(2E)-2-(4-Fluoro-benzyl-idene)hydrazinecarboxamide.

In the title compound, C(8)H(8)FN(3)O, 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 fluoro-benzene ring. In the crystal, mol-ecules 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 = 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

Δρmax = 0.31 e Å−3

Δρmin = −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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811040797/hb6436sup1.cif

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

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

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

C8H8FN3O	F(000) = 376
Mr = 181.17	Dx = 1.413 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2666 reflections
a = 16.522 (2) Å	θ = 2.5–29.4°
b = 4.4381 (6) Å	µ = 0.11 mm−1
c = 11.9457 (15) Å	T = 296 K
β = 103.478 (3)°	Needle, colourless
V = 851.80 (19) Å3	0.72 × 0.18 × 0.12 mm
Z = 4

Bruker APEX DUO CCD diffractometer	2418 independent reflections
Radiation source: fine-focus sealed tube	1657 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 29.9°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −23→23
Tmin = 0.923, Tmax = 0.987	k = −6→6
8746 measured reflections	l = −16→15

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.209	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.1446P)2 + 0.0418P] where P = (Fo2 + 2Fc2)/3
2418 reflections	(Δ/σ)max < 0.001
130 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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	0.51936 (9)	1.2636 (4)	1.15848 (18)	0.1170 (6)
O1	1.01013 (7)	0.7059 (3)	0.87156 (9)	0.0508 (3)
N1	0.83497 (7)	0.8821 (3)	0.97516 (10)	0.0448 (3)
N2	0.90494 (8)	0.7354 (3)	0.96093 (11)	0.0470 (3)
N3	0.91237 (8)	1.0690 (3)	0.81619 (11)	0.0493 (4)
C1	0.71134 (11)	0.8578 (5)	1.18840 (15)	0.0637 (5)
H1A	0.7461	0.7333	1.2413	0.076*
C2	0.63885 (11)	0.9701 (6)	1.21288 (16)	0.0705 (5)
H2A	0.6244	0.9217	1.2814	0.085*
C3	0.58977 (12)	1.1518 (5)	1.1342 (2)	0.0740 (6)
C4	0.60851 (13)	1.2285 (6)	1.0325 (2)	0.0855 (7)
H4A	0.5735	1.3543	0.9805	0.103*
C5	0.68021 (11)	1.1161 (5)	1.00849 (17)	0.0669 (5)
H5A	0.6937	1.1662	0.9394	0.080*
C6	0.73235 (9)	0.9300 (4)	1.08559 (13)	0.0493 (4)
C7	0.80796 (9)	0.8014 (4)	1.06141 (13)	0.0504 (4)
H7A	0.8371	0.6560	1.1109	0.060*
C8	0.94581 (8)	0.8362 (3)	0.88136 (11)	0.0405 (3)
H1N3	0.9423 (12)	1.145 (5)	0.7725 (18)	0.064 (5)*
H1N2	0.9306 (12)	0.599 (5)	1.0133 (16)	0.061 (5)*
H2N3	0.8717 (14)	1.181 (5)	0.8357 (19)	0.074 (6)*

	U11	U22	U33	U12	U13	U23
F1	0.0854 (10)	0.1393 (14)	0.1524 (15)	0.0374 (9)	0.0807 (10)	0.0080 (10)
O1	0.0544 (6)	0.0586 (7)	0.0499 (6)	0.0023 (4)	0.0334 (5)	−0.0022 (4)
N1	0.0447 (6)	0.0544 (7)	0.0417 (6)	0.0019 (5)	0.0228 (5)	−0.0006 (5)
N2	0.0490 (7)	0.0566 (7)	0.0446 (7)	0.0073 (5)	0.0296 (5)	0.0048 (5)
N3	0.0569 (7)	0.0541 (7)	0.0457 (7)	−0.0004 (5)	0.0299 (6)	0.0032 (5)
C1	0.0563 (9)	0.0936 (13)	0.0502 (9)	0.0081 (8)	0.0304 (7)	0.0076 (8)
C2	0.0662 (10)	0.0974 (15)	0.0620 (10)	−0.0021 (9)	0.0438 (9)	−0.0068 (10)
C3	0.0558 (10)	0.0863 (14)	0.0938 (15)	0.0098 (8)	0.0457 (10)	−0.0057 (11)
C4	0.0695 (12)	0.1019 (16)	0.0965 (17)	0.0321 (11)	0.0423 (12)	0.0232 (13)
C5	0.0631 (10)	0.0820 (12)	0.0656 (11)	0.0196 (8)	0.0353 (8)	0.0179 (9)
C6	0.0457 (7)	0.0643 (9)	0.0448 (7)	0.0019 (6)	0.0244 (6)	−0.0001 (6)
C7	0.0482 (8)	0.0673 (9)	0.0425 (8)	0.0090 (6)	0.0245 (6)	0.0085 (6)
C8	0.0461 (7)	0.0452 (7)	0.0361 (6)	−0.0067 (5)	0.0215 (5)	−0.0085 (5)

F1—C3	1.3568 (19)	C1—H1A	0.9300
O1—C8	1.2393 (16)	C2—C3	1.355 (3)
N1—C7	1.2661 (18)	C2—H2A	0.9300
N1—N2	1.3714 (16)	C3—C4	1.365 (3)
N2—C8	1.3634 (17)	C4—C5	1.376 (2)
N2—H1N2	0.90 (2)	C4—H4A	0.9300
N3—C8	1.3333 (18)	C5—C6	1.379 (2)
N3—H1N3	0.87 (2)	C5—H5A	0.9300
N3—H2N3	0.91 (2)	C6—C7	1.4621 (19)
C1—C2	1.390 (2)	C7—H7A	0.9300
C1—C6	1.389 (2)
C7—N1—N2	115.71 (12)	C3—C4—C5	118.7 (2)
C8—N2—N1	119.96 (12)	C3—C4—H4A	120.6
C8—N2—H1N2	118.4 (12)	C5—C4—H4A	120.6
N1—N2—H1N2	120.3 (12)	C4—C5—C6	120.79 (17)
C8—N3—H1N3	115.9 (13)	C4—C5—H5A	119.6
C8—N3—H2N3	120.3 (14)	C6—C5—H5A	119.6
H1N3—N3—H2N3	120 (2)	C5—C6—C1	118.85 (14)
C2—C1—C6	120.56 (17)	C5—C6—C7	122.08 (14)
C2—C1—H1A	119.7	C1—C6—C7	119.06 (15)
C6—C1—H1A	119.7	N1—C7—C6	121.99 (14)
C3—C2—C1	118.24 (16)	N1—C7—H7A	119.0
C3—C2—H2A	120.9	C6—C7—H7A	119.0
C1—C2—H2A	120.9	O1—C8—N3	123.66 (12)
F1—C3—C2	118.27 (19)	O1—C8—N2	119.18 (13)
F1—C3—C4	118.9 (2)	N3—C8—N2	117.15 (12)
C2—C3—C4	122.86 (16)
C7—N1—N2—C8	−170.19 (13)	C4—C5—C6—C7	178.57 (19)
C6—C1—C2—C3	−0.3 (3)	C2—C1—C6—C5	0.3 (3)
C1—C2—C3—F1	−179.4 (2)	C2—C1—C6—C7	−178.40 (17)
C1—C2—C3—C4	0.0 (4)	N2—N1—C7—C6	−177.87 (13)
F1—C3—C4—C5	179.6 (2)	C5—C6—C7—N1	8.7 (3)
C2—C3—C4—C5	0.2 (4)	C1—C6—C7—N1	−172.65 (16)
C3—C4—C5—C6	−0.1 (4)	N1—N2—C8—O1	178.19 (12)
C4—C5—C6—C1	−0.1 (3)	N1—N2—C8—N3	−3.3 (2)

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)

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)

Symmetry codes: (i) ; (ii) .