(E)-2-Fluoro-N′-(4-nitro­benzyl­idene)benzo­hydrazide

Wu, H.-Y.; Ban, H.-Y.; Wang, J.-B.; Zhang, L.-H.

doi:10.1107/S1600536810052268

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 1| January 2011| Page o160

https://doi.org/10.1107/S1600536810052268

Open

access

(E)-2-Fluoro-N′-(4-nitrobenzylidene)benzohydrazide

Hong-Yun Wu,^a Hong-Yan Ban,^a ^* Jia-Bo Wang ^a and Li-Hua Zhang ^a

^aSchool of Chemical Engineering, University of Science and Technology Liaoning, Anshan 114051, People's Republic of China
^*Correspondence e-mail: hongyan_ban@163.com

(Received 5 December 2010; accepted 13 December 2010; online 18 December 2010)

In the title hydrazone compound, C₁₄H₁₀FN₃O₃, the dihedral angle between the two substituted benzene rings is 13.7 (3)°. The molecule exists in a trans configuration with respect to the central methylidene unit. In the crystal, molecules are linked through intermolecular N—H⋯O hydrogen bonds, forming chains along the a axis.

Related literature

For the biological activity of hydrazones, see: Zhong et al. (2007 ); Raj et al. (2007 ); Jimenez-Pulido et al. (2008 ). For related structures, see: Ban (2010 ); Ban & Li (2008a ,b ); Li & Ban (2009a ,b ); Yehye et al. (2008 ); Fun, Patil, Jebas et al. (2008 ); Fun, Patil, Rao et al. (2008 ); Yang et al. (2008 ); Ejsmont et al. (2008 ).

Experimental

Crystal data

C₁₄H₁₀FN₃O₃
M_r = 287.25
Monoclinic, P 2₁ /n
a = 7.077 (2) Å
b = 25.718 (4) Å
c = 7.6844 (17) Å
β = 111.640 (3)°
V = 1300.1 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 298 K
0.17 × 0.15 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.981, T_max = 0.983
6999 measured reflections
2810 independent reflections
1155 reflections with I > 2σ(I)
R_int = 0.074

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.173
S = 0.98
2810 reflections
193 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O3ⁱ	0.90 (1)	2.04 (3)	2.928 (3)	168 (3)
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); 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/S1600536810052268/rz2538sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810052268/rz2538Isup2.hkl

checkCIF report

Comment top

Hydrazone compounds derived from the condensation of aldehydes with hydrazides have been demonstrated to possess excellent biological activities (Zhong et al., 2007; Raj et al., 2007; Jimenez-Pulido et al., 2008). Due to the easy synthesis of such compounds, a large number of hydrazone compounds have been synthesized and structurally characterized (Yehye et al., 2008; Fun, Patil, Jebas et al., 2008; Fun, Patil, Rao et al., 2008; Yang et al., 2008; Ejsmont et al., 2008). Recently, we have reported a few such compounds (Ban, 2010; Ban & Li, 2008a,b; Li & Ban, 2009a,b). We report here the crystal structure of the title new compound.

In the title hydrazone compound, Fig. 1, the dihedral angle between the two substituted benzene rings C1—C6 and C9—C14 is 13.7 (3)°. The molecule exists in a trans configuration with respect to the central methylidene unit.

In the crystal structure, molecules are linked through intermolecular N—H···O hydrogen bonds (Table 1), forming chains along the a axis (Fig. 2).

Related literature top

For the biological activity of hydrazones, see: Zhong et al. (2007); Raj et al. (2007); Jimenez-Pulido et al. (2008). For related structures, see: Ban (2010); Ban & Li (2008a,b); Li & Ban (2009a,b); Yehye et al. (2008); Fun, Patil, Jebas et al. (2008); Fun, Patil, Rao et al. (2008); Yang et al. (2008); Ejsmont et al. (2008).

Experimental top

The title compound was prepared by refluxing 4-nitrobenzaldehyde (1.0 mol) with 2-fluorobenzohydrazide (1.0 mol) in methanol (100 ml). Excess methanol was removed from the mixture by distillation. A colourless solid product was filtered, and washed three times with methanol. Colourless block-shaped crystals of the title compound were obtained from a methanol solution by slow evaporation in air.

Structure description top

In the crystal structure, molecules are linked through intermolecular N—H···O hydrogen bonds (Table 1), forming chains along the a axis (Fig. 2).

For the biological activity of hydrazones, see: Zhong et al. (2007); Raj et al. (2007); Jimenez-Pulido et al. (2008). For related structures, see: Ban (2010); Ban & Li (2008a,b); Li & Ban (2009a,b); Yehye et al. (2008); Fun, Patil, Jebas et al. (2008); Fun, Patil, Rao et al. (2008); Yang et al. (2008); Ejsmont et al. (2008).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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, showing 30% probability displacement ellipsoids for the non-hydrogen atoms.
	Fig. 2. Packing diagram of the title compound, viewed along the c axis. Hydrogen bonds are shown as dashed lines.

(E)-2-Fluoro-N'-(4-nitrobenzylidene)benzohydrazide top

Crystal data top

C₁₄H₁₀FN₃O₃	F(000) = 592
M_r = 287.25	D_x = 1.468 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 680 reflections
a = 7.077 (2) Å	θ = 2.5–24.5°
b = 25.718 (4) Å	µ = 0.12 mm⁻¹
c = 7.6844 (17) Å	T = 298 K
β = 111.640 (3)°	Block, colourless
V = 1300.1 (5) Å³	0.17 × 0.15 × 0.15 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2810 independent reflections
Radiation source: fine-focus sealed tube	1155 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.074
ω scans	θ_max = 27.0°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→8
T_min = 0.981, T_max = 0.983	k = −32→27
6999 measured reflections	l = −5→9

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.173	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ²(F_o²) + (0.0571P)²] where P = (F_o² + 2F_c²)/3
2810 reflections	(Δ/σ)_max < 0.001
193 parameters	Δρ_max = 0.25 e Å⁻³
1 restraint	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₄H₁₀FN₃O₃	V = 1300.1 (5) Å³
M_r = 287.25	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.077 (2) Å	µ = 0.12 mm⁻¹
b = 25.718 (4) Å	T = 298 K
c = 7.6844 (17) Å	0.17 × 0.15 × 0.15 mm
β = 111.640 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2810 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1155 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.983	R_int = 0.074
6999 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	1 restraint
wR(F²) = 0.173	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	Δρ_max = 0.25 e Å⁻³
2810 reflections	Δρ_min = −0.22 e Å⁻³
193 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
F1	0.2225 (4)	0.24829 (9)	0.4967 (3)	0.0822 (8)
N1	0.2495 (5)	0.48648 (15)	−0.5057 (5)	0.0631 (10)
N2	0.2488 (4)	0.29033 (11)	0.0113 (4)	0.0432 (8)
N3	0.2828 (5)	0.25789 (11)	0.1631 (4)	0.0464 (8)
O1	0.2201 (5)	0.47230 (12)	−0.6636 (4)	0.0978 (12)
O2	0.2646 (6)	0.53203 (12)	−0.4634 (5)	0.1069 (13)
O3	0.0937 (4)	0.19271 (9)	−0.0144 (3)	0.0547 (8)
C1	0.2637 (5)	0.44701 (14)	−0.3635 (5)	0.0438 (9)
C2	0.2406 (6)	0.39574 (14)	−0.4128 (5)	0.0486 (10)
H2	0.2183	0.3855	−0.5348	0.058*
C3	0.2511 (5)	0.35963 (14)	−0.2776 (5)	0.0465 (10)
H3	0.2325	0.3246	−0.3094	0.056*
C4	0.2891 (5)	0.37471 (13)	−0.0952 (5)	0.0374 (8)
C5	0.3140 (5)	0.42716 (14)	−0.0505 (5)	0.0474 (10)
H5	0.3419	0.4376	0.0723	0.057*
C6	0.2981 (5)	0.46400 (13)	−0.1853 (5)	0.0494 (10)
H6	0.3103	0.4993	−0.1564	0.059*
C7	0.3085 (5)	0.33691 (14)	0.0518 (5)	0.0448 (10)
H7	0.3652	0.3470	0.1766	0.054*
C8	0.2013 (5)	0.21010 (13)	0.1394 (5)	0.0404 (9)
C9	0.2475 (5)	0.17828 (13)	0.3115 (5)	0.0361 (8)
C10	0.2603 (5)	0.19735 (14)	0.4817 (5)	0.0484 (10)
C11	0.3020 (6)	0.16713 (18)	0.6393 (5)	0.0627 (12)
H11	0.3100	0.1815	0.7529	0.075*
C12	0.3310 (6)	0.11534 (18)	0.6222 (6)	0.0658 (12)
H12	0.3597	0.0940	0.7266	0.079*
C13	0.3190 (5)	0.09383 (15)	0.4558 (6)	0.0595 (11)
H13	0.3399	0.0584	0.4478	0.071*
C14	0.2757 (5)	0.12515 (13)	0.2996 (6)	0.0489 (10)
H14	0.2653	0.1105	0.1858	0.059*
H3A	0.374 (4)	0.2695 (13)	0.272 (3)	0.073*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.130 (2)	0.0599 (16)	0.0721 (18)	−0.0116 (15)	0.0550 (17)	−0.0204 (13)
N1	0.084 (3)	0.055 (2)	0.051 (2)	0.003 (2)	0.026 (2)	0.009 (2)
N2	0.0457 (18)	0.0456 (19)	0.0314 (18)	−0.0036 (15)	0.0062 (15)	0.0066 (15)
N3	0.058 (2)	0.0411 (19)	0.0300 (17)	−0.0090 (16)	0.0044 (15)	0.0041 (16)
O1	0.163 (3)	0.085 (2)	0.053 (2)	−0.007 (2)	0.048 (2)	0.0113 (18)
O2	0.190 (4)	0.051 (2)	0.084 (3)	0.003 (2)	0.054 (2)	0.0158 (19)
O3	0.0665 (18)	0.0531 (17)	0.0306 (15)	−0.0094 (14)	0.0017 (13)	−0.0006 (13)
C1	0.049 (2)	0.043 (2)	0.039 (2)	0.0089 (18)	0.0158 (19)	0.0104 (19)
C2	0.060 (3)	0.051 (3)	0.032 (2)	0.002 (2)	0.0141 (19)	−0.0050 (19)
C3	0.055 (2)	0.041 (2)	0.040 (2)	0.0008 (18)	0.014 (2)	−0.0036 (19)
C4	0.035 (2)	0.038 (2)	0.036 (2)	0.0016 (16)	0.0090 (17)	0.0017 (17)
C5	0.062 (3)	0.041 (2)	0.036 (2)	−0.0033 (19)	0.015 (2)	−0.0045 (18)
C6	0.065 (3)	0.034 (2)	0.050 (3)	0.0008 (19)	0.023 (2)	−0.0022 (19)
C7	0.045 (2)	0.054 (2)	0.033 (2)	−0.0012 (19)	0.0104 (18)	−0.0002 (19)
C8	0.045 (2)	0.040 (2)	0.033 (2)	0.0036 (18)	0.0109 (18)	0.0010 (18)
C9	0.037 (2)	0.039 (2)	0.031 (2)	−0.0037 (16)	0.0101 (16)	−0.0021 (16)
C10	0.056 (2)	0.043 (2)	0.047 (3)	−0.010 (2)	0.020 (2)	−0.010 (2)
C11	0.070 (3)	0.082 (3)	0.035 (2)	−0.023 (3)	0.018 (2)	−0.003 (2)
C12	0.058 (3)	0.076 (3)	0.054 (3)	−0.008 (2)	0.009 (2)	0.025 (3)
C13	0.053 (3)	0.053 (3)	0.070 (3)	0.003 (2)	0.020 (2)	0.015 (2)
C14	0.043 (2)	0.046 (3)	0.056 (3)	0.0008 (18)	0.016 (2)	0.004 (2)

Geometric parameters (Å, º) top

F1—C10	1.350 (4)	C4—C7	1.458 (5)
N1—O2	1.210 (4)	C5—C6	1.377 (5)
N1—O1	1.210 (4)	C5—H5	0.9300
N1—C1	1.468 (5)	C6—H6	0.9300
N2—C7	1.270 (4)	C7—H7	0.9300
N2—N3	1.381 (4)	C8—C9	1.485 (4)
N3—C8	1.341 (4)	C9—C10	1.368 (4)
N3—H3A	0.900 (10)	C9—C14	1.389 (4)
O3—C8	1.230 (4)	C10—C11	1.376 (5)
C1—C2	1.365 (4)	C11—C12	1.361 (5)
C1—C6	1.370 (4)	C11—H11	0.9300
C2—C3	1.375 (5)	C12—C13	1.367 (5)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.382 (4)	C13—C14	1.383 (5)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.387 (4)	C14—H14	0.9300

O2—N1—O1	121.8 (4)	N2—C7—C4	120.8 (3)
O2—N1—C1	119.7 (4)	N2—C7—H7	119.6
O1—N1—C1	118.5 (4)	C4—C7—H7	119.6
C7—N2—N3	115.1 (3)	O3—C8—N3	123.1 (3)
C8—N3—N2	120.4 (3)	O3—C8—C9	120.7 (3)
C8—N3—H3A	124 (2)	N3—C8—C9	116.2 (3)
N2—N3—H3A	115 (2)	C10—C9—C14	117.1 (3)
C2—C1—C6	123.0 (3)	C10—C9—C8	124.7 (3)
C2—C1—N1	119.6 (3)	C14—C9—C8	118.3 (3)
C6—C1—N1	117.5 (3)	F1—C10—C9	118.9 (3)
C1—C2—C3	118.4 (3)	F1—C10—C11	117.3 (4)
C1—C2—H2	120.8	C9—C10—C11	123.8 (4)
C3—C2—H2	120.8	C12—C11—C10	117.3 (4)
C2—C3—C4	120.8 (3)	C12—C11—H11	121.3
C2—C3—H3	119.6	C10—C11—H11	121.3
C4—C3—H3	119.6	C11—C12—C13	121.8 (4)
C3—C4—C5	118.9 (3)	C11—C12—H12	119.1
C3—C4—C7	121.7 (3)	C13—C12—H12	119.1
C5—C4—C7	119.3 (3)	C12—C13—C14	119.6 (4)
C6—C5—C4	121.0 (3)	C12—C13—H13	120.2
C6—C5—H5	119.5	C14—C13—H13	120.2
C4—C5—H5	119.5	C13—C14—C9	120.5 (4)
C1—C6—C5	117.8 (3)	C13—C14—H14	119.8
C1—C6—H6	121.1	C9—C14—H14	119.8
C5—C6—H6	121.1

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O3ⁱ	0.90 (1)	2.04 (3)	2.928 (3)	168 (3)

Symmetry code: (i) x+1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₀FN₃O₃
M_r	287.25
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	7.077 (2), 25.718 (4), 7.6844 (17)
β (°)	111.640 (3)
V (Å³)	1300.1 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.17 × 0.15 × 0.15

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.981, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	6999, 2810, 1155
R_int	0.074
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.173, 0.98
No. of reflections	2810
No. of parameters	193
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)	0.25, −0.22

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), 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
N3—H3A···O3ⁱ	0.900 (10)	2.04 (3)	2.928 (3)	168 (3)

Symmetry code: (i) x+1/2, −y+1/2, z+1/2.

Acknowledgements

The authors acknowledge the support of the Scientific and Technological Training Fund for undergraduates from the University of Science and Technology Liaoning.

References

Ban, H.-Y. (2010). Acta Cryst. E66, o3240. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ban, H.-Y. & Li, C.-M. (2008a). Acta Cryst. E64, o2177. Web of Science CrossRef IUCr Journals Google Scholar
Ban, H.-Y. & Li, C.-M. (2008b). Acta Cryst. E64, o2260. Web of Science CrossRef IUCr Journals Google Scholar
Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ejsmont, K., Zareef, M., Arfan, M., Bashir, S. A. & Zaleski, J. (2008). Acta Cryst. E64, o1128. Web of Science CSD CrossRef IUCr Journals Google Scholar
Fun, H.-K., Patil, P. S., Jebas, S. R., Sujith, K. V. & Kalluraya, B. (2008). Acta Cryst. E64, o1594–o1595. Web of Science CSD CrossRef IUCr Journals Google Scholar
Fun, H.-K., Patil, P. S., Rao, J. N., Kalluraya, B. & Chantrapromma, S. (2008). Acta Cryst. E64, o1707. Web of Science CSD CrossRef IUCr Journals Google Scholar
Jimenez-Pulido, S. B., Linares-Ordonez, F. M., Martinez-Martos, J. M., Moreno-Carretero, M. N., Quiros-Olozabal, M. & Ramirez-Exposito, M. J. (2008). J. Inorg. Biochem. 102, 1677–1683. Web of Science CSD CrossRef PubMed CAS Google Scholar
Li, C.-M. & Ban, H.-Y. (2009a). Acta Cryst. E65, o876. Web of Science CSD CrossRef IUCr Journals Google Scholar
Li, C.-M. & Ban, H.-Y. (2009b). Acta Cryst. E65, o883. Web of Science CSD CrossRef IUCr Journals Google Scholar
Raj, K. K. V., Narayana, B., Ashalatha, B. V., Kumari, N. S. & Sarojini, B. K. (2007). Eur. J. Med. Chem. 42, 425–429. PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yang, T., Cao, G.-B., Xiang, J.-M. & Zhang, L.-H. (2008). Acta Cryst. E64, o1186. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yehye, W. A., Rahman, N. A., Ariffin, A. & Ng, S. W. (2008). Acta Cryst. E64, o1824. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhong, X., Wei, H.-L., Liu, W.-S., Wang, D.-Q. & Wang, X. (2007). Bioorg. Med. Chem. Lett. 17, 3774–3777. Web of Science CSD CrossRef PubMed CAS Google Scholar