N'-[(E)-1-(3-Fluoro-phen-yl)ethyl-idene]formohydrazide.

In the title compound, C(9)H(9)FN(2)O, the dihedral angle between the fluoro-benzene ring and the mean plane of the side chain is 15.59 (14)°. In the crystal, the mol-ecules form inversion dimers linked by pairs of N-H⋯O hydrogen bonds, resulting in R(2) (2)(8) loops. These dimers are reinforced by C-H⋯O inter-actions.

Related literature

For related structures, see: Shafiq et al. (2009a ▶,b ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C9H9FN2O

M = 180.18

Triclinic,

a = 6.8466 (5) Å

b = 7.0258 (6) Å

c = 9.9419 (8) Å

α = 70.558 (5)°

β = 81.267 (5)°

γ = 73.977 (4)°

V = 432.50 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.28 × 0.12 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.986, T max = 0.990

19438 measured reflections

2124 independent reflections

1320 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.148

S = 1.00

2124 reflections

119 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809042809/hb5150sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809042809/hb5150Isup2.hkl

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

C9H9FN2O	Z = 2
Mr = 180.18	F(000) = 188
Triclinic, P1	Dx = 1.384 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8466 (5) Å	Cell parameters from 2124 reflections
b = 7.0258 (6) Å	θ = 3.1–28.3°
c = 9.9419 (8) Å	µ = 0.11 mm−1
α = 70.558 (5)°	T = 296 K
β = 81.267 (5)°	Cut needle, colourless
γ = 73.977 (4)°	0.28 × 0.12 × 0.10 mm
V = 432.50 (6) Å3

Bruker Kappa APEXII CCD diffractometer	2124 independent reflections
Radiation source: fine-focus sealed tube	1320 reflections with I > 2σ(I)
graphite	Rint = 0.028
Detector resolution: 7.40 pixels mm-1	θmax = 28.3°, θmin = 3.1°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −9→9
Tmin = 0.986, Tmax = 0.990	l = −13→12
19438 measured reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0721P)2 + 0.1041P] where P = (Fo2 + 2Fc2)/3
2124 reflections	(Δ/σ)max < 0.001
119 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	−0.17799 (17)	0.19897 (19)	0.11146 (13)	0.0654 (5)
O1	−0.27158 (19)	1.0743 (2)	0.48303 (16)	0.0571 (5)
N1	−0.0361 (2)	0.6861 (2)	0.32755 (15)	0.0397 (4)
N2	−0.0531 (2)	0.8255 (2)	0.40149 (15)	0.0423 (5)
C1	0.1524 (2)	0.4305 (3)	0.22398 (18)	0.0385 (5)
C2	−0.0221 (3)	0.3804 (3)	0.20534 (18)	0.0414 (5)
C3	−0.0068 (3)	0.2466 (3)	0.12916 (19)	0.0443 (6)
C4	0.1727 (3)	0.1578 (3)	0.0688 (3)	0.0600 (8)
C5	0.3447 (3)	0.2084 (4)	0.0867 (3)	0.0734 (10)
C6	0.3367 (3)	0.3417 (3)	0.1637 (2)	0.0582 (7)
C7	0.1417 (2)	0.5780 (3)	0.30417 (18)	0.0395 (5)
C8	0.3324 (3)	0.5870 (4)	0.3542 (3)	0.0689 (8)
C9	−0.2381 (3)	0.9408 (3)	0.4233 (2)	0.0462 (6)
H2	−0.14795	0.43732	0.24433	0.0496*
H2A	0.05215	0.83756	0.43242	0.0507*
H4	0.17812	0.06689	0.01769	0.0720*
H5	0.46934	0.15168	0.04599	0.0882*
H6	0.45566	0.37230	0.17538	0.0698*
H8A	0.30519	0.60432	0.44755	0.1034*
H8B	0.38093	0.70226	0.28885	0.1034*
H8C	0.43388	0.46005	0.35838	0.1034*
H9	−0.34809	0.91844	0.39133	0.0554*

	U11	U22	U33	U12	U13	U23
F1	0.0472 (7)	0.0812 (9)	0.0917 (9)	−0.0205 (6)	−0.0071 (6)	−0.0522 (7)
O1	0.0416 (7)	0.0611 (9)	0.0844 (10)	−0.0063 (6)	0.0031 (6)	−0.0510 (8)
N1	0.0379 (7)	0.0397 (8)	0.0486 (8)	−0.0064 (6)	−0.0014 (6)	−0.0256 (7)
N2	0.0350 (7)	0.0458 (8)	0.0558 (9)	−0.0057 (6)	−0.0034 (6)	−0.0312 (7)
C1	0.0353 (8)	0.0386 (9)	0.0457 (10)	−0.0038 (7)	−0.0042 (7)	−0.0217 (8)
C2	0.0348 (8)	0.0458 (10)	0.0482 (10)	−0.0059 (7)	0.0000 (7)	−0.0247 (8)
C3	0.0392 (9)	0.0480 (10)	0.0543 (11)	−0.0110 (8)	−0.0071 (7)	−0.0248 (9)
C4	0.0485 (11)	0.0681 (13)	0.0841 (15)	−0.0068 (9)	−0.0018 (10)	−0.0570 (12)
C5	0.0407 (10)	0.0940 (18)	0.112 (2)	−0.0058 (10)	0.0056 (11)	−0.0791 (16)
C6	0.0332 (9)	0.0723 (14)	0.0886 (15)	−0.0071 (9)	−0.0009 (9)	−0.0558 (12)
C7	0.0357 (8)	0.0408 (9)	0.0470 (10)	−0.0046 (7)	−0.0058 (7)	−0.0224 (8)
C8	0.0423 (10)	0.0802 (15)	0.1084 (18)	0.0019 (10)	−0.0197 (11)	−0.0673 (14)
C9	0.0356 (9)	0.0491 (10)	0.0638 (12)	−0.0082 (7)	−0.0003 (8)	−0.0330 (9)

F1—C3	1.355 (2)	C4—C5	1.372 (3)
O1—C9	1.223 (3)	C5—C6	1.379 (3)
N1—N2	1.380 (2)	C7—C8	1.490 (3)
N1—C7	1.278 (2)	C2—H2	0.9300
N2—C9	1.332 (3)	C4—H4	0.9300
N2—H2A	0.8600	C5—H5	0.9300
C1—C2	1.389 (3)	C6—H6	0.9300
C1—C7	1.485 (3)	C8—H8A	0.9600
C1—C6	1.388 (3)	C8—H8B	0.9600
C2—C3	1.365 (3)	C8—H8C	0.9600
C3—C4	1.364 (3)	C9—H9	0.9300
N2—N1—C7	117.88 (15)	O1—C9—N2	123.78 (19)
N1—N2—C9	117.74 (15)	C1—C2—H2	120.00
C9—N2—H2A	121.00	C3—C2—H2	120.00
N1—N2—H2A	121.00	C3—C4—H4	121.00
C6—C1—C7	120.83 (15)	C5—C4—H4	121.00
C2—C1—C7	120.92 (16)	C4—C5—H5	119.00
C2—C1—C6	118.24 (18)	C6—C5—H5	119.00
C1—C2—C3	119.28 (19)	C1—C6—H6	120.00
C2—C3—C4	123.5 (2)	C5—C6—H6	120.00
F1—C3—C2	118.80 (18)	C7—C8—H8A	109.00
F1—C3—C4	117.74 (18)	C7—C8—H8B	109.00
C3—C4—C5	117.2 (2)	C7—C8—H8C	109.00
C4—C5—C6	121.4 (2)	H8A—C8—H8B	110.00
C1—C6—C5	120.5 (2)	H8A—C8—H8C	109.00
N1—C7—C1	115.92 (14)	H8B—C8—H8C	109.00
N1—C7—C8	124.86 (19)	O1—C9—H9	118.00
C1—C7—C8	119.20 (17)	N2—C9—H9	118.00
C7—N1—N2—C9	178.74 (16)	C2—C1—C7—C8	164.42 (19)
N2—N1—C7—C1	−179.88 (14)	C6—C1—C7—N1	164.85 (17)
N2—N1—C7—C8	1.7 (3)	C6—C1—C7—C8	−16.6 (3)
N1—N2—C9—O1	−177.46 (17)	C1—C2—C3—F1	−179.92 (16)
C6—C1—C2—C3	0.1 (3)	C1—C2—C3—C4	−0.2 (3)
C7—C1—C2—C3	179.02 (17)	F1—C3—C4—C5	179.6 (2)
C2—C1—C6—C5	0.4 (3)	C2—C3—C4—C5	−0.2 (4)
C7—C1—C6—C5	−178.6 (2)	C3—C4—C5—C6	0.7 (4)
C2—C1—C7—N1	−14.1 (3)	C4—C5—C6—C1	−0.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1i	0.86	2.14	2.989 (2)	168
C8—H8A···O1i	0.96	2.52	3.204 (3)	129

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1i	0.86	2.14	2.989 (2)	168
C8—H8A⋯O1i	0.96	2.52	3.204 (3)	129

Symmetry code: (i) .