(E)-N′-(3-Fluoro­benzyl­idene)-3-nitro­benzohydrazide

Li, X.-Y.

doi:10.1107/S1600536812005478

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o697

doi:10.1107/S1600536812005478

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(E)-N′-(3-Fluorobenzylidene)-3-nitrobenzohydrazide

Xiao-Yan Li ^a ^*

^aZibo Vocational Institute, Zibo 255314, People's Republic of China
^*Correspondence e-mail: lixiaoyan_zb@126.com

(Received 2 February 2012; accepted 7 February 2012; online 17 February 2012)

In the title compound, C₁₄H₁₀FN₃O₃, the molecule exists in a trans conformation with respect to the methylidene unit. The dihedral angle between the benzene rings is 5.1 (2)°. In the crystal, molecules are linked through N—H⋯O hydrogen bonds, forming chains along the c axis.

Related literature

For the syntheses and crystal structures of hydrazone compounds, see: Hashemian et al. (2011 ); Lei (2011 ); Shalash et al. (2010 ). For the crystal structures of similar compounds, reported recently by the author, see: Li (2011a ,b ).

Experimental

Crystal data

C₁₄H₁₀FN₃O₃
M_r = 287.25
Monoclinic, P 2₁ /c
a = 11.823 (2) Å
b = 12.813 (3) Å
c = 8.7020 (17) Å
β = 94.855 (2)°
V = 1313.5 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.17 × 0.17 × 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
9452 measured reflections
2429 independent reflections
1438 reflections with I > 2σ(I)
R_int = 0.075

Refinement

R[F² > 2σ(F²)] = 0.080
wR(F²) = 0.218
S = 1.02
2429 reflections
193 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.59 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
N2—H2⋯O3ⁱ	0.90 (1)	1.96 (1)	2.846 (4)	172 (5)
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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: 10.1107/S1600536812005478/rz2708sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812005478/rz2708Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812005478/rz2708Isup3.cml

checkCIF report

Comment top

In recent years, hydrazone compounds have attracted much attention due to their syntheses and crystal structures (Hashemian et al., 2011; Lei, 2011; Shalash et al., 2010). As a continuation of our work on such compounds (Li, 2011a,b), the author reports herein on the crystal structure of the new title hydrazone compound.

The title compound (Fig. 1) exists in a trans configuration with respect to the methylidene unit. The dihedral angle between the C1–C6 and C9–C14 benzene rings of the molecule is 5.1 (2)°. The N1/O1/O2 nitro group is tilted by 16.3 (3)° with respect to the C1—C6 benzene ring. In the crystal, molecules are linked through N–H···O hydrogen bonds (Table 1) to form chains along the c axis (Fig. 2).

Related literature top

For the syntheses and crystal structures of hydrazone compounds, see: Hashemian et al. (2011); Lei (2011); Shalash et al. (2010). For the crystal structures of similar compounds, reported recently by the author, see: Li (2011a,b).

Experimental top

A mixture of 3-fluorobenzaldehyde (0.124 g, 1 mmol) and 3-nitrobenzohydrazide (0.181 g, 1 mmol) in 30 ml of ethanol containing few drops of acetic acid was refluxed for about 1 h. On cooling to room temperature, a solid precipitate was formed. The solid was filtered and then recrystallized from methanol. Yellow crystals, suitable for X-ray diffraction analysis, were obtained by slow evaporation of the solvent.

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 displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Molecular packing diagram of the title compound, viewed along the b axis. Hydrogen bonds are indicated by dashed lines. The C-bound H-atoms have been omitted for clarity.

(E)-N'-(3-Fluorobenzylidene)-3-nitrobenzohydrazide top

Crystal data top

C₁₄H₁₀FN₃O₃	F(000) = 592
M_r = 287.25	D_x = 1.453 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 690 reflections
a = 11.823 (2) Å	θ = 2.4–26.2°
b = 12.813 (3) Å	µ = 0.11 mm⁻¹
c = 8.7020 (17) Å	T = 298 K
β = 94.855 (2)°	Block, yellow
V = 1313.5 (5) Å³	0.17 × 0.17 × 0.15 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2429 independent reflections
Radiation source: fine-focus sealed tube	1438 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.075
ω scans	θ_max = 25.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
T_min = 0.981, T_max = 0.983	k = −15→15
9452 measured reflections	l = −10→10

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)] = 0.080	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.218	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0985P)² + 0.4222P] where P = (F_o² + 2F_c²)/3
2429 reflections	(Δ/σ)_max < 0.001
193 parameters	Δρ_max = 0.59 e Å⁻³
1 restraint	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₄H₁₀FN₃O₃	V = 1313.5 (5) Å³
M_r = 287.25	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.823 (2) Å	µ = 0.11 mm⁻¹
b = 12.813 (3) Å	T = 298 K
c = 8.7020 (17) Å	0.17 × 0.17 × 0.15 mm
β = 94.855 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2429 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1438 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.983	R_int = 0.075
9452 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.080	1 restraint
wR(F²) = 0.218	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.59 e Å⁻³
2429 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	0.6421 (4)	−0.2974 (2)	1.1301 (4)	0.1160 (14)
N1	1.0252 (3)	0.4021 (4)	0.6545 (5)	0.0679 (12)
N2	0.7281 (3)	0.2345 (2)	0.9891 (3)	0.0395 (8)
N3	0.6810 (3)	0.1600 (2)	1.0796 (3)	0.0378 (8)
O1	1.0149 (4)	0.3120 (3)	0.6079 (6)	0.1118 (16)
O2	1.0930 (3)	0.4628 (3)	0.6109 (4)	0.0929 (13)
O3	0.7513 (2)	0.34723 (19)	1.1894 (3)	0.0479 (8)
C1	0.8197 (3)	0.3996 (3)	0.9543 (4)	0.0342 (9)
C2	0.8882 (3)	0.3651 (3)	0.8433 (4)	0.0375 (9)
H2A	0.8947	0.2943	0.8222	0.045*
C3	0.9466 (3)	0.4386 (3)	0.7646 (4)	0.0427 (10)
C4	0.9357 (4)	0.5431 (3)	0.7881 (5)	0.0527 (11)
H4	0.9744	0.5910	0.7318	0.063*
C5	0.8655 (4)	0.5763 (3)	0.8979 (5)	0.0538 (11)
H5	0.8568	0.6473	0.9156	0.065*
C6	0.8089 (3)	0.5051 (3)	0.9806 (5)	0.0445 (10)
H6	0.7628	0.5282	1.0551	0.053*
C7	0.7631 (3)	0.3250 (3)	1.0550 (4)	0.0354 (9)
C8	0.6781 (3)	0.0680 (3)	1.0258 (4)	0.0367 (9)
H8	0.7070	0.0547	0.9316	0.044*
C9	0.6300 (3)	−0.0173 (3)	1.1103 (4)	0.0385 (9)
C10	0.6562 (4)	−0.1197 (3)	1.0745 (5)	0.0529 (11)
H10	0.7025	−0.1344	0.9961	0.064*
C11	0.6121 (4)	−0.1984 (3)	1.1575 (5)	0.0619 (13)
C12	0.5428 (4)	−0.1806 (4)	1.2734 (5)	0.0634 (13)
H12	0.5138	−0.2358	1.3273	0.076*
C13	0.5176 (4)	−0.0806 (4)	1.3071 (5)	0.0546 (12)
H13	0.4702	−0.0673	1.3848	0.066*
C14	0.5605 (3)	0.0019 (3)	1.2291 (4)	0.0447 (10)
H14	0.5433	0.0701	1.2555	0.054*
H2	0.736 (4)	0.215 (4)	0.891 (2)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.192 (4)	0.0477 (18)	0.111 (3)	−0.004 (2)	0.029 (3)	−0.0008 (17)
N1	0.065 (3)	0.073 (3)	0.069 (3)	−0.009 (2)	0.028 (2)	0.006 (2)
N2	0.054 (2)	0.0383 (18)	0.0278 (16)	−0.0094 (16)	0.0141 (15)	0.0014 (14)
N3	0.0390 (18)	0.0411 (19)	0.0342 (17)	−0.0043 (15)	0.0084 (13)	0.0036 (14)
O1	0.133 (4)	0.077 (3)	0.139 (4)	−0.010 (3)	0.088 (3)	−0.010 (3)
O2	0.087 (3)	0.109 (3)	0.089 (3)	−0.039 (2)	0.042 (2)	0.002 (2)
O3	0.0715 (19)	0.0427 (16)	0.0312 (14)	−0.0021 (14)	0.0154 (13)	−0.0040 (12)
C1	0.036 (2)	0.036 (2)	0.0298 (18)	−0.0029 (17)	−0.0025 (16)	−0.0001 (16)
C2	0.041 (2)	0.039 (2)	0.033 (2)	−0.0069 (18)	0.0019 (17)	0.0001 (16)
C3	0.039 (2)	0.049 (3)	0.041 (2)	−0.0064 (18)	0.0036 (17)	0.0022 (18)
C4	0.058 (3)	0.053 (3)	0.048 (2)	−0.021 (2)	0.004 (2)	0.013 (2)
C5	0.067 (3)	0.034 (2)	0.059 (3)	−0.007 (2)	0.000 (2)	0.003 (2)
C6	0.048 (2)	0.040 (2)	0.044 (2)	0.0012 (19)	0.0018 (19)	−0.0007 (18)
C7	0.040 (2)	0.037 (2)	0.031 (2)	0.0026 (17)	0.0073 (16)	−0.0030 (16)
C8	0.037 (2)	0.039 (2)	0.035 (2)	0.0036 (17)	0.0050 (16)	−0.0006 (17)
C9	0.039 (2)	0.041 (2)	0.035 (2)	−0.0062 (18)	−0.0013 (17)	0.0014 (17)
C10	0.069 (3)	0.039 (2)	0.052 (3)	−0.003 (2)	0.014 (2)	0.001 (2)
C11	0.092 (4)	0.031 (2)	0.063 (3)	−0.001 (2)	0.008 (3)	0.001 (2)
C12	0.080 (3)	0.055 (3)	0.055 (3)	−0.025 (3)	0.000 (2)	0.015 (2)
C13	0.058 (3)	0.057 (3)	0.051 (3)	−0.014 (2)	0.015 (2)	0.006 (2)
C14	0.049 (2)	0.041 (2)	0.045 (2)	−0.0040 (19)	0.0083 (19)	0.0042 (18)

Geometric parameters (Å, º) top

F1—C11	1.344 (5)	C4—H4	0.9300
N1—O2	1.201 (5)	C5—C6	1.372 (6)
N1—O1	1.225 (5)	C5—H5	0.9300
N1—C3	1.467 (5)	C6—H6	0.9300
N2—C7	1.343 (5)	C8—C9	1.459 (5)
N2—N3	1.383 (4)	C8—H8	0.9300
N2—H2	0.897 (10)	C9—C10	1.390 (6)
N3—C8	1.268 (4)	C9—C14	1.396 (5)
O3—C7	1.223 (4)	C10—C11	1.369 (6)
C1—C6	1.379 (5)	C10—H10	0.9300
C1—C2	1.384 (5)	C11—C12	1.371 (7)
C1—C7	1.493 (5)	C12—C13	1.353 (6)
C2—C3	1.384 (5)	C12—H12	0.9300
C2—H2A	0.9300	C13—C14	1.376 (5)
C3—C4	1.362 (6)	C13—H13	0.9300
C4—C5	1.384 (6)	C14—H14	0.9300

O2—N1—O1	123.8 (4)	O3—C7—N2	123.6 (3)
O2—N1—C3	118.4 (4)	O3—C7—C1	120.3 (3)
O1—N1—C3	117.8 (4)	N2—C7—C1	116.0 (3)
C7—N2—N3	118.5 (3)	N3—C8—C9	120.6 (3)
C7—N2—H2	126 (3)	N3—C8—H8	119.7
N3—N2—H2	115 (3)	C9—C8—H8	119.7
C8—N3—N2	115.5 (3)	C10—C9—C14	119.2 (4)
C6—C1—C2	119.8 (3)	C10—C9—C8	119.4 (3)
C6—C1—C7	118.6 (3)	C14—C9—C8	121.4 (3)
C2—C1—C7	121.5 (3)	C11—C10—C9	118.4 (4)
C3—C2—C1	118.3 (4)	C11—C10—H10	120.8
C3—C2—H2A	120.9	C9—C10—H10	120.8
C1—C2—H2A	120.9	F1—C11—C10	118.9 (5)
C4—C3—C2	122.5 (4)	F1—C11—C12	118.1 (4)
C4—C3—N1	119.0 (4)	C10—C11—C12	122.9 (4)
C2—C3—N1	118.5 (4)	C13—C12—C11	118.2 (4)
C3—C4—C5	118.4 (4)	C13—C12—H12	120.9
C3—C4—H4	120.8	C11—C12—H12	120.9
C5—C4—H4	120.8	C12—C13—C14	121.6 (4)
C6—C5—C4	120.4 (4)	C12—C13—H13	119.2
C6—C5—H5	119.8	C14—C13—H13	119.2
C4—C5—H5	119.8	C13—C14—C9	119.7 (4)
C5—C6—C1	120.6 (4)	C13—C14—H14	120.2
C5—C6—H6	119.7	C9—C14—H14	120.2
C1—C6—H6	119.7

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3ⁱ	0.90 (1)	1.96 (1)	2.846 (4)	172 (5)

Symmetry code: (i) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₀FN₃O₃
M_r	287.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	11.823 (2), 12.813 (3), 8.7020 (17)
β (°)	94.855 (2)
V (Å³)	1313.5 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.17 × 0.17 × 0.15

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
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	9452, 2429, 1438
R_int	0.075
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.080, 0.218, 1.02
No. of reflections	2429
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)	0.59, −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
N2—H2···O3ⁱ	0.897 (10)	1.955 (13)	2.846 (4)	172 (5)

Symmetry code: (i) x, −y+1/2, z−1/2.

Acknowledgements

The author is grateful to the Zibo Vocational Institute for supporting this work.

References

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