N,N′-Bis(pyridin-2-yl)benzene-1,4-dicarboxamide

Abstract

Mol­ecules of the title compound, C₁₈H₁₄N₄O₂, are located around an inversion center and connected into chains in the crystal via inter­molecular N—H⋯N hydrogen bonds generating an R ₂ ²(8) motif.

Related literature

For N,N′-bis­(pyridin­yl) derivatives of 1,4-benzene­dicarbox­amide and their metal complexes, see: Tsai et al. (2010 ▶).

Experimental

Crystal data

• C₁₈H₁₄N₄O₂

• M _r = 318.33

• Triclinic,

• a = 5.7895 (4) Å

• b = 7.8315 (6) Å

• c = 8.8460 (5) Å

• α = 82.906 (6)°

• β = 74.083 (5)°

• γ = 73.695 (6)°

• V = 369.72 (4) ų

• Z = 1

• Mo Kα radiation

• μ = 0.10 mm⁻¹

• T = 298 K

• 0.60 × 0.60 × 0.56 mm

Data collection

• Siemens P4 diffractometer

• Absorption correction: ψ scan (XSCANS; Siemens, 1995 ▶) T _min = 0.831, T _max = 0.851

• 1962 measured reflections

• 1787 independent reflections

• 1521 reflections with I > 2σ(I)

• R _int = 0.013

• 3 standard reflections every 97 reflections intensity decay: none

Refinement

• R[F ² > 2σ(F ²)] = 0.040

• wR(F ²) = 0.112

• S = 1.06

• 1787 reflections

• 110 parameters

• H-atom parameters constrained

• Δρ_max = 0.32 e Å⁻³

• Δρ_min = −0.19 e Å⁻³

Data collection: XSCANS (Siemens, 1995 ▶); cell refinement: XSCANS; data reduction: XSCANS 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	2.34	3.1679 (15)	163

Symmetry code: (i) .

supplementary crystallographic information

Comment

Several Cu(II), Cd(II) and Hg(II) complexes containg N,N'-bis(2/3-aryl)-1,4-benzenedicarboxamide ligands have been reported, which show one-dimensional and two-dimensional structures (Tsai, et al., 2010). Within this project the crystal structure of the title compound was determined.

In its crystal structure intermolecular N—H···N hydrogen bonds are found (Tab. 1) and the molecule is located on a center of inversion (Fig. 1).

Experimental

The title compound was prepared according to a published procedure (Tsai, et al., 2010). Block crystals suitable for X-ray crystallography were obtained by slow evaporization of the solvent from a solution of the title compound in methanol.

Refinement

All the hydrogen atoms were placed into idealized positions and refined in the riding atom approximation with C—H = 0.93 Å, N—H = 0.86 Å and U_iso(H) = 1.2 U_eq(C, N).

Figures

Fig. 1.

Crystal structure of the title compound with atom labeling and displacement ellipsoids drawn at the 30% probability level. Symmetry code: (i) =-x + 2,-y,-z.

Crystal data

C18H14N4O2	Z = 1
Mr = 318.33	F(000) = 166
Triclinic, P1	Dx = 1.430 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.7895 (4) Å	Cell parameters from 50 reflections
b = 7.8315 (6) Å	θ = 4.8–15.0°
c = 8.8460 (5) Å	µ = 0.10 mm−1
α = 82.906 (6)°	T = 298 K
β = 74.083 (5)°	Block, pale yellow
γ = 73.695 (6)°	0.60 × 0.60 × 0.56 mm
V = 369.72 (4) Å3

Data collection

Bruker P4 diffractometer	1521 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.013
graphite	θmax = 28.0°, θmin = 2.4°
ω scans	h = 0→7
Absorption correction: ψ scan (XSCANS; Siemens, 1995)	k = −9→10
Tmin = 0.831, Tmax = 0.851	l = −11→11
1962 measured reflections	3 standard reflections every 97 reflections
1787 independent reflections	intensity decay: none

Refinement

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040	H-atom parameters constrained
wR(F2) = 0.112	w = 1/[σ2(Fo2) + (0.0468P)2 + 0.1049P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
1787 reflections	Δρmax = 0.32 e Å−3
110 parameters	Δρmin = −0.19 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.193 (17)

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 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	1.1101 (2)	0.21659 (16)	0.30550 (13)	0.0497 (3)
N1	0.7461 (2)	0.13586 (16)	0.41052 (13)	0.0369 (3)
H1A	0.6695	0.0611	0.3982	0.044*
N2	0.4263 (2)	0.20173 (15)	0.63054 (13)	0.0353 (3)
C1	0.6435 (2)	0.23152 (17)	0.54787 (14)	0.0316 (3)
C2	0.7512 (3)	0.35023 (19)	0.59089 (16)	0.0393 (3)
H2B	0.9066	0.3632	0.5336	0.047*
C3	0.6200 (3)	0.4479 (2)	0.72110 (18)	0.0434 (4)
H3A	0.6853	0.5296	0.7523	0.052*
C4	0.3907 (3)	0.42384 (19)	0.80528 (17)	0.0422 (3)
H4A	0.2982	0.4900	0.8924	0.051*
C5	0.3035 (3)	0.29915 (19)	0.75631 (16)	0.0381 (3)
H5A	0.1507	0.2816	0.8138	0.046*
C6	0.9524 (2)	0.14708 (17)	0.29436 (15)	0.0322 (3)
C7	0.9716 (2)	0.06764 (16)	0.14401 (14)	0.0290 (3)
C8	1.2030 (2)	−0.03051 (17)	0.06322 (14)	0.0314 (3)
H8A	1.3391	−0.0509	0.1057	0.038*
C9	1.2324 (2)	−0.09833 (17)	−0.08032 (15)	0.0321 (3)
H9A	1.3876	−0.1641	−0.1340	0.039*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
O	0.0418 (6)	0.0697 (7)	0.0464 (6)	−0.0318 (5)	−0.0005 (5)	−0.0194 (5)
N1	0.0417 (6)	0.0460 (6)	0.0291 (5)	−0.0261 (5)	−0.0008 (5)	−0.0092 (5)
N2	0.0366 (6)	0.0411 (6)	0.0302 (5)	−0.0166 (5)	−0.0041 (4)	−0.0045 (4)
C1	0.0368 (6)	0.0353 (6)	0.0256 (6)	−0.0148 (5)	−0.0065 (5)	−0.0023 (5)
C2	0.0426 (7)	0.0445 (8)	0.0364 (7)	−0.0224 (6)	−0.0055 (6)	−0.0067 (6)
C3	0.0532 (9)	0.0383 (7)	0.0443 (8)	−0.0182 (6)	−0.0115 (7)	−0.0100 (6)
C4	0.0491 (8)	0.0360 (7)	0.0382 (7)	−0.0074 (6)	−0.0055 (6)	−0.0110 (5)
C5	0.0360 (7)	0.0401 (7)	0.0353 (7)	−0.0101 (6)	−0.0029 (5)	−0.0041 (5)
C6	0.0332 (6)	0.0359 (6)	0.0298 (6)	−0.0144 (5)	−0.0052 (5)	−0.0039 (5)
C7	0.0300 (6)	0.0323 (6)	0.0259 (6)	−0.0139 (5)	−0.0030 (4)	−0.0015 (4)
C8	0.0267 (6)	0.0384 (7)	0.0308 (6)	−0.0119 (5)	−0.0068 (5)	−0.0011 (5)
C9	0.0263 (6)	0.0359 (6)	0.0320 (6)	−0.0084 (5)	−0.0020 (5)	−0.0057 (5)

Geometric parameters (Å, °)

O—C6	1.2169 (16)	C4—C5	1.377 (2)
N1—C6	1.3614 (16)	C4—H4A	0.9300
N1—C1	1.4034 (16)	C5—H5A	0.9300
N1—H1A	0.8600	C6—C7	1.5009 (17)
N2—C1	1.3375 (17)	C7—C8	1.3888 (17)
N2—C5	1.3403 (17)	C7—C9i	1.3936 (17)
C1—C2	1.3932 (18)	C8—C9	1.3860 (17)
C2—C3	1.378 (2)	C8—H8A	0.9300
C2—H2B	0.9300	C9—C7i	1.3936 (17)
C3—C4	1.384 (2)	C9—H9A	0.9300
C3—H3A	0.9300
C6—N1—C1	127.85 (11)	N2—C5—C4	123.77 (13)
C6—N1—H1A	116.1	N2—C5—H5A	118.1
C1—N1—H1A	116.1	C4—C5—H5A	118.1
C1—N2—C5	117.11 (11)	O—C6—N1	124.94 (12)
N2—C1—C2	123.38 (12)	O—C6—C7	120.89 (11)
N2—C1—N1	112.88 (11)	N1—C6—C7	114.16 (11)
C2—C1—N1	123.70 (12)	C8—C7—C9i	119.81 (11)
C3—C2—C1	117.84 (13)	C8—C7—C6	118.37 (11)
C3—C2—H2B	121.1	C9i—C7—C6	121.72 (11)
C1—C2—H2B	121.1	C9—C8—C7	120.42 (12)
C2—C3—C4	119.75 (13)	C9—C8—H8A	119.8
C2—C3—H3A	120.1	C7—C8—H8A	119.8
C4—C3—H3A	120.1	C8—C9—C7i	119.77 (11)
C5—C4—C3	118.06 (13)	C8—C9—H9A	120.1
C5—C4—H4A	121.0	C7i—C9—H9A	120.1
C3—C4—H4A	121.0

Symmetry codes: (i) −x+2, −y, −z.

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2ii	0.86	2.34	3.1679 (15)	163

Symmetry codes: (ii) −x+1, −y, −z+1.