N′-[(E)-(3-Fluoro­pyridin-2-yl)methyl­idene]pyridine-3-carbohydrazide dihydrate

Nair, Y.; Sithambaresan, M.; Nair, S.M.; Kurup, M.R.P.

doi:10.1107/S1600536814006072

organic compounds

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ISSN: 2056-9890

Volume 70| Part 4| April 2014| Pages o483-o484

doi:10.1107/S1600536814006072

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N′-[(E)-(3-Fluoropyridin-2-yl)methylidene]pyridine-3-carbohydrazide dihydrate

Yamuna Nair,^a M. Sithambaresan,^b ^* S. Muraleedharan Nair ^a and M. R. Prathapachandra Kurup ^c

^aDepartment of Chemical Ocenography, Cochin University of Science and Technology, Lakeside Campus, Kochi 682 016, India, ^bDepartment of Chemistry, Faculty of Science, Eastern University, Sri Lanka, Chenkalady, Sri Lanka, and ^cDepartment of Applied Chemistry, Cochin University of Science and Technology, Kochi 682 022, India
^*Correspondence e-mail: eesans@yahoo.com

(Received 5 March 2014; accepted 19 March 2014; online 26 March 2014)

The organic molecule in the title dihydrate, C₁₂H₉FN₄O·2H₂O, exists in the E conformation with respect to the azomethane C=N double bond. The molecule is approximately planar, with a maximum deviation of 0.117 (1) Å for the carbonyl O atom from the mean plane of the molecule. Both pyridine rings are essentially coplanar with the central C(=O)N₂C unit [dihedral angles = 1.99 (7) and 5.71 (8)°], exhibiting a significant difference in dihedral angles from its benzohydrazide analogue. The crystal packing features N—H⋯O, O—H⋯N and O—H⋯O hydrogen-bond interactions, which lead to the formation of a chain along the c-axis direction through one of the water molecules present, and these chains are stacked one over the other by means of π–π interactions [with centroid–centroid distances of 3.7099 (10) and 3.6322 (10) Å] between the aromatic rings in neighbouring antiparallel molecules, building a three-dimensional supramolecular network.

CCDC reference: 992525

Related literature

For the biological activity of carbohydrazide derivatives, see: Sreeja et al. (2004 ); Havanur et al. (2010 ); Despaigne et al. (2010 ). For the synthesis of related compounds, see: Kuriakose et al. (2007 ). For a related structure, see Nair et al. (2012 ).

Experimental

Crystal data

C₁₂H₉FN₄O·2H₂O
M_r = 280.26
Monoclinic, P 2₁ /c
a = 7.3023 (7) Å
b = 14.4031 (17) Å
c = 12.6422 (13) Å
β = 94.842 (3)°
V = 1324.9 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 K
0.41 × 0.21 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.963, T_max = 0.969
9779 measured reflections
3237 independent reflections
2339 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.149
S = 1.04
3237 reflections
202 parameters
7 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3′⋯O1S	0.88 (1)	2.04 (1)	2.8821 (19)	160 (2)
O1S—H1A⋯N4ⁱ	0.87 (1)	2.09 (1)	2.946 (2)	170 (3)
O2S—H2A⋯N1ⁱ	0.87 (1)	2.10 (1)	2.965 (2)	177 (2)
O2S—H2B⋯O1ⁱ	0.86 (1)	1.97 (1)	2.816 (2)	172 (2)
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

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 ).

Supporting information

CCDC reference: 992525

Crystal structure: contains datablocks Global, I. DOI: 10.1107/S1600536814006072/bv2232sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814006072/bv2232Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814006072/bv2232Isup3.cml

checkCIF report

Comment top

Carbohydrazides have attracted much attention for their excellent biological properties. Moreover, carbohydrazides derived from 2-acetylpyridine are known to inhibit the proliferation of tumour cells to a greater extent compared to standard anticancer agents (Havanur et al., 2010; Sreeja et al., 2004). In addition, metal complexes with carbohydrazides exhibit antimicrobial, DNA-binding and cytotoxic activities. It has also been shown that these metal complexes can be potent inhibitors of cell growth and DNA synthesis (Despaigne et al., 2010). We report herein the crystal structure of the title compound, a new carbohydrazide.

This molecule adopts an E configuration (Fig. 1) with respect to the C6=N2 bond and it exists in the amido form with a C7=O1 bond length of 1.2211 (18) Å which is very close to the reported C=O bond length of similar structure of benzene analogue (Nair et al., 2012). The O1 and N2 atoms are in a Z configuration with respect to C7–N3 having a tortional angle of -0.6 (3)°. The molecule is almost planar with maximum deviation of 0.117 (1) Å for the atom O1 from the mean plane of the molecule (r.m.s. deviation, 0.0513). The pyridyl ring having F atom is essentially coplanar with the central C(=O)N₂C unit (dihedral angle 5.71 (8)°), the other pyridyl ring exhibits a torsion angle of 1.99 (7)°.

Whilst one of the water molecules connects two adjacent molecules through two O–H···N and N–H···O H-bonding interactions with D···A distances of 2.946 (2) and 2.882 (1) Å respectively, the other water molecule forms two O–H···N and O–H···O H-bonds with D···A distances of 2.965 (2) and 2.816 (2) Å with the same molecule (Fig. 2, Table 1). One of the water molecules acts as both a hydrogen bond acceptor as well as a donor towards another carbohydrazide molecule while the other acts only as hydrogen bond donor. By means of these interactions the molecules are chained through one of the water molecules to form infinite chains parallel to the c axis of the unit cell (Fig. 3). These parallel chains are stacked one over the other by means of two π–π interactions between the two aromatic rings of the neighbouring anti parallel molecules (Fig. 4) with centeroid-centeroid distances of 3.7099 (10) and 3.6322 (10) Å. Fig. 5 shows the stacked packing of the molecules along a axis in the unit cell.

Related literature top

For the biological activity of carbohydrazide derivatives, see: Sreeja et al. (2004); Havanur et al. (2010); Despaigne et al. (2010). For the synthesis of related compounds, see: Kuriakose et al. (2007). For a related structure, see Nair et al. (2012).

Experimental top

The title compound was prepared by adapting a reported procedure (Kuriakose et al., 2007). A solution of 3-fluoropyridine-2-carbaldehyde (1.25 g,1 mmol) in ethanol (10 ml) was mixed with an ethanolic solution (10 ml) of pyridine-3-carbohydrazide (1.37 g,1 mmol). The mixture was boiled under reflux for 12 h after adding few drops of glacial acetic acid and then cooled to room temperature. Colorless needle shaped crystals, suitable for single-crystal analysis, were obtained after slow evaporation of the solution in air for a few days.

Computing details top

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 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. ORTEP diagram of N'-[(E)-(3-fluoropyridin-2-yl)methylidene]pyridine-3-carbohydrazide dihydrate with 50% probability ellipsoids.
	Fig. 2. Hydrogen-bonding interactions showing the interconnection of the molecules via one of the water molecules in the lattice.
	Fig. 3. Hydrogen-bonding interactions showing the chain progressing along c axis.
	Fig. 4. Hydrogen-bonding and π–π interactions in the lattice.
	Fig. 5. Packing diagram showing the stacked packing arrangement of the molecules along a axis.

N'-[(E)-(3-Fluoropyridin-2-yl)methylidene]pyridine-3-carbohydrazide dihydrate top

Crystal data top

C₁₂H₉FN₄O·2H₂O	F(000) = 584
M_r = 280.26	D_x = 1.405 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4225 reflections
a = 7.3023 (7) Å	θ = 2.8–28.0°
b = 14.4031 (17) Å	µ = 0.11 mm⁻¹
c = 12.6422 (13) Å	T = 296 K
β = 94.842 (3)°	Needle, colorless
V = 1324.9 (2) Å³	0.41 × 0.21 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	3237 independent reflections
Radiation source: fine-focus sealed tube	2339 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
Detector resolution: 8.33 pixels mm^-1	θ_max = 28.2°, θ_min = 2.8°
ω and ϕ scan	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −17→19
T_min = 0.963, T_max = 0.969	l = −16→16
9779 measured reflections

Refinement top

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) = 0.149	w = 1/[σ²(F_o²) + (0.0712P)² + 0.3471P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3237 reflections	Δρ_max = 0.29 e Å⁻³
202 parameters	Δρ_min = −0.20 e Å⁻³
7 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.079 (6)

Crystal data top

C₁₂H₉FN₄O·2H₂O	V = 1324.9 (2) Å³
M_r = 280.26	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.3023 (7) Å	µ = 0.11 mm⁻¹
b = 14.4031 (17) Å	T = 296 K
c = 12.6422 (13) Å	0.41 × 0.21 × 0.20 mm
β = 94.842 (3)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3237 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2339 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.969	R_int = 0.030
9779 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	7 restraints
wR(F²) = 0.149	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.29 e Å⁻³
3237 reflections	Δρ_min = −0.20 e Å⁻³
202 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O2S	0.5863 (3)	0.45901 (12)	0.25212 (11)	0.0835 (5)
F1	0.77433 (17)	1.26247 (8)	0.16447 (8)	0.0683 (4)
O1	0.7242 (2)	0.88186 (10)	−0.13894 (9)	0.0770 (5)
O1S	0.7875 (3)	0.96417 (11)	0.24957 (11)	0.0792 (5)
N1	0.60794 (18)	1.20176 (10)	−0.10083 (10)	0.0470 (3)
C6	0.7337 (2)	1.10213 (11)	0.04205 (11)	0.0427 (4)
H6	0.7710	1.0945	0.1137	0.051*
N2	0.73006 (18)	1.03335 (9)	−0.02053 (10)	0.0440 (3)
N4	0.8628 (2)	0.62144 (10)	−0.03962 (11)	0.0543 (4)
C1	0.5563 (2)	1.28602 (13)	−0.13628 (13)	0.0530 (4)
H1	0.5071	1.2915	−0.2063	0.064*
C2	0.5718 (2)	1.36560 (12)	−0.07482 (15)	0.0548 (4)
H2	0.5331	1.4226	−0.1031	0.066*
C3	0.6450 (3)	1.35901 (12)	0.02835 (14)	0.0540 (4)
H3	0.6583	1.4109	0.0721	0.065*
C4	0.6980 (2)	1.27194 (11)	0.06413 (12)	0.0455 (4)
C5	0.6785 (2)	1.19411 (10)	0.00027 (11)	0.0396 (3)
N3	0.78095 (19)	0.94872 (9)	0.02199 (10)	0.0435 (3)
C7	0.7743 (2)	0.87503 (11)	−0.04464 (11)	0.0452 (4)
C8	0.8311 (2)	0.78321 (10)	0.00146 (11)	0.0396 (3)
C9	0.8966 (2)	0.76657 (11)	0.10573 (12)	0.0475 (4)
H9	0.9101	0.8151	0.1543	0.057*
C10	0.9414 (2)	0.67696 (12)	0.13635 (13)	0.0514 (4)
H10	0.9836	0.6638	0.2062	0.062*
C11	0.9223 (2)	0.60731 (12)	0.06144 (14)	0.0530 (4)
H11	0.9528	0.5471	0.0828	0.064*
C12	0.8172 (2)	0.70823 (12)	−0.06745 (12)	0.0479 (4)
H12	0.7734	0.7191	−0.1376	0.057*
H3'	0.809 (3)	0.9462 (13)	0.0910 (8)	0.057 (5)*
H2A	0.597 (3)	0.4119 (11)	0.2949 (16)	0.088 (8)*
H1A	0.807 (4)	0.9453 (19)	0.3148 (10)	0.110 (9)*
H2B	0.623 (4)	0.5053 (11)	0.2904 (17)	0.097 (9)*
H1B	0.902 (2)	0.962 (3)	0.233 (3)	0.19 (2)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2S	0.1384 (15)	0.0589 (9)	0.0478 (7)	−0.0012 (9)	−0.0228 (8)	−0.0033 (7)
F1	0.1063 (9)	0.0553 (6)	0.0417 (5)	0.0069 (6)	−0.0038 (5)	−0.0027 (4)
O1	0.1404 (14)	0.0510 (8)	0.0373 (6)	0.0225 (8)	−0.0057 (7)	−0.0003 (5)
O1S	0.1276 (15)	0.0674 (9)	0.0409 (7)	0.0091 (9)	−0.0028 (8)	0.0039 (6)
N1	0.0501 (7)	0.0474 (8)	0.0426 (7)	0.0026 (6)	−0.0009 (5)	0.0049 (6)
C6	0.0482 (8)	0.0418 (8)	0.0377 (7)	0.0021 (6)	0.0007 (6)	0.0040 (6)
N2	0.0547 (8)	0.0379 (7)	0.0393 (6)	0.0069 (5)	0.0033 (5)	0.0047 (5)
N4	0.0634 (9)	0.0430 (8)	0.0545 (8)	0.0091 (6)	−0.0071 (6)	−0.0092 (6)
C1	0.0532 (10)	0.0578 (10)	0.0474 (8)	0.0067 (8)	0.0002 (7)	0.0133 (7)
C2	0.0565 (10)	0.0453 (9)	0.0638 (10)	0.0106 (7)	0.0123 (8)	0.0164 (8)
C3	0.0659 (11)	0.0395 (9)	0.0584 (10)	0.0046 (7)	0.0159 (8)	0.0007 (7)
C4	0.0525 (9)	0.0449 (8)	0.0397 (7)	0.0033 (7)	0.0069 (6)	0.0023 (6)
C5	0.0403 (8)	0.0389 (8)	0.0400 (7)	0.0023 (6)	0.0061 (6)	0.0042 (6)
N3	0.0568 (8)	0.0372 (7)	0.0360 (6)	0.0067 (5)	0.0011 (5)	0.0033 (5)
C7	0.0582 (9)	0.0418 (8)	0.0359 (7)	0.0072 (7)	0.0060 (6)	0.0005 (6)
C8	0.0404 (8)	0.0397 (8)	0.0390 (7)	0.0041 (6)	0.0048 (6)	−0.0008 (6)
C9	0.0596 (10)	0.0420 (8)	0.0406 (8)	0.0068 (7)	0.0021 (7)	−0.0035 (6)
C10	0.0610 (10)	0.0500 (9)	0.0419 (8)	0.0113 (7)	−0.0033 (7)	0.0036 (7)
C11	0.0577 (10)	0.0408 (9)	0.0589 (10)	0.0112 (7)	−0.0036 (8)	0.0016 (7)
C12	0.0540 (9)	0.0465 (9)	0.0417 (8)	0.0070 (7)	−0.0041 (6)	−0.0045 (6)

Geometric parameters (Å, º) top

O2S—H2A	0.866 (9)	C2—C3	1.371 (2)
O2S—H2B	0.855 (9)	C2—H2	0.9300
F1—C4	1.3486 (18)	C3—C4	1.377 (2)
O1—C7	1.2211 (18)	C3—H3	0.9300
O1S—H1A	0.869 (10)	C4—C5	1.382 (2)
O1S—H1B	0.881 (10)	N3—C7	1.3534 (19)
N1—C1	1.337 (2)	N3—H3'	0.880 (9)
N1—C5	1.3417 (18)	C7—C8	1.490 (2)
C6—N2	1.267 (2)	C8—C9	1.385 (2)
C6—C5	1.470 (2)	C8—C12	1.386 (2)
C6—H6	0.9300	C9—C10	1.379 (2)
N2—N3	1.3707 (17)	C9—H9	0.9300
N4—C11	1.330 (2)	C10—C11	1.379 (2)
N4—C12	1.333 (2)	C10—H10	0.9300
C1—C2	1.384 (3)	C11—H11	0.9300
C1—H1	0.9300	C12—H12	0.9300

H2A—O2S—H2B	104.5 (17)	C4—C5—C6	120.63 (13)
H1A—O1S—H1B	97.5 (19)	C7—N3—N2	117.32 (12)
C1—N1—C5	117.95 (14)	C7—N3—H3'	125.3 (13)
N2—C6—C5	119.32 (13)	N2—N3—H3'	117.3 (13)
N2—C6—H6	120.3	O1—C7—N3	122.44 (14)
C5—C6—H6	120.3	O1—C7—C8	120.26 (14)
C6—N2—N3	117.37 (13)	N3—C7—C8	117.29 (13)
C11—N4—C12	116.80 (14)	C9—C8—C12	117.69 (14)
N1—C1—C2	123.80 (15)	C9—C8—C7	126.03 (13)
N1—C1—H1	118.1	C12—C8—C7	116.28 (13)
C2—C1—H1	118.1	C10—C9—C8	118.94 (14)
C3—C2—C1	118.92 (15)	C10—C9—H9	120.5
C3—C2—H2	120.5	C8—C9—H9	120.5
C1—C2—H2	120.5	C11—C10—C9	118.72 (15)
C2—C3—C4	116.87 (16)	C11—C10—H10	120.6
C2—C3—H3	121.6	C9—C10—H10	120.6
C4—C3—H3	121.6	N4—C11—C10	123.68 (15)
F1—C4—C3	118.90 (15)	N4—C11—H11	118.2
F1—C4—C5	118.79 (14)	C10—C11—H11	118.2
C3—C4—C5	122.30 (15)	N4—C12—C8	124.16 (14)
N1—C5—C4	120.16 (14)	N4—C12—H12	117.9
N1—C5—C6	119.21 (13)	C8—C12—H12	117.9

C5—C6—N2—N3	−179.37 (13)	N2—N3—C7—O1	−0.6 (3)
C5—N1—C1—C2	0.1 (3)	N2—N3—C7—C8	179.54 (13)
N1—C1—C2—C3	0.4 (3)	O1—C7—C8—C9	177.57 (17)
C1—C2—C3—C4	−0.3 (3)	N3—C7—C8—C9	−2.5 (2)
C2—C3—C4—F1	178.65 (15)	O1—C7—C8—C12	−2.0 (2)
C2—C3—C4—C5	−0.3 (3)	N3—C7—C8—C12	177.88 (14)
C1—N1—C5—C4	−0.8 (2)	C12—C8—C9—C10	−1.2 (2)
C1—N1—C5—C6	179.01 (14)	C7—C8—C9—C10	179.25 (15)
F1—C4—C5—N1	−178.09 (13)	C8—C9—C10—C11	1.1 (3)
C3—C4—C5—N1	0.9 (2)	C12—N4—C11—C10	−1.1 (3)
F1—C4—C5—C6	2.1 (2)	C9—C10—C11—N4	0.0 (3)
C3—C4—C5—C6	−178.89 (15)	C11—N4—C12—C8	1.1 (3)
N2—C6—C5—N1	6.6 (2)	C9—C8—C12—N4	0.0 (3)
N2—C6—C5—C4	−173.62 (15)	C7—C8—C12—N4	179.68 (16)
C6—N2—N3—C7	179.03 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3′···O1S	0.88 (1)	2.04 (1)	2.8821 (19)	160 (2)
O2S—H2A···N1ⁱ	0.87 (1)	2.10 (1)	2.965 (2)	177 (2)
O1S—H1A···N4ⁱ	0.87 (1)	2.09 (1)	2.946 (2)	170 (3)
O2S—H2B···O1ⁱ	0.86 (1)	1.97 (1)	2.816 (2)	172 (2)

Symmetry code: (i) x, −y+3/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3'···O1S	0.880 (9)	2.041 (11)	2.8821 (19)	159.6 (17)
O2S—H2A···N1ⁱ	0.866 (9)	2.100 (10)	2.965 (2)	177 (2)
O1S—H1A···N4ⁱ	0.869 (10)	2.086 (11)	2.946 (2)	170 (3)
O2S—H2B···O1ⁱ	0.855 (9)	1.967 (10)	2.816 (2)	172 (2)

Symmetry code: (i) x, −y+3/2, z+1/2.

Acknowledgements

The authors are thankful to Dr Shibu M. Eapen, SAIF, Cochin University of Science and Technology, for the single-crystal XRD measurements.

References

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Volume 70| Part 4| April 2014| Pages o483-o484

doi:10.1107/S1600536814006072

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N′-[(E)-(3-Fluoro­pyridin-2-yl)methyl­­idene]pyridine-3-carbohydrazide dihydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N′-[(E)-(3-Fluoropyridin-2-yl)methylidene]pyridine-3-carbohydrazide dihydrate