(E)-2-Fluoro-N'-(4-nitro-benzyl-idene)benzo-hydrazide.

In the title hydrazone compound, C(14)H(10)FN(3)O(3), the dihedral angle between the two substituted benzene rings is 13.7 (3)°. The mol-ecule exists in a trans configuration with respect to the central methyl-idene unit. In the crystal, mol-ecules are linked through inter-molecular 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 = 287.25

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.173

S = 0.98

2810 reflections

193 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.22 e Å−3

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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810052268/rz2538sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052268/rz2538Isup2.hkl

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

C14H10FN3O3	F(000) = 592
Mr = 287.25	Dx = 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

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

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(Fo2) + (0.0571P)2] where P = (Fo2 + 2Fc2)/3
2810 reflections	(Δ/σ)max < 0.001
193 parameters	Δρmax = 0.25 e Å−3
1 restraint	Δρmin = −0.22 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
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*

	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)

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

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)

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) .