(E)-1-(4-Fluoro-phen-yl)ethan-1-one semicarbazone.

In the title compound, C(9)H(10)FN(3)O, 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 mol-ecules are linked into a supra-molecular chain by N-H⋯O hydrogen bonds formed along the c axis. The crystal structure is further stabilized by weak inter-molucular C-H⋯π inter-actions; 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 = 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 (; 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

Δρmax = 0.51 e Å−3

Δρmin = −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 ▶).

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

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

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

C9H10FN3O	F(000) = 408
Mr = 195.20	Dx = 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

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

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(Fo2) + (0.078P)2 + 0.1557P] where P = (Fo2 + 2Fc2)/3
3998 reflections	(Δ/σ)max < 0.001
167 parameters	Δρmax = 0.51 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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···Cg1iv	0.976 (14)	2.825 (13)	3.6505 (11)	142.8 (10)

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⋯Cg1iv	0.976 (14)	2.825 (13)	3.6505 (11)	142.8 (10)

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