N,N′-Bis(pyridin-3-yl)oxamide

Abstract

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,

• a = 3.8992 (7) Å

• b = 12.662 (2) Å

• c = 10.9678 (17) Å

• β = 97.983 (4)°

• V = 536.26 (16) ų

• 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[F ² > 2σ(F ²)] = 0.043

• wR(F ²) = 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

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.

Supplementary Material

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

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) .

supplementary crystallographic information

Comment

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).

Experimental

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

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 U_iso(H) = 1.2 or 1.5 U_eq(C/N).

Figures

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.

Crystal data

C12H10N4O2	F(000) = 252
Mr = 242.24	Dx = 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

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

Refinement

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(Fo2) + (0.075P)2] where P = (Fo2 + 2Fc2)/3
1050 reflections	(Δ/σ)max < 0.001
82 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	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)

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)

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.