(2E)-2-(4-Fluoro­benzyl­idene)hydrazinecarboxamide

Hoong-Kun Fun; Tze Shyang Chia; Shridhar Malladi; Arun M Isloor; Kammasandra N Shivananda

doi:10.1107/S1600536811040797

. 2011 Oct 8;67(Pt 11):o2885–o2886. doi: 10.1107/S1600536811040797

(2E)-2-(4-Fluorobenzylidene)hydrazinecarboxamide

Hoong-Kun Fun ^a,^*,^‡, Tze Shyang Chia ^a, Shridhar Malladi ^b, Arun M Isloor ^b, Kammasandra N Shivananda ^c

PMCID: PMC3247616 PMID: 22219921

Abstract

In the title compound, C₈H₈FN₃O, the semicarbazide group is close to being planar, with a maximum deviation of 0.020 (1) Å, and subtends a dihedral angle of 16.63 (9)° with its attached fluorobenzene ring. In the crystal, molecules are linked by N—H⋯O hydrogen bonds, forming layers lying parallel to the bc plane.

Related literature

For background to semicarbazides and semicarbazones, see: Dogan et al. (1999 ▶); Pandeya & Dimmock (1993 ▶); Pandeya et al. (1998 ▶); Sriram et al. (2004 ▶); Yogeeswari et al. (2004 ▶); For further synthetic details, see: Furniss et al. (1978 ▶). For related structures, see: Fun et al. (2009a ▶,b ▶). For reference bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₈H₈FN₃O
M _r = 181.17
Monoclinic,
a = 16.522 (2) Å
b = 4.4381 (6) Å
c = 11.9457 (15) Å
β = 103.478 (3)°
V = 851.80 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 K
0.72 × 0.18 × 0.12 mm

Data collection

Bruker APEX DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.923, T _max = 0.987
8746 measured reflections
2418 independent reflections
1657 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.209
S = 1.00
2418 reflections
130 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.21 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/S1600536811040797/hb6436sup1.cif

e-67-o2885-sup1.cif^{(15KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811040797/hb6436Isup2.hkl

e-67-o2885-Isup2.hkl^{(118.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811040797/hb6436Isup3.cml

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—H1N3⋯O1ⁱ	0.88 (2)	2.07 (2)	2.8954 (19)	158 (2)
N2—H1N2⋯O1ⁱⁱ	0.92 (2)	2.00 (2)	2.9155 (19)	179 (2)

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

Acknowledgments

HKF and TSC thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSC thanks the Malaysian Government and USM for the award of the post of Research Officer under the Structure Determination of kDa Outer Membrane Proteins From S. typhi by X-ray Protein Crystallography Grant (No. 1001/PSKBP/8630013). AMI thanks Professor Sandeep Sanchethi, Director, National Institute of Technology-Karnataka, India, for providing research facilities and the Board for Research in Nuclear Sciences, Department of Atomic Energy, Government of India, for the Young Scientist award.

supplementary crystallographic information

Comment

The semicarbazides, which are the raw material of semicarbazones, have been known to possess biological activities against many of the most common species of bacteria (Dogan et al., 1999). Semicarbazones are of much interest due to their wide spectrum of antibacterial activities (Pandeya & Dimmock, 1993). Recently some workers have reviewed the bioactivity of semicarbazones and they have exhibited anticonvulsant (Pandeya et al., 1998; Yogeeswari et al., 2004) and antitubercular (Sriram et al., 2004) properties. Accordingly and by considering the biological potential of semicarbazones, herein, we have synthesized the title compound to study its crystal structure.

The molecular structure of the title compound is shown in Fig. 1. The semicarbazone group (O1/N1–N3/C8) is essentially planar with maximum deviation of 0.020 (1) Å for atom N2. This plane makes dihedral angle of 16.63 (9)° with its terminal benzene ring (C1–C6). Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to related structures (Fun et al., 2009a,b).

In the crystal structure (Fig. 2), the molecules are interconnected by N3—H1N3···O1 and N2—H1N2···O1 hydrogen bonds (Table 1) forming two-dimensional networks parallel to bc plane.

Experimental

Semicarbazide hydrochloride (0.86 g, 7.70 mmol) and freshly recrystallized sodium acetate (0.77 g, 9.40 mmol) were dissolved in water (10 ml) following a literature procedure (Furniss et al., 1978). The reaction mixture was stirred at room temperature for 10 minutes. To this, 4-fluorobenzaldehyde (0.896 g, 7.23 mmol) was added and the mixture was shaken well. A little alcohol was added to dissolve the turbidity. The mixture was shaken for a further 10 minutes and allowed to stand. The title compound crystallizes out on standing for 6 h. The separated crystals were filtered, washed with cold water and recrystallized from ethanol to yield colourless needles. Yield: 0.98 g, 75.38%. M.p.: 506–508 K.