(2E)-2-Hydroxy­imino-N′-[(E)-2-pyridyl­methyl­ene]propanohydrazide

Moroz, Y.S.; Kalibabchuk, V.A.; Gumienna-Kontecka, E.; Skopenko, V.V.; Pavlova, S.V.

doi:10.1107/S1600536809034400

organic compounds

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Volume 65| Part 10| October 2009| Page o2413

doi:10.1107/S1600536809034400

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(2E)-2-Hydroxyimino-N′-[(E)-2-pyridylmethylene]propanohydrazide

Yurii S. Moroz,^a ^* Valentina A. Kalibabchuk,^b Elżbieta Gumienna-Kontecka,^c Viktor V. Skopenko ^a and Svetlana V. Pavlova ^a

^aDepartment of Chemistry, Kyiv National Taras Shevchenko University, Volodymyrska Str. 64, 01601 Kyiv, Ukraine, ^bDepartment of General Chemistry, O.O. Bohomolets National Medical University, Shevchenko blvd. 13, 01601 Kiev, Ukraine, and ^cFaculty of Chemistry, University of Wrocław, 14 F. Joliot-Curie str., 50-383 Wrocław, Poland
^*Correspondence e-mail: ysmoroz@yahoo.com

(Received 26 August 2009; accepted 27 August 2009; online 9 September 2009)

In the title compound, C₉H₁₀N₄O₂, the pyridine ring is twisted by 16.5 (1)° from the mean plane defined by the remaining non-H atoms. An intramolecular N—H⋯N interaction is present. In the crystal, intermolecular O—H⋯N and N—H⋯O hydrogen bonds link molecules into layers parallel to the bc plane. The crystal packing exhibits π–π interactions indicated by the short distance of 3.649 (1) Å between the centroids of the pyridine rings of neighbouring molecules.

Related literature

For the crystal structures of related oxime derivatives, see: Mokhir et al. (2002 ); Moroz et al. (2009 ). For 2-hydroxyiminopropanamide and amide derivatives of 2-hydroxyiminopropanoic acid, see: Onindo et al. (1995 ); Duda et al. (1997 ); Sliva et al. (1997a ). For the preparation and characterization of 3d-metal complexes with the structural analog of the title compound, see: Moroz et al. (2008a ,b ). For the synthesis of 2-(hydroxyimino)propanehydrazide, see Fritsky et al. (1998 ).

Experimental

Crystal data

C₉H₁₀N₄O₂
M_r = 206.21
Monoclinic, P 2₁ /c
a = 10.274 (4) Å
b = 9.717 (4) Å
c = 10.136 (4) Å
β = 109.28 (4)°
V = 955.2 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 100 K
0.4 × 0.4 × 0.3 mm

Data collection

Kuma KM-4-CCD diffractometer
Absorption correction: none
10648 measured reflections
2680 independent reflections
2449 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.106
S = 1.08
2680 reflections
176 parameters
All H-atom parameters refined
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H21⋯N1ⁱ	0.881 (17)	1.897 (18)	2.7667 (17)	168.6 (15)
N3—H31⋯O1ⁱⁱ	0.879 (16)	2.217 (16)	2.9656 (15)	142.9 (14)
N3—H31⋯N4	0.879 (16)	2.240 (16)	2.6059 (15)	104.7 (12)
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z-{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon,England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon,England.]$ ); data reduction: CrysAlis RED; 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, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809034400/cv2608sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809034400/cv2608Isup2.hkl

checkCIF report

Comment top

As a part of our research study we present the structure of the title compound, 1 (Fig. 1), which comprises several donor groups: oxime, hydrazone, azomethine, and pyridine. It has been shown previously that structurally similiar strand ligand forms mono- and tetranuclear grid-like assemblies with 3d-metal ions (Moroz et al., 2008a,b).

The C—N and N—O bond lengths in the oxime group, i.e. 1.285 (1) and 1.387 (1) Å, respectively, adopt typical values (Mokhir et al., 2002; Moroz et al., 2009). The oxime group is in a trans position with respect to the amide group, in accordance with the structures of 2-hydroxyiminopropanamide and other amide derivatives of 2-hydroxyiminopropanoic acid (Onindo et al., 1995; Duda et al., 1997; Sliva et al., 1997a). This conformation is stabilized by an N3—H···N4 intramolecular interaction (Table 1). The CH₃C(=NOH)C(O)NH fragment deviates from planarity because of a twist between the oxime and amide groups about the C7—C8 bond; the O1—C7—C8—N4 torsion angle is 173.3 (1)°. The C—N bond length in the azomethine group is 1.283 (1) Å, and the N2—C6—C5 angle has almost ideal value 120.5 (1)°. The pyridine nitrogen atom is situated in an anti- position with respect to the azomethine group.

In the crystal packing, molecules are connected by O2—H···N1 and N3—H···O1 hydrogen bonds (Table 1), where the oximic oxygen and hydrazone nitrogen atoms act as donors and the hydrazone oxygen and pyridine nitrogen atoms act as acceptors. Due to the presence of the system of O2—H···N1 and N3—H···O1 hydrogen bonds, layers parallel to bc plane are formed. The layers are connected in three-dimensional structure by π-π contacts with centroid-to-centroid distance of 3.649 (2) Å, which arise between the pyridine rings of neighbour molecules.

Related literature top

For the crystal structures of related oxime derivatives, see: Mokhir et al. (2002); Moroz et al. (2009). For 2-hydroxyiminopropanamide and amide derivatives of 2-hydroxyiminopropanoic acid, see: Onindo et al. (1995); Duda et al. (1997); Sliva et al. (1997a). For the preparation and characterization of 3d-metal complexes with the structural analog of the title compound, see: Moroz et al. (2008a,b). For the synthesis of 2-(hydroxyimino)propanehydrazide, see Fritsky et al. (1998).

Experimental top

The compound 1 has beeen prepared accourding to following procedure: picolinaldehyde (1.1 ml, 0.012 mol) was added to 20 ml of a stirred warm ethanol/water solution of 2-(hydroxyimino)propanehydrazide (1.17 g, 0.01 mol) prepared according to early reported method (Fritsky et al., 1998). After 20 minutes of stirring at 60°C a yellowish precipitate was formed. It was filtered off, washed with water and acetone and recrystalized from methanol. Yield: 1.65 g, 80%. ¹H NMR, 400.13 MHz, (DMSO-d₆): 1.983 (s, 3H, CH₃), 7.393 (dd, 1H, py-5, J = 5.1 Hz, J = 7.2 Hz, py—H), 7.854 (t, 1H, py-4, J = 7.2 Hz, py—H), 7.932 (d, 1H, py-3, J = 7.2 Hz, py—H), 8.494 (s, 1H, CH), 8.594 (d, 1H, py-6, J = 5.1 Hz, py—H), 11.703 (s, 1H, NH), 11.932 (s, 1H, NOH); IR (KBr, cm^-1): 1670 ν(CO_{amid I}), 1040, 895 ν(NO_oxim), 3345 ν(NH_as). Anal. calc. for C₉H₁₀N₄O₂ C, 52.42; H, 4.89; N, 27.17. Found: C, 52.30; H, 4.98; N, 26.98.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); 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, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. A view of 1, with displacement ellipsoids shown at the 40% probability level and atom labelling.

(2E)-2-Hydroxyimino-N'-[(E)-2- pyridylmethylene]propanohydrazide top

Crystal data top

C₉H₁₀N₄O₂	F(000) = 432
M_r = 206.21	D_x = 1.434 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybc	Cell parameters from 11569 reflections
a = 10.274 (4) Å	θ = 3–37°
b = 9.717 (4) Å	µ = 0.11 mm⁻¹
c = 10.136 (4) Å	T = 100 K
β = 109.28 (4)°	Block, white
V = 955.2 (7) Å³	0.4 × 0.4 × 0.3 mm
Z = 4

Data collection top

Kuma KM-4-CCD diffractometer	2449 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	R_int = 0.023
Graphite monochromator	θ_max = 30.0°, θ_min = 3.2°
Detector resolution: 8.3359 pixels mm^-1	h = −14→13
ω scans	k = −13→10
10648 measured reflections	l = −14→14
2680 independent reflections

Refinement top

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	All H-atom parameters refined
S = 1.08	w = 1/[σ²(F_o²) + (0.0621P)² + 0.2439P] where P = (F_o² + 2F_c²)/3
2680 reflections	(Δ/σ)_max < 0.001
176 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₉H₁₀N₄O₂	V = 955.2 (7) Å³
M_r = 206.21	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.274 (4) Å	µ = 0.11 mm⁻¹
b = 9.717 (4) Å	T = 100 K
c = 10.136 (4) Å	0.4 × 0.4 × 0.3 mm
β = 109.28 (4)°

Data collection top

Kuma KM-4-CCD diffractometer	2449 reflections with I > 2σ(I)
10648 measured reflections	R_int = 0.023
2680 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.106	All H-atom parameters refined
S = 1.08	Δρ_max = 0.46 e Å⁻³
2680 reflections	Δρ_min = −0.18 e Å⁻³
176 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
O1	0.59592 (7)	0.23238 (7)	0.23853 (7)	0.01751 (17)
O2	0.24735 (8)	0.10483 (8)	−0.16272 (8)	0.01954 (17)
H21	0.2245 (17)	0.1328 (17)	−0.2501 (18)	0.032 (4)*
N1	0.85431 (9)	0.66853 (8)	−0.05564 (8)	0.01561 (18)
N2	0.70574 (8)	0.39826 (8)	0.08234 (8)	0.01477 (17)
N3	0.59208 (9)	0.31588 (9)	0.02612 (9)	0.01608 (18)
H31	0.5529 (16)	0.3104 (16)	−0.0650 (17)	0.030 (4)*
N4	0.36471 (8)	0.18113 (8)	−0.09566 (8)	0.01500 (17)
C1	0.95964 (11)	0.75821 (10)	−0.01987 (11)	0.0176 (2)
H1	0.9570 (16)	0.8267 (16)	−0.0903 (16)	0.029 (4)*
C2	1.06781 (10)	0.75321 (10)	0.10549 (10)	0.0168 (2)
H2	1.1433 (15)	0.8188 (14)	0.1263 (15)	0.023 (3)*
C3	1.06686 (10)	0.64989 (10)	0.20031 (10)	0.0167 (2)
H3	1.1409 (16)	0.6414 (16)	0.2873 (16)	0.026 (4)*
C4	0.95703 (10)	0.55828 (10)	0.16717 (10)	0.01493 (19)
H4	0.9544 (15)	0.4838 (15)	0.2317 (15)	0.024 (3)*
C5	0.85205 (10)	0.57099 (9)	0.03849 (9)	0.01315 (18)
C6	0.73225 (10)	0.47858 (10)	−0.00602 (10)	0.01499 (19)
H6	0.6756 (15)	0.4825 (15)	−0.1032 (15)	0.026 (3)*
C7	0.54344 (10)	0.23721 (9)	0.11115 (10)	0.01334 (18)
C8	0.41629 (10)	0.15545 (9)	0.03573 (10)	0.01366 (19)
C9	0.36358 (11)	0.05663 (11)	0.11943 (11)	0.0188 (2)
H9A	0.2794 (19)	0.0181 (19)	0.0675 (19)	0.044 (5)*
H9B	0.3462 (17)	0.1013 (17)	0.1967 (18)	0.037 (4)*
H9C	0.4325 (17)	−0.0149 (17)	0.1626 (17)	0.035 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0173 (3)	0.0225 (4)	0.0118 (3)	−0.0006 (3)	0.0036 (3)	0.0006 (2)
O2	0.0176 (4)	0.0249 (4)	0.0133 (3)	−0.0076 (3)	0.0014 (3)	−0.0023 (3)
N1	0.0163 (4)	0.0174 (4)	0.0136 (4)	0.0008 (3)	0.0055 (3)	0.0016 (3)
N2	0.0133 (4)	0.0166 (4)	0.0145 (4)	−0.0022 (3)	0.0046 (3)	−0.0024 (3)
N3	0.0160 (4)	0.0202 (4)	0.0109 (4)	−0.0054 (3)	0.0029 (3)	−0.0011 (3)
N4	0.0128 (4)	0.0168 (4)	0.0146 (4)	−0.0022 (3)	0.0036 (3)	−0.0028 (3)
C1	0.0192 (5)	0.0172 (4)	0.0180 (5)	−0.0002 (3)	0.0084 (4)	0.0029 (3)
C2	0.0155 (4)	0.0163 (4)	0.0198 (5)	−0.0018 (3)	0.0076 (4)	−0.0022 (3)
C3	0.0147 (4)	0.0188 (4)	0.0153 (4)	0.0002 (3)	0.0034 (3)	−0.0017 (3)
C4	0.0161 (4)	0.0153 (4)	0.0132 (4)	0.0001 (3)	0.0046 (3)	0.0007 (3)
C5	0.0139 (4)	0.0138 (4)	0.0128 (4)	0.0006 (3)	0.0058 (3)	−0.0011 (3)
C6	0.0147 (4)	0.0171 (4)	0.0126 (4)	−0.0005 (3)	0.0038 (3)	−0.0014 (3)
C7	0.0133 (4)	0.0139 (4)	0.0133 (4)	0.0011 (3)	0.0050 (3)	−0.0004 (3)
C8	0.0136 (4)	0.0139 (4)	0.0139 (4)	0.0001 (3)	0.0051 (3)	−0.0010 (3)
C9	0.0201 (5)	0.0190 (4)	0.0170 (4)	−0.0037 (4)	0.0058 (4)	0.0024 (3)

Geometric parameters (Å, º) top

O1—C7	1.2249 (13)	C2—H2	0.972 (14)
O2—N4	1.3872 (12)	C3—C4	1.3886 (14)
O2—H21	0.881 (17)	C3—H3	0.959 (15)
N1—C1	1.3427 (13)	C4—C5	1.3967 (15)
N1—C5	1.3505 (12)	C4—H4	0.982 (14)
N2—C6	1.2832 (13)	C5—C6	1.4691 (14)
N2—N3	1.3746 (12)	C6—H6	0.965 (14)
N3—C7	1.3643 (12)	C7—C8	1.5042 (14)
N3—H31	0.879 (16)	C8—C9	1.4962 (13)
N4—C8	1.2848 (14)	C9—H9A	0.930 (19)
C1—C2	1.3854 (16)	C9—H9B	0.962 (17)
C1—H1	0.970 (15)	C9—H9C	0.985 (17)
C2—C3	1.3921 (14)

N4—O2—H21	103.1 (11)	N1—C5—C4	122.25 (9)
C1—N1—C5	117.71 (9)	N1—C5—C6	114.84 (9)
C6—N2—N3	114.32 (9)	C4—C5—C6	122.90 (9)
C7—N3—N2	120.18 (8)	N2—C6—C5	120.45 (9)
C7—N3—H31	119.6 (10)	N2—C6—H6	122.7 (9)
N2—N3—H31	120.2 (10)	C5—C6—H6	116.8 (9)
C8—N4—O2	113.47 (8)	O1—C7—N3	124.18 (9)
N1—C1—C2	123.77 (9)	O1—C7—C8	121.44 (9)
N1—C1—H1	115.0 (9)	N3—C7—C8	114.38 (8)
C2—C1—H1	121.2 (9)	N4—C8—C9	127.58 (9)
C1—C2—C3	118.17 (9)	N4—C8—C7	114.58 (9)
C1—C2—H2	121.1 (9)	C9—C8—C7	117.84 (9)
C3—C2—H2	120.7 (9)	C8—C9—H9A	112.3 (11)
C4—C3—C2	119.06 (10)	C8—C9—H9B	111.8 (10)
C4—C3—H3	120.1 (9)	H9A—C9—H9B	104.7 (15)
C2—C3—H3	120.8 (9)	C8—C9—H9C	111.3 (9)
C3—C4—C5	118.98 (9)	H9A—C9—H9C	111.4 (15)
C3—C4—H4	120.7 (8)	H9B—C9—H9C	104.8 (13)
C5—C4—H4	120.3 (8)

C6—N2—N3—C7	−172.56 (9)	N1—C5—C6—N2	−167.65 (9)
C5—N1—C1—C2	2.31 (14)	C4—C5—C6—N2	13.31 (14)
N1—C1—C2—C3	−0.46 (15)	N2—N3—C7—O1	−1.03 (15)
C1—C2—C3—C4	−1.31 (14)	N2—N3—C7—C8	178.35 (8)
C2—C3—C4—C5	1.19 (14)	O2—N4—C8—C9	−0.54 (14)
C1—N1—C5—C4	−2.42 (14)	O2—N4—C8—C7	−179.80 (7)
C1—N1—C5—C6	178.54 (8)	O1—C7—C8—N4	173.25 (9)
C3—C4—C5—N1	0.71 (14)	N3—C7—C8—N4	−6.14 (12)
C3—C4—C5—C6	179.68 (8)	O1—C7—C8—C9	−6.08 (13)
N3—N2—C6—C5	−178.98 (8)	N3—C7—C8—C9	174.52 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H21···N1ⁱ	0.881 (17)	1.897 (18)	2.7667 (17)	168.6 (15)
N3—H31···O1ⁱⁱ	0.879 (16)	2.217 (16)	2.9656 (15)	142.9 (14)
N3—H31···N4	0.879 (16)	2.240 (16)	2.6059 (15)	104.7 (12)

Symmetry codes: (i) −x+1, y−1/2, −z−1/2; (ii) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₉H₁₀N₄O₂
M_r	206.21
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	10.274 (4), 9.717 (4), 10.136 (4)
β (°)	109.28 (4)
V (Å³)	955.2 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.4 × 0.4 × 0.3

Data collection
Diffractometer	Kuma KM-4-CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10648, 2680, 2449
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.106, 1.08
No. of reflections	2680
No. of parameters	176
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.18

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H21···N1ⁱ	0.881 (17)	1.897 (18)	2.7667 (17)	168.6 (15)
N3—H31···O1ⁱⁱ	0.879 (16)	2.217 (16)	2.9656 (15)	142.9 (14)
N3—H31···N4	0.879 (16)	2.240 (16)	2.6059 (15)	104.7 (12)

Symmetry codes: (i) −x+1, y−1/2, −z−1/2; (ii) x, −y+1/2, z−1/2.

Acknowledgements

The authors thank the Ministry of Education and Science of Ukraine for financial support (grant No. F28/241–2009).

References

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