N 2,N 2,N 4,N 4-Tetra­ethyl-6-{2-[(E)-1-(4-nitro­phen­yl)ethyl­idene]hydrazino}-1,3,5-triazine-2,4-diamine

Xiao-Ru Pan; Fang-Fang Jian

doi:10.1107/S1600536809025677

. 2009 Jul 11;65(Pt 8):o1844. doi: 10.1107/S1600536809025677

N ²,N ²,N ⁴,N ⁴-Tetraethyl-6-{2-[(E)-1-(4-nitrophenyl)ethylidene]hydrazino}-1,3,5-triazine-2,4-diamine

Xiao-Ru Pan ^a, Fang-Fang Jian ^b,^*

PMCID: PMC2977253 PMID: 21583544

Abstract

The title compound, C₁₉H₂₈N₈O₂, was prepared by the reaction of N ²,N ²,N ⁴,N ⁴-tetraethyl-6-hydrazino-1,3,5-triazine-2,4-diamine and 1-(4-nitrophenyl)ethanone in ethanol at room temperature. The molecular conformation is stabilized by intramolecular C—H⋯N hydrogen-bonding interactions. There are also intermolecular N—H⋯O hydrogen bonds, and C—H⋯π and π–π interactions, which help to stabilize the crystal structure. The centroid–centroid distance is 3.6172 (10) Å between adjacent benzene and 1,3,5-triazine rings.

Related literature

For the antimicrobial and anticancer applications of Schiff bases, see: Tarafder et al. (2000 ▶); Deschamps et al. (2003 ▶). For the ability of Schiff bases to form intramolecular hydrogen bonds by electron coupling between acid–base centers, see: Rozwadowski et al. (1999 ▶). For a related structure, see: Jian et al. (2006 ▶).

Experimental

Crystal data

C₁₉H₂₈N₈O₂
M _r = 400.49
Monoclinic,
a = 12.333 (3) Å
b = 9.5286 (19) Å
c = 17.407 (4) Å
β = 92.12 (3)°
V = 2044.3 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.22 × 0.18 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
19318 measured reflections
4667 independent reflections
4054 reflections with I > 2σ(I)
R _int = 0.018

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.104
S = 1.05
4667 reflections
278 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809025677/at2835sup1.cif

e-65-o1844-sup1.cif^{(20.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025677/at2835Isup2.hkl

e-65-o1844-Isup2.hkl^{(228.7KB, 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
N3—H3A⋯O1ⁱ	0.868 (15)	2.491 (15)	3.2751 (15)	150.7 (13)
N3—H3A⋯O2ⁱ	0.868 (15)	2.474 (15)	3.2486 (15)	149.0 (13)
C2—H2C⋯N4	0.97	2.38	2.7252 (15)	100
C7—H7A⋯N5	0.97	2.39	2.7322 (16)	100
C15—H15A⋯N2	0.93	2.39	2.7128 (15)	100
C1—H1A⋯Cg2ⁱⁱ	0.96	2.91	3.7486 (16)	147
C7—H7B⋯Cg1ⁱⁱⁱ	0.97	2.71	3.3835 (15)	127

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) . Cg1 and Cg2 are centroids of the N4–N6/ C9–C11 and C14–C19 rings, respectively.

Acknowledgments

The authors thank Weifang University for support of this research (grant No. 2008Z14) and the Natural Science Foundation of Shandong Province (grant No. Y2008B29).

supplementary crystallographic information

Comment

Schiff bases have antimicrobial (Tarafder et al., 2000) and anticancer applications (Deschamps et al., 2003). The recent growing interest in Schiff bases is also due to their ability to form intramolecular hydrogen bonds by electron coupling between acid-base centers (Rozwadowski et al., 1999). The part of our research is to find Schiff base with higher biological activity, we sythesized the title compound (I) and report its crystal structure here.

In the crystal structure of compound (I) (Fig. 1), the dihedral angle formed by the C14 –C19 and N4–N6/C9–C11 rings was 10.76 (1)°. The C═N bond length [1.2910 (17) Å] is in agreement with that observed before (Jian et al., 2006). There are intermolecular N—H···O hydrogen-bonds, C—H···π and π—π interactions to stabilize the crystal structure. The centroid–centroid distance iss 3.6172 (10) Å between the adjacent benzene and 1,3,5-triazine rings.

Experimental

A mixture of N2,N2,N4,N4-tetraethyl-6-hydrazinyl-1,3,5-triazine-2,4-diamine (0.02 mol) and 1-(4-nitrophenyl)ethanone (0.02 mol) was stirred with ethanol (50 mL) at 298 K for 2 h, affording the title compound (6.40 g, yield 80.0%). Single crystals suitable for X-ray measurements were obtained by recrystallization from ethanol at room temperature.