(E)-3,4,5-Trimeth­oxy-N′-[(6-meth­oxy-4-oxo-4H-chromen-3-yl)methyl­idene]benzohydrazide monohydrate

Yoshinobu Ishikawa; Kohzoh Watanabe

doi:10.1107/S1600536814014937

. 2014 Jul 2;70(Pt 8):o832. doi: 10.1107/S1600536814014937

(E)-3,4,5-Trimethoxy-N′-[(6-methoxy-4-oxo-4H-chromen-3-yl)methylidene]benzohydrazide monohydrate

Yoshinobu Ishikawa ^a,^*, Kohzoh Watanabe ^a

PMCID: PMC4158489 PMID: 25249887

Abstract

In the title chromone-tethered benzohydrazide derivative, C₂₁H₂₀N₂O₇·H₂O, the atoms of the 4H-chromen-4-one segment are essentially coplanar (r.m.s. deviation = 0.0073 Å) with the largest deviation from the mean plane [0.012 (3) Å] being found for the benzene C atom. The dihedral angles between the chromone segment and the hydrazide plane and between the chromone segment and the benzene ring of the trimethoxybenzene unit are 24.67 (9) and 41.28 (8) Å, respectively. The molecule is connected to the solvent water molecule by O—H⋯O hydrogen bonds and weak C—H⋯O interactions. Additional N—H⋯O interactions are observed and together they link the molecules into chains forming a two-dimensional network along (011).

Keywords: crystal structure

Related literature

For the biological activity of related compounds, see: Khan et al. (2009 ▶); Tu et al. (2013 ▶). For related structures, see: Ishikawa et al. (2014a ▶,b ▶).

Experimental

Crystal data

C₂₁H₂₀N₂O₇·H₂O
M _r = 430.41
Triclinic,
a = 7.782 (3) Å
b = 9.015 (5) Å
c = 14.991 (6) Å
α = 103.17 (5)°
β = 96.51 (3)°
γ = 95.52 (4)°
V = 1009.4 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 100 K
0.30 × 0.20 × 0.18 mm

Data collection

Rigaku AFC-7R diffractometer
5621 measured reflections
4621 independent reflections
3518 reflections with F ² > 2σ(F ²)
R _int = 0.111
3 standard reflections every 150 reflections intensity decay: 2.3%

Refinement

R[F ² > 2σ(F ²)] = 0.076
wR(F ²) = 0.230
S = 1.02
4621 reflections
292 parameters
H-atom parameters constrained
Δρ_max = 0.65 e Å⁻³
Δρ_min = −0.57 e Å⁻³

Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999 ▶); cell refinement: WinAFC Diffractometer Control Software; data reduction: WinAFC Diffractometer Control Software; program(s) used to solve structure: SIR2008 (Burla et al., 2007 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: CrystalStructure (Rigaku, 2010 ▶); software used to prepare material for publication: CrystalStructure.

Supplementary Material

Crystal structure: contains datablock(s) General, I. DOI: 10.1107/S1600536814014937/jj2189sup1.cif

e-70-0o832-sup1.cif^{(46.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814014937/jj2189Isup2.hkl

e-70-0o832-Isup2.hkl^{(226.4KB, hkl)}

Click here for additional data file.^{(8.4KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814014937/jj2189Isup3.cml

CCDC reference: 1010096

Additional supporting information: crystallographic information; 3D view; checkCIF report

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8—H21⋯O2ⁱ	0.91	1.93	2.829 (4)	168
O8—H22⋯O4	0.83	2.27	3.036 (3)	153
N2—H9⋯O6ⁱⁱ	0.88	2.28	3.062 (3)	149
C1—H1⋯O8	0.95	2.30	3.214 (4)	161
C4ⁱ—H2ⁱ⋯O8	0.95	2.60	3.489 (4)	155

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

Acknowledgments

We acknowledge the University of Shizuoka for instrumental support.

supplementary crystallographic information

S1. Comment

Schiff base derivatives of 3-formyl chromones have attracted much attention due to their biological functions such as enzyme inhibition (Khan et al. 2009; Tu et al. 2013). We herein report the crystal structure of the title compound, which was obtained from the condensation reaction of 6-methoxy-3-formylchromone with 3,4,5-trimethoxybenzoylhydrazide in benzene.

The mean deviation of the least-square planes for the non-hydrogen atoms of the 4H-chromen-4-one segment is 0.0073 Å, and the largest deviation is 0.012 (3) Å for C6 (Fig.1) showing an essentially coplanar segment. The dihedral angles between this chromone segment and the hydrazide (N1/N2/C12/O4) plane and between the chromone segment and the benzene ring of the trimethoxybenzene unit are 24.67 (9) Å and 41.28 (8) Å, respectively. In the crystal, the molecule is connected to the solvent water molecule by O–H···O hydrogen bonds and weak O—H···O, C–H···O intermolecular interactions (Table 1). Additional weak N—H···O intermolecular interactions are observed and together they link the molecules into chains forming a 2-D network along (011) (Fig. 2).

S2. Experimental

3,4,5-Trimethoxybenzoylhydrazide (1.00 mmol), 6-methoxy-3-formylchromone (1.00mmol), and a few drops of acetic acid were dissolved in 25 ml of benzene, andthe mixture was refluxed with Dean-Stark apparatus for 6 h. After cooling, theprecipitates were collected, washed with n-hexane, and dried (yield 63.6%). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an acetonitrile solution of the title compound at room temperature. DART-MS calcd for [C₂₁H₂₀N₂O₇ + H⁺]: 413.135, found 413.158.