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ISSN: 2056-9890

N,N′-Bis(pyridin-3-yl)oxamide

aCenter for General Education, Hsin Sheng Junior College of Medical Care and Management, Longtan, Taiwan, and bDepartment of Chemistry, Chung-Yuan Christian University, Chung-Li, Taiwan
*Correspondence e-mail: jdchen@cycu.edu.tw

(Received 12 March 2013; accepted 17 March 2013; online 23 March 2013)

The title mol­ecule, C12H10N4O2, located about an inversion centre, is roughly planar, with an r.m.s. deviation from the least-squares plane of all non-H atoms of 0.019 Å. In the crystal, N—H⋯N hydrogen bonds between the amide N—H group and the pyridine N atom connect the mol­ecules into a corrugated layer parallel to (10-1).

Related literature

For N,N'-di(3-pyrid­yl)oxamide and its metal complexes, see: Hu et al. (2012[Hu, H.-L., Hsu, Y.-F., Wu, C.-J., Yeh, C.-W., Chen, J.-D. & Wang, J.-C. (2012). Polyhedron, 33, 280-288.]).

[Scheme 1]

Experimental

Crystal data
  • C12H10N4O2

  • Mr = 242.24

  • Monoclinic, P 21 /n

  • a = 3.8992 (7) Å

  • b = 12.662 (2) Å

  • c = 10.9678 (17) Å

  • β = 97.983 (4)°

  • V = 536.26 (16) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 297 K

  • 0.58 × 0.20 × 0.06 mm

Data collection
  • Bruker SMART 1000 diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1997[Bruker (1997). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 1.000, Tmax = 1.000

  • 2997 measured reflections

  • 1050 independent reflections

  • 768 reflections with I > 2σ(I)

  • Rint = 0.034

Refinement
  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.126

  • S = 1.06

  • 1050 reflections

  • 82 parameters

  • H-atom parameters constrained

  • Δρmax = 0.19 e Å−3

  • Δρmin = −0.26 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1A⋯N2i 0.86 2.26 3.061 (2) 156
Symmetry code: (i) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 1997[Bruker (1997). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Several Zn(II), Cd(II) and Hg(II) complexes containing N,N'-di(3-pyridyl)oxamide ligands have been reported, which show one-dimensional chains and metallocycles (Hu et al., 2012). Within this project the crystal structure of the title compound was determined (Fig. 1). In its crystal structure intermolecular N—H···N hydrogen bonds are found (Table 1 & Fig. 2).

Related literature top

For N,N'-di(3-pyridyl)oxamide and its metal complexes, see: Hu et al. (2012).

Experimental top

The title compound was prepared according to a published procedure (Hu et al., 2012). Block crystals suitable for X-ray crystallography were obtained by slow evaporation of the solvent from a solution of the title compound in methanol.

Refinement top

H atoms bound to C and N atoms were placed in idealized positions and constrained to ride on their parent atoms, with C—H = 0.93 Å and N—H = 0.86 Å, and with Uiso(H) = 1.2 or 1.5 Ueq(C/N).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997) and SHELXTL (Sheldrick, 2008); 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
[Figure 1] Fig. 1. Molecular structure of the title compound with atom labeling and displacement ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. Hydrogen bonding interactions in the title compound.
N,N'-Bis(pyridin-3-yl)oxamide top
Crystal data top
C12H10N4O2F(000) = 252
Mr = 242.24Dx = 1.500 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1108 reflections
a = 3.8992 (7) Åθ = 2.5–25.6°
b = 12.662 (2) ŵ = 0.11 mm1
c = 10.9678 (17) ÅT = 297 K
β = 97.983 (4)°Parallelepiped, colorless
V = 536.26 (16) Å30.58 × 0.20 × 0.06 mm
Z = 2
Data collection top
Bruker SMART 1000
diffractometer
1050 independent reflections
Radiation source: fine-focus sealed tube768 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
ϕ and ω scansθmax = 26.0°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 44
Tmin = 1.000, Tmax = 1.000k = 1514
2997 measured reflectionsl = 1213
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.075P)2]
where P = (Fo2 + 2Fc2)/3
1050 reflections(Δ/σ)max < 0.001
82 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.26 e Å3
Crystal data top
C12H10N4O2V = 536.26 (16) Å3
Mr = 242.24Z = 2
Monoclinic, P21/nMo Kα radiation
a = 3.8992 (7) ŵ = 0.11 mm1
b = 12.662 (2) ÅT = 297 K
c = 10.9678 (17) Å0.58 × 0.20 × 0.06 mm
β = 97.983 (4)°
Data collection top
Bruker SMART 1000
diffractometer
1050 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
768 reflections with I > 2σ(I)
Tmin = 1.000, Tmax = 1.000Rint = 0.034
2997 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.126H-atom parameters constrained
S = 1.06Δρmax = 0.19 e Å3
1050 reflectionsΔρmin = 0.26 e Å3
82 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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) top
xyzUiso*/Ueq
O0.1096 (4)0.96926 (10)1.15577 (12)0.0530 (5)
N10.2264 (4)0.87848 (10)0.98550 (13)0.0342 (4)
H1A0.20330.88270.90650.041*
N20.6079 (4)0.67892 (12)1.21174 (13)0.0421 (5)
C10.0929 (5)0.95887 (12)1.04473 (16)0.0344 (4)
C20.3993 (4)0.78835 (13)1.03865 (15)0.0309 (4)
C30.4530 (5)0.76739 (14)1.16394 (16)0.0382 (5)
H3A0.37840.81681.21730.046*
C40.7184 (5)0.60928 (14)1.13512 (17)0.0416 (5)
H4A0.82380.54761.16760.050*
C50.6832 (5)0.62458 (14)1.00998 (17)0.0404 (5)
H5A0.76670.57470.95930.048*
C60.5223 (5)0.71506 (13)0.96066 (16)0.0367 (5)
H6A0.49640.72690.87620.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O0.0796 (11)0.0451 (9)0.0339 (8)0.0183 (7)0.0064 (7)0.0030 (6)
N10.0433 (9)0.0310 (8)0.0283 (8)0.0024 (6)0.0057 (6)0.0002 (6)
N20.0547 (11)0.0349 (9)0.0351 (9)0.0016 (7)0.0012 (7)0.0017 (7)
C10.0387 (10)0.0312 (9)0.0337 (9)0.0020 (7)0.0065 (7)0.0017 (7)
C20.0339 (9)0.0277 (8)0.0313 (9)0.0046 (7)0.0048 (7)0.0007 (7)
C30.0501 (12)0.0311 (9)0.0335 (10)0.0017 (7)0.0066 (8)0.0028 (8)
C40.0479 (11)0.0324 (9)0.0428 (11)0.0021 (8)0.0001 (8)0.0030 (8)
C50.0446 (11)0.0354 (10)0.0411 (10)0.0039 (8)0.0061 (8)0.0042 (8)
C60.0416 (11)0.0380 (10)0.0305 (9)0.0014 (8)0.0050 (7)0.0009 (8)
Geometric parameters (Å, º) top
O—C11.218 (2)C2—C61.392 (2)
N1—C11.350 (2)C3—H3A0.9300
N1—C21.410 (2)C4—C51.374 (3)
N1—H1A0.8600C4—H4A0.9300
N2—C41.330 (2)C5—C61.380 (2)
N2—C31.344 (2)C5—H5A0.9300
C1—C1i1.541 (3)C6—H6A0.9300
C2—C31.387 (2)
C1—N1—C2127.27 (14)N2—C3—H3A118.5
C1—N1—H1A116.4C2—C3—H3A118.5
C2—N1—H1A116.4N2—C4—C5122.78 (17)
C4—N2—C3118.26 (15)N2—C4—H4A118.6
O—C1—N1126.31 (16)C5—C4—H4A118.6
O—C1—C1i121.25 (19)C4—C5—C6119.04 (17)
N1—C1—C1i112.44 (17)C4—C5—H5A120.5
C3—C2—C6117.65 (16)C6—C5—H5A120.5
C3—C2—N1124.21 (15)C5—C6—C2119.30 (16)
C6—C2—N1118.14 (14)C5—C6—H6A120.3
N2—C3—C2122.94 (16)C2—C6—H6A120.3
Symmetry code: (i) x, y+2, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···N2ii0.862.263.061 (2)156
Symmetry code: (ii) x1/2, y+3/2, z1/2.

Experimental details

Crystal data
Chemical formulaC12H10N4O2
Mr242.24
Crystal system, space groupMonoclinic, P21/n
Temperature (K)297
a, b, c (Å)3.8992 (7), 12.662 (2), 10.9678 (17)
β (°) 97.983 (4)
V3)536.26 (16)
Z2
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.58 × 0.20 × 0.06
Data collection
DiffractometerBruker SMART 1000
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 1997)
Tmin, Tmax1.000, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
2997, 1050, 768
Rint0.034
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.126, 1.06
No. of reflections1050
No. of parameters82
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.19, 0.26

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997) and SHELXTL (Sheldrick, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···N2i0.862.263.061 (2)156
Symmetry code: (i) x1/2, y+3/2, z1/2.
 

Acknowledgements

We are grateful to the National Science Council of the Republic of China for support.

References

First citationBruker (1997). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationHu, H.-L., Hsu, Y.-F., Wu, C.-J., Yeh, C.-W., Chen, J.-D. & Wang, J.-C. (2012). Polyhedron, 33, 280–288.  Web of Science CSD CrossRef CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
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