2-Cyano-N'-[1-(pyridin-2-yl)ethyl-idene]acetohydrazide.

In the title compound, C(10)H(10)N(4)O, the dihedral angle between the pyridine ring and the -C=O(CH(2))CN group is 24.08 (12)°. In the crystal, inversion dimers linked by pairs of N-H⋯N hydrogen bonds generate R(2) (2)(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 = 202.22

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.143

S = 1.03

2222 reflections

140 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.18 e Å−3

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.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812042869/hb6969sup1.cif

Click here for additional data file.

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812042869/hb6969Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H10N4O	F(000) = 424
Mr = 202.22	Dx = 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

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

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(Fo2) + (0.0562P)2 + 0.0523P] where P = (Fo2 + 2Fc2)/3
2222 reflections	(Δ/σ)max < 0.001
140 parameters	Δρmax = 0.14 e Å−3
1 restraint	Δρmin = −0.18 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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

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)

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) .