(E,E)-1,2-Bis(2,4,6-trimeth­oxy­benzyl­idene)hydrazine

Hoong-Kun Fun; Patcharaporn Jansrisewangwong; Suchada Chantrapromma

doi:10.1107/S1600536810033684

. 2010 Aug 25;66(Pt 9):o2401–o2402. doi: 10.1107/S1600536810033684

(E,E)-1,2-Bis(2,4,6-trimethoxybenzylidene)hydrazine

Hoong-Kun Fun ^a,^*,^‡, Patcharaporn Jansrisewangwong ^b, Suchada Chantrapromma ^c,^§

PMCID: PMC3008086 PMID: 21588733

Abstract

The title molecule, C₂₀H₂₄N₂O₆, lies on an inversion centre. All non-H atoms are essentially coplanar, with an r.m.s. deviation of 0.0415 (1) Å and a maximum deviation of 0.1476 (1) Å for the methoxy C atom at the 4-position of the benzene ring. The crystal structure is stabilized by weak C—H⋯N and C—H⋯π interactions.

Related literature

For standard bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Jansrisewangwong et al. (2010 ▶); Zhao et al. (2006 ▶). For background and the biological activity of hydrozones, see: El-Tabl et al. (2008 ▶); Qin et al. (2009 ▶); Ramamohan et al. (1995 ▶); Rollas & Küçükgüzel (2007 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986 ▶).

Experimental

Crystal data

C₂₀H₂₄N₂O₆
M _r = 388.41
Triclinic,
a = 7.3851 (2) Å
b = 7.4043 (2) Å
c = 9.5440 (2) Å
α = 71.412 (1)°
β = 78.095 (1)°
γ = 79.449 (1)°
V = 480.13 (2) Å³
Z = 1
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.29 × 0.14 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.972, T _max = 0.992
11100 measured reflections
2791 independent reflections
2244 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.115
S = 1.03
2791 reflections
134 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810033684/lh5117sup1.cif

e-66-o2401-sup1.cif^{(16.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033684/lh5117Isup2.hkl

e-66-o2401-Isup2.hkl^{(137KB, hkl)}

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

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

Cg is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10B⋯N1ⁱ	0.96	2.49	3.3876 (15)	155
C8—H8C⋯Cgⁱⁱ	0.97	2.79	3.6678 (13)	152
C10—H10C⋯Cgⁱⁱⁱ	0.97	2.63	3.4385 (13)	142

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

Acknowledgments

PJ thanks the Center of Excellence for Innovation in Chemistry (PERCH-CIC), the Commission on Higher Education, Ministry of Education and the Graduate School, Prince of Songkla University, for financial support. The authors thank the Prince of Songkla University for financial support through the Crystal Materials Research Unit (CMRU) and Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

supplementary crystallographic information

Comment

Hydrazones and their complexes are interesting due to their fluorescence properties (Qin et al., 2009) and various biological activities such as insecticidal, antitumor, antioxidant, antifungal, antibacterial and antiviral properties (El-Tabl et al., 2008; Ramamohan et al., 1995; Rollas & Küçükgüzel, 2007). These interesting properties led us to synthesize the title hydrazone derivative (I) in order to study its antibacterial activity and fluorescence property. Experiments show that (I) does not possess antibacterial activities, however it does exhibit fluorescence with the maximum emission at 410 nm when the compound is excited at 280 nm. Herein the crystal structure of (I) is reported.

The asymmetric unit of (I), (Fig. 1), C₂₀H₂₄N₂O₆, contains one half-molecule and the complete molecule is generated by an inversion centre (symmetry code -x, 2-y, 1-z). The mean plane through the C=N-N=C bridge forms a dihedral angle of 4.96 (9)° with the benzene rings. The methoxy groups attached to atoms C1 and C5 (positions 2 and 6) are approximately coplanar with the benzene ring whereas the one attached to atom C3 (position 4) is slightly twisted with respect to the benzene ring as described by the torsion angles of C8–O1–C1–C2 = 2.86 (15)°, C10–O3–C5–C4 = 3.58 (14)° and C9–O2–C3–C4 = 8.39 (15)°, respectively. The N-N bond length, 1.4117 (18) Å is comparable with 1.419 (3) Å and the C=N-N angle = 110.7 (2)°, is almost similar to 112.2 (2)° observed in (E,E)-1,2-bis(3,4,5-trimethoxybenzylidene)hydrazine (Zhao et al., 2006). The bond distances have normal values (Allen et al., 1987) and are comparable with related structures (Jansrisewangwong et al., 2010; Zhao et al., 2006). The crystal structure is stabilized by weak C—H···N and C—H···π interactions (Fig. 2).

Experimental

The title compound was synthesized by mixing a solution (1:2 molar ratio) of hydrazine hydrate (0.097 ml, 2 mmol) and 2,4,6-trimethoxybenzaldehyde (0.785 mg, 4 mmol) in ethanol (20 ml). The resulting solution was refluxed for 5 h, yielding the yellow solid. The resultant solid was filtered off and washed with methanol. Yellow block-shaped single crystals of the title compound suitable for x-ray structure determination were recrystalized from acetone by slow evaporation of the solvent at room temperature over several days, mp. 484–486 K.