(E)-N′-[2-(4-Chloro-3-nitro­phenyl­sulfon­yloxy)-3-methoxy­benzyl­idene]isonicotinohydrazide acetic acid tetra­solvate

Xiao-Li Zhen; Xiao-Liu Li

doi:10.1107/S1600536808034089

. 2008 Oct 22;64(Pt 11):o2170. doi: 10.1107/S1600536808034089

(E)-N′-[2-(4-Chloro-3-nitrophenylsulfonyloxy)-3-methoxybenzylidene]isonicotinohydrazide acetic acid tetrasolvate

Xiao-Li Zhen ^a,^b, Xiao-Liu Li ^a,^*

PMCID: PMC2959596 PMID: 21581030

Abstract

In the title compound, C₂₀H₁₅ClN₄O₇S·4CH₃COOH, the central o-vanillin group makes dihedral angles of 9.50 (11) and 42.86 (7)°, respectively, with its attached pyridine and nitrobenzene rings. The crystal packing is stabilized by N—H⋯O, O—H⋯O and O—H⋯N hydrogen bonds and C—H⋯O interactions, leading to an infinite three-dimensional network. A short intramolecular C—H⋯O contact is also seen.

Related literature

For general background, see: Allen et al. (1987 ▶); Jones et al. (1979 ▶); Larson & Pecoraro, (1991 ▶); Santos et al. (2001 ▶).

Experimental

Crystal data

C₂₀H₁₅ClN₄O₇S·4C₂H₄O₂
M _r = 731.09
Triclinic,
a = 8.0565 (16) Å
b = 13.876 (3) Å
c = 16.097 (3) Å
α = 79.01 (3)°
β = 76.01 (3)°
γ = 75.44 (3)°
V = 1673.8 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 294 (2) K
0.23 × 0.18 × 0.12 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.913, T _max = 0.970
9794 measured reflections
5882 independent reflections
4448 reflections with I > 2σ(I)
R _int = 0.081

Refinement

R[F ² > 2σ(F ²)] = 0.059
wR(F ²) = 0.146
S = 1.01
5882 reflections
451 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808034089/at2646sup1.cif

e-64-o2170-sup1.cif^{(27.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034089/at2646Isup2.hkl

e-64-o2170-Isup2.hkl^{(287.9KB, 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
O71—H71⋯N11ⁱ	0.82	1.84	2.661 (3)	176
C35—H35⋯O17ⁱⁱ	0.93	2.51	3.360 (3)	152
O41—H41⋯O17ⁱⁱⁱ	0.82	1.96	2.698 (3)	150
O41—H41⋯N27ⁱⁱⁱ	0.82	2.59	3.211 (3)	134
N17—H17⋯O42^iv	0.86	2.10	2.875 (3)	150
C27—H27⋯O42^iv	0.93	2.43	3.206 (4)	140
O51—H51⋯O52ⁱⁱⁱ	0.82	1.87	2.672 (3)	167
C24—H24⋯O62ⁱⁱⁱ	0.93	2.54	3.461 (3)	170
O61—H61⋯O62^v	0.82	1.83	2.648 (3)	178
C12—H12⋯O72ⁱ	0.93	2.59	3.255 (3)	129
C32—H32⋯O72	0.93	2.37	3.122 (4)	137

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

supplementary crystallographic information

Comment

There has been a steady growth of interest in the synthesis, structure, and reactivity of Schiff bases due to their potential applications in areas such as biological modelling, catalysis, and molecular magnets (Jones et al., 1979; Larson & Pecoraro, 1991). One of the aims of investigating the structural chemistry of Schiff bases is to develop protein and enzyme mimics (Santos et al., 2001). As part of an investigation of the coordination properties of Schiff bases functioning as ligands, we report the synthesis and structure of the title compound (I).

In the title molecule (Fig. 1), bond lengths and angles are within normal ranges (Allen et al., 1987). The o-vanillin group (C21–C27/O22/O23) is essentially planar, with an r.m.s. deviation for fitted atoms of 0.0236 Å. This group makes dihedral angles of 9.50 (11)° and 42.86 (7)°, respectively, with the pyridine ring (C12—C16/N11) and the benzene ring (C31—C36). Furthermore, the dihedral angle between the pyridine ring (C12—C16/N11) and the benzene ring (C31—C36) is 50.43 (8)°.

The crystal packing is stabilized by N—H···O, O—H···O, O—H···N hydrogen bonds and C—H···O interactions (Table 1, Fig. 2), leading to an infinite network.

Experimental

An anhydrous ethanol solution (50 ml) of 2-formyl-6-methoxyphenyl 4-chloro-3-nitrobenzenesulfonate (3.72 g, 10 mmol) was added to an anhydrous ethanol solution (50 ml) of isonicotinohydrazide (1.37 g, 10 mmol) and the mixture stirred at 350 K for 5 h under nitrogen, giving a yellow precipitate. The product was isolated, recrystallized from ethanol and then dried in a vacuum to give the pure compound in 78% yield. Yellow single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an acetic acid solution.