2,2'-(2,6-Pyridinedi-yl)diquinoline.

The title mol-ecule, C(23)H(15)N(3), is a terpyridine derivative resulting from the Friedländer annulation between 2,6-diacetyl-pyridine and N,N'-bis-(2-amino-benz-yl)ethyl-ene-di-amine. The asymmetric unit contains one half-mol-ecule, the complete mol-ecule being generated by a mirror plane (one N atom and one C atom lie on the plane). The mol-ecule, although aromatic, is deformed from planarity as a result of crystal packing forces: mol-ecules are stacked along the short c axis, with a short separation of 3.605 (1) Å between the mean planes. The bent mol-ecular shape is reflected in the dihedral angle of 16.10 (5)° between the essentially planar quinoline groups. In addition to π⋯π inter-actions, the crystal structure features weak inter-stack C-H⋯N contacts involving atoms of the central pyridine rings which lie in a common crystallographic m plane.

Related literature

For the synthesis and the coordination behavior of the title mol­ecule, see: Bertrand et al. (2009 ▶); Harris et al. (1969 ▶); Klassen et al. (1975 ▶). For a terpyridine derivative closely related to the title mol­ecule, see: Sasaki et al. (1998 ▶). For the Friedländer condensation as a tool for the preparation of quinolines, see: Da Costa et al. (2009 ▶); Sridharan et al. (2009 ▶).

Experimental

Crystal data

C23H15N3

M = 333.38

Orthorhombic,

a = 11.960 (2) Å

b = 34.509 (6) Å

c = 3.9509 (5) Å

V = 1630.7 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.40 × 0.20 × 0.10 mm

Data collection

Siemens P4 diffractometer

5603 measured reflections

1469 independent reflections

1032 reflections with I > 2σ(I)

R int = 0.031

2 standard reflections every 48 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.118

S = 1.02

1469 reflections

122 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.11 e Å−3

Data collection: XSCANS (Siemens, 1996 ▶); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL-Plus (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL-Plus; molecular graphics: SHELXTL-Plus and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXTL-Plus.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810006033/xu2726sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810006033/xu2726Isup2.hkl

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

C23H15N3	Dx = 1.358 Mg m−3
Mr = 333.38	Melting point = 495–497 K
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 100 reflections
a = 11.960 (2) Å	θ = 5.5–11.7°
b = 34.509 (6) Å	µ = 0.08 mm−1
c = 3.9509 (5) Å	T = 298 K
V = 1630.7 (5) Å3	Plate, orange
Z = 4	0.40 × 0.20 × 0.10 mm
F(000) = 696

Siemens P4 diffractometer	Rint = 0.031
Radiation source: X-ray	θmax = 25.1°, θmin = 2.4°
graphite	h = −14→14
ω scans	k = −41→41
5603 measured reflections	l = −4→4
1469 independent reflections	2 standard reflections every 48 reflections
1032 reflections with I > 2σ(I)	intensity decay: 1%

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)] = 0.041	H-atom parameters constrained
wR(F2) = 0.118	w = 1/[σ2(Fo2) + (0.0614P)2 + 0.1644P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
1469 reflections	Δρmax = 0.16 e Å−3
122 parameters	Δρmin = −0.11 e Å−3
0 restraints	Extinction correction: SHELXTL-Plus, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraints	Extinction coefficient: 0.0069 (16)
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
N1	0.05056 (13)	0.2500	0.0324 (4)	0.0465 (5)
C1	−0.15745 (18)	0.2500	−0.2714 (6)	0.0572 (6)
H1A	−0.2280	0.2500	−0.3703	0.069*
C2	−0.10509 (12)	0.28415 (5)	−0.1980 (4)	0.0539 (4)
H2A	−0.1388	0.3077	−0.2506	0.065*
C3	−0.00108 (11)	0.28327 (4)	−0.0443 (4)	0.0465 (4)
C4	0.05844 (12)	0.32017 (4)	0.0278 (4)	0.0468 (4)
N5	0.00977 (10)	0.35190 (4)	−0.0808 (3)	0.0522 (4)
C6	0.06408 (13)	0.38627 (4)	−0.0411 (4)	0.0522 (4)
C7	0.01369 (16)	0.42018 (5)	−0.1667 (5)	0.0667 (5)
H7A	−0.0563	0.4188	−0.2686	0.080*
C8	0.06583 (19)	0.45476 (5)	−0.1410 (5)	0.0752 (6)
H8A	0.0319	0.4769	−0.2279	0.090*
C9	0.17008 (19)	0.45757 (5)	0.0147 (5)	0.0762 (6)
H9A	0.2049	0.4816	0.0326	0.091*
C10	0.22110 (16)	0.42554 (5)	0.1402 (5)	0.0660 (5)
H10A	0.2907	0.4278	0.2437	0.079*
C11	0.16971 (13)	0.38897 (4)	0.1153 (4)	0.0528 (4)
C12	0.21698 (13)	0.35438 (4)	0.2379 (4)	0.0555 (4)
H12A	0.2859	0.3549	0.3468	0.067*
C13	0.16215 (12)	0.32044 (4)	0.1973 (4)	0.0511 (4)
H13A	0.1925	0.2975	0.2804	0.061*

	U11	U22	U33	U12	U13	U23
N1	0.0355 (9)	0.0555 (11)	0.0484 (10)	0.000	0.0022 (8)	0.000
C1	0.0364 (11)	0.0734 (16)	0.0619 (14)	0.000	−0.0071 (11)	0.000
C2	0.0404 (8)	0.0637 (10)	0.0576 (10)	0.0072 (7)	−0.0014 (7)	−0.0021 (8)
C3	0.0361 (7)	0.0586 (9)	0.0448 (8)	0.0043 (7)	0.0045 (6)	−0.0018 (7)
C4	0.0395 (8)	0.0554 (9)	0.0456 (8)	0.0054 (7)	0.0048 (7)	−0.0030 (7)
N5	0.0442 (7)	0.0569 (8)	0.0555 (8)	0.0078 (6)	0.0016 (6)	−0.0002 (7)
C6	0.0506 (9)	0.0563 (10)	0.0498 (9)	0.0089 (8)	0.0066 (7)	−0.0027 (8)
C7	0.0688 (11)	0.0654 (11)	0.0659 (11)	0.0147 (9)	0.0013 (9)	0.0016 (9)
C8	0.0985 (16)	0.0599 (12)	0.0672 (12)	0.0145 (11)	0.0066 (12)	0.0053 (10)
C9	0.0981 (16)	0.0617 (11)	0.0687 (13)	−0.0086 (11)	0.0121 (11)	−0.0025 (10)
C10	0.0672 (11)	0.0673 (11)	0.0635 (11)	−0.0064 (10)	0.0044 (9)	−0.0083 (9)
C11	0.0522 (9)	0.0561 (10)	0.0501 (9)	0.0020 (7)	0.0060 (8)	−0.0062 (8)
C12	0.0443 (8)	0.0648 (11)	0.0575 (10)	0.0031 (8)	−0.0032 (7)	−0.0078 (8)
C13	0.0426 (8)	0.0545 (9)	0.0561 (9)	0.0077 (7)	−0.0033 (7)	−0.0043 (7)

N1—C3i	1.3383 (16)	C7—C8	1.350 (2)
N1—C3	1.3383 (16)	C7—H7A	0.9300
C1—C2	1.3658 (18)	C8—C9	1.394 (3)
C1—C2i	1.3658 (18)	C8—H8A	0.9300
C1—H1A	0.9300	C9—C10	1.357 (2)
C2—C3	1.385 (2)	C9—H9A	0.9300
C2—H2A	0.9300	C10—C11	1.407 (2)
C3—C4	1.486 (2)	C10—H10A	0.9300
C4—N5	1.3123 (18)	C11—C12	1.407 (2)
C4—C13	1.410 (2)	C12—C13	1.352 (2)
N5—C6	1.3615 (19)	C12—H12A	0.9300
C6—C7	1.407 (2)	C13—H13A	0.9300
C6—C11	1.410 (2)
C3i—N1—C3	118.13 (17)	C6—C7—H7A	119.6
C2—C1—C2i	119.3 (2)	C7—C8—C9	120.52 (18)
C2—C1—H1A	120.3	C7—C8—H8A	119.7
C2i—C1—H1A	120.3	C9—C8—H8A	119.7
C1—C2—C3	119.07 (15)	C10—C9—C8	120.48 (18)
C1—C2—H2A	120.5	C10—C9—H9A	119.8
C3—C2—H2A	120.5	C8—C9—H9A	119.8
N1—C3—C2	122.20 (14)	C9—C10—C11	120.57 (18)
N1—C3—C4	118.07 (13)	C9—C10—H10A	119.7
C2—C3—C4	119.69 (13)	C11—C10—H10A	119.7
N5—C4—C13	122.69 (14)	C12—C11—C10	124.15 (16)
N5—C4—C3	116.09 (13)	C12—C11—C6	117.07 (14)
C13—C4—C3	121.21 (13)	C10—C11—C6	118.78 (15)
C4—N5—C6	118.54 (13)	C13—C12—C11	119.96 (14)
N5—C6—C7	118.67 (15)	C13—C12—H12A	120.0
N5—C6—C11	122.39 (14)	C11—C12—H12A	120.0
C7—C6—C11	118.92 (15)	C12—C13—C4	119.27 (14)
C8—C7—C6	120.72 (18)	C12—C13—H13A	120.4
C8—C7—H7A	119.6	C4—C13—H13A	120.4
C2i—C1—C2—C3	−1.4 (3)	C6—C7—C8—C9	−0.8 (3)
C3i—N1—C3—C2	0.1 (3)	C7—C8—C9—C10	0.5 (3)
C3i—N1—C3—C4	−177.46 (10)	C8—C9—C10—C11	0.0 (3)
C1—C2—C3—N1	0.6 (3)	C9—C10—C11—C12	179.83 (16)
C1—C2—C3—C4	178.17 (16)	C9—C10—C11—C6	−0.3 (3)
N1—C3—C4—N5	173.63 (14)	N5—C6—C11—C12	−1.3 (2)
C2—C3—C4—N5	−4.0 (2)	C7—C6—C11—C12	179.88 (15)
N1—C3—C4—C13	−5.2 (2)	N5—C6—C11—C10	178.75 (14)
C2—C3—C4—C13	177.17 (14)	C7—C6—C11—C10	0.0 (2)
C13—C4—N5—C6	3.0 (2)	C10—C11—C12—C13	−178.88 (16)
C3—C4—N5—C6	−175.81 (13)	C6—C11—C12—C13	1.2 (2)
C4—N5—C6—C7	178.05 (14)	C11—C12—C13—C4	0.8 (2)
C4—N5—C6—C11	−0.7 (2)	N5—C4—C13—C12	−3.1 (2)
N5—C6—C7—C8	−178.24 (16)	C3—C4—C13—C12	175.65 (14)
C11—C6—C7—C8	0.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···N1ii	0.93	2.72	3.641 (3)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯N1i	0.93	2.72	3.641 (3)	169

Symmetry code: (i) .