N′-(4-Fluoro­benzyl­idene)acetohydrazide

Guo, H.; Liu, L.; Yang, J.; Liu, Y.

doi:10.1107/S1600536810042765

organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o2952

https://doi.org/10.1107/S1600536810042765

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N′-(4-Fluorobenzylidene)acetohydrazide

Huan-mei Guo,^a ^* Li Liu,^a Jie Yang ^a and Yang-chun Liu ^b

^aMicroscale Science Institute, Weifang University, Weifang 261061, People's Republic of China, and ^bDepartment of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: ffjian2008@163.com

(Received 10 October 2010; accepted 21 October 2010; online 30 October 2010)

The title compound, C₉H₉FN₂O, was prepared by the reaction of 4-fluorobenzophenone and acethydrazide. In the molecule, all non-H atoms are essentially coplanar [r.m.s. deviation = 0.065 (2) Å]. In the crystal, molecules are linked into centrosymmetric dimers by pairs of intermolecular 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_r = 180.18
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.052
wR(F²) = 0.176
S = 1.12
2033 reflections
118 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.23 e Å⁻³

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) -x+1, -y+1, -z.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810042765/lh5151sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810042765/lh5151Isup2.hkl

checkCIF report

Comment top

Schiff bases have received considerable attention in the literature (Zhang et al., 2010; Goswami et al., 2009). As part of our search for new schiff base compounds we synthesized the title compound(I) and its crystal structure is reported herein. In the title compound (Fig. 1), the bond lengths and angles are similar to those in related structures (Li & Jian, 2008; Yang et al., 2010). The C3═N2 bond length of 1.269 (2)Å is slight shorter than the C═N double bond [1.281 (2) Å and 1.2732 (18)] reported by Girgis (2006) and Yang et al. (2010). In the crystal structure, molecules are linked into centrosymmetric dimers by pairs of intermolecular N—H···O hydrogen bonds (Table 1).

Related literature top

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 top

A mixture of the 4-fluorobenzophenone (0.02 mol) and acethydrazide (0.02 mol) was stirred in refluxing ethanol (30 ml) for 2 h to afford the title compound (yield 65%). Single crystals suitable for X-ray measurements were obtained by recrystallization from a solution of the title compound in ethanol at room temperature.

Structure description top

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);

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound with the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level.

N'-(4-Fluorobenzylidene)acetohydrazide top

Crystal data top

C₉H₉FN₂O	F(000) = 376
M_r = 180.18	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.1001P)² + 0.0565P] where P = (F_o² + 2F_c²)/3
2033 reflections	(Δ/σ)_max < 0.001
118 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₉H₉FN₂O	V = 887.5 (3) Å³
M_r = 180.18	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.443 (2) Å	µ = 0.11 mm⁻¹
b = 4.0418 (8) Å	T = 293 K
c = 21.172 (4) Å	0.24 × 0.22 × 0.22 mm
β = 96.71 (3)°

Data collection top

Bruker SMART CCD diffractometer	1412 reflections with I > σ(I)
7536 measured reflections	R_int = 0.025
2033 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.176	H-atom parameters constrained
S = 1.12	Δρ_max = 0.31 e Å⁻³
2033 reflections	Δρ_min = −0.23 e Å⁻³
118 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₉H₉FN₂O
M_r	180.18
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	10.443 (2), 4.0418 (8), 21.172 (4)
β (°)	96.71 (3)
V (Å³)	887.5 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.24 × 0.22 × 0.22

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	–
No. of measured, independent and observed [I > σ(I)] reflections	7536, 2033, 1412
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.176, 1.12
No. of reflections	2033
No. of parameters	118
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.23

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.86	2.0398	2.899 (2)	176.3

Symmetry code: (i) −x+1, −y+1, −z.

Acknowledgements

The authors would like to thank the National Natural Science Foundation of Shandong Province (Y2008B29) and Yuandu Scholar of Weifang City.

References

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