(E)-N'-(3-Fluoro-benzyl-idene)-3-nitro-benzohydrazide.

In the title compound, C(14)H(10)FN(3)O(3), the mol-ecule exists in a trans conformation with respect to the methyl-idene unit. The dihedral angle between the benzene rings is 5.1 (2)°. In the crystal, mol-ecules 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 = 287.25

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.080

wR(F 2) = 0.218

S = 1.02

2429 reflections

193 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.59 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 datablock(s) global, I. DOI: 10.1107/S1600536812005478/rz2708sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812005478/rz2708Isup3.cml

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

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

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

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(Fo2) + (0.0985P)2 + 0.4222P] where P = (Fo2 + 2Fc2)/3
2429 reflections	(Δ/σ)max < 0.001
193 parameters	Δρmax = 0.59 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	0.6421 (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*

	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)

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

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)

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) .