(E)-N′-(3-Fluoro­benzyl­idene)-4-methyl­benzohydrazide

Hu, H.-N.; Liu, S.-Y.

doi:10.1107/S1600536812019484

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1643

doi:10.1107/S1600536812019484

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(E)-N′-(3-Fluorobenzylidene)-4-methylbenzohydrazide

Hua-Nan Hu ^a and Shi-Yong Liu ^a ^*

^aCollege of Chemistry and Pharmacy, Taizhou University, Taizhou Zhejiang 317000, People's Republic of China
^*Correspondence e-mail: liushiyong2012@yahoo.cn

(Received 30 April 2012; accepted 1 May 2012; online 5 May 2012)

In the title compound, C₁₅H₁₃FN₂O, the dihedral angle between the benzene rings is 16.9 (2)°. The F atom and the O atom are in a syn conformation. In the crystal, molecules are linked by N—H⋯O hydrogen bonds to generate C(4) chains propagating along the b-axis direction.

Related literature

For hydrazones that we have reported previously, see: Liu & You (2010 ); Liu & Wang (2010 ). For the crystal structures of other similar hydrazone compounds, see: Vijayakumar et al. (2009 ); Xu et al. (2009 ); Shafiq et al. (2009 ).

Experimental

Crystal data

C₁₅H₁₃FN₂O
M_r = 256.27
Orthorhombic, P b c a
a = 13.2629 (5) Å
b = 7.9118 (3) Å
c = 24.9235 (8) Å
V = 2615.31 (16) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.17 × 0.15 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.984, T_max = 0.986
26269 measured reflections
2424 independent reflections
1997 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.123
S = 1.04
2424 reflections
176 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1ⁱ	0.90 (1)	2.04 (1)	2.9322 (17)	169 (2)
Symmetry code: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812019484/hb6775sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812019484/hb6775Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812019484/hb6775Isup3.cml

checkCIF report

Comment top

The crystal structures of hydrazones are of ongoing interest (Vijayakumar et al., 2009). As a continuation of our work on similar compounds (Liu & You, 2010; Liu & Wang, 2010), we report herein the crystal structure of the title compound a new hydrazone.

The molecular structure of the title compound is shown in Fig. 1. The two benzene ring system are inclined at a dihedral angle of 16.9 (2)°. All the bond lengths are comparable to those observed in related structures (Xu et al., 2009; Shafiq et al., 2009) and those we reported previously.

In the crystal structure, molecules are linked through N–H···O hydrogen bonds, to form one-dimensional chains running along the b axis (Fig. 2 and Table 1).

Related literature top

For hydrazones that we have reported previously, see: Liu & You (2010); Liu & Wang (2010). For the crystal structures of other similar hydrazone compounds, see: Vijayakumar et al. (2009); Xu et al. (2009); Shafiq et al. (2009).

Experimental top

The title compound was prepared by the condensation reaction of 3-fluorobenzaldehyde (0.05 mol, 6.2 g) and 4-methylbenzohydrazide (0.05 mol, 7.5 g) in anhydrous methanol (100 ml) at ambient temperature. Colourless blocks were obtained by slow evaporation of the solution for several days.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (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. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The molecular packing of the title compound, viewed along the a axis. Hydrogen bonds are shown as dashed lines. Hydrogen atoms not involved in hydrogen bonding have been omitted.

(E)-N'-(3-Fluorobenzylidene)-4-methylbenzohydrazide top

Crystal data top

C₁₅H₁₃FN₂O	D_x = 1.302 Mg m⁻³
M_r = 256.27	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 12661 reflections
a = 13.2629 (5) Å	θ = 2.4–26.6°
b = 7.9118 (3) Å	µ = 0.09 mm⁻¹
c = 24.9235 (8) Å	T = 298 K
V = 2615.31 (16) Å³	Block, colourless
Z = 8	0.17 × 0.15 × 0.15 mm
F(000) = 1072

Data collection top

Bruker SMART CCD diffractometer	2424 independent reflections
Radiation source: fine-focus sealed tube	1997 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω scans	θ_max = 25.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −15→16
T_min = 0.984, T_max = 0.986	k = −9→9
26269 measured reflections	l = −26→30

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0664P)² + 0.6653P] where P = (F_o² + 2F_c²)/3
2424 reflections	(Δ/σ)_max < 0.001
176 parameters	Δρ_max = 0.33 e Å⁻³
1 restraint	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₅H₁₃FN₂O	V = 2615.31 (16) Å³
M_r = 256.27	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 13.2629 (5) Å	µ = 0.09 mm⁻¹
b = 7.9118 (3) Å	T = 298 K
c = 24.9235 (8) Å	0.17 × 0.15 × 0.15 mm

Data collection top

Bruker SMART CCD diffractometer	2424 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1997 reflections with I > 2σ(I)
T_min = 0.984, T_max = 0.986	R_int = 0.027
26269 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	1 restraint
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.33 e Å⁻³
2424 reflections	Δρ_min = −0.21 e Å⁻³
176 parameters

Special details top

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 > 2sigma(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
F1	0.78383 (10)	1.16955 (17)	0.83669 (4)	0.0913 (4)
N1	0.77048 (10)	0.87893 (16)	0.65528 (5)	0.0465 (3)
N2	0.74744 (10)	0.79810 (16)	0.60759 (5)	0.0479 (3)
O1	0.63068 (8)	0.99556 (13)	0.58731 (4)	0.0490 (3)
C1	0.86862 (11)	0.87814 (19)	0.73528 (6)	0.0455 (4)
C2	0.81042 (12)	0.9977 (2)	0.76159 (6)	0.0511 (4)
H2A	0.7516	1.0388	0.7461	0.061*
C3	0.84119 (13)	1.0540 (2)	0.81085 (6)	0.0544 (4)
C4	0.92785 (14)	0.9988 (2)	0.83548 (6)	0.0575 (4)
H4	0.9470	1.0400	0.8689	0.069*
C5	0.98513 (14)	0.8808 (2)	0.80907 (7)	0.0614 (5)
H5	1.0444	0.8418	0.8246	0.074*
C6	0.95580 (13)	0.8195 (2)	0.75978 (6)	0.0568 (4)
H6	0.9948	0.7379	0.7427	0.068*
C7	0.83918 (12)	0.8096 (2)	0.68307 (6)	0.0486 (4)
H7	0.8713	0.7136	0.6700	0.058*
C8	0.67452 (11)	0.86358 (18)	0.57603 (5)	0.0406 (3)
C9	0.64991 (11)	0.76616 (18)	0.52671 (5)	0.0413 (3)
C10	0.55246 (12)	0.7776 (2)	0.50671 (6)	0.0528 (4)
H10	0.5052	0.8451	0.5241	0.063*
C11	0.52533 (14)	0.6893 (2)	0.46127 (7)	0.0610 (5)
H11	0.4594	0.6969	0.4488	0.073*
C12	0.59315 (13)	0.5906 (2)	0.43399 (6)	0.0540 (4)
C13	0.69117 (13)	0.5831 (2)	0.45316 (6)	0.0547 (4)
H13	0.7389	0.5193	0.4348	0.066*
C14	0.71912 (12)	0.6688 (2)	0.49895 (6)	0.0499 (4)
H14	0.7851	0.6610	0.5113	0.060*
C15	0.56269 (19)	0.4938 (3)	0.38453 (8)	0.0806 (6)
H15A	0.4905	0.4864	0.3829	0.121*
H15B	0.5908	0.3821	0.3860	0.121*
H15C	0.5873	0.5512	0.3532	0.121*
H2	0.7769 (14)	0.6969 (16)	0.6020 (8)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.1050 (10)	0.0996 (9)	0.0693 (7)	0.0196 (8)	−0.0026 (6)	−0.0352 (7)
N1	0.0550 (8)	0.0461 (7)	0.0383 (6)	−0.0006 (6)	−0.0032 (5)	−0.0095 (6)
N2	0.0587 (8)	0.0447 (7)	0.0404 (7)	0.0068 (6)	−0.0079 (6)	−0.0115 (5)
O1	0.0539 (6)	0.0436 (6)	0.0495 (6)	0.0052 (5)	0.0031 (5)	−0.0070 (5)
C1	0.0524 (8)	0.0445 (8)	0.0398 (8)	−0.0040 (7)	−0.0021 (6)	−0.0010 (6)
C2	0.0546 (9)	0.0536 (9)	0.0452 (9)	0.0010 (7)	−0.0062 (7)	−0.0052 (7)
C3	0.0666 (10)	0.0526 (9)	0.0439 (8)	−0.0038 (8)	0.0036 (7)	−0.0089 (7)
C4	0.0739 (11)	0.0597 (10)	0.0390 (8)	−0.0164 (9)	−0.0092 (8)	0.0003 (7)
C5	0.0638 (10)	0.0673 (11)	0.0532 (9)	−0.0023 (9)	−0.0163 (8)	0.0061 (9)
C6	0.0613 (10)	0.0582 (10)	0.0509 (9)	0.0069 (8)	−0.0062 (8)	−0.0037 (8)
C7	0.0562 (9)	0.0468 (8)	0.0427 (8)	0.0036 (7)	−0.0028 (7)	−0.0070 (7)
C8	0.0447 (8)	0.0385 (7)	0.0385 (7)	−0.0020 (6)	0.0045 (6)	−0.0009 (6)
C9	0.0489 (8)	0.0374 (7)	0.0378 (7)	0.0004 (6)	−0.0020 (6)	0.0013 (6)
C10	0.0514 (9)	0.0525 (9)	0.0545 (9)	0.0080 (7)	−0.0060 (7)	−0.0057 (7)
C11	0.0565 (10)	0.0663 (11)	0.0602 (10)	0.0056 (8)	−0.0186 (8)	−0.0059 (9)
C12	0.0715 (10)	0.0489 (9)	0.0415 (8)	0.0001 (8)	−0.0133 (7)	−0.0010 (7)
C13	0.0673 (10)	0.0565 (10)	0.0402 (8)	0.0120 (8)	−0.0040 (7)	−0.0082 (7)
C14	0.0514 (9)	0.0580 (9)	0.0402 (8)	0.0087 (7)	−0.0062 (6)	−0.0056 (7)
C15	0.1006 (16)	0.0834 (14)	0.0579 (11)	−0.0013 (12)	−0.0259 (11)	−0.0184 (10)

Geometric parameters (Å, º) top

F1—C3	1.352 (2)	C7—H7	0.9300
N1—C7	1.269 (2)	C8—C9	1.487 (2)
N1—N2	1.3841 (16)	C9—C14	1.384 (2)
N2—C8	1.3498 (19)	C9—C10	1.388 (2)
N2—H2	0.902 (9)	C10—C11	1.378 (2)
O1—C8	1.2278 (17)	C10—H10	0.9300
C1—C2	1.386 (2)	C11—C12	1.372 (2)
C1—C6	1.388 (2)	C11—H11	0.9300
C1—C7	1.463 (2)	C12—C13	1.386 (2)
C2—C3	1.368 (2)	C12—C15	1.506 (2)
C2—H2A	0.9300	C13—C14	1.378 (2)
C3—C4	1.374 (3)	C13—H13	0.9300
C4—C5	1.372 (3)	C14—H14	0.9300
C4—H4	0.9300	C15—H15A	0.9600
C5—C6	1.377 (2)	C15—H15B	0.9600
C5—H5	0.9300	C15—H15C	0.9600
C6—H6	0.9300

C7—N1—N2	115.30 (13)	O1—C8—C9	121.74 (13)
C8—N2—N1	118.77 (12)	N2—C8—C9	116.10 (12)
C8—N2—H2	124.2 (13)	C14—C9—C10	118.31 (14)
N1—N2—H2	116.6 (13)	C14—C9—C8	123.80 (13)
C2—C1—C6	118.96 (14)	C10—C9—C8	117.87 (13)
C2—C1—C7	121.69 (14)	C11—C10—C9	120.35 (15)
C6—C1—C7	119.33 (14)	C11—C10—H10	119.8
C3—C2—C1	118.74 (15)	C9—C10—H10	119.8
C3—C2—H2A	120.6	C12—C11—C10	121.65 (16)
C1—C2—H2A	120.6	C12—C11—H11	119.2
F1—C3—C2	118.67 (16)	C10—C11—H11	119.2
F1—C3—C4	118.20 (15)	C11—C12—C13	117.91 (15)
C2—C3—C4	123.13 (16)	C11—C12—C15	121.29 (16)
C5—C4—C3	117.72 (15)	C13—C12—C15	120.80 (17)
C5—C4—H4	121.1	C14—C13—C12	121.13 (15)
C3—C4—H4	121.1	C14—C13—H13	119.4
C4—C5—C6	120.76 (16)	C12—C13—H13	119.4
C4—C5—H5	119.6	C13—C14—C9	120.62 (14)
C6—C5—H5	119.6	C13—C14—H14	119.7
C5—C6—C1	120.67 (16)	C9—C14—H14	119.7
C5—C6—H6	119.7	C12—C15—H15A	109.5
C1—C6—H6	119.7	C12—C15—H15B	109.5
N1—C7—C1	121.10 (15)	H15A—C15—H15B	109.5
N1—C7—H7	119.4	C12—C15—H15C	109.5
C1—C7—H7	119.4	H15A—C15—H15C	109.5
O1—C8—N2	122.16 (13)	H15B—C15—H15C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ⁱ	0.90 (1)	2.04 (1)	2.9322 (17)	169 (2)

Symmetry code: (i) −x+3/2, y−1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃FN₂O
M_r	256.27
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	13.2629 (5), 7.9118 (3), 24.9235 (8)
V (Å³)	2615.31 (16)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.17 × 0.15 × 0.15

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.984, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	26269, 2424, 1997
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.123, 1.04
No. of reflections	2424
No. of parameters	176
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.21

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ⁱ	0.902 (9)	2.043 (10)	2.9322 (17)	168.5 (19)

Symmetry code: (i) −x+3/2, y−1/2, z.

Acknowledgements

The authors acknowledge the Zhejiang Provincial Natural Science Foundation of China (project No. Y12B020017).

References

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