4′-Vinyl-2,2′:6′,2′′-ter­pyridine

The title compound, C₁₇H₁₃N₃, is a versatile precursor for polymeric ter­pyridine derivatives and their metal complexes. The mol­ecule has transoid and near-coplanar pyridine rings. However, the vinyl group is forced out of the plane of the terpyridyl moiety by a close H...H contact.

Computing details

Data collection: COLLECT (Nonius, 1999); cell refinement: DENZO-SMN (Otwinowski & Minor, 1996); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: local program.

4'-Vinyl-2,2':6',2''-terpyridine

Crystal data

C17H13N3	F(000) = 1088
Mr = 259.30	Dx = 1.275 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 14681 reflections
a = 7.9476 (2) Å	θ = 2.8–27.5°
b = 11.5546 (3) Å	µ = 0.08 mm^−1
c = 29.4257 (8) Å	T = 150 K
V = 2702.20 (12) Å^3	Plate, colourless
Z = 8	0.67 × 0.50 × 0.25 mm

Data collection

Nonius KappaCCD area detector diffractometer	3093 independent reflections
Radiation source: fine-focus sealed tube	2246 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.074
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 2.8°
Area detector scans	h = −10→10
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −14→15
Tmin = 0.950, Tmax = 0.981	l = −38→38
14681 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.052	Hydrogen site location: located in Fourier map
wR(F^2) = 0.147	All H-atom parameters refined
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0781P)^2 + 0.3186P] where P = (Fo^2 + 2Fc^2)/3
3093 reflections	(Δ/σ)max < 0.001
233 parameters	Δρmax = 0.41 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

Special details

Experimental. Detector set at 30 mm from sample with different 2theta offsets 1 degree phi exposures for chi=0 degree settings 1 degree omega exposures for chi=90 degree settings

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
N1	0.11351 (15)	0.63412 (10)	0.10094 (4)	0.0371 (3)
C2	0.11929 (17)	0.54003 (12)	0.07399 (5)	0.0349 (3)
C3	0.04888 (18)	0.43444 (13)	0.08620 (5)	0.0374 (3)
H3	0.0541 (18)	0.3694 (13)	0.0645 (5)	0.037 (4)*
C4	−0.03288 (18)	0.42401 (13)	0.12804 (5)	0.0397 (4)
C5	−0.04299 (19)	0.52254 (14)	0.15501 (5)	0.0421 (4)
H5	−0.097 (2)	0.5187 (13)	0.1838 (6)	0.046 (4)*
C6	0.03330 (18)	0.62459 (13)	0.14113 (5)	0.0388 (4)
C7	0.20661 (17)	0.55401 (11)	0.02958 (5)	0.0342 (3)
N8	0.22931 (16)	0.45608 (10)	0.00554 (4)	0.0403 (3)
C9	0.3114 (2)	0.46491 (14)	−0.03393 (5)	0.0446 (4)
H9	0.325 (2)	0.3943 (15)	−0.0512 (6)	0.050 (4)*
C10	0.3737 (2)	0.56747 (15)	−0.05100 (5)	0.0460 (4)
H10	0.430 (2)	0.5674 (14)	−0.0797 (6)	0.052 (5)*
C11	0.3488 (2)	0.66726 (14)	−0.02642 (5)	0.0441 (4)
H11	0.390 (2)	0.7436 (15)	−0.0368 (6)	0.052 (4)*
C12	0.26260 (19)	0.66111 (13)	0.01435 (5)	0.0391 (4)
H12	0.2470 (19)	0.7287 (14)	0.0326 (5)	0.042 (4)*
C13	0.03053 (19)	0.73034 (14)	0.17016 (5)	0.0427 (4)
N14	−0.04703 (18)	0.71973 (13)	0.21089 (4)	0.0535 (4)
C15	−0.0578 (3)	0.81609 (19)	0.23649 (6)	0.0613 (5)
H15	−0.107 (3)	0.8048 (16)	0.2666 (7)	0.071 (6)*
C16	0.0045 (3)	0.92223 (19)	0.22361 (6)	0.0639 (5)
H16	−0.011 (2)	0.9919 (16)	0.2438 (7)	0.074 (6)*
C17	0.0891 (2)	0.93078 (16)	0.18251 (7)	0.0558 (5)
H17	0.135 (2)	1.0037 (18)	0.1732 (6)	0.070 (6)*
C18	0.1020 (2)	0.83315 (14)	0.15556 (6)	0.0467 (4)
H18	0.158 (2)	0.8369 (13)	0.1263 (6)	0.044 (4)*
C19	−0.1059 (2)	0.31411 (15)	0.14391 (6)	0.0485 (4)
H19	−0.193 (3)	0.3249 (16)	0.1693 (7)	0.075 (6)*
C20	−0.0585 (2)	0.21034 (16)	0.13078 (6)	0.0526 (4)
H20A	−0.109 (2)	0.1377 (16)	0.1435 (6)	0.057 (5)*
H20B	0.032 (3)	0.1976 (15)	0.1070 (7)	0.069 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0368 (6)	0.0400 (6)	0.0344 (6)	0.0051 (5)	−0.0002 (5)	0.0011 (5)
C2	0.0318 (7)	0.0388 (7)	0.0340 (7)	0.0050 (6)	−0.0010 (6)	0.0032 (6)
C3	0.0363 (8)	0.0402 (8)	0.0355 (7)	0.0001 (6)	0.0000 (6)	0.0028 (6)
C4	0.0347 (8)	0.0469 (8)	0.0376 (8)	−0.0008 (7)	−0.0005 (6)	0.0077 (6)
C5	0.0386 (8)	0.0554 (9)	0.0321 (8)	0.0031 (7)	0.0034 (6)	0.0047 (7)
C6	0.0362 (8)	0.0466 (8)	0.0336 (7)	0.0070 (7)	−0.0017 (6)	0.0014 (6)
C7	0.0308 (7)	0.0368 (7)	0.0349 (7)	0.0036 (6)	0.0007 (6)	0.0030 (6)
N8	0.0428 (7)	0.0403 (7)	0.0379 (7)	0.0027 (6)	0.0049 (5)	−0.0002 (5)
C9	0.0463 (9)	0.0500 (9)	0.0374 (8)	0.0032 (7)	0.0049 (7)	−0.0033 (7)
C10	0.0408 (8)	0.0614 (10)	0.0358 (8)	0.0019 (8)	0.0062 (7)	0.0052 (7)
C11	0.0405 (8)	0.0482 (9)	0.0437 (9)	−0.0037 (7)	0.0026 (7)	0.0104 (7)
C12	0.0384 (8)	0.0388 (8)	0.0402 (8)	−0.0003 (7)	0.0014 (6)	0.0024 (6)
C13	0.0401 (8)	0.0529 (9)	0.0351 (8)	0.0114 (7)	−0.0043 (6)	−0.0032 (7)
N14	0.0593 (9)	0.0668 (9)	0.0344 (7)	0.0150 (7)	−0.0014 (6)	−0.0044 (6)
C15	0.0673 (12)	0.0805 (14)	0.0363 (9)	0.0217 (11)	−0.0048 (8)	−0.0118 (9)
C16	0.0721 (12)	0.0704 (13)	0.0493 (11)	0.0234 (10)	−0.0180 (9)	−0.0215 (9)
C17	0.0573 (11)	0.0542 (10)	0.0559 (11)	0.0097 (9)	−0.0144 (8)	−0.0126 (9)
C18	0.0439 (9)	0.0518 (9)	0.0443 (9)	0.0078 (8)	−0.0058 (7)	−0.0059 (7)
C19	0.0451 (9)	0.0577 (10)	0.0427 (9)	−0.0090 (8)	0.0034 (7)	0.0091 (7)
C20	0.0567 (10)	0.0510 (10)	0.0501 (10)	−0.0132 (9)	−0.0013 (8)	0.0094 (8)

Geometric parameters (Å, º)

N1—C2	1.3464 (18)	C11—H11	0.989 (18)
N1—C6	1.3481 (18)	C11—C12	1.383 (2)
C2—C3	1.390 (2)	C12—H12	0.956 (16)
C2—C7	1.4882 (19)	C13—N14	1.3534 (19)
C3—H3	0.987 (15)	C13—C18	1.385 (2)
C3—C4	1.397 (2)	N14—C15	1.347 (2)
C4—C5	1.390 (2)	C15—H15	0.98 (2)
C4—C19	1.472 (2)	C15—C16	1.376 (3)
C5—H5	0.951 (16)	C16—H16	1.01 (2)
C5—C6	1.387 (2)	C16—C17	1.387 (3)
C6—C13	1.491 (2)	C17—H17	0.96 (2)
C7—N8	1.3466 (17)	C17—C18	1.383 (2)
C7—C12	1.3894 (19)	C18—H18	0.972 (17)
N8—C9	1.3359 (19)	C19—H19	1.03 (2)
C9—H9	0.967 (17)	C19—C20	1.315 (2)
C9—C10	1.379 (2)	C20—H20A	1.004 (19)
C10—H10	0.956 (18)	C20—H20B	1.01 (2)
C10—C11	1.375 (2)
C2—N1—C6	117.83 (12)	H11—C11—C12	118.4 (10)
N1—C2—C3	122.88 (13)	C10—C11—C12	118.96 (14)
N1—C2—C7	116.45 (12)	H12—C12—C11	120.7 (9)
C3—C2—C7	120.67 (13)	H12—C12—C7	120.3 (9)
H3—C3—C2	119.0 (8)	C11—C12—C7	118.95 (14)
H3—C3—C4	121.6 (8)	N14—C13—C18	122.62 (14)
C2—C3—C4	119.40 (14)	N14—C13—C6	116.10 (14)
C5—C4—C3	117.34 (13)	C18—C13—C6	121.27 (14)
C5—C4—C19	120.18 (14)	C15—N14—C13	116.70 (16)
C3—C4—C19	122.49 (14)	H15—C15—N14	115.0 (11)
H5—C5—C6	120.0 (10)	H15—C15—C16	120.8 (11)
H5—C5—C4	119.8 (10)	N14—C15—C16	124.07 (18)
C6—C5—C4	120.19 (13)	H16—C16—C15	120.4 (12)
N1—C6—C5	122.30 (13)	H16—C16—C17	121.1 (12)
N1—C6—C13	116.28 (13)	C15—C16—C17	118.55 (17)
C5—C6—C13	121.42 (13)	H17—C17—C18	121.7 (12)
N8—C7—C12	122.42 (13)	H17—C17—C16	119.7 (12)
N8—C7—C2	115.63 (12)	C18—C17—C16	118.55 (19)
C12—C7—C2	121.95 (12)	H18—C18—C17	120.4 (9)
C9—N8—C7	117.26 (12)	H18—C18—C13	120.1 (9)
H9—C9—N8	116.5 (10)	C17—C18—C13	119.44 (17)
H9—C9—C10	119.6 (10)	H19—C19—C20	121.2 (11)
N8—C9—C10	123.88 (15)	H19—C19—C4	113.1 (11)
H10—C10—C11	122.2 (10)	C20—C19—C4	125.49 (16)
H10—C10—C9	119.3 (10)	H20A—C20—H20B	114.9 (14)
C11—C10—C9	118.51 (14)	H20A—C20—C19	122.5 (10)
H11—C11—C10	122.6 (10)	H20B—C20—C19	122.6 (10)
C6—N1—C2—C3	−1.0 (2)	H11—C11—C12—C7	−179.0 (11)
C6—N1—C2—C7	179.14 (12)	C10—C11—C12—C7	1.2 (2)
N1—C2—C3—H3	178.1 (10)	N8—C7—C12—H12	−178.4 (11)
C7—C2—C3—H3	−2.1 (10)	C2—C7—C12—H12	0.8 (11)
N1—C2—C3—C4	0.4 (2)	N8—C7—C12—C11	−1.8 (2)
C7—C2—C3—C4	−179.77 (12)	C2—C7—C12—C11	177.44 (13)
H3—C3—C4—C5	−176.0 (10)	N1—C6—C13—N14	−178.66 (13)
C2—C3—C4—C5	1.7 (2)	C5—C6—C13—N14	1.4 (2)
H3—C3—C4—C19	4.3 (10)	N1—C6—C13—C18	2.1 (2)
C2—C3—C4—C19	−178.07 (13)	C5—C6—C13—C18	−177.85 (14)
C3—C4—C5—H5	−179.5 (11)	C18—C13—N14—C15	2.5 (2)
C19—C4—C5—H5	0.2 (12)	C6—C13—N14—C15	−176.80 (14)
C3—C4—C5—C6	−3.1 (2)	C13—N14—C15—H15	−175.8 (13)
C19—C4—C5—C6	176.66 (14)	C13—N14—C15—C16	0.0 (3)
C2—N1—C6—C5	−0.5 (2)	H15—C15—C16—H16	−6.6 (19)
C2—N1—C6—C13	179.60 (12)	N14—C15—C16—H16	177.8 (13)
H5—C5—C6—N1	179.0 (11)	H15—C15—C16—C17	173.2 (14)
C4—C5—C6—N1	2.6 (2)	N14—C15—C16—C17	−2.4 (3)
H5—C5—C6—C13	−1.1 (12)	H16—C16—C17—H17	0.8 (19)
C4—C5—C6—C13	−177.51 (13)	C15—C16—C17—H17	−179.0 (14)
N1—C2—C7—N8	172.21 (12)	H16—C16—C17—C18	−178.0 (13)
C3—C2—C7—N8	−7.64 (19)	C15—C16—C17—C18	2.2 (3)
N1—C2—C7—C12	−7.0 (2)	H17—C17—C18—H18	−0.1 (18)
C3—C2—C7—C12	173.11 (13)	C16—C17—C18—H18	178.6 (11)
C12—C7—N8—C9	1.0 (2)	H17—C17—C18—C13	−178.6 (14)
C2—C7—N8—C9	−178.22 (12)	C16—C17—C18—C13	0.1 (2)
C7—N8—C9—H9	−178.7 (11)	N14—C13—C18—H18	178.9 (11)
C7—N8—C9—C10	0.3 (2)	C6—C13—C18—H18	−1.9 (11)
H9—C9—C10—H10	−0.3 (16)	N14—C13—C18—C17	−2.5 (2)
N8—C9—C10—H10	−179.3 (12)	C6—C13—C18—C17	176.67 (14)
H9—C9—C10—C11	178.2 (11)	C5—C4—C19—H19	19.2 (12)
N8—C9—C10—C11	−0.8 (3)	C3—C4—C19—H19	−161.1 (12)
H10—C10—C11—H11	−1.3 (17)	C5—C4—C19—C20	−155.28 (17)
C9—C10—C11—H11	−179.8 (11)	C3—C4—C19—C20	24.4 (3)
H10—C10—C11—C12	178.5 (12)	H19—C19—C20—H20A	3.5 (18)
C9—C10—C11—C12	0.0 (2)	C4—C19—C20—H20A	177.5 (12)
H11—C11—C12—H12	−2.4 (16)	H19—C19—C20—H20B	−176.6 (18)
C10—C11—C12—H12	177.8 (11)	C4—C19—C20—H20B	−2.6 (13)