N′-(4-Fluoro­benzyl­idene)-2-(4-fluoro­phen­yl)acetohydrazide

Hoong-Kun Fun; Madhukar Hemamalini; V Sumangala; G K Nagaraja; Boja Poojary

doi:10.1107/S1600536811039845

. 2011 Oct 5;67(Pt 11):o2835. doi: 10.1107/S1600536811039845

N′-(4-Fluorobenzylidene)-2-(4-fluorophenyl)acetohydrazide

Hoong-Kun Fun ^a,^*,^‡, Madhukar Hemamalini ^a, V Sumangala ^b, G K Nagaraja ^b, Boja Poojary ^b

PMCID: PMC3247574 PMID: 22219879

Abstract

In the title compound, C₁₅H₁₂F₂N₂O, the dihedral angle between the two benzene rings is 48.73 (8)°. The hydrazine group is twisted slightly, with a C—N—N—C torsion angle of 172.48 (12)°. In the crystal, molecules are connected by strong N—H⋯O and weak C—H⋯O hydrogen bonds, forming supramolecular chains along the c axis. The structure is consolidated by π–π [centroid–centroid separation = 3.6579 (10) Å] and C—H⋯π interactions.

Related literature

For further details of aroylhydrozones, see: Li & Qu (2011 ▶); Zhang (2011 ▶); Fan et al. (2008 ▶). Ajani et al. (2010 ▶); Avaji et al. (2009 ▶); Rasras et al. (2010 ▶).

Experimental

Crystal data

C₁₅H₁₂F₂N₂O
M _r = 274.27
Monoclinic,
a = 13.8754 (15) Å
b = 12.5349 (13) Å
c = 7.7093 (8) Å
β = 93.566 (2)°
V = 1338.3 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 K
0.85 × 0.26 × 0.12 mm

Data collection

Bruker APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.915, T _max = 0.988
17153 measured reflections
4415 independent reflections
2586 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.153
S = 1.02
4415 reflections
229 parameters
All H-atom parameters refined
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536811039845/hb6416sup1.cif

e-67-o2835-sup1.cif^{(17.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039845/hb6416Isup2.hkl

e-67-o2835-Isup2.hkl^{(212KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811039845/hb6416Isup3.cml

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

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

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N1⋯O1ⁱ	0.892 (15)	2.013 (15)	2.8841 (14)	165.2 (14)
C4—H4⋯O1ⁱⁱ	0.92 (2)	2.47 (2)	3.370 (2)	168 (2)
C1—H1⋯Cg1ⁱⁱⁱ	0.98 (2)	2.92 (2)	3.7025 (18)	138.0 (15)

Open in a new tab

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

Acknowledgments

HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

supplementary crystallographic information

Comment

Large number of aroylhydrozones have been synthesized in the recent years (Li & Qu, 2011; Zhang, 2011; Fan et al., 2008) which can serve as intermediates in synthesizing biologically active compounds (Ajani et al., 2010; Avaji et al., 2009; Rasras et al., 2010).

The asymmetric unit of the title compound is shown in Fig. 1. The dihedral angle between the two benzene rings (C1–C6/C10–C15) is 48.73 (8)°. The hydrazine group is twisted slightly with C9-N1-N2-C8, N1-N2-C8-C7 and N2-N1-C9-C10 torsion angles of 172.48 (12)°, 169.41 (12)° and 174.13 (11)°, respectively.

In the crystal structure, (Fig. 2), the molecules are connected via intermolecular strong N—H···O and weak C—H···.O (Table 1) hydrogen bonds forming one-dimensional supramolecular chains along the c-axis. The crystal structure is further stabilized by π–π interactions between the benzene (Cg2; C10–C15) rings [Cg2···Cg2 = 3.6579 (10) Å; -x, 2-y, 1-z] and C—H···π interaction involving the centroid of the C1–C6 (Cg1) ring.

Experimental

An equimolar mixture of 2-(4-fluorophenyl)acetohydrazide and 4-fluorobenzaldehyde was refluxed for four hours in the presence of few drops of acid catalyst and ethanol as solvent. The compound obtained was filtered, washed, dried and recrystalised from ethanol to yield colourless needles.