolecular complexes, which have multiple coordination modes and form regular hydrogen bonds functioning as both a hydrogen-bond donor and acceptor (Kozlevcar et al., 2006, Liu et al., 2007, Moncol et al., 2006). Recently, we obtained the title compound of (I) under hydrothermal condition.

The asymmetric unit of the title compound (I) contains two molecules which are connected by the water molecules trough O—H···O hydrogen bonds building up a R₄⁴(12) ring (Etter et al., 1990; Bernstein et al., 1995) (Table 1, Fig. 1). The C—C and C—O distances ranging from 1.225 (2) to 1.425 (2) Å, show no remarkable features. These rings are further connected to each other by O—H···O hydrogen bonds buiding a R₆⁶ (18) ring to form helical chains arranged around the [0 1/2 0] axis (Table 1, Fig. 2). These helical chains are further assembled through offset π-π stacking interactions between the aromatic rings of neigboring chains (centroid to centroid distance of 3.6432 (8) Å [Symmetry code: 1 - x,1 - y,-1 - z]; interplanar distance of 3.44 Å and slippest distances of 1.20 Å) to form a supramolecular network.

Experimental

2-Hydroxy-3-methoxybenzoic acid was dissolved in hot water with stirring. Colorless single crystals suitable for X-ray diffraction were obtained at room temperature by slow evaporation of the solvent over a period of several days.