N'-(4-Fluoro-benzyl-idene)acetohydrazide.

The title compound, C(9)H(9)FN(2)O, was prepared by the reaction of 4-fluoro-benzophenone and acethydrazide. In the mol-ecule, all non-H atoms are essentially coplanar [r.m.s. deviation = 0.065 (2) Å]. In the crystal, mol-ecules are linked into centrosymmetric dimers by pairs of inter-molecular N-H⋯O hydrogen bonds.

Related literature

For general background to Schiff bases, see: Goswami et al. (2009 ▶); Zhang et al. (2010 ▶). For related structures, see: Li & Jian (2008 ▶); Girgis (2006 ▶); Yang et al. (2010 ▶);

Experimental

Crystal data

C9H9FN2O

M = 180.18

Monoclinic,

a = 10.443 (2) Å

b = 4.0418 (8) Å

c = 21.172 (4) Å

β = 96.71 (3)°

V = 887.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.24 × 0.22 × 0.22 mm

Data collection

Bruker SMART CCD diffractometer

7536 measured reflections

2033 independent reflections

1412 reflections with I > σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.176

S = 1.12

2033 reflections

118 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.23 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/S1600536810042765/lh5151sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042765/lh5151Isup2.hkl

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

C9H9FN2O	F(000) = 376
Mr = 180.18	Dx = 1.349 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2033 reflections
a = 10.443 (2) Å	θ = 3.7–27.5°
b = 4.0418 (8) Å	µ = 0.11 mm−1
c = 21.172 (4) Å	T = 293 K
β = 96.71 (3)°	Bar, colourless
V = 887.5 (3) Å3	0.24 × 0.22 × 0.22 mm
Z = 4

Bruker SMART CCD diffractometer	1412 reflections with I > σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.025
graphite	θmax = 27.5°, θmin = 3.3°
φ and ω scans	h = −13→13
7536 measured reflections	k = −5→5
2033 independent reflections	l = −27→27

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.176	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.1001P)2 + 0.0565P] where P = (Fo2 + 2Fc2)/3
2033 reflections	(Δ/σ)max < 0.001
118 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.23 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
N2	0.41309 (13)	0.8047 (4)	0.12439 (6)	0.0506 (4)
C4	0.50404 (14)	0.7947 (4)	0.23307 (7)	0.0448 (4)
C3	0.50479 (15)	0.7172 (4)	0.16566 (7)	0.0517 (4)
H3A	0.5741	0.6012	0.1527	0.062*
N1	0.42670 (14)	0.7124 (4)	0.06305 (6)	0.0574 (4)
H1A	0.4921	0.5941	0.0561	0.069*
O1	0.35986 (12)	0.7130 (4)	−0.04043 (5)	0.0692 (4)
F1	0.50984 (11)	0.9900 (3)	0.42320 (4)	0.0807 (4)
C2	0.34069 (16)	0.8017 (4)	0.01332 (7)	0.0533 (4)
C8	0.40253 (16)	1.0213 (4)	0.31985 (7)	0.0545 (4)
H8A	0.3333	1.1268	0.3352	0.065*
C7	0.50862 (17)	0.9235 (4)	0.36057 (7)	0.0536 (4)
C5	0.60833 (15)	0.6986 (4)	0.27603 (7)	0.0518 (4)
H5A	0.6772	0.5882	0.2613	0.062*
C9	0.40169 (14)	0.9588 (4)	0.25596 (7)	0.0497 (4)
H9A	0.3318	1.0270	0.2277	0.060*
C6	0.61129 (16)	0.7648 (4)	0.34044 (7)	0.0557 (4)
H6A	0.6815	0.7025	0.3691	0.067*
C1	0.22542 (17)	0.9959 (4)	0.02534 (8)	0.0631 (5)
H1B	0.1738	1.0404	−0.0143	0.095*
H1C	0.2522	1.2011	0.0456	0.095*
H1D	0.1757	0.8720	0.0525	0.095*

	U11	U22	U33	U12	U13	U23
N2	0.0517 (8)	0.0632 (8)	0.0366 (7)	−0.0062 (6)	0.0045 (5)	−0.0048 (5)
C4	0.0445 (8)	0.0502 (8)	0.0393 (8)	−0.0073 (6)	0.0030 (6)	−0.0030 (6)
C3	0.0471 (8)	0.0647 (10)	0.0433 (8)	−0.0038 (7)	0.0058 (6)	−0.0067 (7)
N1	0.0497 (8)	0.0851 (10)	0.0374 (7)	0.0001 (7)	0.0045 (5)	−0.0076 (6)
O1	0.0619 (7)	0.1067 (11)	0.0384 (6)	−0.0006 (7)	0.0029 (5)	−0.0048 (6)
F1	0.0863 (8)	0.1149 (10)	0.0392 (6)	0.0063 (7)	0.0000 (5)	−0.0137 (5)
C2	0.0511 (9)	0.0682 (10)	0.0400 (8)	−0.0107 (8)	0.0033 (6)	−0.0005 (7)
C8	0.0513 (9)	0.0650 (10)	0.0472 (9)	0.0041 (7)	0.0059 (6)	−0.0074 (7)
C7	0.0600 (9)	0.0648 (10)	0.0350 (7)	−0.0067 (8)	0.0017 (6)	−0.0056 (7)
C5	0.0432 (8)	0.0635 (10)	0.0484 (8)	0.0001 (7)	0.0035 (6)	−0.0029 (7)
C9	0.0451 (8)	0.0584 (9)	0.0441 (8)	−0.0002 (7)	−0.0011 (6)	−0.0030 (6)
C6	0.0488 (9)	0.0697 (10)	0.0458 (8)	−0.0026 (7)	−0.0061 (6)	0.0018 (7)
C1	0.0681 (11)	0.0673 (11)	0.0533 (9)	0.0041 (9)	0.0043 (7)	0.0044 (8)

N2—C3	1.269 (2)	C8—C9	1.375 (2)
N2—N1	1.3744 (17)	C8—C7	1.380 (2)
C4—C5	1.390 (2)	C8—H8A	0.9300
C4—C9	1.392 (2)	C7—C6	1.360 (2)
C4—C3	1.462 (2)	C5—C6	1.386 (2)
C3—H3A	0.9300	C5—H5A	0.9300
N1—C2	1.351 (2)	C9—H9A	0.9300
N1—H1A	0.8600	C6—H6A	0.9300
O1—C2	1.2317 (17)	C1—H1B	0.9600
F1—C7	1.3516 (17)	C1—H1C	0.9600
C2—C1	1.484 (2)	C1—H1D	0.9600
C3—N2—N1	114.97 (14)	F1—C7—C8	118.09 (15)
C5—C4—C9	118.69 (14)	C6—C7—C8	122.96 (14)
C5—C4—C3	119.05 (15)	C6—C5—C4	121.01 (15)
C9—C4—C3	122.25 (14)	C6—C5—H5A	119.5
N2—C3—C4	121.53 (15)	C4—C5—H5A	119.5
N2—C3—H3A	119.2	C8—C9—C4	120.87 (14)
C4—C3—H3A	119.2	C8—C9—H9A	119.6
C2—N1—N2	122.09 (15)	C4—C9—H9A	119.6
C2—N1—H1A	119.0	C7—C6—C5	118.13 (15)
N2—N1—H1A	119.0	C7—C6—H6A	120.9
O1—C2—N1	118.51 (16)	C5—C6—H6A	120.9
O1—C2—C1	122.36 (15)	C2—C1—H1B	109.5
N1—C2—C1	119.12 (14)	C2—C1—H1C	109.5
C9—C8—C7	118.32 (15)	H1B—C1—H1C	109.5
C9—C8—H8A	120.8	C2—C1—H1D	109.5
C7—C8—H8A	120.8	H1B—C1—H1D	109.5
F1—C7—C6	118.94 (15)	H1C—C1—H1D	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.86	2.04	2.899 (2)	176

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.86	2.04	2.899 (2)	176

Symmetry code: (i) .