N'-[(E)-1-(2-Fluoro-phen-yl)ethyl-idene]pyridine-4-carbohydrazide.

The title compound, C14H12FN3O, adopts an E conformation with respect to the azomethine bond. The pyridyl and fluoro-benzene rings make dihedral angles of 38.58 (6) and 41.61 (5)° respectively with the central C(=O)N2CC unit, resulting in a non-planar mol-ecule. The inter-molecular inter-actions comprise two classical N-H⋯O and N-H⋯N hydrogen bonds and four non-classical C-H⋯O and C-H⋯F hydrogen bonds. These inter-actions are augmented by a weak π-π inter-action between the benzene and pyridyl rings of neighbouring mol-ecules, with a centroid-centroid distance of 3.9226 (10) Å. This leads to a three-dimensional supra-molecular assembly in the crystal system. The F atom is disordered over two sites in a 0.559 (3): 0.441 (3) ratio, through a 180° rotation of the fluoro-benzene ring.

Related literature

For biological properties of hydrazones, see: Kahwa et al. (1986 ▶); Santos et al. (2001 ▶); Rollas & Kucukguzel (2007 ▶). For the synthesis of related compounds, see: Mangalam & Kurup (2011 ▶). For related structures, see: Sreeja et al. (2013 ▶, 2014 ▶).

Experimental

Crystal data

C14H12FN3O

M = 257.27

Monoclinic,

a = 8.2649 (6) Å

b = 19.2127 (14) Å

c = 8.0554 (5) Å

β = 99.244 (3)°

V = 1262.51 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.35 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.965, T max = 0.976

9610 measured reflections

3137 independent reflections

2262 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.152

S = 1.04

3113 reflections

179 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.21 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/S1600536814007545/fj2669sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814007545/fj2669Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814007545/fj2669Isup3.cml

CCDC reference: 995414

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

C14H12FN3O	F(000) = 536
Mr = 257.27	Dx = 1.354 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3938 reflections
a = 8.2649 (6) Å	θ = 2.5–28.2°
b = 19.2127 (14) Å	µ = 0.10 mm−1
c = 8.0554 (5) Å	T = 296 K
β = 99.244 (3)°	Block, colorless
V = 1262.51 (15) Å3	0.35 × 0.30 × 0.25 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	3137 independent reflections
Radiation source: fine-focus sealed tube	2262 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
Detector resolution: 8.33 pixels mm-1	θmax = 28.3°, θmin = 2.5°
ω and φ scan	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −25→25
Tmin = 0.965, Tmax = 0.976	l = −6→10
9610 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)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.152	w = 1/[σ2(Fo2) + (0.0851P)2 + 0.152P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
3113 reflections	Δρmax = 0.24 e Å−3
179 parameters	Δρmin = −0.21 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: 0.091 (9)

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)
F1	1.2954 (2)	0.23496 (9)	0.7843 (2)	0.0687 (7)	0.559 (3)
F1B	1.1039 (4)	0.01885 (12)	0.6026 (3)	0.0868 (11)	0.441 (3)
O1	0.85862 (15)	0.33623 (6)	0.55332 (12)	0.0580 (3)
N1	1.02285 (13)	0.21790 (6)	0.53744 (12)	0.0407 (3)
N2	0.93699 (14)	0.24882 (6)	0.39513 (13)	0.0412 (3)
N3	0.5574 (2)	0.40011 (8)	−0.01035 (19)	0.0675 (4)
C1	1.27207 (19)	0.16966 (8)	0.80753 (18)	0.0496 (4)
H1	1.2797	0.2175	0.7923	0.059*	0.441 (3)
C2	1.3481 (2)	0.14096 (11)	0.9566 (2)	0.0674 (5)
H2	1.4056	0.1691	1.0399	0.081*
C3	1.3382 (3)	0.07038 (11)	0.9809 (2)	0.0726 (5)
H3	1.3889	0.0505	1.0811	0.087*
C4	1.2544 (3)	0.02970 (10)	0.8585 (3)	0.0734 (5)
H4	1.2473	−0.0181	0.8746	0.088*
C5	1.17979 (10)	0.05957 (4)	0.71021 (9)	0.0592 (4)
H5	1.1236	0.0310	0.6271	0.071*	0.559 (3)
C6	1.18520 (10)	0.13048 (4)	0.68017 (9)	0.0411 (3)
C7	1.10140 (10)	0.16188 (4)	0.52091 (9)	0.0399 (3)
C8	1.11560 (10)	0.12603 (4)	0.35878 (9)	0.0566 (4)
H8A	1.0211	0.0972	0.3257	0.085*
H8B	1.2126	0.0977	0.3735	0.085*
H8C	1.1222	0.1602	0.2732	0.085*
C9	0.85653 (17)	0.30834 (7)	0.41681 (15)	0.0409 (3)
C10	0.75600 (16)	0.33873 (7)	0.26301 (16)	0.0390 (3)
C11	0.7454 (2)	0.40996 (8)	0.2466 (2)	0.0546 (4)
H11	0.8047	0.4389	0.3269	0.066*
C12	0.6454 (2)	0.43775 (9)	0.1093 (2)	0.0676 (5)
H12	0.6392	0.4860	0.1000	0.081*
C13	0.5681 (2)	0.33184 (9)	0.0080 (2)	0.0604 (4)
H13	0.5069	0.3043	−0.0741	0.073*
C14	0.66414 (18)	0.29849 (8)	0.14078 (18)	0.0476 (3)
H14	0.6667	0.2502	0.1475	0.057*
H2'	0.944 (2)	0.2338 (8)	0.2948 (14)	0.053 (4)*

	U11	U22	U33	U12	U13	U23
F1	0.0844 (14)	0.0480 (10)	0.0645 (11)	−0.0090 (8)	−0.0157 (9)	−0.0032 (8)
F1B	0.129 (3)	0.0477 (14)	0.0729 (16)	−0.0225 (13)	−0.0185 (15)	0.0026 (11)
O1	0.0791 (8)	0.0563 (7)	0.0350 (5)	0.0115 (5)	−0.0015 (5)	−0.0073 (4)
N1	0.0442 (6)	0.0490 (6)	0.0280 (5)	0.0044 (5)	0.0026 (4)	0.0053 (5)
N2	0.0477 (7)	0.0498 (7)	0.0248 (5)	0.0072 (5)	0.0021 (4)	0.0029 (4)
N3	0.0639 (9)	0.0691 (9)	0.0618 (8)	0.0087 (7)	−0.0132 (7)	0.0126 (7)
C1	0.0514 (8)	0.0522 (8)	0.0421 (7)	0.0001 (6)	−0.0015 (6)	0.0027 (6)
C2	0.0646 (11)	0.0874 (13)	0.0435 (8)	−0.0005 (9)	−0.0116 (7)	0.0025 (8)
C3	0.0748 (12)	0.0848 (13)	0.0540 (10)	0.0174 (10)	−0.0023 (9)	0.0261 (9)
C4	0.0912 (14)	0.0584 (10)	0.0680 (11)	0.0085 (9)	0.0046 (10)	0.0226 (9)
C5	0.0708 (11)	0.0504 (9)	0.0540 (9)	−0.0012 (8)	0.0025 (8)	0.0085 (7)
C6	0.0409 (7)	0.0462 (7)	0.0356 (6)	0.0027 (6)	0.0043 (5)	0.0051 (5)
C7	0.0413 (7)	0.0444 (7)	0.0328 (6)	−0.0021 (5)	0.0021 (5)	0.0031 (5)
C8	0.0755 (11)	0.0520 (8)	0.0381 (7)	0.0112 (8)	−0.0038 (7)	−0.0036 (6)
C9	0.0458 (7)	0.0446 (7)	0.0307 (6)	−0.0009 (5)	0.0017 (5)	0.0009 (5)
C10	0.0393 (7)	0.0440 (7)	0.0334 (6)	0.0040 (5)	0.0050 (5)	0.0009 (5)
C11	0.0611 (10)	0.0434 (8)	0.0539 (9)	−0.0009 (6)	−0.0071 (7)	0.0002 (6)
C12	0.0733 (12)	0.0476 (9)	0.0741 (11)	0.0041 (8)	−0.0117 (9)	0.0125 (8)
C13	0.0566 (9)	0.0658 (10)	0.0514 (9)	0.0039 (8)	−0.0139 (7)	−0.0045 (8)
C14	0.0492 (8)	0.0455 (7)	0.0452 (7)	0.0031 (6)	−0.0013 (6)	−0.0030 (6)

F1—C1	1.288 (2)	C3—C4	1.358 (3)
F1B—C5	1.258 (2)	C4—C5	1.3782 (19)
O1—C9	1.2208 (16)	C5—C6	1.3856
N1—C7	1.2748 (13)	C6—C7	1.4846
N1—N2	1.3818 (15)	C7—C8	1.4977
N2—C9	1.3483 (18)	C9—C10	1.4951 (18)
N3—C13	1.321 (2)	C10—C11	1.376 (2)
N3—C12	1.325 (2)	C10—C14	1.380 (2)
C1—C6	1.3777 (16)	C11—C12	1.378 (2)
C1—C2	1.378 (2)	C13—C14	1.383 (2)
C2—C3	1.374 (3)
C7—N1—N2	118.60 (9)	C5—C6—C7	121.8
C9—N2—N1	117.10 (10)	N1—C7—C6	115.31 (5)
C13—N3—C12	116.19 (14)	N1—C7—C8	126.29 (5)
F1—C1—C6	119.78 (13)	C6—C7—C8	118.4
F1—C1—C2	117.28 (16)	O1—C9—N2	123.57 (12)
C6—C1—C2	122.72 (15)	O1—C9—C10	120.04 (12)
C3—C2—C1	119.32 (17)	N2—C9—C10	116.35 (11)
C4—C3—C2	119.98 (16)	C11—C10—C14	118.00 (13)
C3—C4—C5	119.64 (16)	C11—C10—C9	119.08 (12)
F1B—C5—C4	116.26 (16)	C14—C10—C9	122.78 (12)
F1B—C5—C6	121.17 (12)	C10—C11—C12	118.87 (15)
C4—C5—C6	122.56 (10)	N3—C12—C11	124.12 (16)
C1—C6—C5	115.77 (7)	N3—C13—C14	124.51 (15)
C1—C6—C7	122.44 (7)	C10—C14—C13	118.29 (14)
C7—N1—N2—C9	−179.39 (11)	C5—C6—C7—N1	136.27 (7)
F1—C1—C2—C3	−174.5 (2)	C1—C6—C7—C8	136.79 (9)
C6—C1—C2—C3	0.1 (3)	C5—C6—C7—C8	−43.6
C1—C2—C3—C4	0.1 (3)	N1—N2—C9—O1	1.4 (2)
C2—C3—C4—C5	0.1 (3)	N1—N2—C9—C10	−176.38 (11)
C3—C4—C5—F1B	−179.8 (2)	O1—C9—C10—C11	37.3 (2)
C3—C4—C5—C6	−0.6 (2)	N2—C9—C10—C11	−144.86 (14)
F1—C1—C6—C5	173.92 (14)	O1—C9—C10—C14	−138.39 (15)
C2—C1—C6—C5	−0.56 (18)	N2—C9—C10—C14	39.45 (18)
F1—C1—C6—C7	−6.5 (2)	C14—C10—C11—C12	−0.5 (2)
C2—C1—C6—C7	179.04 (12)	C9—C10—C11—C12	−176.42 (15)
F1B—C5—C6—C1	180.0 (2)	C13—N3—C12—C11	0.6 (3)
C4—C5—C6—C1	0.80 (13)	C10—C11—C12—N3	−0.1 (3)
F1B—C5—C6—C7	0.39 (19)	C12—N3—C13—C14	−0.4 (3)
C4—C5—C6—C7	−178.81 (11)	C11—C10—C14—C13	0.7 (2)
N2—N1—C7—C6	−177.77 (8)	C9—C10—C14—C13	176.42 (13)
N2—N1—C7—C8	2.13 (14)	N3—C13—C14—C10	−0.2 (3)
C1—C6—C7—N1	−43.30 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2′···N1i	0.87 (1)	2.45 (1)	3.1420 (15)	137 (1)
N2—H2′···O1i	0.87 (1)	2.38 (1)	3.1777 (15)	154 (2)
C8—H8C···F1i	0.96	2.46	3.1603 (19)	129
C8—H8C···O1i	0.96	2.58	3.0680 (13)	112
C13—H13···F1ii	0.93	2.34	3.238 (2)	161
C14—H14···O1i	0.93	2.50	3.1849 (19)	131

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2′⋯N1i	0.87 (1)	2.45 (1)	3.1420 (15)	137 (1)
N2—H2′⋯O1i	0.87 (1)	2.38 (1)	3.1777 (15)	154 (2)
C8—H8C⋯F1i	0.96	2.46	3.1603 (19)	129
C8—H8C⋯O1i	0.96	2.58	3.0680 (13)	112
C13—H13⋯F1ii	0.93	2.34	3.238 (2)	161
C14—H14⋯O1i	0.93	2.50	3.1849 (19)	131

Symmetry codes: (i) ; (ii) .