organic compounds
2-Cyano-N′-[1-(pyridin-2-yl)ethylidene]acetohydrazide
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
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
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Refinement
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Data collection: SMART (Bruker, 1998); cell 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
10.1107/S1600536812042869/hb6969sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812042869/hb6969Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812042869/hb6969Isup3.cml
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.
H3A attached to N3 was located in a difference Fourier map and was refined isotropically, with N—H distance of 0.90 (1) Å. The remaining hydrogen atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.93–0.97 Å for aromatic and CH2 and 0.96 Å for CH3. The Uiso values were constrained to be 1.5Ueq of the
for methyl and 1.2Ueq for the remaining H atoms. A rotating group model was used for the methyl group.Data collection: SMART (Bruker, 1998); cell
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).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 |
C10H10N4O | V = 1027.6 (4) Å3 |
Mr = 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)° |
Bruker SMART CCD diffractometer | 2222 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1128 reflections with I > 2σ(I) |
Tmin = 0.985, Tmax = 0.989 | Rint = 0.040 |
6189 measured reflections |
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 | Δρmax = 0.14 e Å−3 |
2222 reflections | Δρmin = −0.18 e Å−3 |
140 parameters |
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) |
Symmetry code: (i) −x+2, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C10H10N4O |
Mr | 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) |
Tmin, Tmax | 0.985, 0.989 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6189, 2222, 1128 |
Rint | 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 |
Δρmax, Δρmin (e Å−3) | 0.14, −0.18 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
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
Bruker (1998). SMART and SAINT . Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kargar, H., Kia, R. & Tahir, M. N. (2012). Acta Cryst. E68, o2118–o2119. CSD CrossRef IUCr Journals Google Scholar
Rassem, H. H., Salhin, A., Bin Salleh, B., Rosli, M. M. & Fun, H.-K. (2012). Acta Cryst. E68, o2279. CSD CrossRef IUCr Journals Google Scholar
Rauf, A., Banday, M. R. & Mattoo, R. H. (2008). Acta Chim. Slov. 55, 448-452. CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Taha, M., Naz, H., Rahman, A. A., Ismail, N. H. & Yousuf, S. (2012). Acta Cryst. E68, o2846. CSD CrossRef IUCr Journals Google Scholar
Zhang, M., Xian, D.-M., Li, H.-H., Zhang, J.-C. & You, Z.-L. (2012). Aust. J. Chem. 65, 343–350. CAS Google Scholar
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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).