N'-[(1E)-1-(2-Fluoro-phen-yl)ethyl-idene]pyridine-3-carbohydrazide.

The title compound, C14H12FN3O, adopts an E conformation with respect to the azomethine double bond whereas the N and methyl C atoms are in a Z conformation with respect to the same bond. The ketonic O and azomethine N atoms are cis to each other. The non-planar mol-ecule [the dihedral angle between the benzene rings is 7.44 (11)°] exists in an amido form with a C=O bond length of 1.221 (2) Å. In the crystal, a bifurcated N-H⋯(O,N) hydrogen bond is formed between the amide H atom and the keto O and imine N atoms of an adjacent mol-ecule, leading to the formation of chains propagating along the b-axis direction. Through a 180° rotation of the fluoro-phenyl ring, the F atom is disordered over two sites with an occupancy ratio of 0.632 (4):0.368 (4).

Related literature

For biological properties of hydrazones, see: Sreeja et al. (2004 ▶); Ajani et al. (2010 ▶). For the synthesis of related compounds and for related work, see: Mangalam & Kurup (2011 ▶). For a related structure, see: Nair et al. (2012 ▶). For di­fluoro­phenyl compounds, see: Nayak et al. (2012 ▶).

Experimental

Crystal data

C14H12FN3O

M = 257.27

Orthorhombic,

a = 18.926 (3) Å

b = 8.0486 (9) Å

c = 16.337 (3) Å

V = 2488.6 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.50 × 0.25 × 0.20 mm

Data collection

Bruker ApexII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.952, T max = 0.980

19111 measured reflections

3009 independent reflections

1755 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.161

S = 1.01

2999 reflections

188 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 2010 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) Global, I. DOI: 10.1107/S1600536813035009/zl2571sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813035009/zl2571Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813035009/zl2571Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C14H12FN3O	F(000) = 1072
Mr = 257.27	Dx = 1.373 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 2433 reflections
a = 18.926 (3) Å	θ = 2.5–22.6°
b = 8.0486 (9) Å	µ = 0.10 mm−1
c = 16.337 (3) Å	T = 296 K
V = 2488.6 (7) Å3	Needle, colourless
Z = 8	0.50 × 0.25 × 0.20 mm

Bruker ApexII CCD diffractometer	3009 independent reflections
Radiation source: fine-focus sealed tube	1755 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.056
Detector resolution: 8.33 pixels mm-1	θmax = 28.0°, θmin = 2.5°
ω and φ scan	h = −24→25
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −10→10
Tmin = 0.952, Tmax = 0.980	l = −21→21
19111 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.161	w = 1/[σ2(Fo2) + (0.0806P)2 + 0.3159P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
2999 reflections	Δρmax = 0.29 e Å−3
188 parameters	Δρmin = −0.22 e Å−3
1 restraint	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0048 (13)

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	Occ. (<1)
O1	0.16369 (8)	1.08491 (17)	0.92895 (10)	0.0564 (5)
N1	0.28297 (9)	1.04304 (17)	1.01301 (10)	0.0379 (4)
N2	0.25250 (9)	0.91485 (18)	0.96943 (10)	0.0384 (4)
N3	0.05671 (13)	0.6619 (3)	0.84194 (16)	0.0827 (8)
F1	0.26405 (10)	1.2489 (2)	1.14815 (13)	0.0557 (7)	0.632 (4)
F1B	0.4820 (2)	1.1072 (5)	1.0493 (3)	0.0761 (16)	0.368 (4)
C6	0.44269 (12)	1.1919 (3)	1.09238 (15)	0.0533 (6)
H6	0.4719	1.1180	1.0646	0.064*	0.632 (4)
C2	0.33059 (12)	1.2728 (2)	1.13857 (13)	0.0447 (5)
H2	0.2822	1.2548	1.1430	0.054*	0.368 (4)
C5	0.47260 (14)	1.3288 (3)	1.12899 (17)	0.0672 (7)
H5	0.5211	1.3466	1.1259	0.081*
C4	0.43039 (15)	1.4381 (3)	1.16994 (18)	0.0717 (8)
H4	0.4501	1.5317	1.1943	0.086*
C3	0.35920 (15)	1.4110 (3)	1.17547 (16)	0.0628 (7)
H3	0.3305	1.4850	1.2038	0.075*
C1	0.37091 (10)	1.1596 (2)	1.09523 (12)	0.0378 (5)
C7	0.33978 (10)	1.0136 (2)	1.05237 (12)	0.0371 (4)
C8	0.37763 (12)	0.8504 (2)	1.05763 (16)	0.0551 (6)
H8A	0.3441	0.7635	1.0681	0.083*
H8B	0.4116	0.8544	1.1013	0.083*
H8C	0.4015	0.8289	1.0069	0.083*
C9	0.19212 (11)	0.9487 (2)	0.92867 (12)	0.0386 (5)
C10	0.16141 (11)	0.8085 (2)	0.88031 (11)	0.0374 (5)
C11	0.08970 (12)	0.7822 (3)	0.88351 (15)	0.0545 (6)
H11	0.0626	0.8519	0.9164	0.065*
C12	0.09829 (18)	0.5653 (4)	0.79477 (19)	0.0829 (9)
H12	0.0769	0.4795	0.7658	0.099*
C13	0.16935 (14)	0.5845 (3)	0.78654 (15)	0.0601 (6)
H13	0.1954	0.5155	0.7522	0.072*
C14	0.20124 (11)	0.7080 (2)	0.83009 (13)	0.0460 (5)
H14	0.2498	0.7242	0.8259	0.055*
H2'	0.2692 (10)	0.8137 (15)	0.9722 (14)	0.051 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0594 (10)	0.0345 (8)	0.0752 (12)	0.0116 (7)	−0.0128 (8)	−0.0112 (7)
N1	0.0495 (10)	0.0247 (7)	0.0393 (9)	−0.0057 (7)	−0.0023 (8)	−0.0022 (6)
N2	0.0499 (10)	0.0222 (7)	0.0431 (9)	−0.0004 (7)	−0.0070 (8)	−0.0031 (6)
N3	0.0724 (15)	0.0924 (17)	0.0834 (18)	−0.0245 (13)	−0.0065 (13)	−0.0225 (14)
F1	0.0434 (13)	0.0599 (13)	0.0639 (14)	0.0009 (9)	0.0058 (9)	−0.0186 (10)
F1B	0.053 (2)	0.072 (3)	0.103 (3)	−0.0039 (19)	0.026 (2)	−0.023 (2)
C6	0.0507 (13)	0.0508 (13)	0.0583 (14)	−0.0085 (11)	0.0020 (11)	−0.0027 (11)
C2	0.0508 (13)	0.0406 (11)	0.0426 (11)	0.0015 (9)	−0.0056 (10)	−0.0032 (8)
C5	0.0579 (15)	0.0559 (14)	0.088 (2)	−0.0180 (12)	−0.0146 (14)	−0.0041 (13)
C4	0.0798 (19)	0.0495 (14)	0.086 (2)	−0.0141 (13)	−0.0316 (16)	−0.0113 (13)
C3	0.0851 (19)	0.0412 (12)	0.0621 (15)	0.0095 (12)	−0.0157 (13)	−0.0182 (11)
C1	0.0479 (12)	0.0306 (9)	0.0347 (10)	−0.0059 (8)	−0.0019 (9)	0.0009 (7)
C7	0.0423 (11)	0.0307 (9)	0.0384 (10)	−0.0041 (8)	0.0034 (9)	−0.0009 (7)
C8	0.0528 (13)	0.0374 (11)	0.0751 (16)	0.0050 (10)	−0.0097 (12)	−0.0117 (10)
C9	0.0479 (11)	0.0262 (9)	0.0417 (11)	−0.0001 (8)	−0.0002 (9)	−0.0021 (7)
C10	0.0449 (11)	0.0305 (9)	0.0368 (10)	0.0001 (8)	−0.0059 (8)	0.0018 (7)
C11	0.0489 (13)	0.0561 (13)	0.0584 (15)	−0.0020 (11)	−0.0031 (11)	−0.0108 (11)
C12	0.106 (2)	0.0739 (18)	0.0687 (18)	−0.0330 (18)	−0.0120 (17)	−0.0239 (15)
C13	0.0832 (18)	0.0477 (12)	0.0492 (13)	−0.0034 (12)	0.0003 (12)	−0.0194 (10)
C14	0.0496 (12)	0.0428 (11)	0.0457 (12)	−0.0013 (9)	−0.0019 (10)	−0.0070 (9)

O1—C9	1.221 (2)	C4—C3	1.368 (4)
N1—C7	1.275 (2)	C4—H4	0.9300
N1—N2	1.380 (2)	C3—H3	0.9300
N2—C9	1.350 (3)	C1—C7	1.490 (3)
N2—H2'	0.875 (9)	C7—C8	1.498 (3)
N3—C11	1.338 (3)	C8—H8A	0.9600
N3—C12	1.348 (4)	C8—H8B	0.9600
F1—C2	1.284 (3)	C8—H8C	0.9600
F1B—C6	1.230 (4)	C9—C10	1.495 (3)
C6—C5	1.376 (3)	C10—C11	1.375 (3)
C6—C1	1.384 (3)	C10—C14	1.377 (3)
C6—H6	0.9300	C11—H11	0.9300
C2—C3	1.376 (3)	C12—C13	1.360 (4)
C2—C1	1.383 (3)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.363 (3)
C5—C4	1.364 (4)	C13—H13	0.9300
C5—H5	0.9300	C14—H14	0.9300
C7—N1—N2	118.26 (15)	C6—C1—C7	121.36 (18)
C9—N2—N1	117.22 (15)	N1—C7—C1	115.06 (16)
C9—N2—H2'	121.3 (14)	N1—C7—C8	126.53 (17)
N1—N2—H2'	121.2 (14)	C1—C7—C8	118.40 (17)
C11—N3—C12	115.8 (2)	C7—C8—H8A	109.5
F1B—C6—C5	116.3 (3)	C7—C8—H8B	109.5
F1B—C6—C1	120.6 (3)	H8A—C8—H8B	109.5
C5—C6—C1	122.7 (2)	C7—C8—H8C	109.5
F1B—C6—H6	6.8	H8A—C8—H8C	109.5
C5—C6—H6	118.7	H8B—C8—H8C	109.5
C1—C6—H6	118.7	O1—C9—N2	123.50 (17)
F1—C2—C3	117.0 (2)	O1—C9—C10	120.55 (18)
F1—C2—C1	120.32 (19)	N2—C9—C10	115.94 (15)
C3—C2—C1	122.6 (2)	C11—C10—C14	118.21 (19)
F1—C2—H2	2.6	C11—C10—C9	118.68 (18)
C3—C2—H2	118.7	C14—C10—C9	123.06 (18)
C1—C2—H2	118.7	N3—C11—C10	123.6 (2)
C4—C5—C6	119.3 (2)	N3—C11—H11	118.2
C4—C5—H5	120.4	C10—C11—H11	118.2
C6—C5—H5	120.4	N3—C12—C13	124.6 (2)
C5—C4—C3	120.4 (2)	N3—C12—H12	117.7
C5—C4—H4	119.8	C13—C12—H12	117.7
C3—C4—H4	119.8	C12—C13—C14	118.0 (2)
C4—C3—C2	119.2 (2)	C12—C13—H13	121.0
C4—C3—H3	120.4	C14—C13—H13	121.0
C2—C3—H3	120.4	C13—C14—C10	119.8 (2)
C2—C1—C6	115.79 (18)	C13—C14—H14	120.1
C2—C1—C7	122.84 (18)	C10—C14—H14	120.1
C7—N1—N2—C9	179.58 (18)	C6—C1—C7—N1	−135.9 (2)
F1B—C6—C5—C4	172.7 (4)	C2—C1—C7—C8	−138.5 (2)
C1—C6—C5—C4	0.0 (4)	C6—C1—C7—C8	42.9 (3)
C6—C5—C4—C3	0.8 (4)	N1—N2—C9—O1	−0.3 (3)
C5—C4—C3—C2	−0.6 (4)	N1—N2—C9—C10	178.48 (16)
F1—C2—C3—C4	177.3 (2)	O1—C9—C10—C11	−44.3 (3)
C1—C2—C3—C4	−0.5 (4)	N2—C9—C10—C11	136.9 (2)
F1—C2—C1—C6	−176.5 (2)	O1—C9—C10—C14	133.2 (2)
C3—C2—C1—C6	1.2 (3)	N2—C9—C10—C14	−45.7 (3)
F1—C2—C1—C7	4.8 (3)	C12—N3—C11—C10	−0.5 (4)
C3—C2—C1—C7	−177.5 (2)	C14—C10—C11—N3	1.6 (3)
F1B—C6—C1—C2	−173.4 (3)	C9—C10—C11—N3	179.1 (2)
C5—C6—C1—C2	−1.0 (3)	C11—N3—C12—C13	−1.0 (5)
F1B—C6—C1—C7	5.3 (4)	N3—C12—C13—C14	1.3 (5)
C5—C6—C1—C7	177.7 (2)	C12—C13—C14—C10	−0.1 (4)
N2—N1—C7—C1	177.76 (16)	C11—C10—C14—C13	−1.2 (3)
N2—N1—C7—C8	−0.9 (3)	C9—C10—C14—C13	−178.7 (2)
C2—C1—C7—N1	42.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2′···O1i	0.88 (1)	2.35 (1)	3.163 (2)	156 (2)
N2—H2′···N1i	0.88 (1)	2.48 (2)	3.148 (2)	133 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2′⋯O1i	0.88 (1)	2.35 (1)	3.163 (2)	156 (2)
N2—H2′⋯N1i	0.88 (1)	2.48 (2)	3.148 (2)	133 (2)

Symmetry code: (i) .