2-Cyano-N′-[1-(pyridin-2-yl)ethyl­idene]acetohydrazide

Zhang, X.-Y.; Han, X.-L.; Qian, Z.-B.

doi:10.1107/S1600536812042869

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3203

doi:10.1107/S1600536812042869

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2-Cyano-N′-[1-(pyridin-2-yl)ethylidene]acetohydrazide

Xiao-Yi Zhang,^a Xiao-Lin Han ^b and Zhi-Bin Qian ^c ^*

^aSchool of Pharmacy, Xinxiang Medical University, Xinxiang Henan 453003, People's Republic of China, ^bThe Hematology Department of the First Affiliated Hospital of Xinxiang Medical University, Weihui Henan 453100, People's Republic of China, and ^cSchool of Basic Medical Sciences, Xinxiang Medical University, Xinxiang Henan 453003, People's Republic of China
^*Correspondence e-mail: qianzhibin2012@163.com

(Received 7 October 2012; accepted 13 October 2012; online 24 October 2012)

In the title compound, C₁₀H₁₀N₄O, the dihedral angle between the pyridine ring and the –C=O(CH₂)CN group is 24.08 (12)°. In the crystal, inversion dimers linked by pairs of N—H⋯N hydrogen bonds generate R₂²(8) loops.

Related literature

For the biological activity of hydrazone compounds, see: Rauf et al. (2008 ); Zhang et al. (2012 ). For related structures, see: Taha et al. (2012 ); Kargar et al. (2012 ); Rassem et al. (2012 ).

Experimental

Crystal data

C₁₀H₁₀N₄O
M_r = 202.22
Monoclinic, P 2₁ /c
a = 8.192 (2) Å
b = 14.520 (2) Å
c = 8.7340 (17) Å
β = 98.466 (2)°
V = 1027.6 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.17 × 0.13 × 0.12 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.985, T_max = 0.989
6189 measured reflections
2222 independent reflections
1128 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.143
S = 1.03
2222 reflections
140 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.14 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
N3—H3A⋯O1ⁱ	0.90 (1)	2.05 (1)	2.929 (2)	167 (2)
Symmetry code: (i) -x+2, -y, -z.

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812042869/hb6969sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812042869/hb6969Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812042869/hb6969Isup3.cml

checkCIF report

Comment top

Hydrazone compounds bearing biological active functional groups -C(O)-NH-N=CH- are readily prepared by the condensation reactions of hydrazines with various aldehydes (e.g. Rauf et al., 2008; Zhang et al., 2012). In the present work, the title new hydrazone compound, derived from 2-acetylpyridine and cyanoacetohydrazide, is reported.

The molecule of the compound adopts a trans conformation about the C6=N2 double bond (Fig. 1). The torsion angles of C6-N2-N3-C8, N2-N3-C8-C9, and N3-C8-C9-C10 are 4.8 (3), 5.1 (3), and 6.5 (3)°, respectively. The bond lengths are comparable to those in similar compounds (Taha et al., 2012; Kargar et al., 2012; Rassem et al., 2012). The crystal structure of the compound features N—H···O hydrogen bonds (Table 1), generating dimers (Fig. 2).

Related literature top

For the biological activity of hydrazone compounds, see: Rauf et al. (2008); Zhang et al. (2012). For related structures, see: Taha et al. (2012); Kargar et al. (2012); Rassem et al. (2012).

Experimental top

2-Acetylpyridine (1.0 mmol, 0.121 g) and cyanoacetohydrazide (1.0 mmol, 0.991 g) were mixed and stirred in methanol (50 mL) at room temperature for 1 h. Colorless block-shaped single crystals were obtained after slow evaporation of the solution in air for a few days.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound with 30% thermal ellipsoids.
	Fig. 2. Molecular packing diagram of the title compound, viewed down the c axis. Hydrogen bonds are drawn as dashed lines.

2-Cyano-N'-[1-(pyridin-2-yl)ethylidene]acetohydrazide top

Crystal data top

C₁₀H₁₀N₄O	F(000) = 424
M_r = 202.22	D_x = 1.307 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.192 (2) Å	Cell parameters from 1009 reflections
b = 14.520 (2) Å	θ = 2.7–24.5°
c = 8.7340 (17) Å	µ = 0.09 mm⁻¹
β = 98.466 (2)°	T = 298 K
V = 1027.6 (4) Å³	Block, colorless
Z = 4	0.17 × 0.13 × 0.12 mm

Data collection top

Bruker SMART CCD diffractometer	2222 independent reflections
Radiation source: fine-focus sealed tube	1128 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ω scans	θ_max = 27.0°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→10
T_min = 0.985, T_max = 0.989	k = −18→12
6189 measured reflections	l = −11→11

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.143	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0562P)² + 0.0523P] where P = (F_o² + 2F_c²)/3
2222 reflections	(Δ/σ)_max < 0.001
140 parameters	Δρ_max = 0.14 e Å⁻³
1 restraint	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₀H₁₀N₄O	V = 1027.6 (4) Å³
M_r = 202.22	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.192 (2) Å	µ = 0.09 mm⁻¹
b = 14.520 (2) Å	T = 298 K
c = 8.7340 (17) Å	0.17 × 0.13 × 0.12 mm
β = 98.466 (2)°

Data collection top

Bruker SMART CCD diffractometer	2222 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1128 reflections with I > 2σ(I)
T_min = 0.985, T_max = 0.989	R_int = 0.040
6189 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	1 restraint
wR(F²) = 0.143	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.14 e Å⁻³
2222 reflections	Δρ_min = −0.18 e Å⁻³
140 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
N1	0.3684 (2)	0.07074 (13)	0.3032 (2)	0.0623 (6)
N2	0.6478 (2)	0.10204 (13)	0.0382 (2)	0.0537 (5)
N3	0.7946 (2)	0.06818 (13)	0.0033 (2)	0.0583 (5)
N4	0.8363 (3)	0.17583 (17)	−0.4976 (3)	0.0901 (8)
O1	0.97937 (19)	0.06914 (12)	−0.16256 (18)	0.0727 (5)
C1	0.4400 (3)	0.11185 (15)	0.1938 (2)	0.0504 (6)
C2	0.3705 (3)	0.18833 (17)	0.1157 (3)	0.0667 (7)
H2	0.4223	0.2167	0.0404	0.080*
C3	0.2244 (3)	0.22169 (19)	0.1506 (3)	0.0805 (9)
H3	0.1764	0.2733	0.0993	0.097*
C4	0.1494 (3)	0.17926 (19)	0.2605 (3)	0.0714 (7)
H4	0.0494	0.2006	0.2851	0.086*
C5	0.2256 (3)	0.10466 (18)	0.3330 (3)	0.0686 (7)
H5	0.1747	0.0755	0.4082	0.082*
C6	0.5976 (3)	0.07141 (15)	0.1606 (2)	0.0512 (6)
C7	0.6822 (3)	−0.00024 (17)	0.2651 (3)	0.0675 (7)
H7A	0.6830	−0.0574	0.2098	0.101*
H7B	0.6246	−0.0083	0.3522	0.101*
H7C	0.7936	0.0187	0.3006	0.101*
C8	0.8458 (3)	0.09339 (15)	−0.1295 (3)	0.0554 (6)
C9	0.7285 (3)	0.15165 (16)	−0.2381 (2)	0.0587 (6)
H9A	0.6215	0.1218	−0.2570	0.070*
H9B	0.7146	0.2109	−0.1904	0.070*
C10	0.7896 (3)	0.16532 (16)	−0.3836 (3)	0.0594 (6)
H3A	0.860 (2)	0.0304 (13)	0.066 (2)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0625 (14)	0.0709 (13)	0.0578 (12)	0.0094 (11)	0.0226 (10)	0.0093 (10)
N2	0.0449 (11)	0.0645 (13)	0.0536 (11)	0.0050 (9)	0.0137 (9)	0.0024 (9)
N3	0.0490 (13)	0.0724 (14)	0.0548 (12)	0.0110 (10)	0.0125 (9)	0.0116 (10)
N4	0.0921 (18)	0.1099 (19)	0.0729 (15)	0.0051 (14)	0.0278 (13)	0.0163 (14)
O1	0.0543 (11)	0.0962 (13)	0.0717 (11)	0.0180 (9)	0.0226 (9)	0.0185 (9)
C1	0.0485 (14)	0.0581 (14)	0.0448 (12)	−0.0002 (12)	0.0069 (10)	−0.0003 (11)
C2	0.0622 (17)	0.0784 (18)	0.0631 (15)	0.0105 (14)	0.0215 (13)	0.0169 (13)
C3	0.0741 (19)	0.091 (2)	0.0809 (19)	0.0283 (16)	0.0261 (16)	0.0236 (16)
C4	0.0623 (17)	0.0910 (19)	0.0649 (16)	0.0209 (15)	0.0232 (14)	0.0064 (15)
C5	0.0664 (17)	0.0843 (19)	0.0610 (15)	0.0076 (15)	0.0291 (13)	0.0074 (14)
C6	0.0486 (14)	0.0581 (14)	0.0471 (12)	−0.0015 (11)	0.0081 (11)	0.0011 (11)
C7	0.0607 (17)	0.0816 (17)	0.0616 (15)	0.0133 (14)	0.0131 (12)	0.0181 (13)
C8	0.0481 (15)	0.0633 (16)	0.0568 (14)	0.0015 (12)	0.0143 (12)	0.0027 (12)
C9	0.0536 (15)	0.0676 (16)	0.0564 (13)	0.0062 (12)	0.0132 (11)	0.0058 (12)
C10	0.0594 (16)	0.0618 (15)	0.0583 (14)	0.0026 (12)	0.0131 (13)	0.0045 (12)

Geometric parameters (Å, º) top

N1—C5	1.331 (3)	C3—H3	0.9300
N1—C1	1.333 (2)	C4—C5	1.359 (3)
N2—C6	1.280 (2)	C4—H4	0.9300
N2—N3	1.374 (2)	C5—H5	0.9300
N3—C8	1.341 (3)	C6—C7	1.486 (3)
N3—H3A	0.899 (10)	C7—H7A	0.9600
N4—C10	1.128 (3)	C7—H7B	0.9600
O1—C8	1.224 (2)	C7—H7C	0.9600
C1—C2	1.382 (3)	C8—C9	1.506 (3)
C1—C6	1.486 (3)	C9—C10	1.446 (3)
C2—C3	1.366 (3)	C9—H9A	0.9700
C2—H2	0.9300	C9—H9B	0.9700
C3—C4	1.361 (3)

C5—N1—C1	117.8 (2)	N2—C6—C1	114.9 (2)
C6—N2—N3	117.41 (19)	N2—C6—C7	125.31 (19)
C8—N3—N2	119.3 (2)	C1—C6—C7	119.78 (18)
C8—N3—H3A	117.5 (15)	C6—C7—H7A	109.5
N2—N3—H3A	123.2 (15)	C6—C7—H7B	109.5
N1—C1—C2	121.4 (2)	H7A—C7—H7B	109.5
N1—C1—C6	116.7 (2)	C6—C7—H7C	109.5
C2—C1—C6	121.88 (19)	H7A—C7—H7C	109.5
C3—C2—C1	119.1 (2)	H7B—C7—H7C	109.5
C3—C2—H2	120.5	O1—C8—N3	122.0 (2)
C1—C2—H2	120.5	O1—C8—C9	121.5 (2)
C4—C3—C2	119.9 (2)	N3—C8—C9	116.48 (19)
C4—C3—H3	120.1	C10—C9—C8	111.03 (18)
C2—C3—H3	120.1	C10—C9—H9A	109.4
C5—C4—C3	117.7 (2)	C8—C9—H9A	109.4
C5—C4—H4	121.1	C10—C9—H9B	109.4
C3—C4—H4	121.1	C8—C9—H9B	109.4
N1—C5—C4	124.1 (2)	H9A—C9—H9B	108.0
N1—C5—H5	118.0	N4—C10—C9	179.6 (3)
C4—C5—H5	118.0

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1ⁱ	0.90 (1)	2.05 (1)	2.929 (2)	167 (2)

Symmetry code: (i) −x+2, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₀N₄O
M_r	202.22
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	8.192 (2), 14.520 (2), 8.7340 (17)
β (°)	98.466 (2)
V (Å³)	1027.6 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.17 × 0.13 × 0.12

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.985, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	6189, 2222, 1128
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.143, 1.03
No. of reflections	2222
No. of parameters	140
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.18

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1ⁱ	0.899 (10)	2.048 (11)	2.929 (2)	167 (2)

Symmetry code: (i) −x+2, −y, −z.

Acknowledgements

The intensity data were collected by Xiao-Lin Han under the guidance of Mr Yanglu Zhu at Dalian Institute of Technology.

References

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