N,N'-(Ethane-1,2-diyldi-o-phenyl-ene)bis-(pyridine-2-carboxamide).

The title mol-ecule, C(26)H(22)N(4)O(2), is centrosymmetric and adopts an anti conformation. Two intra-molecular hydrogen bonds, viz. amide-pyridine N-H⋯N and phen-yl-amide C-H⋯O, stabilize the trans conformation of the (pyridine-2-carboxamido)-phenyl group about the amide plane. In the crystal, the presence of weak inter-molecular C-H⋯O hydrogen bonds results in the formation of a three-dimensional network.

Related literature

For a related structure, see: Meghdadi et al. (2006 ▶). For applications of the pyridine-bearing carboxamides, see: Song et al. (2010 ▶); Piguet et al. (1997 ▶); Lessmann & Horrocks (2000 ▶); Singh et al. (2008 ▶). For the synthesis of the ligand, see: Jain et al. (2004 ▶).

Experimental

Crystal data

C26H22N4O2

M = 422.48

Monoclinic,

a = 5.9548 (5) Å

b = 11.9548 (10) Å

c = 14.8133 (12) Å

β = 91.429 (2)°

V = 1054.21 (15) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 200 K

0.25 × 0.16 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer

7762 measured reflections

2616 independent reflections

1118 reflections with I > 2σ(I)

R int = 0.074

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.090

S = 0.84

2616 reflections

149 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶) and CrystalMaker (CrystalMaker, 2007 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811042309/kp2356sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811042309/kp2356Isup2.hkl

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

C26H22N4O2	F(000) = 444
Mr = 422.48	Dx = 1.331 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1330 reflections
a = 5.9548 (5) Å	θ = 2.8–25.8°
b = 11.9548 (10) Å	µ = 0.09 mm−1
c = 14.8133 (12) Å	T = 200 K
β = 91.429 (2)°	Block, colourless
V = 1054.21 (15) Å3	0.25 × 0.16 × 0.12 mm
Z = 2

Bruker SMART CCD area-detector diffractometer	1118 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.074
graphite	θmax = 28.3°, θmin = 2.2°
phi and ω scans	h = −7→7
7762 measured reflections	k = −15→11
2616 independent reflections	l = −19→19

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 0.84	w = 1/[σ2(Fo2) + (0.0126P)2] where P = (Fo2 + 2Fc2)/3
2616 reflections	(Δ/σ)max < 0.001
149 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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.

	x	y	z	Uiso*/Ueq
N1	0.8708 (3)	0.71472 (14)	0.45440 (12)	0.0405 (5)
C1	0.8708 (4)	0.64611 (19)	0.38332 (15)	0.0499 (7)
H1	0.7466	0.6485	0.3418	0.060*
C2	1.0440 (5)	0.57144 (19)	0.36728 (17)	0.0516 (8)
H2	1.0382	0.5237	0.3160	0.062*
C3	1.2230 (5)	0.5680 (2)	0.42681 (17)	0.0545 (8)
H3	1.3435	0.5176	0.4174	0.065*
C4	1.2270 (4)	0.63841 (18)	0.50077 (15)	0.0452 (7)
H4	1.3501	0.6378	0.5428	0.054*
C5	1.0471 (4)	0.70976 (17)	0.51194 (14)	0.0321 (6)
C6	1.0488 (4)	0.78986 (18)	0.59027 (14)	0.0316 (6)
O1	1.1900 (3)	0.78453 (12)	0.65163 (10)	0.0425 (4)
N2	0.8816 (3)	0.86669 (15)	0.58299 (12)	0.0333 (5)
H14	0.789 (4)	0.8555 (18)	0.5327 (15)	0.073 (9)*
C7	0.8427 (4)	0.96392 (17)	0.63478 (13)	0.0282 (5)
C8	0.6431 (4)	1.02237 (17)	0.61789 (13)	0.0282 (5)
C9	0.4708 (4)	0.98304 (17)	0.54855 (12)	0.0308 (5)
H9A	0.3226	1.0149	0.5632	0.037*
H9B	0.4587	0.9006	0.5518	0.037*
C10	0.6084 (4)	1.12198 (18)	0.66456 (14)	0.0379 (6)
H10	0.4734	1.1627	0.6539	0.046*
C11	0.7673 (4)	1.16257 (18)	0.72620 (15)	0.0425 (7)
H11	0.7412	1.2308	0.7571	0.051*
C12	0.9627 (4)	1.10390 (19)	0.74251 (14)	0.0421 (7)
H12	1.0720	1.1318	0.7845	0.051*
C13	1.0005 (4)	1.00386 (18)	0.69758 (13)	0.0352 (6)
H13	1.1343	0.9627	0.7098	0.042*

	U11	U22	U33	U12	U13	U23
N1	0.0473 (15)	0.0353 (12)	0.0385 (12)	0.0060 (10)	−0.0035 (10)	−0.0072 (10)
C1	0.059 (2)	0.0470 (17)	0.0437 (16)	0.0059 (14)	−0.0067 (14)	−0.0121 (13)
C2	0.074 (2)	0.0395 (17)	0.0413 (16)	0.0124 (14)	0.0094 (15)	−0.0059 (13)
C3	0.068 (2)	0.0478 (18)	0.0481 (17)	0.0240 (15)	0.0113 (16)	−0.0006 (14)
C4	0.0487 (19)	0.0428 (16)	0.0442 (16)	0.0168 (13)	0.0035 (13)	0.0024 (13)
C5	0.0394 (16)	0.0260 (13)	0.0314 (13)	0.0055 (10)	0.0068 (11)	0.0065 (10)
C6	0.0353 (16)	0.0290 (14)	0.0306 (13)	0.0010 (11)	0.0038 (11)	0.0084 (11)
O1	0.0430 (12)	0.0442 (10)	0.0399 (10)	0.0075 (8)	−0.0103 (8)	0.0046 (8)
N2	0.0355 (14)	0.0330 (12)	0.0311 (12)	0.0081 (9)	−0.0053 (10)	−0.0056 (9)
C7	0.0318 (15)	0.0292 (13)	0.0239 (12)	−0.0006 (10)	0.0034 (10)	−0.0018 (10)
C8	0.0305 (15)	0.0296 (13)	0.0249 (12)	0.0001 (10)	0.0053 (10)	0.0028 (10)
C9	0.0291 (14)	0.0310 (13)	0.0324 (13)	0.0025 (10)	0.0043 (11)	0.0031 (10)
C10	0.0444 (18)	0.0344 (15)	0.0354 (14)	0.0044 (11)	0.0102 (13)	0.0012 (11)
C11	0.059 (2)	0.0331 (15)	0.0365 (14)	−0.0052 (13)	0.0141 (14)	−0.0064 (11)
C12	0.0527 (19)	0.0460 (17)	0.0278 (13)	−0.0140 (13)	0.0034 (13)	−0.0024 (12)
C13	0.0375 (16)	0.0404 (15)	0.0278 (13)	−0.0035 (11)	0.0026 (11)	0.0015 (11)

N1—C1	1.335 (3)	C7—C13	1.390 (3)
N1—C5	1.337 (3)	C7—C8	1.396 (3)
C1—C2	1.389 (3)	C8—C10	1.395 (3)
C1—H1	0.9500	C8—C9	1.509 (3)
C2—C3	1.367 (3)	C9—C9i	1.543 (3)
C2—H2	0.9500	C9—H9A	0.9900
C3—C4	1.381 (3)	C9—H9B	0.9900
C3—H3	0.9500	C10—C11	1.386 (3)
C4—C5	1.382 (3)	C10—H10	0.9500
C4—H4	0.9500	C11—C12	1.375 (3)
C5—C6	1.504 (3)	C11—H11	0.9500
C6—O1	1.224 (2)	C12—C13	1.390 (3)
C6—N2	1.357 (3)	C12—H12	0.9500
N2—C7	1.415 (2)	C13—H13	0.9500
N2—H14	0.93 (2)
C1—N1—C5	117.4 (2)	C13—C7—N2	121.9 (2)
N1—C1—C2	123.0 (2)	C8—C7—N2	117.7 (2)
N1—C1—H1	118.5	C10—C8—C7	118.3 (2)
C2—C1—H1	118.5	C10—C8—C9	119.8 (2)
C3—C2—C1	118.6 (2)	C7—C8—C9	121.84 (19)
C3—C2—H2	120.7	C8—C9—C9i	112.8 (2)
C1—C2—H2	120.7	C8—C9—H9A	109.0
C2—C3—C4	119.4 (2)	C9i—C9—H9A	109.0
C2—C3—H3	120.3	C8—C9—H9B	109.0
C4—C3—H3	120.3	C9i—C9—H9B	109.0
C3—C4—C5	118.2 (2)	H9A—C9—H9B	107.8
C3—C4—H4	120.9	C11—C10—C8	121.2 (2)
C5—C4—H4	120.9	C11—C10—H10	119.4
N1—C5—C4	123.3 (2)	C8—C10—H10	119.4
N1—C5—C6	116.96 (19)	C12—C11—C10	119.9 (2)
C4—C5—C6	119.7 (2)	C12—C11—H11	120.1
O1—C6—N2	125.7 (2)	C10—C11—H11	120.1
O1—C6—C5	122.1 (2)	C11—C12—C13	120.1 (2)
N2—C6—C5	112.3 (2)	C11—C12—H12	120.0
C6—N2—C7	130.0 (2)	C13—C12—H12	120.0
C6—N2—H14	112.8 (15)	C12—C13—C7	120.1 (2)
C7—N2—H14	116.9 (15)	C12—C13—H13	120.0
C13—C7—C8	120.4 (2)	C7—C13—H13	120.0
C5—N1—C1—C2	−0.1 (4)	C6—N2—C7—C8	−173.7 (2)
N1—C1—C2—C3	−0.1 (4)	C13—C7—C8—C10	0.9 (3)
C1—C2—C3—C4	−0.1 (4)	N2—C7—C8—C10	−176.24 (18)
C2—C3—C4—C5	0.4 (4)	C13—C7—C8—C9	178.45 (17)
C1—N1—C5—C4	0.5 (3)	N2—C7—C8—C9	1.3 (3)
C1—N1—C5—C6	178.20 (18)	C10—C8—C9—C9i	96.1 (3)
C3—C4—C5—N1	−0.6 (4)	C7—C8—C9—C9i	−81.4 (3)
C3—C4—C5—C6	−178.3 (2)	C7—C8—C10—C11	0.1 (3)
N1—C5—C6—O1	172.4 (2)	C9—C8—C10—C11	−177.55 (19)
C4—C5—C6—O1	−9.8 (3)	C8—C10—C11—C12	−0.4 (3)
N1—C5—C6—N2	−8.7 (3)	C10—C11—C12—C13	−0.3 (3)
C4—C5—C6—N2	169.2 (2)	C11—C12—C13—C7	1.2 (3)
O1—C6—N2—C7	8.3 (4)	C8—C7—C13—C12	−1.5 (3)
C5—C6—N2—C7	−170.7 (2)	N2—C7—C13—C12	175.5 (2)
C6—N2—C7—C13	9.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H14···N1	0.93 (2)	2.11 (3)	2.632 (2)	114.7 (18)
C13—H13···O1	0.95	2.33	2.941 (3)	122
C12—H12···O1ii	0.95	2.48	3.352 (3)	152
C9—H9B···O1iii	0.99	2.61	3.299 (2)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H14⋯N1	0.93 (2)	2.11 (3)	2.632 (2)	114.7 (18)
C13—H13⋯O1	0.95	2.33	2.941 (3)	122
C12—H12⋯O1i	0.95	2.48	3.352 (3)	152
C9—H9B⋯O1ii	0.99	2.61	3.299 (2)	127

Symmetry codes: (i) ; (ii) .