4-[(1E,3E,5E)-6-(4-Pyrid-yl)hexa-1,3,5-trien-yl]pyridine.

The two independent mol-ecules in the asymmetric unit of the title compound, C(16)H(14)N(2), are planar [dihedral angle between the terminal pyridine rings = 1.76 (2)°] and each display an all-trans configuration of C=C double bonds. One of the two mol-ecules lies about a center of inversion. The dihedral angle between the two pyridine rings in the mol-ecule lying on a general position is 1.65 (2)°.

Related literature

For acceptor-terminated polyenes, see: Gao et al. (2004 ▶). For the synthesis, see: Woitellier et al. (1989 ▶). For a related structure, see: Pham (2009 ▶).

Experimental

Crystal data

C16H14N2

M = 234.29

Monoclinic,

a = 5.837 (1) Å

b = 17.171 (4) Å

c = 19.227 (4) Å

β = 97.685 (4)°

V = 1909.8 (7) Å3

Z = 6

Mo Kα radiation

μ = 0.07 mm−1

T = 173 K

0.44 × 0.24 × 0.22 mm

Data collection

Bruker SMART Platform CCD diffractometer

Absorption correction: none

18771 measured reflections

3366 independent reflections

2460 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.089

S = 1.01

3366 reflections

328 parameters

All H-atom parameters refined

Δρmax = 0.09 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809029092/ng2615sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809029092/ng2615Isup2.hkl

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

C16H14N2	F(000) = 744
Mr = 234.29	Dx = 1.222 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 867 reflections
a = 5.837 (1) Å	θ = 2.5–27.5°
b = 17.171 (4) Å	µ = 0.07 mm−1
c = 19.227 (4) Å	T = 173 K
β = 97.685 (4)°	Block, yellow
V = 1909.8 (7) Å3	0.44 × 0.24 × 0.22 mm
Z = 6

Bruker SMART Platform CCD diffractometer	2460 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tube	Rint = 0.028
graphite	θmax = 25.0°, θmin = 1.6°
ω scans	h = −6→6
18771 measured reflections	k = −20→20
3366 independent reflections	l = −22→22

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089	All H-atom parameters refined
S = 1.01	w = 1/[σ2(Fo2) + (0.048P)2 + 0.1535P] where P = (Fo2 + 2Fc2)/3
3366 reflections	(Δ/σ)max = 0.001
328 parameters	Δρmax = 0.09 e Å−3
0 restraints	Δρmin = −0.15 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	0.5720 (2)	0.58755 (7)	−0.07734 (6)	0.0569 (3)
N2	−0.45576 (19)	1.10512 (6)	0.36976 (5)	0.0481 (3)
N3	−0.00550 (19)	1.24674 (6)	0.23495 (6)	0.0497 (3)
C1	0.6991 (3)	0.65228 (9)	−0.06772 (8)	0.0543 (4)
H1	0.838 (3)	0.6547 (8)	−0.0931 (7)	0.062 (4)*
C2	0.6494 (2)	0.71361 (8)	−0.02588 (7)	0.0462 (3)
H2	0.751 (2)	0.7581 (8)	−0.0194 (7)	0.052 (4)*
C3	0.4553 (2)	0.71081 (7)	0.00886 (6)	0.0388 (3)
C4	0.3222 (2)	0.64283 (7)	−0.00011 (7)	0.0431 (3)
H4	0.185 (2)	0.6363 (7)	0.0227 (6)	0.044 (3)*
C5	0.3870 (3)	0.58440 (8)	−0.04271 (7)	0.0511 (4)
H5	0.293 (2)	0.5370 (8)	−0.0495 (6)	0.056 (4)*
C6	−0.5830 (2)	1.04076 (8)	0.35549 (7)	0.0479 (3)
H6	−0.722 (3)	1.0359 (8)	0.3800 (7)	0.060 (4)*
C7	−0.5305 (2)	0.98292 (8)	0.31014 (7)	0.0445 (3)
H7	−0.628 (2)	0.9374 (8)	0.3018 (6)	0.049 (4)*
C8	−0.3348 (2)	0.98987 (7)	0.27589 (6)	0.0385 (3)
C9	−0.2039 (2)	1.05746 (7)	0.29001 (6)	0.0411 (3)
H9	−0.064 (2)	1.0657 (7)	0.2688 (6)	0.041 (3)*
C10	−0.2692 (2)	1.11169 (8)	0.33646 (7)	0.0449 (3)
H10	−0.176 (2)	1.1575 (7)	0.3472 (6)	0.044 (3)*
C11	−0.1535 (2)	1.23391 (8)	0.17687 (7)	0.0487 (3)
H11	−0.298 (2)	1.2632 (7)	0.1723 (7)	0.055 (4)*
C12	−0.1104 (2)	1.18348 (8)	0.12416 (7)	0.0453 (3)
H12	−0.223 (2)	1.1766 (8)	0.0831 (7)	0.057 (4)*
C13	0.0985 (2)	1.14333 (7)	0.12916 (6)	0.0384 (3)
C14	0.2518 (2)	1.15541 (7)	0.19037 (7)	0.0415 (3)
H14	0.401 (2)	1.1294 (7)	0.1986 (6)	0.049 (4)*
C15	0.1931 (2)	1.20645 (8)	0.24030 (7)	0.0473 (3)
H15	0.300 (2)	1.2158 (8)	0.2839 (7)	0.059 (4)*
C16	0.3959 (2)	0.77741 (7)	0.05039 (6)	0.0414 (3)
H16	0.504 (2)	0.8205 (7)	0.0528 (6)	0.040 (3)*
C17	0.2082 (2)	0.78441 (7)	0.08307 (6)	0.0404 (3)
H17	0.100 (2)	0.7412 (7)	0.0822 (6)	0.043 (3)*
C18	0.1516 (2)	0.85257 (7)	0.12091 (6)	0.0432 (3)
H18	0.260 (2)	0.8965 (7)	0.1235 (6)	0.049 (4)*
C19	−0.0351 (2)	0.85901 (7)	0.15427 (7)	0.0431 (3)
H19	−0.140 (2)	0.8147 (7)	0.1538 (6)	0.047 (4)*
C20	−0.0919 (2)	0.92526 (7)	0.19440 (6)	0.0414 (3)
H20	0.012 (2)	0.9683 (8)	0.1966 (6)	0.044 (3)*
C21	−0.2736 (2)	0.92738 (7)	0.23017 (6)	0.0420 (3)
H21	−0.376 (2)	0.8825 (8)	0.2281 (6)	0.049 (4)*
C22	0.1515 (2)	1.09529 (7)	0.07030 (7)	0.0420 (3)
H22	0.030 (2)	1.0935 (7)	0.0295 (7)	0.050 (4)*
C23	0.3498 (2)	1.05781 (7)	0.06546 (7)	0.0417 (3)
H23	0.473 (2)	1.0581 (7)	0.1052 (6)	0.044 (3)*
C24	0.3997 (2)	1.01778 (7)	0.00320 (7)	0.0439 (3)
H24	0.275 (2)	1.0192 (7)	−0.0377 (7)	0.052 (4)*

	U11	U22	U33	U12	U13	U23
N1	0.0517 (7)	0.0549 (8)	0.0644 (8)	0.0045 (6)	0.0091 (6)	−0.0115 (6)
N2	0.0471 (7)	0.0512 (7)	0.0468 (6)	0.0063 (5)	0.0095 (5)	0.0009 (5)
N3	0.0557 (7)	0.0448 (6)	0.0486 (7)	0.0072 (5)	0.0073 (6)	−0.0015 (5)
C1	0.0454 (9)	0.0607 (9)	0.0581 (9)	0.0038 (7)	0.0118 (7)	−0.0031 (7)
C2	0.0441 (8)	0.0453 (8)	0.0494 (8)	−0.0044 (6)	0.0065 (6)	0.0033 (6)
C3	0.0428 (7)	0.0382 (7)	0.0340 (6)	0.0018 (5)	0.0002 (5)	0.0060 (5)
C4	0.0428 (8)	0.0420 (7)	0.0441 (7)	−0.0017 (6)	0.0049 (6)	0.0013 (6)
C5	0.0499 (9)	0.0437 (8)	0.0587 (9)	−0.0027 (6)	0.0034 (7)	−0.0047 (7)
C6	0.0413 (8)	0.0560 (9)	0.0477 (8)	0.0050 (6)	0.0107 (6)	0.0079 (7)
C7	0.0410 (8)	0.0444 (8)	0.0479 (8)	−0.0026 (6)	0.0052 (6)	0.0071 (6)
C8	0.0396 (7)	0.0377 (7)	0.0371 (7)	0.0021 (5)	0.0012 (5)	0.0065 (5)
C9	0.0384 (7)	0.0425 (7)	0.0431 (7)	−0.0015 (6)	0.0076 (6)	0.0014 (6)
C10	0.0451 (8)	0.0422 (8)	0.0473 (8)	−0.0008 (6)	0.0060 (6)	−0.0024 (6)
C11	0.0467 (8)	0.0480 (8)	0.0518 (8)	0.0099 (6)	0.0080 (7)	0.0049 (6)
C12	0.0437 (8)	0.0490 (8)	0.0417 (8)	0.0016 (6)	−0.0003 (6)	0.0050 (6)
C13	0.0437 (7)	0.0339 (6)	0.0377 (7)	−0.0030 (5)	0.0060 (6)	0.0042 (5)
C14	0.0411 (8)	0.0376 (7)	0.0450 (7)	0.0022 (6)	0.0027 (6)	−0.0003 (6)
C15	0.0531 (9)	0.0423 (7)	0.0445 (8)	0.0033 (6)	−0.0009 (6)	−0.0040 (6)
C16	0.0497 (8)	0.0359 (7)	0.0379 (7)	−0.0048 (6)	0.0029 (6)	0.0035 (5)
C17	0.0504 (8)	0.0361 (7)	0.0340 (7)	−0.0020 (6)	0.0027 (6)	0.0031 (5)
C18	0.0553 (9)	0.0364 (7)	0.0370 (7)	−0.0019 (6)	0.0026 (6)	0.0023 (6)
C19	0.0517 (8)	0.0369 (7)	0.0394 (7)	−0.0006 (6)	0.0011 (6)	0.0013 (6)
C20	0.0476 (8)	0.0364 (7)	0.0391 (7)	−0.0025 (6)	0.0022 (6)	0.0018 (5)
C21	0.0463 (8)	0.0356 (7)	0.0431 (7)	−0.0027 (6)	0.0022 (6)	0.0030 (6)
C22	0.0480 (8)	0.0395 (7)	0.0377 (7)	−0.0033 (6)	0.0028 (6)	0.0017 (5)
C23	0.0503 (8)	0.0351 (7)	0.0394 (7)	−0.0046 (6)	0.0049 (6)	0.0004 (5)
C24	0.0541 (8)	0.0363 (7)	0.0415 (7)	−0.0046 (6)	0.0073 (7)	0.0006 (6)

N1—C1	1.3355 (18)	C11—H11	0.975 (14)
N1—C5	1.3436 (18)	C12—C13	1.3931 (18)
N2—C6	1.3394 (17)	C12—H12	0.964 (14)
N2—C10	1.3396 (16)	C13—C14	1.3952 (17)
N3—C11	1.3354 (17)	C13—C22	1.4663 (17)
N3—C15	1.3422 (17)	C14—C15	1.3765 (18)
C1—C2	1.380 (2)	C14—H14	0.971 (13)
C1—H1	0.999 (15)	C15—H15	0.989 (13)
C2—C3	1.3910 (18)	C16—C17	1.3394 (18)
C2—H2	0.964 (13)	C16—H16	0.969 (12)
C3—C4	1.3999 (18)	C17—C18	1.4395 (18)
C3—C16	1.4627 (18)	C17—H17	0.973 (13)
C4—C5	1.3796 (19)	C18—C19	1.3408 (19)
C4—H4	0.970 (13)	C18—H18	0.982 (13)
C5—H5	0.980 (14)	C19—C20	1.4382 (18)
C6—C7	1.3830 (19)	C19—H19	0.976 (13)
C6—H6	0.997 (14)	C20—C21	1.3390 (18)
C7—C8	1.3974 (18)	C20—H20	0.954 (13)
C7—H7	0.969 (13)	C21—H21	0.973 (13)
C8—C9	1.3961 (17)	C22—C23	1.3380 (18)
C8—C21	1.4616 (17)	C22—H22	0.985 (13)
C9—C10	1.3788 (18)	C23—C24	1.4436 (18)
C9—H9	0.969 (12)	C23—H23	0.978 (12)
C10—H10	0.964 (13)	C24—C24i	1.341 (3)
C11—C12	1.3815 (18)	C24—H24	0.997 (13)
C1—N1—C5	115.69 (12)	C13—C12—H12	119.3 (8)
C6—N2—C10	115.81 (12)	C12—C13—C14	116.18 (12)
C11—N3—C15	115.75 (12)	C12—C13—C22	119.88 (11)
N1—C1—C2	124.04 (14)	C14—C13—C22	123.85 (12)
N1—C1—H1	116.0 (8)	C15—C14—C13	119.46 (12)
C2—C1—H1	120.0 (8)	C15—C14—H14	118.7 (7)
C1—C2—C3	120.14 (13)	C13—C14—H14	121.9 (7)
C1—C2—H2	120.4 (8)	N3—C15—C14	124.58 (13)
C3—C2—H2	119.5 (8)	N3—C15—H15	115.0 (8)
C2—C3—C4	116.35 (12)	C14—C15—H15	120.4 (8)
C2—C3—C16	120.18 (12)	C17—C16—C3	126.49 (12)
C4—C3—C16	123.45 (12)	C17—C16—H16	118.4 (7)
C5—C4—C3	119.21 (13)	C3—C16—H16	115.1 (7)
C5—C4—H4	119.6 (7)	C16—C17—C18	124.57 (13)
C3—C4—H4	121.2 (7)	C16—C17—H17	119.5 (7)
N1—C5—C4	124.55 (13)	C18—C17—H17	115.9 (7)
N1—C5—H5	116.1 (8)	C19—C18—C17	124.39 (13)
C4—C5—H5	119.3 (8)	C19—C18—H18	118.2 (7)
N2—C6—C7	123.92 (13)	C17—C18—H18	117.4 (7)
N2—C6—H6	116.0 (8)	C18—C19—C20	125.63 (13)
C7—C6—H6	120.1 (8)	C18—C19—H19	118.8 (7)
C6—C7—C8	119.99 (13)	C20—C19—H19	115.5 (8)
C6—C7—H7	120.5 (8)	C21—C20—C19	123.54 (13)
C8—C7—H7	119.5 (8)	C21—C20—H20	119.9 (7)
C9—C8—C7	116.10 (12)	C19—C20—H20	116.5 (7)
C9—C8—C21	123.76 (12)	C20—C21—C8	127.09 (12)
C7—C8—C21	120.12 (12)	C20—C21—H21	118.8 (7)
C10—C9—C8	119.73 (12)	C8—C21—H21	114.1 (8)
C10—C9—H9	119.7 (7)	C23—C22—C13	126.71 (12)
C8—C9—H9	120.5 (7)	C23—C22—H22	117.8 (7)
N2—C10—C9	124.44 (13)	C13—C22—H22	115.3 (7)
N2—C10—H10	115.9 (7)	C22—C23—C24	124.00 (13)
C9—C10—H10	119.6 (7)	C22—C23—H23	119.9 (7)
N3—C11—C12	123.79 (13)	C24—C23—H23	116.1 (7)
N3—C11—H11	116.4 (8)	C24i—C24—C23	124.67 (17)
C12—C11—H11	119.8 (8)	C24i—C24—H24	119.5 (8)
C11—C12—C13	120.21 (13)	C23—C24—H24	115.8 (8)
C11—C12—H12	120.5 (8)
C5—N1—C1—C2	−0.5 (2)	C11—C12—C13—C22	−174.59 (11)
N1—C1—C2—C3	−0.7 (2)	C12—C13—C14—C15	−1.72 (18)
C1—C2—C3—C4	1.43 (18)	C22—C13—C14—C15	174.85 (12)
C1—C2—C3—C16	−176.92 (12)	C11—N3—C15—C14	1.1 (2)
C2—C3—C4—C5	−1.03 (18)	C13—C14—C15—N3	0.1 (2)
C16—C3—C4—C5	177.26 (11)	C2—C3—C16—C17	175.93 (12)
C1—N1—C5—C4	0.9 (2)	C4—C3—C16—C17	−2.3 (2)
C3—C4—C5—N1	−0.1 (2)	C3—C16—C17—C18	−177.16 (11)
C10—N2—C6—C7	0.60 (19)	C16—C17—C18—C19	−179.16 (12)
N2—C6—C7—C8	−0.2 (2)	C17—C18—C19—C20	177.79 (11)
C6—C7—C8—C9	−0.64 (17)	C18—C19—C20—C21	−176.06 (13)
C6—C7—C8—C21	177.48 (11)	C19—C20—C21—C8	175.54 (11)
C7—C8—C9—C10	1.12 (17)	C9—C8—C21—C20	−1.5 (2)
C21—C8—C9—C10	−176.93 (11)	C7—C8—C21—C20	−179.51 (12)
C6—N2—C10—C9	−0.08 (19)	C12—C13—C22—C23	175.18 (13)
C8—C9—C10—N2	−0.8 (2)	C14—C13—C22—C23	−1.3 (2)
C15—N3—C11—C12	−0.6 (2)	C13—C22—C23—C24	−173.53 (11)
N3—C11—C12—C13	−1.0 (2)	C22—C23—C24—C24i	177.66 (15)
C11—C12—C13—C14	2.12 (18)