Sodium 2-nitro­cinnamate dihydrate: a one-dimensional hydrogen-bonded coordination polymer

Graham Smith; Urs D Wermuth

doi:10.1107/S1600536809030402

. 2009 Aug 8;65(Pt 9):m1048. doi: 10.1107/S1600536809030402

Sodium 2-nitrocinnamate dihydrate: a one-dimensional hydrogen-bonded coordination polymer

Graham Smith ^a,^*, Urs D Wermuth ^a

PMCID: PMC2969855 PMID: 21577409

Abstract

The title compound catena-poly[aquasodium-μ₂-aqua-μ₃-2-nitrocinnamato], [Na(C₉H₆NO₄)(H₂O)₂]_n, the sodium salt of trans-2-nitrocinnamic acid, is a one-dimensional coordination polymer based on six-coordinate octahedral NaO₆ centres, comprising three facially related monodentate carboxylate O-atom donors from separate ligands (all bridging) [Na—O = 2.4370 (13)–2.5046 (13) Å], and three water molecules (two bridging and one monodentate) [Na—O = 2.3782 (13)–2.4404 (17) Å]. The structure is also stabilized by intra-chain water–carboxylate and water–nitro O—H⋯O hydrogen bonds.

Related literature

For literature on similar compounds, see: Crowther et al. (2008 ▶); Kariuki et al. (1995 ▶); Kula et al. (2007 ▶); Schmidt (1964 ▶); Smith et al. (2006 ▶); Trividi et al. (2005 ▶).

Experimental

Crystal data

[Na(C₉H₆NO₄)(H₂O)₂]
M _r = 251.17
Monoclinic,
a = 19.4179 (7) Å
b = 3.6899 (2) Å
c = 14.8738 (7) Å
β = 92.239 (4)°
V = 1064.90 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 297 K
0.40 × 0.30 × 0.13 mm

Data collection

Oxford Diffraction Gemini-S CCD-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.93, T _max = 0.98
6531 measured reflections
2100 independent reflections
1626 reflections with I > 2σ(I)
R _int = 0.019

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.113
S = 1.09
2100 reflections
170 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: CrysAlis Pro (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis Pro; data reduction: CrysAlis Pro; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809030402/su2131sup1.cif

e-65-m1048-sup1.cif^{(18.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030402/su2131Isup2.hkl

e-65-m1048-Isup2.hkl^{(101.2KB, 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
O1W—H11W⋯O32ⁱ	0.78 (3)	2.14 (3)	2.8871 (17)	162 (2)
O1W—H12W⋯O32ⁱⁱ	0.89 (2)	1.90 (2)	2.7852 (17)	171 (2)
O2W—H21W⋯O21ⁱⁱⁱ	0.77 (3)	2.49 (3)	3.050 (2)	131 (3)
O2W—H22W⋯O32ⁱ	0.91 (4)	2.04 (5)	2.882 (2)	153 (4)

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

Acknowledgments

The authors acknowledge financial support from the Australian Research Council and the School of Physical and Chemical Sciences, Queensland University of Technology.

supplementary crystallographic information

Comment

Although the structures of two polymorphs of trans-cinnamic acid have been determined (Schmidt, 1964; Smith et al., 2006), the structures of neither trans-2-nitrocinnamic acid [(E)-3-(2-nitrophenyl)propenoic acid] nor any of its alkali metal salts are known, although the dicyclohexylaminium salt has been reported (Trividi et al., 2005). The only structures of alkali metal compounds of analogous ring-substituted trans-cinnamic acids are the sodium complexes with 2-chlorocinnamic acid (Kariuki et al., 1995), 3-chlorocinnamic acid (Crowther et al., 2008), and 4-hydroxy-2-methoxycinnamic acid (Kula et al., 2007). We have now prepared the sodium salt of trans-2-nitrocinnamic acid, a dihydrate [Na(C₉H₆NO₄)(H₂O)₂]_n and its structure is reported here.

The molecular structure of the title compound is illustrated in Fig. 1. The polymeric structure is based on octahadral six-coordinate NaO₆ centres comprising three facially related monodentate carboxylate O-donors from separate ligands (all bridging) [Na–O, 2.4370 (13)– 2.5046 (13) Å] and three water molecules (two bridging, one monodentate) [Na–O, 2.3782 (13)–2.4404 (17) Å]. These units are linked into one-dimensional coordination polymer chains which extend along direction [010] (Fig. 1). The structure is similar to that of the sodium 2-chlorocinnamate complex (Kariuki et al., 1995). The polymer chains are stabilized by intra-chain water O–H···O_carboxylate and O–H···O_nitrohydrogen bonds (Table 1).

In the substituted cinnamate ligand molecule, the nitro group is rotated out of the plane of the benzene ring [torsion angle C1–C2–N21–O22, 144.65 (17)°], while the carboxylate group is similarly non-coplanar [C11–C21–C31–O31, -169.51 (17)°].

Experimental

The title compound was synthesized by heating together for 10 minutes under reflux 1 mmol quantities of trans-cinnamic acid [(E-3-(2-nitrophenyl)propenoic acid] and sodium carbonate in 50 ml of 50% ethanol-water. After concentration to ca 30 ml, partial rt evaporation of the hot-filtered solution gave thin colourless plate-like crystals, suitable for X-ray analysis.