(E)-1-(4-Fluoro­phen­yl)ethan-1-one semicarbazone

Hoong-Kun Fun; Chin Sing Yeap; Mahesh Padaki; Shridhar Malladi; Arun M Isloor

doi:10.1107/S1600536809022521

. 2009 Jun 20;65(Pt 7):o1619–o1620. doi: 10.1107/S1600536809022521

(E)-1-(4-Fluorophenyl)ethan-1-one semicarbazone

Hoong-Kun Fun ^a,^*,^‡, Chin Sing Yeap ^a,^§, Mahesh Padaki ^b, Shridhar Malladi ^b, Arun M Isloor ^b

PMCID: PMC2969237 PMID: 21582889

Abstract

In the title compound, C₉H₁₀FN₃O, the semicarbazone group is nearly planar, with the maximum deviation of 0.044 (1) Å for one of the N atoms. The mean plane of semicarbazone group forms a dihedral angle of 30.94 (4)° with the benzene ring. The molecules are linked into a supramolecular chain by N—H⋯O hydrogen bonds formed along the c axis. The crystal structure is further stabilized by weak intermolucular C—H⋯π interactions; the closest C⋯Cg contact is 3.6505 (11) Å.

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For applications of semicarbazone derivatives, see: Chandra & Gupta (2005 ▶); Jain et al. (2002 ▶); Pilgram (1978 ▶); Warren et al. (1977 ▶); Yogeeswari et al. (2004 ▶). For the preparation of the compound, see: Furniss et al. (1978 ▶). For related structures, see: Fun et al. (2009a ▶,b ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₉H₁₀FN₃O
M _r = 195.20
Monoclinic,
a = 18.8207 (3) Å
b = 6.6387 (1) Å
c = 7.3074 (1) Å
β = 95.887 (1)°
V = 908.21 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 100 K
0.30 × 0.10 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.876, T _max = 0.991
17523 measured reflections
3998 independent reflections
2766 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.151
S = 1.07
3998 reflections
167 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.30 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/S1600536809022521/tk2477sup1.cif

e-65-o1619-sup1.cif^{(16.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022521/tk2477Isup2.hkl

e-65-o1619-Isup2.hkl^{(196KB, 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
N2—H1N2⋯O1ⁱ	0.96 (2)	1.94 (2)	2.8998 (11)	179.2 (18)
N3—H2N3⋯O1ⁱⁱ	0.82 (2)	2.07 (2)	2.8901 (12)	176 (2)
C2—H2A⋯Cg1ⁱⁱⁱ	0.989 (17)	2.927 (18)	3.7250 (12)	138.5 (12)
C5—H5A⋯Cg1^iv	0.976 (14)	2.825 (13)	3.6505 (11)	142.8 (10)

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) . Cg1 is the centroid of C1–C6 benzene ring.

Acknowledgments

HKF thanks Universiti Sains Malaysia for the Research University Golden Goose Grant No. 1001/PFIZIK/811012. CSY thanks the Malaysian Government and Universiti Sains Malaysia for the award of the post of Research Officer under the Science Fund grant No. 305/PFIZIK/613312. AMI is grateful to the Head of the Department of Chemistry and the Director, NITK, Surathkal, India, for providing research facilities.

supplementary crystallographic information

Comment

In organic chemistry, a semicarbazone is a derivative of an aldehyde or ketone formed by a condensation between a ketone or aldehyde and semicarbazide. Semicarbazones find a large number of applications in the field of synthetic chemistry, such as in medicinal chemistry (Warren et al., 1977), organometallics (Chandra & Gupta, 2005), polymers (Jain et al., 2002), and herbicides (Pilgram, 1978). 4-Sulphamoylphenyl semicarbazones were found to possess anti-convulsant activity (Yogeeswari et al., 2004). We hereby report the crystal structure of a semicarbazone of commercial importance, (I).

The bond lengths and angles for (I), Fig. 1, are comparable to those found in related structures (Fun et al., 2009a, b). A maximum deviation of 0.044 (1) Å for atom N2 from the mean plane formed by atoms O1, N1, N2, N3, C6, C7, C8 and C9, indicates that the semicarbazone group is nearly planar. This mean plane makes a dihedral angle of 30.94 (4)° with the C1–C6 benzene ring. The molecules are linked into one-dimensional chains by intermolecular N—H···O hydrogen bonds along the c axis (Fig. 2); these hydrogen bonding interactions generate R₂²(8) ring motifs (Bernstein et al., 1995). The crystal structure is stabilized by weak intermolecular C—H···π interactions (Table 1).

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-fluoroacetophenone (1.00 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 (I) crystallizes on standing for 6 h. The separated crystals were filtered, washed with cold water and recrystallized from ethanol. Yield: 1.34 g (95%). M.p. 485-486 K.