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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2734.
Published online 2009 October 17. doi:  10.1107/S1600536809040902
PMCID: PMC2971095

N,N′-Bis(6-methyl-2-pyrid­yl)oxamide

Abstract

In the crystal structure of the title compound, C14H14N4O2, the mol­ecules are almost planar (mean deviation 0.028 Å) and a weak intra­molecular N—H(...)O hydrogen bond between the H atom bound to an oxamide N atom and a carbonyl O atom is found. The asymmetric unit consits of one half-mol­ecule which is located on a centre of inversion.

Related literature

For the synthesis, see: Siedel et al. (1970 [triangle]). For a series of Ag(I) coordination polymers containing N1,N2-bis­(2-pyrid­yl)­oxamide ligands, see: Hsu & Chen (2004 [triangle]); Hu et al. (2004 [triangle]).

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Object name is e-65-o2734-scheme1.jpg

Experimental

Crystal data

  • C14H14N4O2
  • M r = 270.29
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2734-efi1.jpg
  • a = 3.8925 (6) Å
  • b = 15.964 (2) Å
  • c = 10.8353 (14) Å
  • β = 94.461 (13)°
  • V = 671.26 (16) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 295 K
  • 0.4 × 0.2 × 0.1 mm

Data collection

  • Bruker P4 diffractometer
  • Absorption correction: multi-scan (XSCANS; Siemens, 1995 [triangle]) T min = 0.741, T max = 0.762
  • 1867 measured reflections
  • 1190 independent reflections
  • 767 reflections with I > 2σ(I)
  • R int = 0.028
  • 3 standard reflections every 97 reflections intensity decay: none

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.101
  • S = 1.01
  • 1190 reflections
  • 93 parameters
  • H-atom parameters constrained
  • Δρmax = 0.14 e Å−3
  • Δρmin = −0.12 e Å−3

Data collection: XSCANS (Siemens, 1995 [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/S1600536809040902/nc2161sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809040902/nc2161Isup2.hkl

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

Acknowledgments

We are grateful to the National Science Council of the Republic of China for support. This research was also supported by the project of the specific research fields in Chung-Yuan Christian University, Taiwan, under grant No. CYCU-98-CR—CH.

supplementary crystallographic information

Comment

A series of Ag(I) coordination polymers containg N1,N2-bis(2-pyridyl)oxamide ligands have been prepared, which show one-dimensional and two-dimensional structures (Hsu, et al., 2004; Hu, et al., 2004). To investigate the steric effect of the alkyl groups on the structural type of such coordination polymers, we have synthesized the title compound. Within this project its crystal structure was determined.

In its crystal structure weak intramolecular N-H···O hydrogen bonding is found (Tab. 1) and the molecules are almost planar (Fig. 1).

Experimental

2-Amino-6-methylpyridine (6.2 g, 57.3 mmol) was dissolved in 200 ml CH2Cl2, followed by addition of triethyl amine (10.0 ml, 72.1 mmol) at 0° C. The mixture was then stirred for 10 min. Oxalyl chloride (2.5 ml, 28.7 mmol) in 10 ml CH2Cl2 was then added slowly to the above mixture. After continuous stirring for 3 h at 0° give maximu[C, 200 ml hexanes was added to the mixture to induce precipitate. The solid was filtered, washed with water to give a white product. Yield: 2.8 g (36%). Coloress plate crystals suitable for X-ray crystallography were obtained by slow evaporization of the solvent from a solution in CH2Cl2.

Refinement

All the hydrogen atoms were placed into idealized positions and constrained by the riding atom approximation with C—H = 0.93 — 0.96 Å, N—H = 0.86 Å and Uiso(H) = 1.5 Ueq(C) or 1.2 Ueq(C, N). The methyl H atoms are disordered and were refined in two different orientations.

Figures

Fig. 1.
Crystal structure of the title compound with labeling and displacement ellipsoids drawn at the 30% probability level. Symmetry code: i = -x + 1, -y + 1, -z + 2. The disorder is shown with open bonds.

Crystal data

C14H14N4O2F(000) = 284
Mr = 270.29Dx = 1.337 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 23 reflections
a = 3.8925 (6) Åθ = 7.5–12.6°
b = 15.964 (2) ŵ = 0.09 mm1
c = 10.8353 (14) ÅT = 295 K
β = 94.461 (13)°Plate, colorless
V = 671.26 (16) Å30.4 × 0.2 × 0.1 mm
Z = 2

Data collection

Bruker P4 diffractometer767 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.028
graphiteθmax = 25.0°, θmin = 2.3°
ω scansh = −1→4
Absorption correction: multi-scan (XSCANS; Siemens, 1995)k = −1→18
Tmin = 0.741, Tmax = 0.762l = −12→12
1867 measured reflections3 standard reflections every 97 reflections
1190 independent reflections intensity decay: none

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.101w = 1/[σ2(Fo2) + (0.0467P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
1190 reflectionsΔρmax = 0.14 e Å3
93 parametersΔρmin = −0.11 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.021 (4)

Special details

Experimental. 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.
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)

xyzUiso*/UeqOcc. (<1)
O0.2331 (4)0.50956 (7)0.86392 (12)0.0677 (5)
N10.4420 (4)0.25146 (8)0.92913 (12)0.0454 (4)
N20.4631 (4)0.39274 (9)0.95953 (12)0.0487 (5)
H2A0.58920.37841.02480.058*
C10.4561 (6)0.10020 (12)0.92021 (19)0.0675 (6)
H1A0.60450.10960.99390.101*0.50
H1B0.57730.06850.86210.101*0.50
H1C0.25600.06960.94070.101*0.50
H1D0.35400.05560.87060.101*0.50
H1E0.38120.09671.00240.101*0.50
H1F0.70250.09550.92370.101*0.50
C20.3474 (5)0.18289 (10)0.86378 (16)0.0482 (5)
C30.1571 (5)0.18820 (12)0.75053 (17)0.0548 (6)
H3A0.09470.13990.70640.066*
C40.0617 (5)0.26555 (11)0.70415 (17)0.0552 (6)
H4A−0.06650.26980.62830.066*
C50.1561 (5)0.33684 (12)0.77004 (15)0.0489 (5)
H5A0.09490.38990.74050.059*
C60.3460 (5)0.32573 (10)0.88206 (15)0.0421 (5)
C70.4079 (5)0.47496 (11)0.94694 (16)0.0460 (5)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O0.0921 (11)0.0427 (8)0.0626 (9)0.0079 (7)−0.0296 (8)0.0000 (6)
N10.0530 (10)0.0360 (9)0.0464 (9)0.0001 (8)−0.0011 (7)−0.0017 (7)
N20.0639 (11)0.0342 (9)0.0452 (8)0.0019 (8)−0.0138 (7)−0.0021 (7)
C10.0770 (16)0.0412 (12)0.0839 (14)0.0009 (11)0.0040 (12)−0.0021 (10)
C20.0500 (12)0.0391 (10)0.0562 (11)−0.0025 (9)0.0076 (9)−0.0051 (9)
C30.0605 (13)0.0481 (12)0.0558 (11)−0.0083 (10)0.0035 (10)−0.0146 (9)
C40.0585 (13)0.0594 (13)0.0461 (10)−0.0065 (11)−0.0056 (9)−0.0078 (9)
C50.0549 (12)0.0467 (11)0.0438 (9)0.0028 (10)−0.0052 (9)0.0006 (9)
C60.0470 (11)0.0371 (10)0.0419 (9)−0.0002 (9)0.0016 (8)−0.0026 (8)
C70.0551 (12)0.0377 (11)0.0441 (10)0.0024 (9)−0.0038 (9)0.0005 (8)

Geometric parameters (Å, °)

O—C71.217 (2)C1—H1E0.9600
N1—C61.333 (2)C1—H1F0.9600
N1—C21.340 (2)C2—C31.386 (3)
N2—C71.335 (2)C3—C41.373 (3)
N2—C61.413 (2)C3—H3A0.9300
N2—H2A0.8600C4—C51.378 (2)
C1—C21.502 (3)C4—H4A0.9300
C1—H1A0.9600C5—C61.383 (2)
C1—H1B0.9600C5—H5A0.9300
C1—H1C0.9600C7—C7i1.532 (3)
C1—H1D0.9600
C6—N1—C2117.86 (14)H1C—C1—H1F141.1
C7—N2—C6129.90 (15)H1D—C1—H1F109.5
C7—N2—H2A115.1H1E—C1—H1F109.5
C6—N2—H2A115.1N1—C2—C3121.61 (16)
C2—C1—H1A109.5N1—C2—C1116.48 (16)
C2—C1—H1B109.5C3—C2—C1121.91 (16)
H1A—C1—H1B109.5C4—C3—C2119.32 (17)
C2—C1—H1C109.5C4—C3—H3A120.3
H1A—C1—H1C109.5C2—C3—H3A120.3
H1B—C1—H1C109.5C3—C4—C5119.96 (17)
C2—C1—H1D109.5C3—C4—H4A120.0
H1A—C1—H1D141.1C5—C4—H4A120.0
H1B—C1—H1D56.3C4—C5—C6116.85 (16)
H1C—C1—H1D56.3C4—C5—H5A121.6
C2—C1—H1E109.5C6—C5—H5A121.6
H1A—C1—H1E56.3N1—C6—C5124.40 (15)
H1B—C1—H1E141.1N1—C6—N2112.23 (14)
H1C—C1—H1E56.3C5—C6—N2123.37 (15)
H1D—C1—H1E109.5O—C7—N2126.71 (17)
C2—C1—H1F109.5O—C7—C7i121.3 (2)
H1A—C1—H1F56.3N2—C7—C7i111.96 (19)
H1B—C1—H1F56.3

Symmetry codes: (i) −x+1, −y+1, −z+2.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2A···Oi0.862.242.6718 (18)111

Symmetry codes: (i) −x+1, −y+1, −z+2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2161).

References

  • Hsu, Y.-F. & Chen, J.-D. (2004). Eur. J. Inorg. Chem. pp. 1488–1493.
  • Hu, H.-L., Yeh, C.-W. & Chen, J.-D. (2004). Eur. J. Inorg. Chem. pp. 4696–4701.
  • Sheldrick, G. M. (2008). Acta Cryst A64, 112–122. [PubMed]
  • Siedel, M. C., Tuyle, G. C. V. & Weir, W. D. (1970). J. Org. Chem.35, 1662–1664.
  • Siemens (1995). XSCANS Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

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