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

Fun, H.-K.; Yeap, C.S.; Padaki, M.; Malladi, S.; Isloor, A.M.

doi:10.1107/S1600536809022521

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Pages o1619-o1620

doi:10.1107/S1600536809022521

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

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

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, National Institute of Technology–Karnataka, Surathkal, Mangalore 575 025, India
^*Correspondence e-mail: hkfun@usm.my

(Received 11 June 2009; accepted 12 June 2009; online 20 June 2009)

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, P 2₁ /c
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[F² > 2σ(F²)] = 0.049
wR(F²) = 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

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)
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x, -y+1, -z+2; (iii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iv) $[x, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]$ . Cg1 is the centroid of C1–C6 benzene ring.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809022521/tk2477sup1.cif

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

checkCIF report

Comment top

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).

Related literature top

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). Cg1 is the centroid of C1–C6 benzene ring.

Experimental top

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.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I) with atom labels and 50% probability ellipsoids for non-H atoms.
	Fig. 2. The crystal packing of (I), viewed down the b axis, showing the molecules are linked along the c axis. Hydrogen bonds are shown in as dashed lines.

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

Crystal data top

C₉H₁₀FN₃O	F(000) = 408
M_r = 195.20	D_x = 1.428 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5018 reflections
a = 18.8207 (3) Å	θ = 4.2–38.8°
b = 6.6387 (1) Å	µ = 0.11 mm⁻¹
c = 7.3074 (1) Å	T = 100 K
β = 95.887 (1)°	Needle, colourless
V = 908.21 (2) Å³	0.30 × 0.10 × 0.08 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3998 independent reflections
Radiation source: fine-focus sealed tube	2766 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ϕ and ω scans	θ_max = 35.0°, θ_min = 1.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −29→30
T_min = 0.876, T_max = 0.991	k = −10→10
17523 measured reflections	l = −7→11

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.151	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.078P)² + 0.1557P] where P = (F_o² + 2F_c²)/3
3998 reflections	(Δ/σ)_max < 0.001
167 parameters	Δρ_max = 0.51 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₉H₁₀FN₃O	V = 908.21 (2) Å³
M_r = 195.20	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 18.8207 (3) Å	µ = 0.11 mm⁻¹
b = 6.6387 (1) Å	T = 100 K
c = 7.3074 (1) Å	0.30 × 0.10 × 0.08 mm
β = 95.887 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3998 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2766 reflections with I > 2σ(I)
T_min = 0.876, T_max = 0.991	R_int = 0.033
17523 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.151	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.51 e Å⁻³
3998 reflections	Δρ_min = −0.30 e Å⁻³
167 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
F1	0.50077 (4)	0.48694 (11)	0.79001 (10)	0.02274 (17)
O1	−0.01336 (4)	0.50372 (12)	0.73484 (10)	0.01547 (16)
N1	0.16753 (5)	0.50702 (12)	0.66798 (11)	0.01257 (16)
N2	0.09495 (5)	0.50670 (13)	0.62389 (11)	0.01339 (17)
N3	0.08724 (5)	0.50728 (15)	0.93755 (12)	0.01734 (19)
C1	0.31185 (5)	0.59520 (16)	0.76477 (14)	0.01595 (19)
C2	0.38374 (6)	0.59368 (17)	0.82935 (14)	0.0178 (2)
C3	0.43028 (5)	0.49203 (16)	0.72738 (15)	0.01591 (19)
C4	0.40812 (6)	0.39453 (17)	0.56461 (14)	0.0177 (2)
C5	0.33579 (5)	0.39948 (17)	0.50051 (13)	0.01569 (19)
C6	0.28652 (5)	0.49812 (14)	0.60026 (13)	0.01153 (17)
C7	0.20888 (5)	0.49673 (14)	0.53803 (13)	0.01158 (17)
C8	0.05269 (5)	0.50588 (15)	0.76711 (13)	0.01249 (18)
C9	0.18228 (6)	0.48336 (16)	0.33718 (13)	0.01471 (19)
H1A	0.2783 (8)	0.667 (2)	0.8362 (19)	0.023 (4)*
H2A	0.4017 (8)	0.666 (3)	0.943 (2)	0.031 (4)*
H4A	0.4422 (7)	0.324 (2)	0.4966 (19)	0.021 (3)*
H5A	0.3214 (7)	0.328 (2)	0.3860 (19)	0.017 (3)*
H9A	0.1565 (9)	0.602 (3)	0.303 (2)	0.035 (4)*
H9B	0.1536 (9)	0.364 (3)	0.317 (2)	0.037 (5)*
H9C	0.2216 (10)	0.480 (2)	0.254 (2)	0.031 (5)*
H1N2	0.0681 (10)	0.502 (2)	0.505 (3)	0.029 (4)*
H1N3	0.1329 (10)	0.506 (2)	0.947 (2)	0.025 (4)*
H2N3	0.0643 (10)	0.505 (2)	1.027 (3)	0.030 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0096 (3)	0.0346 (4)	0.0230 (3)	0.0012 (2)	−0.0031 (2)	−0.0014 (3)
O1	0.0103 (3)	0.0256 (4)	0.0103 (3)	−0.0002 (3)	0.0004 (2)	−0.0005 (3)
N1	0.0098 (3)	0.0167 (4)	0.0110 (3)	0.0002 (3)	0.0002 (3)	0.0005 (3)
N2	0.0101 (3)	0.0220 (4)	0.0080 (3)	−0.0003 (3)	0.0004 (3)	0.0000 (3)
N3	0.0120 (4)	0.0317 (5)	0.0082 (3)	−0.0002 (3)	0.0003 (3)	−0.0006 (3)
C1	0.0137 (4)	0.0188 (5)	0.0150 (4)	0.0013 (4)	−0.0002 (3)	−0.0034 (3)
C2	0.0152 (4)	0.0214 (5)	0.0161 (4)	0.0001 (4)	−0.0022 (3)	−0.0036 (4)
C3	0.0097 (4)	0.0205 (5)	0.0169 (4)	0.0002 (3)	−0.0017 (3)	0.0026 (3)
C4	0.0131 (4)	0.0230 (5)	0.0173 (4)	0.0029 (4)	0.0021 (3)	−0.0016 (4)
C5	0.0134 (4)	0.0202 (5)	0.0133 (4)	0.0012 (3)	0.0006 (3)	−0.0024 (3)
C6	0.0107 (4)	0.0134 (4)	0.0103 (4)	0.0005 (3)	0.0002 (3)	0.0007 (3)
C7	0.0116 (4)	0.0128 (4)	0.0102 (4)	0.0005 (3)	0.0003 (3)	−0.0006 (3)
C8	0.0114 (4)	0.0167 (4)	0.0094 (4)	0.0000 (3)	0.0009 (3)	−0.0005 (3)
C9	0.0122 (4)	0.0211 (5)	0.0105 (4)	−0.0010 (4)	−0.0003 (3)	−0.0006 (3)

Geometric parameters (Å, º) top

F1—C3	1.3587 (12)	C2—C3	1.3826 (15)
O1—C8	1.2413 (12)	C2—H2A	0.989 (17)
N1—C7	1.2900 (13)	C3—C4	1.3805 (15)
N1—N2	1.3709 (12)	C4—C5	1.3939 (14)
N2—C8	1.3779 (13)	C4—H4A	0.971 (14)
N2—H1N2	0.957 (19)	C5—C6	1.3995 (14)
N3—C8	1.3446 (13)	C5—H5A	0.976 (14)
N3—H1N3	0.856 (18)	C6—C7	1.4851 (13)
N3—H2N3	0.820 (19)	C7—C9	1.5040 (13)
C1—C2	1.3866 (14)	C9—H9A	0.945 (19)
C1—C6	1.4037 (14)	C9—H9B	0.964 (18)
C1—H1A	0.983 (14)	C9—H9C	1.005 (18)

C7—N1—N2	119.27 (8)	C4—C5—C6	120.83 (9)
N1—N2—C8	117.41 (8)	C4—C5—H5A	116.8 (8)
N1—N2—H1N2	129.3 (10)	C6—C5—H5A	122.3 (8)
C8—N2—H1N2	113.3 (10)	C5—C6—C1	118.42 (9)
C8—N3—H1N3	117.6 (12)	C5—C6—C7	121.42 (8)
C8—N3—H2N3	119.6 (13)	C1—C6—C7	120.14 (8)
H1N3—N3—H2N3	122.7 (18)	N1—C7—C6	115.04 (8)
C2—C1—C6	121.47 (9)	N1—C7—C9	123.77 (9)
C2—C1—H1A	118.7 (8)	C6—C7—C9	121.19 (8)
C6—C1—H1A	119.8 (8)	O1—C8—N3	123.76 (9)
C3—C2—C1	118.04 (9)	O1—C8—N2	120.04 (9)
C3—C2—H2A	120.6 (9)	N3—C8—N2	116.20 (9)
C1—C2—H2A	121.4 (9)	C7—C9—H9A	108.5 (11)
F1—C3—C4	118.48 (9)	C7—C9—H9B	108.7 (10)
F1—C3—C2	118.77 (9)	H9A—C9—H9B	112.6 (16)
C4—C3—C2	122.75 (10)	C7—C9—H9C	113.6 (11)
C3—C4—C5	118.48 (10)	H9A—C9—H9C	104.5 (14)
C3—C4—H4A	120.7 (8)	H9B—C9—H9C	109.0 (14)
C5—C4—H4A	120.8 (8)

C7—N1—N2—C8	176.26 (9)	C2—C1—C6—C7	177.96 (9)
C6—C1—C2—C3	−0.43 (16)	N2—N1—C7—C6	179.99 (8)
C1—C2—C3—F1	−179.17 (10)	N2—N1—C7—C9	−0.23 (14)
C1—C2—C3—C4	0.56 (17)	C5—C6—C7—N1	150.01 (10)
F1—C3—C4—C5	179.90 (9)	C1—C6—C7—N1	−28.31 (13)
C2—C3—C4—C5	0.17 (17)	C5—C6—C7—C9	−29.77 (14)
C3—C4—C5—C6	−1.05 (16)	C1—C6—C7—C9	151.91 (10)
C4—C5—C6—C1	1.16 (15)	N1—N2—C8—O1	−179.35 (9)
C4—C5—C6—C7	−177.18 (9)	N1—N2—C8—N3	0.57 (13)
C2—C1—C6—C5	−0.41 (15)

Hydrogen-bond geometry (Å, º) top

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)

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, −y+1, −z+2; (iii) x, −y+1/2, z−1/2; (iv) x, −y−1/2, z−3/2.

Experimental details

Crystal data
Chemical formula	C₉H₁₀FN₃O
M_r	195.20
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	18.8207 (3), 6.6387 (1), 7.3074 (1)
β (°)	95.887 (1)
V (Å³)	908.21 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.30 × 0.10 × 0.08

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.876, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	17523, 3998, 2766
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.807

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.151, 1.07
No. of reflections	3998
No. of parameters	167
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.30

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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)

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, −y+1, −z+2; (iii) x, −y+1/2, z−1/2; (iv) x, −y−1/2, z−3/2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5523-2009.

Acknowledgements

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.

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