N,N′-Bis(pyridin-3-yl)oxamide

Liu, S.-M.; He, H.-Y.; Chen, J.-D.

doi:10.1107/S1600536813007277

organic compounds

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ISSN: 2056-9890

Volume 69| Part 4| April 2013| Page o560

doi:10.1107/S1600536813007277

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N,N′-Bis(pyridin-3-yl)oxamide

Shih-Miao Liu,^a Hsiu-Yi He ^b and Jhy-Der Chen ^b ^*

^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 ).

Experimental

Crystal data

C₁₂H₁₀N₄O₂
M_r = 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 ) T_min = 1.000, T_max = 1.000
2997 measured reflections
1050 independent reflections
768 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.126
S = 1.06
1050 reflections
82 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT 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; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813007277/gk2563sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813007277/gk2563Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813007277/gk2563Isup3.cml

checkCIF report

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.

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

	Fig. 1. Molecular structure of the title compound with atom labeling and displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Hydrogen bonding interactions in the title compound.

N,N'-Bis(pyridin-3-yl)oxamide top

Crystal data top

C₁₂H₁₀N₄O₂	F(000) = 252
M_r = 242.24	D_x = 1.500 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1108 reflections
a = 3.8992 (7) Å	θ = 2.5–25.6°
b = 12.662 (2) Å	µ = 0.11 mm⁻¹
c = 10.9678 (17) Å	T = 297 K
β = 97.983 (4)°	Parallelepiped, colorless
V = 536.26 (16) Å³	0.58 × 0.20 × 0.06 mm
Z = 2

Data collection top

Bruker SMART 1000 diffractometer	1050 independent reflections
Radiation source: fine-focus sealed tube	768 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −4→4
T_min = 1.000, T_max = 1.000	k = −15→14
2997 measured reflections	l = −12→13

Refinement top

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.075P)²] where P = (F_o² + 2F_c²)/3
1050 reflections	(Δ/σ)_max < 0.001
82 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₂H₁₀N₄O₂	V = 536.26 (16) Å³
M_r = 242.24	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 3.8992 (7) Å	µ = 0.11 mm⁻¹
b = 12.662 (2) Å	T = 297 K
c = 10.9678 (17) Å	0.58 × 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)
T_min = 1.000, T_max = 1.000	R_int = 0.034
2997 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.06	Δρ_max = 0.19 e Å⁻³
1050 reflections	Δρ_min = −0.26 e Å⁻³
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

	x	y	z	U_iso*/U_eq
O	0.1096 (4)	0.96926 (10)	1.15577 (12)	0.0530 (5)
N1	0.2264 (4)	0.87848 (10)	0.98550 (13)	0.0342 (4)
H1A	0.2033	0.8827	0.9065	0.041*
N2	0.6079 (4)	0.67892 (12)	1.21174 (13)	0.0421 (5)
C1	0.0929 (5)	0.95887 (12)	1.04473 (16)	0.0344 (4)
C2	0.3993 (4)	0.78835 (13)	1.03865 (15)	0.0309 (4)
C3	0.4530 (5)	0.76739 (14)	1.16394 (16)	0.0382 (5)
H3A	0.3784	0.8168	1.2173	0.046*
C4	0.7184 (5)	0.60928 (14)	1.13512 (17)	0.0416 (5)
H4A	0.8238	0.5476	1.1676	0.050*
C5	0.6832 (5)	0.62458 (14)	1.00998 (17)	0.0404 (5)
H5A	0.7667	0.5747	0.9593	0.048*
C6	0.5223 (5)	0.71506 (13)	0.96066 (16)	0.0367 (5)
H6A	0.4964	0.7269	0.8762	0.044*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O	0.0796 (11)	0.0451 (9)	0.0339 (8)	0.0183 (7)	0.0064 (7)	−0.0030 (6)
N1	0.0433 (9)	0.0310 (8)	0.0283 (8)	0.0024 (6)	0.0057 (6)	0.0002 (6)
N2	0.0547 (11)	0.0349 (9)	0.0351 (9)	−0.0016 (7)	0.0012 (7)	0.0017 (7)
C1	0.0387 (10)	0.0312 (9)	0.0337 (9)	−0.0020 (7)	0.0065 (7)	−0.0017 (7)
C2	0.0339 (9)	0.0277 (8)	0.0313 (9)	−0.0046 (7)	0.0048 (7)	−0.0007 (7)
C3	0.0501 (12)	0.0311 (9)	0.0335 (10)	−0.0017 (7)	0.0066 (8)	−0.0028 (8)
C4	0.0479 (11)	0.0324 (9)	0.0428 (11)	0.0021 (8)	0.0001 (8)	0.0030 (8)
C5	0.0446 (11)	0.0354 (10)	0.0411 (10)	0.0039 (8)	0.0061 (8)	−0.0042 (8)
C6	0.0416 (11)	0.0380 (10)	0.0305 (9)	0.0014 (8)	0.0050 (7)	−0.0009 (8)

Geometric parameters (Å, º) top

O—C1	1.218 (2)	C2—C6	1.392 (2)
N1—C1	1.350 (2)	C3—H3A	0.9300
N1—C2	1.410 (2)	C4—C5	1.374 (3)
N1—H1A	0.8600	C4—H4A	0.9300
N2—C4	1.330 (2)	C5—C6	1.380 (2)
N2—C3	1.344 (2)	C5—H5A	0.9300
C1—C1ⁱ	1.541 (3)	C6—H6A	0.9300
C2—C3	1.387 (2)

C1—N1—C2	127.27 (14)	N2—C3—H3A	118.5
C1—N1—H1A	116.4	C2—C3—H3A	118.5
C2—N1—H1A	116.4	N2—C4—C5	122.78 (17)
C4—N2—C3	118.26 (15)	N2—C4—H4A	118.6
O—C1—N1	126.31 (16)	C5—C4—H4A	118.6
O—C1—C1ⁱ	121.25 (19)	C4—C5—C6	119.04 (17)
N1—C1—C1ⁱ	112.44 (17)	C4—C5—H5A	120.5
C3—C2—C6	117.65 (16)	C6—C5—H5A	120.5
C3—C2—N1	124.21 (15)	C5—C6—C2	119.30 (16)
C6—C2—N1	118.14 (14)	C5—C6—H6A	120.3
N2—C3—C2	122.94 (16)	C2—C6—H6A	120.3

Symmetry code: (i) −x, −y+2, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2ⁱⁱ	0.86	2.26	3.061 (2)	156

Symmetry code: (ii) x−1/2, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₀N₄O₂
M_r	242.24
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	297
a, b, c (Å)	3.8992 (7), 12.662 (2), 10.9678 (17)
β (°)	97.983 (4)
V (Å³)	536.26 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.58 × 0.20 × 0.06

Data collection
Diffractometer	Bruker SMART 1000 diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	1.000, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	2997, 1050, 768
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.126, 1.06
No. of reflections	1050
No. of parameters	82
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2ⁱ	0.86	2.26	3.061 (2)	156

Symmetry code: (i) x−1/2, −y+3/2, z−1/2.

Acknowledgements

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

References

Bruker (1997). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hu, 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 Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar