(1E,3E,5E,7E)-4,4'-(Octa-1,3,5,7-tetra-ene-1,8-di-yl)dipyridine.

The title compound, C(18)H(16)N(2), crystallizes with one and a half independent mol-ecules in the asymmetric unit, with the half-mol-ecule being completed by crystallographic inversion symmetry. Both independent mol-ecules are almost planar, with the non-H atoms exhibiting r.m.s. deviations from the least-squares mol-ecular plane of 0.175 and 0.118 Å, respectively.

Related literature

For the synthesis, see: Woitellier et al. (1989 ▶). For the use of the diene and the triene in the synthesis of ladderanes via template-directed photochemistry, see: Gao et al. (2004 ▶). For a related structure, see: Bader (2009 ▶).

Experimental

Crystal data

C18H16N2

M = 260.33

Monoclinic,

a = 5.5565 (12) Å

b = 17.950 (4) Å

c = 21.542 (5) Å

β = 94.809 (5)°

V = 2141.0 (8) Å3

Z = 6

Mo Kα radiation

μ = 0.07 mm−1

T = 173 K

0.50 × 0.23 × 0.20 mm

Data collection

Siemens SMART 1K diffractometer

Absorption correction: multi-scan (SADABS; Bruker 2001 ▶) T min = 0.979, T max = 0.986

13659 measured reflections

4727 independent reflections

2195 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.102

S = 0.87

4727 reflections

343 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶), PLATON (Spek, 2009 ▶) and X-SEED (Barbour, 2001 ▶)’; software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681000317X/ng2706sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681000317X/ng2706Isup2.hkl

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

C18H16N2	F(000) = 828
Mr = 260.33	Dx = 1.211 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1908 reflections
a = 5.5565 (12) Å	θ = 2.3–24.0°
b = 17.950 (4) Å	µ = 0.07 mm−1
c = 21.542 (5) Å	T = 173 K
β = 94.809 (5)°	Needle, brown
V = 2141.0 (8) Å3	0.50 × 0.23 × 0.20 mm
Z = 6

Siemens SMART 1K diffractometer	2195 reflections with I > 2σ(I)
ω scans	Rint = 0.061
Absorption correction: multi-scan (SADABS; Bruker 2001)	θmax = 27.2°, θmin = 1.9°
Tmin = 0.979, Tmax = 0.986	h = −5→7
13659 measured reflections	k = −20→23
4727 independent reflections	l = −27→21

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 0.87	w = 1/[σ2(Fo2) + (0.0357P)2] where P = (Fo2 + 2Fc2)/3
4727 reflections	(Δ/σ)max < 0.001
343 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	−0.3021 (3)	0.65494 (9)	0.12504 (7)	0.0448 (4)
N2	1.1856 (3)	0.05066 (10)	0.59878 (8)	0.0536 (5)
N3	0.7464 (3)	0.29359 (9)	0.24722 (7)	0.0469 (4)
C1	−0.4416 (4)	0.59659 (12)	0.13700 (9)	0.0436 (5)
C2	−0.3757 (3)	0.54235 (11)	0.18034 (9)	0.0384 (5)
C3	−0.1522 (3)	0.54509 (10)	0.21419 (8)	0.0343 (5)
C4	−0.0079 (3)	0.60627 (11)	0.20284 (8)	0.0376 (5)
C5	−0.0885 (4)	0.65812 (12)	0.15892 (9)	0.0433 (5)
C6	−0.0763 (4)	0.48508 (11)	0.25731 (9)	0.0385 (5)
C7	0.1333 (4)	0.47926 (11)	0.29196 (8)	0.0385 (5)
C8	0.2023 (4)	0.41530 (11)	0.32953 (8)	0.0381 (5)
C9	0.4162 (4)	0.40603 (11)	0.36246 (8)	0.0389 (5)
C10	0.4835 (4)	0.33966 (11)	0.39705 (8)	0.0379 (5)
C11	0.6999 (4)	0.32671 (11)	0.42754 (8)	0.0386 (5)
C12	0.7613 (4)	0.25807 (11)	0.45946 (8)	0.0375 (5)
C13	0.9763 (4)	0.24363 (11)	0.48963 (8)	0.0383 (5)
C14	1.0455 (3)	0.17596 (10)	0.52440 (8)	0.0346 (5)
C15	0.8974 (4)	0.11369 (11)	0.52742 (9)	0.0418 (5)
C16	0.9740 (4)	0.05425 (12)	0.56460 (10)	0.0480 (6)
C17	1.3282 (4)	0.11009 (13)	0.59511 (10)	0.0526 (6)
C18	1.2671 (3)	0.17204 (12)	0.55905 (9)	0.0436 (5)
C19	0.5479 (4)	0.25131 (12)	0.24915 (9)	0.0444 (5)
C20	0.4693 (3)	0.20009 (11)	0.20450 (9)	0.0391 (5)
C21	0.5991 (3)	0.18927 (10)	0.15268 (8)	0.0346 (5)
C22	0.8084 (3)	0.23195 (11)	0.15099 (9)	0.0415 (5)
C23	0.8709 (4)	0.28191 (12)	0.19777 (10)	0.0459 (5)
C24	0.5221 (3)	0.14039 (11)	0.10062 (9)	0.0388 (5)
C25	0.3179 (4)	0.10021 (10)	0.09310 (9)	0.0388 (5)
C26	0.2444 (4)	0.05851 (11)	0.03763 (9)	0.0409 (5)
C27	0.0375 (4)	0.01998 (10)	0.02796 (8)	0.0410 (5)
H1	−0.601 (3)	0.5947 (10)	0.1124 (7)	0.049*
H2	−0.481 (3)	0.5029 (10)	0.1877 (8)	0.049*
H4	0.151 (3)	0.6145 (9)	0.2237 (7)	0.049*
H5	0.016 (3)	0.6982 (10)	0.1492 (7)	0.049*
H6	−0.194 (3)	0.4458 (10)	0.2585 (8)	0.049*
H7	0.258 (3)	0.5183 (10)	0.2906 (7)	0.049*
H8	0.077 (3)	0.3763 (10)	0.3290 (7)	0.049*
H9	0.539 (3)	0.4467 (10)	0.3614 (7)	0.049*
H10	0.361 (3)	0.3004 (10)	0.3966 (7)	0.049*
H11	0.826 (3)	0.3624 (10)	0.4272 (8)	0.049*
H12	0.633 (3)	0.2204 (10)	0.4577 (7)	0.049*
H13	1.103 (3)	0.2809 (10)	0.4894 (7)	0.049*
H15	0.739 (3)	0.1129 (10)	0.5057 (8)	0.049*
H16	0.864 (3)	0.0118 (10)	0.5671 (8)	0.049*
H17	1.483 (3)	0.1070 (10)	0.6207 (8)	0.049*
H18	1.381 (3)	0.2120 (10)	0.5576 (7)	0.049*
H19	0.457 (3)	0.2596 (9)	0.2858 (7)	0.049*
H20	0.319 (3)	0.1734 (10)	0.2092 (7)	0.049*
H22	0.903 (3)	0.2249 (9)	0.1158 (7)	0.049*
H23	1.019 (3)	0.3124 (10)	0.1963 (7)	0.049*
H24	0.628 (3)	0.1390 (9)	0.0662 (8)	0.049*
H25	0.207 (3)	0.1001 (9)	0.1263 (7)	0.049*
H26	0.355 (3)	0.0600 (9)	0.0042 (8)	0.049*
H27	−0.071 (3)	0.0190 (9)	0.0619 (7)	0.049*

	U11	U22	U33	U12	U13	U23
N1	0.0449 (11)	0.0430 (12)	0.0459 (10)	0.0082 (9)	0.0007 (9)	0.0022 (8)
N2	0.0463 (11)	0.0473 (12)	0.0672 (13)	0.0057 (9)	0.0044 (10)	0.0136 (9)
N3	0.0500 (11)	0.0411 (11)	0.0501 (11)	−0.0068 (9)	0.0065 (9)	−0.0035 (8)
C1	0.0402 (13)	0.0470 (15)	0.0424 (13)	0.0078 (11)	−0.0024 (10)	−0.0058 (11)
C2	0.0378 (12)	0.0369 (13)	0.0405 (12)	−0.0004 (9)	0.0029 (10)	−0.0054 (10)
C3	0.0378 (11)	0.0324 (12)	0.0330 (11)	0.0023 (9)	0.0049 (9)	−0.0040 (9)
C4	0.0335 (11)	0.0393 (13)	0.0400 (12)	−0.0003 (10)	0.0028 (9)	0.0024 (10)
C5	0.0424 (13)	0.0398 (14)	0.0480 (13)	0.0016 (10)	0.0059 (11)	0.0071 (11)
C6	0.0437 (13)	0.0315 (13)	0.0401 (12)	−0.0002 (9)	0.0029 (10)	−0.0028 (9)
C7	0.0488 (13)	0.0311 (13)	0.0358 (12)	−0.0022 (9)	0.0034 (10)	0.0012 (9)
C8	0.0476 (13)	0.0310 (12)	0.0357 (11)	0.0008 (9)	0.0040 (10)	0.0001 (9)
C9	0.0520 (13)	0.0308 (13)	0.0336 (11)	−0.0021 (10)	0.0022 (10)	−0.0011 (9)
C10	0.0508 (14)	0.0306 (13)	0.0321 (11)	−0.0005 (9)	0.0025 (10)	−0.0023 (9)
C11	0.0504 (14)	0.0326 (13)	0.0330 (11)	−0.0035 (10)	0.0033 (10)	−0.0007 (9)
C12	0.0480 (13)	0.0311 (13)	0.0335 (11)	0.0002 (9)	0.0033 (10)	−0.0022 (9)
C13	0.0449 (13)	0.0324 (13)	0.0373 (11)	−0.0021 (9)	0.0023 (10)	−0.0011 (9)
C14	0.0358 (11)	0.0353 (12)	0.0333 (11)	0.0026 (9)	0.0061 (9)	−0.0032 (9)
C15	0.0415 (12)	0.0382 (13)	0.0454 (13)	−0.0001 (10)	0.0022 (10)	0.0002 (10)
C16	0.0471 (14)	0.0398 (14)	0.0572 (14)	−0.0024 (11)	0.0062 (11)	0.0082 (11)
C17	0.0419 (14)	0.0562 (17)	0.0590 (15)	0.0076 (12)	0.0009 (11)	0.0135 (12)
C18	0.0401 (13)	0.0400 (14)	0.0505 (13)	−0.0019 (10)	0.0030 (11)	0.0037 (11)
C19	0.0505 (14)	0.0421 (14)	0.0416 (13)	−0.0030 (11)	0.0100 (10)	−0.0022 (10)
C20	0.0375 (12)	0.0356 (13)	0.0444 (12)	−0.0053 (9)	0.0050 (10)	0.0029 (10)
C21	0.0400 (11)	0.0290 (12)	0.0345 (11)	0.0022 (9)	0.0022 (9)	0.0049 (9)
C22	0.0436 (13)	0.0411 (14)	0.0408 (12)	−0.0033 (10)	0.0082 (10)	0.0017 (10)
C23	0.0424 (13)	0.0440 (14)	0.0514 (14)	−0.0091 (10)	0.0039 (11)	0.0035 (11)
C24	0.0457 (13)	0.0344 (12)	0.0372 (12)	0.0035 (10)	0.0090 (10)	0.0019 (9)
C25	0.0463 (13)	0.0298 (12)	0.0407 (13)	0.0033 (10)	0.0053 (10)	0.0005 (10)
C26	0.0510 (14)	0.0332 (13)	0.0386 (13)	0.0036 (10)	0.0045 (10)	0.0014 (10)
C27	0.0510 (14)	0.0309 (12)	0.0409 (13)	0.0030 (10)	0.0031 (10)	0.0015 (9)

N1—C1	1.341 (2)	C12—H12	0.982 (17)
N1—C5	1.341 (2)	C13—C14	1.462 (2)
N2—C17	1.335 (2)	C13—H13	0.972 (17)
N2—C16	1.335 (2)	C14—C18	1.387 (2)
N3—C23	1.334 (2)	C14—C15	1.393 (2)
N3—C19	1.342 (2)	C15—C16	1.380 (3)
C1—C2	1.377 (3)	C15—H15	0.962 (16)
C1—H1	0.996 (16)	C16—H16	0.981 (17)
C2—C3	1.387 (2)	C17—C18	1.382 (3)
C2—H2	0.942 (17)	C17—H17	0.984 (16)
C3—C4	1.394 (2)	C18—H18	0.960 (17)
C3—C6	1.461 (3)	C19—C20	1.375 (3)
C4—C5	1.375 (2)	C19—H19	0.983 (16)
C4—H4	0.968 (16)	C20—C21	1.392 (2)
C5—H5	0.960 (17)	C20—H20	0.974 (17)
C6—C7	1.334 (2)	C21—C22	1.396 (2)
C6—H6	0.964 (17)	C21—C24	1.460 (2)
C7—C8	1.438 (2)	C22—C23	1.372 (3)
C7—H7	0.986 (17)	C22—H22	0.966 (16)
C8—C9	1.343 (2)	C23—H23	0.990 (17)
C8—H8	0.987 (17)	C24—C25	1.343 (2)
C9—C10	1.438 (3)	C24—H24	0.985 (16)
C9—H9	1.000 (17)	C25—C26	1.440 (2)
C10—C11	1.341 (2)	C25—H25	0.983 (16)
C10—H10	0.981 (17)	C26—C27	1.343 (2)
C11—C12	1.438 (2)	C26—H26	0.986 (16)
C11—H11	0.951 (17)	C27—C27i	1.434 (4)
C12—C13	1.337 (2)	C27—H27	0.985 (16)
C1—N1—C5	115.34 (17)	C18—C14—C15	115.83 (19)
C17—N2—C16	115.36 (19)	C18—C14—C13	120.08 (18)
C23—N3—C19	114.71 (18)	C15—C14—C13	124.05 (17)
N1—C1—C2	123.89 (19)	C16—C15—C14	119.54 (19)
N1—C1—H1	115.4 (10)	C16—C15—H15	119.8 (11)
C2—C1—H1	120.7 (10)	C14—C15—H15	120.6 (11)
C1—C2—C3	120.4 (2)	N2—C16—C15	124.9 (2)
C1—C2—H2	120.7 (11)	N2—C16—H16	117.1 (10)
C3—C2—H2	118.8 (11)	C15—C16—H16	118.0 (10)
C2—C3—C4	116.02 (18)	N2—C17—C18	123.9 (2)
C2—C3—C6	120.39 (18)	N2—C17—H17	114.7 (11)
C4—C3—C6	123.57 (17)	C18—C17—H17	121.5 (11)
C5—C4—C3	119.67 (18)	C17—C18—C14	120.5 (2)
C5—C4—H4	116.6 (10)	C17—C18—H18	119.2 (10)
C3—C4—H4	123.7 (10)	C14—C18—H18	120.3 (10)
N1—C5—C4	124.6 (2)	N3—C19—C20	124.76 (19)
N1—C5—H5	116.0 (10)	N3—C19—H19	114.6 (10)
C4—C5—H5	119.2 (10)	C20—C19—H19	120.6 (10)
C7—C6—C3	127.26 (19)	C19—C20—C21	119.91 (18)
C7—C6—H6	119.5 (10)	C19—C20—H20	118.8 (10)
C3—C6—H6	113.3 (10)	C21—C20—H20	121.3 (10)
C6—C7—C8	123.8 (2)	C20—C21—C22	115.66 (18)
C6—C7—H7	120.6 (10)	C20—C21—C24	124.18 (18)
C8—C7—H7	115.5 (10)	C22—C21—C24	120.07 (17)
C9—C8—C7	125.36 (19)	C23—C22—C21	119.98 (19)
C9—C8—H8	120.8 (10)	C23—C22—H22	122.8 (10)
C7—C8—H8	113.8 (10)	C21—C22—H22	117.2 (10)
C8—C9—C10	123.8 (2)	N3—C23—C22	124.97 (19)
C8—C9—H9	118.2 (10)	N3—C23—H23	115.3 (10)
C10—C9—H9	117.9 (10)	C22—C23—H23	119.8 (10)
C11—C10—C9	125.5 (2)	C25—C24—C21	127.29 (18)
C11—C10—H10	118.3 (10)	C25—C24—H24	116.6 (10)
C9—C10—H10	116.1 (10)	C21—C24—H24	116.0 (10)
C10—C11—C12	123.34 (19)	C24—C25—C26	123.86 (19)
C10—C11—H11	120.8 (11)	C24—C25—H25	119.3 (10)
C12—C11—H11	115.8 (11)	C26—C25—H25	116.8 (10)
C13—C12—C11	124.4 (2)	C27—C26—C25	125.16 (19)
C13—C12—H12	120.2 (10)	C27—C26—H26	118.6 (10)
C11—C12—H12	115.4 (10)	C25—C26—H26	116.3 (10)
C12—C13—C14	126.60 (19)	C26—C27—C27i	124.9 (3)
C12—C13—H13	118.8 (10)	C26—C27—H27	117.6 (10)
C14—C13—H13	114.6 (10)	C27i—C27—H27	117.5 (10)
C5—N1—C1—C2	−0.4 (3)	C13—C14—C15—C16	−176.12 (18)
N1—C1—C2—C3	−1.0 (3)	C17—N2—C16—C15	−0.3 (3)
C1—C2—C3—C4	2.1 (3)	C14—C15—C16—N2	−0.6 (3)
C1—C2—C3—C6	−176.14 (17)	C16—N2—C17—C18	0.1 (3)
C2—C3—C4—C5	−1.7 (3)	N2—C17—C18—C14	0.9 (3)
C6—C3—C4—C5	176.43 (18)	C15—C14—C18—C17	−1.7 (3)
C1—N1—C5—C4	0.8 (3)	C13—C14—C18—C17	176.04 (18)
C3—C4—C5—N1	0.3 (3)	C23—N3—C19—C20	−1.0 (3)
C2—C3—C6—C7	178.71 (19)	N3—C19—C20—C21	0.1 (3)
C4—C3—C6—C7	0.7 (3)	C19—C20—C21—C22	1.2 (3)
C3—C6—C7—C8	−174.69 (18)	C19—C20—C21—C24	−175.40 (18)
C6—C7—C8—C9	176.5 (2)	C20—C21—C22—C23	−1.6 (3)
C7—C8—C9—C10	−176.75 (17)	C24—C21—C22—C23	175.19 (17)
C8—C9—C10—C11	176.03 (19)	C19—N3—C23—C22	0.6 (3)
C9—C10—C11—C12	−177.47 (17)	C21—C22—C23—N3	0.7 (3)
C10—C11—C12—C13	179.32 (19)	C20—C21—C24—C25	1.7 (3)
C11—C12—C13—C14	177.90 (17)	C22—C21—C24—C25	−174.80 (18)
C12—C13—C14—C18	−172.99 (19)	C21—C24—C25—C26	174.09 (18)
C12—C13—C14—C15	4.5 (3)	C24—C25—C26—C27	−177.56 (19)
C18—C14—C15—C16	1.5 (3)	C25—C26—C27—C27i	178.4 (2)