N'-(2-Fluoro-benzyl-idene)acetohydrazide.

The title compound, C(9)H(9)FN(2)O, was prepared by the reaction between 2-fluoro-benzophenone and acetohydrazide. In the crystal structure, inversion dimers linked by pairs of N-H⋯O hydrogen bonds occur, generating R(2) (2)(8) loops.

Related literature

For background to Schiff bases, see: Cimerman et al. (1997 ▶); For related structures, see: Girgis (2006 ▶); Li & Jian (2008 ▶).

Experimental

Crystal data

C9H9FN2O

M = 180.18

Monoclinic,

a = 5.3227 (11) Å

b = 8.4603 (17) Å

c = 19.656 (4) Å

β = 93.70 (3)°

V = 883.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.30 × 0.30 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

7687 measured reflections

2010 independent reflections

1515 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.128

S = 1.04

2010 reflections

119 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810010627/hb5371sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010627/hb5371Isup2.hkl

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

C9H9FN2O	F(000) = 376
Mr = 180.18	Dx = 1.355 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1515 reflections
a = 5.3227 (11) Å	θ = 3.2–27.5°
b = 8.4603 (17) Å	µ = 0.11 mm−1
c = 19.656 (4) Å	T = 293 K
β = 93.70 (3)°	Block, colourless
V = 883.3 (3) Å3	0.30 × 0.30 × 0.20 mm
Z = 4

Bruker SMART CCD diffractometer	1515 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.036
graphite	θmax = 27.5°, θmin = 3.2°
ω scans	h = −6→6
7687 measured reflections	k = −9→10
2010 independent reflections	l = −25→25

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042	H-atom parameters constrained
wR(F2) = 0.128	w = 1/[σ2(Fo2) + (0.0696P)2 + 0.0888P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2010 reflections	Δρmax = 0.14 e Å−3
119 parameters	Δρmin = −0.21 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.035 (6)

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 > 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
N2	0.4557 (2)	0.26752 (14)	0.01843 (6)	0.0474 (3)
O1	0.04461 (18)	0.48232 (13)	−0.09198 (5)	0.0578 (3)
N1	0.2546 (2)	0.35774 (14)	−0.00633 (6)	0.0505 (3)
H1A	0.1453	0.3885	0.0212	0.061*
C1	0.6693 (3)	0.15209 (16)	0.11622 (7)	0.0479 (3)
C8	0.2245 (2)	0.39930 (17)	−0.07282 (7)	0.0473 (3)
C7	0.4679 (3)	0.24649 (16)	0.08270 (7)	0.0477 (3)
H7A	0.3469	0.2919	0.1086	0.057*
F1	0.5354 (2)	0.23104 (15)	0.22231 (5)	0.0865 (4)
C9	0.4142 (3)	0.3418 (2)	−0.11987 (7)	0.0583 (4)
H9A	0.3699	0.3789	−0.1652	0.087*
H9B	0.4168	0.2284	−0.1197	0.087*
H9C	0.5777	0.3812	−0.1049	0.087*
C6	0.8398 (3)	0.0646 (2)	0.08064 (8)	0.0592 (4)
H6A	0.8267	0.0649	0.0332	0.071*
C2	0.6989 (3)	0.1453 (2)	0.18648 (7)	0.0586 (4)
C5	1.0271 (3)	−0.0222 (2)	0.11457 (10)	0.0708 (5)
H5A	1.1397	−0.0794	0.0900	0.085*
C3	0.8824 (4)	0.0594 (2)	0.22135 (9)	0.0756 (5)
H3A	0.8947	0.0580	0.2688	0.091*
C4	1.0489 (3)	−0.0250 (2)	0.18462 (10)	0.0756 (5)
H4A	1.1760	−0.0839	0.2072	0.091*

	U11	U22	U33	U12	U13	U23
N2	0.0448 (6)	0.0508 (6)	0.0460 (6)	0.0032 (5)	−0.0023 (5)	0.0011 (5)
O1	0.0518 (6)	0.0700 (7)	0.0507 (6)	0.0133 (5)	−0.0049 (4)	0.0030 (5)
N1	0.0475 (6)	0.0591 (7)	0.0447 (6)	0.0106 (5)	0.0006 (5)	0.0019 (5)
C1	0.0475 (7)	0.0482 (7)	0.0471 (7)	−0.0069 (6)	−0.0046 (5)	0.0041 (5)
C8	0.0434 (7)	0.0520 (7)	0.0455 (7)	−0.0015 (6)	−0.0035 (5)	−0.0004 (5)
C7	0.0482 (7)	0.0490 (7)	0.0455 (7)	−0.0010 (6)	0.0006 (5)	−0.0021 (5)
F1	0.0899 (8)	0.1230 (10)	0.0462 (5)	0.0075 (6)	0.0006 (5)	−0.0129 (5)
C9	0.0538 (8)	0.0733 (10)	0.0478 (7)	0.0058 (7)	0.0039 (6)	0.0000 (7)
C6	0.0601 (9)	0.0623 (9)	0.0545 (8)	0.0069 (7)	−0.0007 (6)	0.0061 (7)
C2	0.0588 (9)	0.0683 (10)	0.0475 (7)	−0.0101 (7)	−0.0058 (6)	0.0002 (6)
C5	0.0599 (10)	0.0664 (11)	0.0850 (12)	0.0100 (8)	−0.0034 (8)	0.0118 (9)
C3	0.0764 (11)	0.0912 (13)	0.0558 (9)	−0.0153 (10)	−0.0222 (8)	0.0153 (8)
C4	0.0619 (10)	0.0734 (12)	0.0880 (12)	−0.0051 (8)	−0.0233 (9)	0.0253 (10)

N2—C7	1.2732 (18)	C9—H9A	0.9600
N2—N1	1.3775 (16)	C9—H9B	0.9600
O1—C8	1.2269 (17)	C9—H9C	0.9600
N1—C8	1.3529 (17)	C6—C5	1.376 (2)
N1—H1A	0.8600	C6—H6A	0.9300
C1—C2	1.3809 (19)	C2—C3	1.366 (2)
C1—C6	1.394 (2)	C5—C4	1.375 (3)
C1—C7	1.4595 (19)	C5—H5A	0.9300
C8—C9	1.494 (2)	C3—C4	1.379 (3)
C7—H7A	0.9300	C3—H3A	0.9300
F1—C2	1.363 (2)	C4—H4A	0.9300
C7—N2—N1	114.63 (11)	H9A—C9—H9C	109.5
C8—N1—N2	121.75 (11)	H9B—C9—H9C	109.5
C8—N1—H1A	119.1	C5—C6—C1	121.01 (15)
N2—N1—H1A	119.1	C5—C6—H6A	119.5
C2—C1—C6	116.37 (14)	C1—C6—H6A	119.5
C2—C1—C7	120.46 (13)	F1—C2—C3	118.90 (14)
C6—C1—C7	123.17 (12)	F1—C2—C1	117.35 (14)
O1—C8—N1	119.12 (13)	C3—C2—C1	123.74 (16)
O1—C8—C9	122.79 (13)	C4—C5—C6	120.45 (17)
N1—C8—C9	118.08 (12)	C4—C5—H5A	119.8
N2—C7—C1	120.89 (13)	C6—C5—H5A	119.8
N2—C7—H7A	119.6	C2—C3—C4	118.43 (16)
C1—C7—H7A	119.6	C2—C3—H3A	120.8
C8—C9—H9A	109.5	C4—C3—H3A	120.8
C8—C9—H9B	109.5	C5—C4—C3	120.00 (16)
H9A—C9—H9B	109.5	C5—C4—H4A	120.0
C8—C9—H9C	109.5	C3—C4—H4A	120.0

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.86	2.08	2.915 (2)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.86	2.08	2.915 (2)	163

Symmetry code: (i) .