(E)-1-(2,4-Dinitro-phen-yl)-2-[1-(3-fluoro-phen-yl)ethyl-idene]hydrazine.

The mol-ecule of the title hydrazone derivative, C(14)H(11)FN(4)O(4), is nearly planar, with a dihedral angle between the benzene rings of 3.71 (7)°. The central ethyl-idenehydrazine N-N=C-C plane makes dihedral angles of 5.32 (10) and 9.02 (10)° with the 2,4-dinitro- and 3-fluoro-substituted benzene rings, respectively. An intra-molecular N-H⋯O bond generates an S(6) ring motif. In the crystal, mol-ecules are linked by weak C-H⋯O inter-actions into a sheet parallel to (10-1). The mol-ecules are further stacked along the a axis by π-π inter-actions with centroid-centroid distances of 3.6314 (9) and 3.7567 (10) Å. A C⋯F short contact [2.842 (3) Å] is observed. The 3-fluoro-phenyl group is disordered over two orientations with a site-occupancy ratio of 0.636 (3):0.364 (3).

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Chantrapromma et al. (2011 ▶); Fun et al. (2011 ▶, 2012 ▶); Nilwanna et al. (2011 ▶). For background to and the biological activity of hydro­zones, see: Cui et al. (2010 ▶); Gokce et al. (2009 ▶); Krishnamoorthy et al. (2011 ▶); Molyneux (2004 ▶); Wang et al. (2009 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C14H11FN4O4

M = 318.27

Monoclinic,

a = 7.0165 (6) Å

b = 13.3336 (11) Å

c = 14.4498 (12) Å

β = 94.791 (2)°

V = 1347.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 100 K

0.39 × 0.15 × 0.14 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.952, T max = 0.982

15079 measured reflections

3874 independent reflections

3126 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.155

S = 1.07

3874 reflections

223 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.70 e Å−3

Δρmin = −0.59 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681201937X/is5116sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201937X/is5116Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681201937X/is5116Isup3.cml

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

C14H11FN4O4	F(000) = 656
Mr = 318.27	Dx = 1.569 Mg m−3
Monoclinic, P21/c	Melting point = 503–504 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.0165 (6) Å	Cell parameters from 3874 reflections
b = 13.3336 (11) Å	θ = 2.1–30.0°
c = 14.4498 (12) Å	µ = 0.13 mm−1
β = 94.791 (2)°	T = 100 K
V = 1347.1 (2) Å3	Block, yellow
Z = 4	0.39 × 0.15 × 0.14 mm

Bruker APEX DUO CCD area-detector diffractometer	3874 independent reflections
Radiation source: sealed tube	3126 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.054
φ and ω scans	θmax = 30.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
Tmin = 0.952, Tmax = 0.982	k = −18→18
15079 measured reflections	l = −20→19

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0567P)2 + 0.806P] where P = (Fo2 + 2Fc2)/3
3874 reflections	(Δ/σ)max = 0.001
223 parameters	Δρmax = 0.70 e Å−3
2 restraints	Δρmin = −0.59 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.16769 (19)	0.27587 (9)	0.33374 (8)	0.0286 (3)
O2	0.2526 (2)	0.12572 (9)	0.37606 (9)	0.0362 (3)
O3	0.4548 (2)	0.04192 (10)	0.68409 (10)	0.0395 (3)
O4	0.5525 (2)	0.15695 (12)	0.78252 (10)	0.0421 (4)
N1	0.22627 (19)	0.52482 (9)	0.47367 (9)	0.0204 (3)
N2	0.2316 (2)	0.42615 (10)	0.44717 (9)	0.0211 (3)
H1N2	0.187 (4)	0.4037 (18)	0.3918 (17)	0.039 (6)*
N3	0.2368 (2)	0.21543 (10)	0.39303 (9)	0.0239 (3)
N4	0.4801 (2)	0.13015 (11)	0.70636 (10)	0.0283 (3)
C1	0.2965 (2)	0.35508 (11)	0.50920 (10)	0.0190 (3)
C2	0.2999 (2)	0.25164 (11)	0.48499 (10)	0.0197 (3)
C3	0.3613 (2)	0.17866 (11)	0.54990 (11)	0.0212 (3)
H3A	0.3624	0.1113	0.5332	0.025*
C4	0.4199 (2)	0.20773 (12)	0.63873 (11)	0.0224 (3)
C5	0.4229 (2)	0.30902 (13)	0.66526 (11)	0.0231 (3)
H5A	0.4656	0.3272	0.7256	0.028*
C6	0.3626 (2)	0.38075 (12)	0.60177 (10)	0.0210 (3)
H6A	0.3649	0.4478	0.6196	0.025*
C7	0.1518 (2)	0.58571 (11)	0.41102 (10)	0.0202 (3)
C8	0.1511 (2)	0.69296 (11)	0.43865 (11)	0.0205 (3)
C9	0.1014 (2)	0.76901 (13)	0.37412 (12)	0.0264 (3)
H9A	0.0644	0.7534	0.3125	0.032*
C10	0.1085 (3)	0.86754 (13)	0.40379 (13)	0.0332 (4)
H10A	0.0755	0.9175	0.3605	0.040*	0.636 (4)
F1A	0.2507 (3)	0.84685 (12)	0.64414 (10)	0.0370 (5)	0.636 (4)
C11	0.1615 (3)	0.89560 (13)	0.49351 (14)	0.0310 (4)
H11A	0.1654	0.9626	0.5115	0.037*
C12	0.2086 (2)	0.81953 (12)	0.55571 (10)	0.0277 (3)
H12A	0.2449	0.8363	0.6171	0.033*	0.364 (4)
F1B	0.0366 (5)	0.9380 (2)	0.3455 (2)	0.0441 (10)	0.364 (4)
C13	0.2046 (2)	0.71958 (11)	0.53113 (11)	0.0227 (3)
H13A	0.2369	0.6704	0.5753	0.027*
C14	0.0737 (3)	0.55223 (14)	0.31617 (11)	0.0284 (4)
H14A	−0.0124	0.4970	0.3219	0.043*
H14B	0.1771	0.5314	0.2811	0.043*
H14C	0.0064	0.6068	0.2848	0.043*

	U11	U22	U33	U12	U13	U23
O1	0.0396 (7)	0.0257 (6)	0.0197 (5)	0.0008 (5)	−0.0015 (5)	−0.0019 (4)
O2	0.0563 (9)	0.0211 (6)	0.0306 (6)	0.0018 (6)	0.0001 (6)	−0.0088 (5)
O3	0.0511 (9)	0.0265 (6)	0.0403 (7)	−0.0014 (6)	−0.0006 (6)	0.0095 (5)
O4	0.0501 (9)	0.0426 (8)	0.0307 (7)	0.0046 (7)	−0.0129 (6)	0.0045 (6)
N1	0.0226 (6)	0.0174 (6)	0.0214 (6)	−0.0015 (5)	0.0035 (5)	−0.0011 (5)
N2	0.0264 (7)	0.0184 (6)	0.0183 (6)	−0.0002 (5)	0.0016 (5)	−0.0019 (4)
N3	0.0285 (7)	0.0220 (6)	0.0212 (6)	−0.0015 (5)	0.0027 (5)	−0.0042 (5)
N4	0.0263 (7)	0.0300 (7)	0.0285 (7)	0.0008 (6)	0.0015 (6)	0.0062 (6)
C1	0.0179 (6)	0.0197 (6)	0.0198 (6)	−0.0015 (5)	0.0037 (5)	−0.0013 (5)
C2	0.0191 (7)	0.0213 (7)	0.0188 (6)	−0.0017 (5)	0.0029 (5)	−0.0025 (5)
C3	0.0196 (7)	0.0195 (6)	0.0248 (7)	−0.0017 (5)	0.0034 (5)	−0.0002 (5)
C4	0.0192 (7)	0.0257 (7)	0.0223 (7)	−0.0008 (6)	0.0019 (5)	0.0039 (6)
C5	0.0205 (7)	0.0279 (8)	0.0207 (7)	−0.0027 (6)	0.0014 (5)	−0.0017 (5)
C6	0.0206 (7)	0.0218 (7)	0.0207 (7)	−0.0019 (5)	0.0013 (5)	−0.0033 (5)
C7	0.0197 (7)	0.0216 (7)	0.0197 (6)	0.0008 (5)	0.0037 (5)	−0.0017 (5)
C8	0.0184 (7)	0.0201 (7)	0.0233 (7)	0.0005 (5)	0.0029 (5)	0.0011 (5)
C9	0.0234 (7)	0.0276 (8)	0.0278 (8)	0.0030 (6)	0.0003 (6)	0.0044 (6)
C10	0.0272 (8)	0.0261 (8)	0.0454 (10)	0.0061 (7)	−0.0008 (7)	0.0070 (7)
F1A	0.0497 (11)	0.0250 (8)	0.0343 (9)	0.0030 (7)	−0.0078 (8)	−0.0097 (6)
C11	0.0257 (8)	0.0192 (7)	0.0478 (10)	0.0025 (6)	0.0020 (7)	−0.0024 (7)
C12	0.0258 (8)	0.0222 (7)	0.0353 (9)	−0.0019 (6)	0.0031 (7)	−0.0064 (6)
F1B	0.059 (2)	0.0236 (15)	0.048 (2)	0.0038 (14)	−0.0056 (16)	0.0141 (13)
C13	0.0247 (7)	0.0192 (7)	0.0241 (7)	−0.0009 (6)	0.0023 (6)	−0.0003 (5)
C14	0.0348 (9)	0.0297 (8)	0.0203 (7)	0.0060 (7)	−0.0011 (6)	−0.0033 (6)

O1—N3	1.2447 (18)	C7—C8	1.485 (2)
O2—N3	1.2279 (18)	C7—C14	1.501 (2)
O3—N4	1.229 (2)	C8—C9	1.402 (2)
O4—N4	1.226 (2)	C8—C13	1.403 (2)
N1—C7	1.293 (2)	C9—C10	1.381 (3)
N1—N2	1.3716 (18)	C9—H9A	0.9300
N2—C1	1.357 (2)	C10—F1B	1.3322 (10)
N2—H1N2	0.89 (2)	C10—C11	1.371 (3)
N3—C2	1.4478 (19)	C10—H10A	0.9300
N4—C4	1.461 (2)	F1A—C12	1.3377 (10)
C1—C6	1.420 (2)	C11—C12	1.377 (2)
C1—C2	1.424 (2)	C11—H11A	0.9300
C2—C3	1.395 (2)	C12—C13	1.379 (2)
C3—C4	1.371 (2)	C12—H12A	0.9300
C3—H3A	0.9300	C13—H13A	0.9300
C4—C5	1.404 (2)	C14—H14A	0.9600
C5—C6	1.368 (2)	C14—H14B	0.9600
C5—H5A	0.9300	C14—H14C	0.9600
C6—H6A	0.9300
C7—N1—N2	115.18 (13)	C8—C7—C14	121.53 (14)
C1—N2—N1	120.07 (13)	C9—C8—C13	118.84 (15)
C1—N2—H1N2	115.7 (16)	C9—C8—C7	121.61 (14)
N1—N2—H1N2	124.1 (16)	C13—C8—C7	119.55 (13)
O2—N3—O1	121.97 (14)	C10—C9—C8	118.75 (16)
O2—N3—C2	118.85 (14)	C10—C9—H9A	120.6
O1—N3—C2	119.18 (13)	C8—C9—H9A	120.6
O4—N4—O3	123.64 (15)	F1B—C10—C11	117.6 (2)
O4—N4—C4	117.97 (15)	F1B—C10—C9	118.2 (2)
O3—N4—C4	118.39 (15)	C11—C10—C9	123.58 (15)
N2—C1—C6	121.26 (14)	C11—C10—H10A	118.2
N2—C1—C2	121.73 (13)	C9—C10—H10A	118.2
C6—C1—C2	117.01 (13)	C10—C11—C12	116.59 (15)
C3—C2—C1	121.42 (14)	C10—C11—H11A	121.7
C3—C2—N3	115.98 (13)	C12—C11—H11A	121.7
C1—C2—N3	122.59 (13)	F1A—C12—C11	116.40 (16)
C4—C3—C2	118.96 (14)	F1A—C12—C13	120.49 (16)
C4—C3—H3A	120.5	C11—C12—C13	123.03 (14)
C2—C3—H3A	120.5	C11—C12—H12A	118.5
C3—C4—C5	121.62 (14)	C13—C12—H12A	118.5
C3—C4—N4	118.27 (14)	C12—C13—C8	119.20 (14)
C5—C4—N4	120.11 (14)	C12—C13—H13A	120.4
C6—C5—C4	119.53 (14)	C8—C13—H13A	120.4
C6—C5—H5A	120.2	C7—C14—H14A	109.5
C4—C5—H5A	120.2	C7—C14—H14B	109.5
C5—C6—C1	121.44 (14)	H14A—C14—H14B	109.5
C5—C6—H6A	119.3	C7—C14—H14C	109.5
C1—C6—H6A	119.3	H14A—C14—H14C	109.5
N1—C7—C8	115.24 (13)	H14B—C14—H14C	109.5
N1—C7—C14	123.22 (14)
C7—N1—N2—C1	−176.16 (14)	C4—C5—C6—C1	0.1 (2)
N1—N2—C1—C6	−0.9 (2)	N2—C1—C6—C5	178.07 (14)
N1—N2—C1—C2	178.42 (13)	C2—C1—C6—C5	−1.3 (2)
N2—C1—C2—C3	−178.00 (14)	N2—N1—C7—C8	−178.27 (12)
C6—C1—C2—C3	1.4 (2)	N2—N1—C7—C14	0.8 (2)
N2—C1—C2—N3	0.7 (2)	N1—C7—C8—C9	170.45 (14)
C6—C1—C2—N3	−179.90 (13)	C14—C7—C8—C9	−8.6 (2)
O2—N3—C2—C3	−4.7 (2)	N1—C7—C8—C13	−8.4 (2)
O1—N3—C2—C3	174.98 (14)	C14—C7—C8—C13	172.56 (15)
O2—N3—C2—C1	176.52 (15)	C13—C8—C9—C10	0.5 (2)
O1—N3—C2—C1	−3.8 (2)	C7—C8—C9—C10	−178.31 (15)
C1—C2—C3—C4	−0.2 (2)	C8—C9—C10—F1B	−171.0 (2)
N3—C2—C3—C4	−178.96 (13)	C8—C9—C10—C11	−0.1 (3)
C2—C3—C4—C5	−1.2 (2)	F1B—C10—C11—C12	170.7 (2)
C2—C3—C4—N4	178.77 (13)	C9—C10—C11—C12	−0.3 (3)
O4—N4—C4—C3	171.96 (16)	C10—C11—C12—F1A	−176.64 (18)
O3—N4—C4—C3	−8.3 (2)	C10—C11—C12—C13	0.1 (3)
O4—N4—C4—C5	−8.1 (2)	F1A—C12—C13—C8	176.95 (17)
O3—N4—C4—C5	171.62 (16)	C11—C12—C13—C8	0.3 (3)
C3—C4—C5—C6	1.3 (2)	C9—C8—C13—C12	−0.6 (2)
N4—C4—C5—C6	−178.70 (14)	C7—C8—C13—C12	178.24 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O1	0.89 (2)	1.90 (2)	2.6038 (18)	135 (2)
C9—H9A···O1i	0.93	2.58	3.413 (2)	150
C13—H13A···O4ii	0.93	2.44	3.176 (2)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O1	0.89 (2)	1.90 (2)	2.6038 (18)	135 (2)
C9—H9A⋯O1i	0.93	2.58	3.413 (2)	150
C13—H13A⋯O4ii	0.93	2.44	3.176 (2)	137

Symmetry codes: (i) ; (ii) .