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Acta Crystallogr Sect E Struct Rep Online. 2010 April 1; 66(Pt 4): o920.
Published online 2010 March 27. doi:  10.1107/S1600536810010135
PMCID: PMC2983969

4-Eth­oxy-N′-propanoylpyridine-2-carbohydrazide

Abstract

In the crystal structure of the title compound, C11H15N3O3, mol­ecules are linked into a chain by inter­molecular N—H(...)O hydrogen bonds.

Related literature

For the structure of N-propionylpicoloylhydrazide, see: Wu & Liu (2001 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o920-scheme1.jpg

Experimental

Crystal data

  • C11H15N3O3
  • M r = 237.26
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o920-efi1.jpg
  • a = 11.377 (5) Å
  • b = 4.745 (2) Å
  • c = 23.244 (10) Å
  • β = 99.534 (5)°
  • V = 1237.3 (9) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 293 K
  • 1.00 × 0.45 × 0.10 mm

Data collection

  • Bruker P4 diffractometer
  • 9032 measured reflections
  • 2803 independent reflections
  • 2297 reflections with I > 2σ(I)
  • R int = 0.022

Refinement

  • R[F 2 > 2σ(F 2)] = 0.053
  • wR(F 2) = 0.150
  • S = 0.96
  • 2803 reflections
  • 154 parameters
  • H-atom parameters constrained
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.28 e Å−3

Data collection: XSCANS (Bruker, 1999 [triangle]); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810010135/jh2133sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010135/jh2133Isup2.hkl

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

Acknowledgments

We are grateful for financial support from the National Science Foundation of Fujian Province of China (No. E0610017, 2003 F006).

supplementary crystallographic information

Comment

It has been reported that the structure of N-propionylpicoloylhydrazide (II, Wu et al., 2001), based on which we reported the structure of 4-ethoxy-N-propionyl-2-pyridine formylhydrazine (I), C11H15N3O3. The structure of the title compound shown in Fig. 1 exhibits a stable one-dimension chain structure which is stabilized by inter-molecular hydrogen bonds of N2—H2A···O2i, N3—H3A···O2ii. All these bonds are detailed in Fig. 2 and Table 1.

In this title compound, the torsion angle of C6—N2—N3—C7 is -77.1 (2) ° which is slightly smaller than the torsion angle of the structure (II) (-73.5 (2) ° for C6—N2—N3—C7). The distances of C6—N2, N2—N3 and C7—N3 are 1.345 (2) Å, 1.335 (2) and 1.380 (2) Å respectively. They are similar to homologous bonds of structure (II) with distances 1.334 (2) Å for C6—N2, 1.383 (2) Å for N2—N3 and 1.337 (2) Å for C7—N3. And in structure (I), it's almost coplanar for C1, C2, C3, C4, C5, N1, C6, O1, N2, N3, O3, C10 and C11, and the maximum atomic deviation being 0.0920 Å. The dihedral angle between the mean planes of the C1, C2, C3, C4, C5, N1, C6, O1, N2, N3, O3, C10 and C11 and the mean planes of the N3, C7 and O2 is 72.44 (8) °.

Experimental

4-ethoxyl-2-pyridine formylhydrazine (3.42 g, 14.41 mmol) was dissolved in a mixed solution of CHCl3 (30 ml) and EtOH (20 ml), then filtered. Propionic anhydride (3.64 ml) was added and refluxed 2hrs with whisked. Colorless needle crystals of the title compound were obtained by slow evaporation of solvent at room temperature. Melting point: 407 - 407.5 K.

Refinement

The positions of the N2-, N3-bound H atoms were placed at fixed positions and refined accord to the riding model. The C-bound H atoms were included in the riding model approximation with C—H = 0.93 Å and Uiso of each H atom = 1.2Ueq(C).

Figures

Fig. 1.
View of the title compound showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented by circles of arbitrary radius.
Fig. 2.
Hydrogen bonds diagram of the title compound, showing the H-bonded interactions (dashed lines). O2I, O2II represent O2i, O2ii, respectively.

Crystal data

C11H15N3O3F(000) = 504
Mr = 237.26Dx = 1.274 Mg m3
Monoclinic, P21/cMelting point = 407–407.5 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 11.377 (5) ÅCell parameters from 2827 reflections
b = 4.745 (2) Åθ = 2.7–27.5°
c = 23.244 (10) ŵ = 0.09 mm1
β = 99.534 (5)°T = 293 K
V = 1237.3 (9) Å3Prism, colourless
Z = 41.00 × 0.45 × 0.10 mm

Data collection

Bruker P4 diffractometer2297 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.022
graphiteθmax = 27.5°, θmin = 2.7°
Detector resolution: 0 pixels mm-1h = −14→11
ω scansk = −6→6
9032 measured reflectionsl = −24→30
2803 independent reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150H-atom parameters constrained
S = 0.96w = 1/[σ2(Fo2) + (0.080P)2 + 0.3962P] where P = (Fo2 + 2Fc2)/3
2803 reflections(Δ/σ)max < 0.001
154 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = −0.28 e Å3

Special details

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 > 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)

xyzUiso*/Ueq
C10.16780 (13)0.4979 (3)0.41169 (7)0.0451 (4)
C20.18448 (13)0.3174 (3)0.45907 (7)0.0476 (4)
H20.12110.26180.47710.057*
C30.29993 (13)0.2221 (4)0.47874 (6)0.0467 (4)
C40.39038 (13)0.3146 (4)0.45039 (7)0.0552 (4)
H40.46820.25310.46220.066*
C50.36375 (14)0.4981 (4)0.40462 (8)0.0608 (5)
H50.42600.56190.38670.073*
C60.04284 (13)0.5972 (4)0.38881 (7)0.0493 (4)
C7−0.15075 (13)0.6370 (3)0.27838 (7)0.0446 (4)
C8−0.26718 (18)0.7610 (4)0.24930 (10)0.0732 (6)
H8A−0.29380.89480.27600.088*
H8B−0.25300.86540.21520.088*
C9−0.36264 (19)0.5625 (6)0.23120 (15)0.1004 (9)
H9D−0.43270.66240.21340.151*
H9A−0.37950.46070.26460.151*
H9B−0.33910.43250.20360.151*
C100.24191 (15)−0.0530 (4)0.55627 (8)0.0557 (4)
H10A0.1822−0.16240.53110.067*
H10B0.20290.10470.57180.067*
C110.30482 (18)−0.2325 (5)0.60472 (9)0.0708 (6)
H11A0.2481−0.30410.62740.106*
H11B0.3636−0.12160.62920.106*
H11C0.3431−0.38710.58860.106*
N10.25346 (11)0.5917 (3)0.38402 (6)0.0540 (4)
N20.03317 (11)0.7407 (3)0.33833 (6)0.0506 (3)
H2A0.09600.78220.32400.061*
N3−0.07761 (11)0.8213 (3)0.30948 (6)0.0490 (3)
H3A−0.09990.99370.31160.059*
O1−0.04003 (11)0.5488 (4)0.41406 (6)0.0787 (5)
O2−0.12542 (11)0.3873 (2)0.27472 (6)0.0604 (4)
O30.33191 (10)0.0459 (3)0.52425 (5)0.0598 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0370 (7)0.0495 (8)0.0482 (8)0.0069 (6)0.0051 (6)−0.0025 (6)
C20.0360 (7)0.0558 (9)0.0511 (8)0.0084 (6)0.0075 (6)0.0029 (7)
C30.0396 (7)0.0533 (9)0.0463 (8)0.0093 (6)0.0044 (6)0.0002 (7)
C40.0325 (7)0.0737 (11)0.0576 (9)0.0083 (7)0.0025 (6)0.0038 (8)
C50.0358 (8)0.0857 (13)0.0609 (10)0.0011 (8)0.0083 (7)0.0104 (9)
C60.0391 (8)0.0530 (9)0.0554 (9)0.0111 (7)0.0062 (6)0.0044 (7)
C70.0503 (8)0.0319 (7)0.0501 (8)0.0043 (6)0.0037 (6)0.0105 (6)
C80.0658 (11)0.0457 (9)0.0953 (15)0.0063 (8)−0.0247 (10)0.0110 (9)
C90.0567 (12)0.0702 (14)0.162 (3)0.0015 (10)−0.0182 (14)0.0214 (15)
C100.0455 (8)0.0638 (10)0.0591 (10)0.0094 (7)0.0124 (7)0.0056 (8)
C110.0607 (11)0.0857 (14)0.0659 (11)0.0081 (10)0.0104 (9)0.0210 (10)
N10.0393 (7)0.0669 (9)0.0549 (8)0.0039 (6)0.0054 (6)0.0076 (7)
N20.0378 (6)0.0494 (7)0.0627 (8)0.0066 (5)0.0027 (6)0.0113 (6)
N30.0445 (7)0.0314 (6)0.0666 (8)0.0084 (5)−0.0034 (6)0.0054 (6)
O10.0440 (7)0.1159 (12)0.0797 (9)0.0281 (7)0.0204 (6)0.0354 (8)
O20.0739 (8)0.0305 (6)0.0743 (8)0.0092 (5)0.0053 (6)0.0045 (5)
O30.0407 (6)0.0781 (8)0.0612 (7)0.0186 (5)0.0099 (5)0.0205 (6)

Geometric parameters (Å, °)

C1—N11.330 (2)C8—C91.446 (3)
C1—C21.383 (2)C8—H8A0.9700
C1—C61.508 (2)C8—H8B0.9700
C2—C31.393 (2)C9—H9D0.9600
C2—H20.9300C9—H9A0.9600
C3—O31.3502 (19)C9—H9B0.9600
C3—C41.382 (2)C10—O31.440 (2)
C4—C51.369 (3)C10—C111.496 (3)
C4—H40.9300C10—H10A0.9700
C5—N11.342 (2)C10—H10B0.9700
C5—H50.9300C11—H11A0.9600
C6—O11.212 (2)C11—H11B0.9600
C6—N21.345 (2)C11—H11C0.9600
C7—O21.2256 (19)N2—N31.3800 (17)
C7—N31.335 (2)N2—H2A0.8600
C7—C81.504 (2)N3—H3A0.8600
N1—C1—C2125.26 (14)C8—C9—H9D109.5
N1—C1—C6116.63 (14)C8—C9—H9A109.5
C2—C1—C6118.10 (14)H9D—C9—H9A109.5
C1—C2—C3117.38 (14)C8—C9—H9B109.5
C1—C2—H2121.3H9D—C9—H9B109.5
C3—C2—H2121.3H9A—C9—H9B109.5
O3—C3—C4116.42 (13)O3—C10—C11106.39 (14)
O3—C3—C2125.11 (14)O3—C10—H10A110.5
C4—C3—C2118.46 (15)C11—C10—H10A110.5
C5—C4—C3119.08 (14)O3—C10—H10B110.5
C5—C4—H4120.5C11—C10—H10B110.5
C3—C4—H4120.5H10A—C10—H10B108.6
N1—C5—C4124.12 (16)C10—C11—H11A109.5
N1—C5—H5117.9C10—C11—H11B109.5
C4—C5—H5117.9H11A—C11—H11B109.5
O1—C6—N2124.08 (14)C10—C11—H11C109.5
O1—C6—C1122.24 (15)H11A—C11—H11C109.5
N2—C6—C1113.69 (14)H11B—C11—H11C109.5
O2—C7—N3122.59 (14)C1—N1—C5115.67 (15)
O2—C7—C8123.14 (15)C6—N2—N3120.02 (13)
N3—C7—C8114.25 (13)C6—N2—H2A120.0
C9—C8—C7116.04 (16)N3—N2—H2A120.0
C9—C8—H8A108.3C7—N3—N2121.25 (12)
C7—C8—H8A108.3C7—N3—H3A119.4
C9—C8—H8B108.3N2—N3—H3A119.4
C7—C8—H8B108.3C3—O3—C10118.97 (12)
H8A—C8—H8B107.4
N1—C1—C2—C3−1.2 (3)N3—C7—C8—C9−161.1 (2)
C6—C1—C2—C3178.43 (14)C2—C1—N1—C50.4 (3)
C1—C2—C3—O3179.96 (15)C6—C1—N1—C5−179.20 (15)
C1—C2—C3—C40.6 (2)C4—C5—N1—C11.0 (3)
O3—C3—C4—C5−178.73 (17)O1—C6—N2—N3−5.8 (3)
C2—C3—C4—C50.7 (3)C1—C6—N2—N3173.92 (13)
C3—C4—C5—N1−1.6 (3)O2—C7—N3—N21.7 (2)
N1—C1—C6—O1−172.29 (17)C8—C7—N3—N2−179.35 (16)
C2—C1—C6—O18.0 (3)C6—N2—N3—C7−77.1 (2)
N1—C1—C6—N28.0 (2)C4—C3—O3—C10178.74 (16)
C2—C1—C6—N2−171.66 (14)C2—C3—O3—C10−0.7 (3)
O2—C7—C8—C917.9 (3)C11—C10—O3—C3−177.84 (16)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2A···O2i0.862.433.067 (2)132
N3—H3A···O2ii0.862.062.831 (2)150

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JH2133).

References

  • Bruker (1999). XSCANS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wu, W. S. & Liu, S. X. (2001). Chin. J. Struct. Chem.20, 226–228.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography