N-[1-(Biphenyl-4-yl)ethyl­idene]-N′-(2,4-dinitro­phen­yl)hydrazine

Reza Kia; Hoong-Kun Fun; Bijan Etemadi; Hadi Kargar

doi:10.1107/S1600536809009593

. 2009 Apr 8;65(Pt 5):o966–o967. doi: 10.1107/S1600536809009593

N-[1-(Biphenyl-4-yl)ethylidene]-N′-(2,4-dinitrophenyl)hydrazine

Reza Kia ^a, Hoong-Kun Fun ^a,^*, Bijan Etemadi ^b, Hadi Kargar ^c

PMCID: PMC2977666 PMID: 21584009

Abstract

The title compound, C₂₀H₁₆N₄O₄, contains two crystallographically independent molecules (A and B) in the asymmetric unit. Intramolecular N—H⋯O hydrogen bonds generate S(6) ring motifs in both molecules. The dihedral angles between the nitro-substituted benzene rings and the two benzene rings in molecules A and B are 14.32 (9), 17.89 (9)° and 13.04 (9) and 25.71 (9)°. The ortho and para nitro groups form dihedral angles of 6.2 (2) and 8.5 (2)° in molecule A, and 5.3 (3) and 13.8 (2)° in molecule B, with the benzene rings to which they are attached. The crystal structure is stabilized by intermolecular C—H⋯O interactions.

Related literature

For bond length data, see: Allen et al. (1987 ▶). For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For general background and related structures, see: Fun et al. (2009 ▶); Kia et al. (2009 ▶); Cordis et al. (1998 ▶); Guillaumont & Nakamura (2000 ▶); Lamberton et al. (1974 ▶); Niknam et al. (2005 ▶); Raj & Kurup (2006 ▶); Zegota (1999 ▶); Zlotorzynska & Lai (1999 ▶); Okabe et al. (1993 ▶). For stability of the temperature controller used for data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₂₀H₁₆N₄O₄
M _r = 376.37
Monoclinic,
a = 10.0108 (5) Å
b = 14.9422 (8) Å
c = 23.3401 (14) Å
β = 99.871 (4)°
V = 3439.6 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.51 × 0.20 × 0.04 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.949, T _max = 0.996
38703 measured reflections
10018 independent reflections
6820 reflections with I > 2˘I)
R _int = 0.063

Refinement

R[F ² > 2σ(F ²)] = 0.070
wR(F ²) = 0.162
S = 1.05
10018 reflections
515 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.32 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/S1600536809009593/at2742sup1.cif

e-65-0o966-sup1.cif^{(31.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809009593/at2742Isup2.hkl

e-65-0o966-Isup2.hkl^{(489.9KB, 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
N1A—H1NA⋯O1A	0.87 (3)	1.89 (2)	2.596 (2)	137 (2)
N1B—H1NB⋯O1B	0.78 (2)	1.99 (2)	2.600 (2)	134 (2)
C9A—H9AA⋯O2Aⁱ	0.95	2.41	3.084 (2)	127
C3B—H3BA⋯O1Bⁱⁱ	0.95	2.51	3.199 (2)	130
C9B—H9BA⋯O2Bⁱⁱ	0.95	2.39	3.174 (3)	139
C17A—H17A⋯O3Aⁱⁱⁱ	0.95	2.59	3.498 (3)	161

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

Acknowledgments

HKF and RK thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. RK thanks Universiti Sains Malaysia for a postdoctoral research fellowship. BE thanks Shiraz University for financial support. HK thanks PNU for financial support. HKF also thanks Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

supplementary crystallographic information

Comment

2,4-Dinitrophenylhydrazones play a more important role as stabilizers for the detection, characterization and protection of the carbonyl groups than phenylhydrazones (Niknam et al., 2005). 2,4-Dinitrophenylhydrazone derivatives are widely used in various forms of analytical chemistry (Lamberton et al., 1974; Zegota, 1999; Cordis et al., 1998; Zlotorzynska & Lai, 1999) and are also used as dyes (Guillaumont & Nakamura, 2000). They are also found to have versatile coordinating abilities towards different metal ions (Raj & Kurup, 2006). In addition, some phenylhydrazone derivatives have been shown to be potentially DNA-damaging and mutagenic agents (Okabe et al., 1993). For these reasons, the structure of the title compound was reported here.

The bond lengths (Allen et al., 1987) and angles in the title compound (Fig. 1) have normal values and are comparable to the related structures (Fun et al. 2009; Kia et al. 2009). Intramolecular N—H···O hydrogen bonds generate S(6) ring motifs (Bernstein et al.,1995). The dihedral angle between the two benzene rings and the nitro-substituted benzene rings in molecules A and B are 14.32 (9), 17.89 (9), 13.04 (9), and 25.71 (9)°, respectively. The ortho and para-substituted nitro groups form dihedral angles of 6.2 (2), 8.5 (2)° in molecule A and 5.3 (3) and 13.8 (2)° in molecule B, to the benzene rings to which they are attached. The crystal structure is further stabilized by intermolecular C—H···O interactions (Table 1 and Fig.2 ).

Experimental

The title compound was synthesized based on the reported procedure (Okabe et al. 1993) except that p-phenyl-acetophenone (1 mmol) was used instead. Single crystals suitable for X-ray diffraction analysis were grown by slow evaporation of a saturated solution of the resulted compound in acetone.