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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100008295/bm1415sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100008295/bm1415Isup2.hkl
Contains datablock I

CCDC reference: 150853

Computing details top

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 top
Crystal data top
C17H13N3F(000) = 1088
Mr = 259.30Dx = 1.275 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 14681 reflections
a = 7.9476 (2) Åθ = 2.8–27.5°
b = 11.5546 (3) ŵ = 0.08 mm1
c = 29.4257 (8) ÅT = 150 K
V = 2702.20 (12) Å3Plate, colourless
Z = 80.67 × 0.50 × 0.25 mm
Data collection top
Nonius KappaCCD area detector
diffractometer
3093 independent reflections
Radiation source: fine-focus sealed tube2246 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.074
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 2.8°
Area detector scansh = 1010
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
k = 1415
Tmin = 0.950, Tmax = 0.981l = 3838
14681 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: located in Fourier map
wR(F2) = 0.147All H-atom parameters refined
S = 1.04 w = 1/[σ2(Fo2) + (0.0781P)2 + 0.3186P]
where P = (Fo2 + 2Fc2)/3
3093 reflections(Δ/σ)max < 0.001
233 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = 0.20 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
N10.11351 (15)0.63412 (10)0.10094 (4)0.0371 (3)
C20.11929 (17)0.54003 (12)0.07399 (5)0.0349 (3)
C30.04888 (18)0.43444 (13)0.08620 (5)0.0374 (3)
H30.0541 (18)0.3694 (13)0.0645 (5)0.037 (4)*
C40.03288 (18)0.42401 (13)0.12804 (5)0.0397 (4)
C50.04299 (19)0.52254 (14)0.15501 (5)0.0421 (4)
H50.097 (2)0.5187 (13)0.1838 (6)0.046 (4)*
C60.03330 (18)0.62459 (13)0.14113 (5)0.0388 (4)
C70.20661 (17)0.55401 (11)0.02958 (5)0.0342 (3)
N80.22931 (16)0.45608 (10)0.00554 (4)0.0403 (3)
C90.3114 (2)0.46491 (14)0.03393 (5)0.0446 (4)
H90.325 (2)0.3943 (15)0.0512 (6)0.050 (4)*
C100.3737 (2)0.56747 (15)0.05100 (5)0.0460 (4)
H100.430 (2)0.5674 (14)0.0797 (6)0.052 (5)*
C110.3488 (2)0.66726 (14)0.02642 (5)0.0441 (4)
H110.390 (2)0.7436 (15)0.0368 (6)0.052 (4)*
C120.26260 (19)0.66111 (13)0.01435 (5)0.0391 (4)
H120.2470 (19)0.7287 (14)0.0326 (5)0.042 (4)*
C130.03053 (19)0.73034 (14)0.17016 (5)0.0427 (4)
N140.04703 (18)0.71973 (13)0.21089 (4)0.0535 (4)
C150.0578 (3)0.81609 (19)0.23649 (6)0.0613 (5)
H150.107 (3)0.8048 (16)0.2666 (7)0.071 (6)*
C160.0045 (3)0.92223 (19)0.22361 (6)0.0639 (5)
H160.011 (2)0.9919 (16)0.2438 (7)0.074 (6)*
C170.0891 (2)0.93078 (16)0.18251 (7)0.0558 (5)
H170.135 (2)1.0037 (18)0.1732 (6)0.070 (6)*
C180.1020 (2)0.83315 (14)0.15556 (6)0.0467 (4)
H180.158 (2)0.8369 (13)0.1263 (6)0.044 (4)*
C190.1059 (2)0.31411 (15)0.14391 (6)0.0485 (4)
H190.193 (3)0.3249 (16)0.1693 (7)0.075 (6)*
C200.0585 (2)0.21034 (16)0.13078 (6)0.0526 (4)
H20A0.109 (2)0.1377 (16)0.1435 (6)0.057 (5)*
H20B0.032 (3)0.1976 (15)0.1070 (7)0.069 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0368 (6)0.0400 (6)0.0344 (6)0.0051 (5)0.0002 (5)0.0011 (5)
C20.0318 (7)0.0388 (7)0.0340 (7)0.0050 (6)0.0010 (6)0.0032 (6)
C30.0363 (8)0.0402 (8)0.0355 (7)0.0001 (6)0.0000 (6)0.0028 (6)
C40.0347 (8)0.0469 (8)0.0376 (8)0.0008 (7)0.0005 (6)0.0077 (6)
C50.0386 (8)0.0554 (9)0.0321 (8)0.0031 (7)0.0034 (6)0.0047 (7)
C60.0362 (8)0.0466 (8)0.0336 (7)0.0070 (7)0.0017 (6)0.0014 (6)
C70.0308 (7)0.0368 (7)0.0349 (7)0.0036 (6)0.0007 (6)0.0030 (6)
N80.0428 (7)0.0403 (7)0.0379 (7)0.0027 (6)0.0049 (5)0.0002 (5)
C90.0463 (9)0.0500 (9)0.0374 (8)0.0032 (7)0.0049 (7)0.0033 (7)
C100.0408 (8)0.0614 (10)0.0358 (8)0.0019 (8)0.0062 (7)0.0052 (7)
C110.0405 (8)0.0482 (9)0.0437 (9)0.0037 (7)0.0026 (7)0.0104 (7)
C120.0384 (8)0.0388 (8)0.0402 (8)0.0003 (7)0.0014 (6)0.0024 (6)
C130.0401 (8)0.0529 (9)0.0351 (8)0.0114 (7)0.0043 (6)0.0032 (7)
N140.0593 (9)0.0668 (9)0.0344 (7)0.0150 (7)0.0014 (6)0.0044 (6)
C150.0673 (12)0.0805 (14)0.0363 (9)0.0217 (11)0.0048 (8)0.0118 (9)
C160.0721 (12)0.0704 (13)0.0493 (11)0.0234 (10)0.0180 (9)0.0215 (9)
C170.0573 (11)0.0542 (10)0.0559 (11)0.0097 (9)0.0144 (8)0.0126 (9)
C180.0439 (9)0.0518 (9)0.0443 (9)0.0078 (8)0.0058 (7)0.0059 (7)
C190.0451 (9)0.0577 (10)0.0427 (9)0.0090 (8)0.0034 (7)0.0091 (7)
C200.0567 (10)0.0510 (10)0.0501 (10)0.0132 (9)0.0013 (8)0.0094 (8)
Geometric parameters (Å, º) top
N1—C21.3464 (18)C11—H110.989 (18)
N1—C61.3481 (18)C11—C121.383 (2)
C2—C31.390 (2)C12—H120.956 (16)
C2—C71.4882 (19)C13—N141.3534 (19)
C3—H30.987 (15)C13—C181.385 (2)
C3—C41.397 (2)N14—C151.347 (2)
C4—C51.390 (2)C15—H150.98 (2)
C4—C191.472 (2)C15—C161.376 (3)
C5—H50.951 (16)C16—H161.01 (2)
C5—C61.387 (2)C16—C171.387 (3)
C6—C131.491 (2)C17—H170.96 (2)
C7—N81.3466 (17)C17—C181.383 (2)
C7—C121.3894 (19)C18—H180.972 (17)
N8—C91.3359 (19)C19—H191.03 (2)
C9—H90.967 (17)C19—C201.315 (2)
C9—C101.379 (2)C20—H20A1.004 (19)
C10—H100.956 (18)C20—H20B1.01 (2)
C10—C111.375 (2)
C2—N1—C6117.83 (12)H11—C11—C12118.4 (10)
N1—C2—C3122.88 (13)C10—C11—C12118.96 (14)
N1—C2—C7116.45 (12)H12—C12—C11120.7 (9)
C3—C2—C7120.67 (13)H12—C12—C7120.3 (9)
H3—C3—C2119.0 (8)C11—C12—C7118.95 (14)
H3—C3—C4121.6 (8)N14—C13—C18122.62 (14)
C2—C3—C4119.40 (14)N14—C13—C6116.10 (14)
C5—C4—C3117.34 (13)C18—C13—C6121.27 (14)
C5—C4—C19120.18 (14)C15—N14—C13116.70 (16)
C3—C4—C19122.49 (14)H15—C15—N14115.0 (11)
H5—C5—C6120.0 (10)H15—C15—C16120.8 (11)
H5—C5—C4119.8 (10)N14—C15—C16124.07 (18)
C6—C5—C4120.19 (13)H16—C16—C15120.4 (12)
N1—C6—C5122.30 (13)H16—C16—C17121.1 (12)
N1—C6—C13116.28 (13)C15—C16—C17118.55 (17)
C5—C6—C13121.42 (13)H17—C17—C18121.7 (12)
N8—C7—C12122.42 (13)H17—C17—C16119.7 (12)
N8—C7—C2115.63 (12)C18—C17—C16118.55 (19)
C12—C7—C2121.95 (12)H18—C18—C17120.4 (9)
C9—N8—C7117.26 (12)H18—C18—C13120.1 (9)
H9—C9—N8116.5 (10)C17—C18—C13119.44 (17)
H9—C9—C10119.6 (10)H19—C19—C20121.2 (11)
N8—C9—C10123.88 (15)H19—C19—C4113.1 (11)
H10—C10—C11122.2 (10)C20—C19—C4125.49 (16)
H10—C10—C9119.3 (10)H20A—C20—H20B114.9 (14)
C11—C10—C9118.51 (14)H20A—C20—C19122.5 (10)
H11—C11—C10122.6 (10)H20B—C20—C19122.6 (10)
C6—N1—C2—C31.0 (2)H11—C11—C12—C7179.0 (11)
C6—N1—C2—C7179.14 (12)C10—C11—C12—C71.2 (2)
N1—C2—C3—H3178.1 (10)N8—C7—C12—H12178.4 (11)
C7—C2—C3—H32.1 (10)C2—C7—C12—H120.8 (11)
N1—C2—C3—C40.4 (2)N8—C7—C12—C111.8 (2)
C7—C2—C3—C4179.77 (12)C2—C7—C12—C11177.44 (13)
H3—C3—C4—C5176.0 (10)N1—C6—C13—N14178.66 (13)
C2—C3—C4—C51.7 (2)C5—C6—C13—N141.4 (2)
H3—C3—C4—C194.3 (10)N1—C6—C13—C182.1 (2)
C2—C3—C4—C19178.07 (13)C5—C6—C13—C18177.85 (14)
C3—C4—C5—H5179.5 (11)C18—C13—N14—C152.5 (2)
C19—C4—C5—H50.2 (12)C6—C13—N14—C15176.80 (14)
C3—C4—C5—C63.1 (2)C13—N14—C15—H15175.8 (13)
C19—C4—C5—C6176.66 (14)C13—N14—C15—C160.0 (3)
C2—N1—C6—C50.5 (2)H15—C15—C16—H166.6 (19)
C2—N1—C6—C13179.60 (12)N14—C15—C16—H16177.8 (13)
H5—C5—C6—N1179.0 (11)H15—C15—C16—C17173.2 (14)
C4—C5—C6—N12.6 (2)N14—C15—C16—C172.4 (3)
H5—C5—C6—C131.1 (12)H16—C16—C17—H170.8 (19)
C4—C5—C6—C13177.51 (13)C15—C16—C17—H17179.0 (14)
N1—C2—C7—N8172.21 (12)H16—C16—C17—C18178.0 (13)
C3—C2—C7—N87.64 (19)C15—C16—C17—C182.2 (3)
N1—C2—C7—C127.0 (2)H17—C17—C18—H180.1 (18)
C3—C2—C7—C12173.11 (13)C16—C17—C18—H18178.6 (11)
C12—C7—N8—C91.0 (2)H17—C17—C18—C13178.6 (14)
C2—C7—N8—C9178.22 (12)C16—C17—C18—C130.1 (2)
C7—N8—C9—H9178.7 (11)N14—C13—C18—H18178.9 (11)
C7—N8—C9—C100.3 (2)C6—C13—C18—H181.9 (11)
H9—C9—C10—H100.3 (16)N14—C13—C18—C172.5 (2)
N8—C9—C10—H10179.3 (12)C6—C13—C18—C17176.67 (14)
H9—C9—C10—C11178.2 (11)C5—C4—C19—H1919.2 (12)
N8—C9—C10—C110.8 (3)C3—C4—C19—H19161.1 (12)
H10—C10—C11—H111.3 (17)C5—C4—C19—C20155.28 (17)
C9—C10—C11—H11179.8 (11)C3—C4—C19—C2024.4 (3)
H10—C10—C11—C12178.5 (12)H19—C19—C20—H20A3.5 (18)
C9—C10—C11—C120.0 (2)C4—C19—C20—H20A177.5 (12)
H11—C11—C12—H122.4 (16)H19—C19—C20—H20B176.6 (18)
C10—C11—C12—H12177.8 (11)C4—C19—C20—H20B2.6 (13)
 

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