2,2-Dimethyl-N,N′-bis­(4-nitro­benzyl­idene)propane-1,3-diamine

Hoong-Kun Fun; Hadi Kargar; Reza Kia

doi:10.1107/S1600536808037033

. 2008 Nov 13;64(Pt 12):o2335. doi: 10.1107/S1600536808037033

2,2-Dimethyl-N,N′-bis(4-nitrobenzylidene)propane-1,3-diamine

Hoong-Kun Fun ^a,^*, Hadi Kargar ^b,^‡, Reza Kia ^a

PMCID: PMC2960098 PMID: 21581310

Abstract

In the title compound, C₁₉H₂₀N₄O₄, a potential bidentate Schiff base ligand, each imino (C=N) functional group is coplanar with the adjacent benzene ring. The two benzene rings form a dihedral angle of 10.52 (6)°. Intermolecular C—H⋯O contacts link neighbouring molecules into supramolecular array with an R ² ₂(32) ring motif and a C—H⋯π contact is also present.

Related literature

For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Li et al. (2005 ▶); Bomfim et al. (2005 ▶); Glidewell et al. (2005 ▶, 2006 ▶); Sun et al. (2004 ▶); Fun et al. (2008a ▶,b ▶).

Experimental

Crystal data

C₁₉H₂₀N₄O₄
M _r = 368.39
Monoclinic,
a = 7.8219 (1) Å
b = 19.9716 (4) Å
c = 12.0125 (3) Å
β = 92.831 (1)°
V = 1874.25 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 (1) K
0.45 × 0.19 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.959, T _max = 0.993
21845 measured reflections
6784 independent reflections
4307 reflections with I > 2σ(I)
R _int = 0.048

Refinement

R[F ² > 2σ(F ²)] = 0.061
wR(F ²) = 0.152
S = 1.04
6784 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.36 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, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808037033/tk2324sup1.cif

e-64-o2335-sup1.cif^{(20.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808037033/tk2324Isup2.hkl

e-64-o2335-Isup2.hkl^{(332KB, 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
C1—H1A⋯O4ⁱ	0.93	2.52	3.4330 (18)	168
C17—H17A⋯O2ⁱⁱ	0.93	2.48	3.4063 (18)	171
C19—H19A⋯Cg1ⁱⁱⁱ	0.96	2.86	3.8058 (16)	171

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) . Cg1 is the centroid of the C12–C17 benzene ring.

Acknowledgments

HKF and RK thank the Malaysian Government and Universiti Sains Malaysia for Science Fund grant No. 305/PFIZIK/613312. RK thanks Universiti Sains Malaysia for a post-doctoral research fellowship. HK thanks PNU for financial support.

supplementary crystallographic information

Comment

Schiff bases are one of most prevalent mixed-donor ligands in the field of coordination chemistry. They play an important role in the development of coordination chemistry related to catalysis and enzymatic reactions, magnetism, and supramolecular architectures. Structures of Schiff bases derived from substituted benzaldehydes and closely related to the title compound, (I), have been reported previously (Li et al., 2005; Bomfim et al., 2005; Glidewell et al., 2005, 2006; Sun et al., 2004; Fun et al., 2008a,b).

Each imino (C ═N) functional group in (I), Fig. 1, is co-planar with the adjacent benzene ring. Intramolecular C—H···O contacts form five-membered rings, producing S(5) ring motifs (Bernstein et al., 1995). The two benzene rings form a dihedral angle of 10.52 (6)°. Intermolecular C—H···O contacts link neighbouring molecules into supramolecular array with R²₂(32) ring motif, Fig. 2 and Table 1. The crystal structure is further stabilized by weak C—H···π interactions, ( Table 1.

Experimental

The synthetic method has been described earlier (Fun et al., 2008). Single crystals suitable for X-ray diffraction were obtained by evaporation of an ethanol solution of (I) held at room temperature.