organic compounds
2,6-Bis[1-(2-methylphenylimino)ethyl]pyridine
aDepartment of Chemistry, Harbin Institute of Technology, Harbin 150001, People's Republic of China
*Correspondence e-mail: fanruiqing@163.com
The molecule of the title compound, C23H23N3, which was synthesized by the condensation reaction between 2,6-diacetylpyridine and 2-dimethylaniline, adopts an E configuration about both C=N imine bonds. The dihedral angles formed by the benzene rings with the pyridine ring are 89.68 (5) and 53.62 (6)°.
Related literature
For the applications of pyridine-based ligands in sensor technologies and electro-luminescent devices, see: Tang & Vanslyke (1987); Wang (2001). For the crystal structures of related compounds, see: Mentes et al. (2001); Huang et al. (2006). For the synthesis, see: Fan et al. (2004).
Experimental
Crystal data
|
Data collection: SMART (Bruker, 2000); cell SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536809020522/rz2329sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809020522/rz2329Isup2.hkl
The title compound was synthesized according to the literatute method (Fan et al., 2004). To a solution of 2,6-diacetylpyridine (1.1 g, 6.7 mmol) in absolute methanol (25 ml) was added 2-dimethylaniline (2.2 ml, 20.5 mmol). After the addition of several drops of formic acid, the reaction mixture was refluxed for 24 h and then allowed to cool down to room temperature. The crude product precipitated as yellow powder. Yellow block crystals suitable for X-ray
were obtained by slow evaporation of a methanol solution in 85% yield (1.96 g).All H atoms were positioned geometrically with C—H = 0.93–0.96 Å, and allowed to ride on their parent atoms with Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(C) for methyl H atoms.
Data collection: SMART (Bruker, 2000); cell
SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C23H23N3 | F(000) = 728 |
Mr = 341.44 | Dx = 1.162 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 18526 reflections |
a = 12.966 (3) Å | θ = 3.1–27.5° |
b = 11.304 (2) Å | µ = 0.07 mm−1 |
c = 14.767 (3) Å | T = 193 K |
β = 115.62 (3)° | Block, yellow |
V = 1951.6 (8) Å3 | 0.56 × 0.41 × 0.36 mm |
Z = 4 |
Bruker SMART APEX CCD area-detector diffractometer | 4435 independent reflections |
Radiation source: fine-focus sealed tube | 2804 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
phi and ω scans | θmax = 27.5°, θmin = 3.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −16→16 |
Tmin = 0.960, Tmax = 0.972 | k = −14→13 |
18526 measured reflections | l = −19→19 |
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.157 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0848P)2 + 0.041P] where P = (Fo2 + 2Fc2)/3 |
4435 reflections | (Δ/σ)max < 0.001 |
235 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
C23H23N3 | V = 1951.6 (8) Å3 |
Mr = 341.44 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 12.966 (3) Å | µ = 0.07 mm−1 |
b = 11.304 (2) Å | T = 193 K |
c = 14.767 (3) Å | 0.56 × 0.41 × 0.36 mm |
β = 115.62 (3)° |
Bruker SMART APEX CCD area-detector diffractometer | 4435 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 2804 reflections with I > 2σ(I) |
Tmin = 0.960, Tmax = 0.972 | Rint = 0.037 |
18526 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
wR(F2) = 0.157 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.22 e Å−3 |
4435 reflections | Δρmin = −0.16 e Å−3 |
235 parameters |
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 | ||
N2 | 0.27847 (10) | 0.74889 (10) | 0.16139 (9) | 0.0458 (3) | |
N1 | −0.01920 (11) | 0.79913 (11) | 0.03667 (10) | 0.0527 (3) | |
C6 | 0.37804 (12) | 0.80381 (12) | 0.18433 (11) | 0.0448 (4) | |
N3 | 0.57761 (11) | 0.77842 (11) | 0.25205 (11) | 0.0565 (4) | |
C2 | 0.18145 (13) | 0.80916 (12) | 0.10943 (11) | 0.0457 (4) | |
C1 | 0.07290 (13) | 0.74430 (12) | 0.08606 (11) | 0.0476 (4) | |
C7 | 0.48407 (13) | 0.73369 (12) | 0.24317 (11) | 0.0466 (4) | |
C3 | 0.18154 (13) | 0.92576 (13) | 0.08007 (12) | 0.0524 (4) | |
H3B | 0.1130 | 0.9656 | 0.0444 | 0.063* | |
C5 | 0.38449 (14) | 0.92051 (13) | 0.15758 (13) | 0.0543 (4) | |
H5A | 0.4550 | 0.9567 | 0.1751 | 0.065* | |
C10 | −0.12858 (13) | 0.74706 (12) | 0.00704 (12) | 0.0489 (4) | |
C17 | 0.68397 (13) | 0.72253 (14) | 0.30780 (13) | 0.0523 (4) | |
C15 | −0.18677 (13) | 0.75912 (12) | 0.06699 (12) | 0.0522 (4) | |
C4 | 0.28403 (14) | 0.98142 (13) | 0.10444 (13) | 0.0586 (4) | |
H4A | 0.2858 | 1.0595 | 0.0853 | 0.070* | |
C14 | −0.29933 (15) | 0.72146 (15) | 0.02802 (15) | 0.0620 (5) | |
H14A | −0.3395 | 0.7298 | 0.0668 | 0.074* | |
C22 | 0.71360 (14) | 0.61751 (15) | 0.27656 (14) | 0.0633 (5) | |
H22A | 0.6602 | 0.5788 | 0.2202 | 0.076* | |
C9 | 0.47073 (15) | 0.62046 (14) | 0.28932 (15) | 0.0633 (5) | |
H9A | 0.5443 | 0.5840 | 0.3248 | 0.095* | |
H9B | 0.4213 | 0.5681 | 0.2375 | 0.095* | |
H9C | 0.4381 | 0.6366 | 0.3353 | 0.095* | |
C18 | 0.76376 (15) | 0.78082 (15) | 0.39198 (13) | 0.0579 (4) | |
C8 | 0.08130 (16) | 0.61968 (15) | 0.12366 (17) | 0.0764 (6) | |
H8A | 0.0058 | 0.5882 | 0.1037 | 0.115* | |
H8B | 0.1217 | 0.6191 | 0.1956 | 0.115* | |
H8C | 0.1217 | 0.5721 | 0.0958 | 0.115* | |
C13 | −0.35352 (16) | 0.67238 (16) | −0.06562 (16) | 0.0697 (5) | |
H13A | −0.4295 | 0.6487 | −0.0902 | 0.084* | |
C11 | −0.18236 (16) | 0.69527 (15) | −0.08650 (14) | 0.0634 (5) | |
H11A | −0.1426 | 0.6850 | −0.1254 | 0.076* | |
C20 | 0.90039 (16) | 0.62620 (19) | 0.41061 (16) | 0.0742 (6) | |
H20A | 0.9733 | 0.5946 | 0.4454 | 0.089* | |
C12 | −0.29465 (17) | 0.65852 (17) | −0.12285 (15) | 0.0721 (5) | |
H12A | −0.3304 | 0.6243 | −0.1862 | 0.087* | |
C19 | 0.87169 (16) | 0.72988 (18) | 0.44214 (14) | 0.0708 (5) | |
H19A | 0.9259 | 0.7674 | 0.4988 | 0.085* | |
C16 | −0.12855 (18) | 0.81252 (18) | 0.17075 (15) | 0.0768 (6) | |
H16A | −0.1809 | 0.8138 | 0.2009 | 0.115* | |
H16B | −0.1049 | 0.8918 | 0.1659 | 0.115* | |
H16C | −0.0629 | 0.7659 | 0.2114 | 0.115* | |
C21 | 0.82176 (17) | 0.56955 (18) | 0.32815 (17) | 0.0744 (5) | |
H21A | 0.8407 | 0.4990 | 0.3066 | 0.089* | |
C23 | 0.7334 (2) | 0.89394 (18) | 0.42839 (17) | 0.0874 (6) | |
H23A | 0.6561 | 0.9154 | 0.3847 | 0.131* | |
H23B | 0.7842 | 0.9558 | 0.4283 | 0.131* | |
H23C | 0.7407 | 0.8829 | 0.4953 | 0.131* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N2 | 0.0389 (7) | 0.0437 (7) | 0.0531 (7) | 0.0021 (5) | 0.0183 (6) | 0.0030 (5) |
N1 | 0.0407 (7) | 0.0476 (7) | 0.0659 (9) | 0.0017 (5) | 0.0193 (6) | 0.0079 (6) |
C6 | 0.0412 (8) | 0.0442 (8) | 0.0508 (8) | 0.0034 (6) | 0.0217 (7) | 0.0030 (6) |
N3 | 0.0409 (8) | 0.0550 (7) | 0.0719 (9) | 0.0030 (6) | 0.0227 (7) | 0.0109 (6) |
C2 | 0.0413 (8) | 0.0460 (8) | 0.0493 (8) | 0.0043 (6) | 0.0191 (7) | 0.0026 (6) |
C1 | 0.0423 (8) | 0.0458 (8) | 0.0533 (9) | 0.0019 (6) | 0.0193 (7) | 0.0031 (6) |
C7 | 0.0421 (8) | 0.0441 (7) | 0.0537 (9) | 0.0027 (6) | 0.0208 (7) | −0.0005 (6) |
C3 | 0.0439 (9) | 0.0460 (8) | 0.0631 (10) | 0.0072 (6) | 0.0191 (7) | 0.0075 (7) |
C5 | 0.0434 (9) | 0.0472 (8) | 0.0721 (11) | −0.0002 (6) | 0.0247 (8) | 0.0068 (7) |
C10 | 0.0394 (8) | 0.0399 (7) | 0.0619 (9) | 0.0040 (6) | 0.0166 (7) | 0.0108 (6) |
C17 | 0.0384 (8) | 0.0541 (9) | 0.0654 (10) | 0.0012 (7) | 0.0234 (8) | 0.0113 (7) |
C15 | 0.0446 (9) | 0.0435 (8) | 0.0658 (10) | 0.0024 (6) | 0.0212 (8) | 0.0074 (7) |
C4 | 0.0521 (10) | 0.0421 (8) | 0.0790 (11) | 0.0036 (7) | 0.0260 (8) | 0.0122 (7) |
C14 | 0.0454 (9) | 0.0622 (10) | 0.0774 (12) | 0.0018 (8) | 0.0256 (9) | 0.0112 (9) |
C22 | 0.0455 (9) | 0.0639 (10) | 0.0785 (12) | 0.0029 (8) | 0.0248 (9) | 0.0004 (8) |
C9 | 0.0487 (10) | 0.0548 (9) | 0.0876 (13) | 0.0091 (7) | 0.0305 (9) | 0.0182 (8) |
C18 | 0.0542 (10) | 0.0614 (9) | 0.0583 (10) | −0.0042 (8) | 0.0245 (8) | 0.0091 (7) |
C8 | 0.0511 (10) | 0.0542 (10) | 0.1118 (16) | 0.0021 (8) | 0.0239 (10) | 0.0249 (10) |
C13 | 0.0429 (9) | 0.0704 (11) | 0.0806 (13) | −0.0085 (8) | 0.0125 (9) | 0.0122 (10) |
C11 | 0.0589 (11) | 0.0667 (10) | 0.0621 (11) | −0.0051 (8) | 0.0238 (9) | 0.0013 (8) |
C20 | 0.0415 (10) | 0.0890 (14) | 0.0863 (14) | 0.0123 (9) | 0.0222 (10) | 0.0223 (11) |
C12 | 0.0647 (12) | 0.0717 (11) | 0.0630 (11) | −0.0148 (9) | 0.0116 (10) | −0.0010 (9) |
C19 | 0.0518 (11) | 0.0886 (13) | 0.0613 (11) | −0.0094 (9) | 0.0143 (9) | 0.0121 (9) |
C16 | 0.0730 (13) | 0.0819 (13) | 0.0805 (14) | −0.0175 (10) | 0.0380 (11) | −0.0189 (10) |
C21 | 0.0567 (11) | 0.0729 (11) | 0.1024 (15) | 0.0155 (9) | 0.0428 (11) | 0.0108 (11) |
C23 | 0.1025 (18) | 0.0732 (12) | 0.0791 (14) | −0.0003 (12) | 0.0323 (13) | −0.0034 (10) |
N2—C6 | 1.3374 (18) | C22—H22A | 0.9300 |
N2—C2 | 1.3420 (18) | C9—H9A | 0.9600 |
N1—C1 | 1.2606 (18) | C9—H9B | 0.9600 |
N1—C10 | 1.4187 (19) | C9—H9C | 0.9600 |
C6—C5 | 1.390 (2) | C18—C19 | 1.394 (3) |
C6—C7 | 1.497 (2) | C18—C23 | 1.504 (3) |
N3—C7 | 1.2674 (19) | C8—H8A | 0.9600 |
N3—C17 | 1.413 (2) | C8—H8B | 0.9600 |
C2—C3 | 1.388 (2) | C8—H8C | 0.9600 |
C2—C1 | 1.489 (2) | C13—C12 | 1.371 (3) |
C1—C8 | 1.501 (2) | C13—H13A | 0.9300 |
C7—C9 | 1.495 (2) | C11—C12 | 1.380 (3) |
C3—C4 | 1.370 (2) | C11—H11A | 0.9300 |
C3—H3B | 0.9300 | C20—C21 | 1.363 (3) |
C5—C4 | 1.379 (2) | C20—C19 | 1.371 (3) |
C5—H5A | 0.9300 | C20—H20A | 0.9300 |
C10—C11 | 1.380 (2) | C12—H12A | 0.9300 |
C10—C15 | 1.396 (2) | C19—H19A | 0.9300 |
C17—C22 | 1.387 (2) | C16—H16A | 0.9600 |
C17—C18 | 1.392 (2) | C16—H16B | 0.9600 |
C15—C14 | 1.384 (2) | C16—H16C | 0.9600 |
C15—C16 | 1.511 (3) | C21—H21A | 0.9300 |
C4—H4A | 0.9300 | C23—H23A | 0.9600 |
C14—C13 | 1.369 (3) | C23—H23B | 0.9600 |
C14—H14A | 0.9300 | C23—H23C | 0.9600 |
C22—C21 | 1.385 (2) | ||
C6—N2—C2 | 118.22 (12) | C7—C9—H9C | 109.5 |
C1—N1—C10 | 123.03 (12) | H9A—C9—H9C | 109.5 |
N2—C6—C5 | 122.59 (13) | H9B—C9—H9C | 109.5 |
N2—C6—C7 | 116.43 (12) | C17—C18—C19 | 117.84 (17) |
C5—C6—C7 | 120.96 (13) | C17—C18—C23 | 120.89 (17) |
C7—N3—C17 | 122.08 (13) | C19—C18—C23 | 121.26 (18) |
N2—C2—C3 | 122.25 (14) | C1—C8—H8A | 109.5 |
N2—C2—C1 | 116.17 (12) | C1—C8—H8B | 109.5 |
C3—C2—C1 | 121.58 (13) | H8A—C8—H8B | 109.5 |
N1—C1—C2 | 117.13 (13) | C1—C8—H8C | 109.5 |
N1—C1—C8 | 125.07 (14) | H8A—C8—H8C | 109.5 |
C2—C1—C8 | 117.79 (13) | H8B—C8—H8C | 109.5 |
N3—C7—C9 | 126.06 (14) | C14—C13—C12 | 119.32 (17) |
N3—C7—C6 | 116.53 (13) | C14—C13—H13A | 120.3 |
C9—C7—C6 | 117.37 (13) | C12—C13—H13A | 120.3 |
C4—C3—C2 | 119.07 (14) | C10—C11—C12 | 120.57 (19) |
C4—C3—H3B | 120.5 | C10—C11—H11A | 119.7 |
C2—C3—H3B | 120.5 | C12—C11—H11A | 119.7 |
C4—C5—C6 | 118.51 (14) | C21—C20—C19 | 119.81 (17) |
C4—C5—H5A | 120.7 | C21—C20—H20A | 120.1 |
C6—C5—H5A | 120.7 | C19—C20—H20A | 120.1 |
C11—C10—C15 | 119.90 (15) | C13—C12—C11 | 120.05 (18) |
C11—C10—N1 | 119.33 (16) | C13—C12—H12A | 120.0 |
C15—C10—N1 | 120.41 (15) | C11—C12—H12A | 120.0 |
C22—C17—C18 | 119.76 (15) | C20—C19—C18 | 122.03 (18) |
C22—C17—N3 | 121.99 (15) | C20—C19—H19A | 119.0 |
C18—C17—N3 | 118.04 (15) | C18—C19—H19A | 119.0 |
C14—C15—C10 | 117.91 (16) | C15—C16—H16A | 109.5 |
C14—C15—C16 | 121.28 (17) | C15—C16—H16B | 109.5 |
C10—C15—C16 | 120.81 (15) | H16A—C16—H16B | 109.5 |
C3—C4—C5 | 119.35 (14) | C15—C16—H16C | 109.5 |
C3—C4—H4A | 120.3 | H16A—C16—H16C | 109.5 |
C5—C4—H4A | 120.3 | H16B—C16—H16C | 109.5 |
C13—C14—C15 | 122.21 (18) | C20—C21—C22 | 119.73 (18) |
C13—C14—H14A | 118.9 | C20—C21—H21A | 120.1 |
C15—C14—H14A | 118.9 | C22—C21—H21A | 120.1 |
C21—C22—C17 | 120.83 (17) | C18—C23—H23A | 109.5 |
C21—C22—H22A | 119.6 | C18—C23—H23B | 109.5 |
C17—C22—H22A | 119.6 | H23A—C23—H23B | 109.5 |
C7—C9—H9A | 109.5 | C18—C23—H23C | 109.5 |
C7—C9—H9B | 109.5 | H23A—C23—H23C | 109.5 |
H9A—C9—H9B | 109.5 | H23B—C23—H23C | 109.5 |
C2—N2—C6—C5 | 0.8 (2) | C11—C10—C15—C14 | −2.1 (2) |
C2—N2—C6—C7 | 179.43 (13) | N1—C10—C15—C14 | 170.93 (13) |
C6—N2—C2—C3 | −0.6 (2) | C11—C10—C15—C16 | 178.34 (15) |
C6—N2—C2—C1 | −179.79 (13) | N1—C10—C15—C16 | −8.6 (2) |
C10—N1—C1—C2 | 178.32 (14) | C2—C3—C4—C5 | −0.1 (3) |
C10—N1—C1—C8 | −2.3 (3) | C6—C5—C4—C3 | 0.3 (3) |
N2—C2—C1—N1 | −179.50 (14) | C10—C15—C14—C13 | 0.8 (2) |
C3—C2—C1—N1 | 1.3 (2) | C16—C15—C14—C13 | −179.72 (16) |
N2—C2—C1—C8 | 1.0 (2) | C18—C17—C22—C21 | 0.1 (3) |
C3—C2—C1—C8 | −178.12 (16) | N3—C17—C22—C21 | 174.74 (16) |
C17—N3—C7—C9 | 1.0 (3) | C22—C17—C18—C19 | −0.2 (2) |
C17—N3—C7—C6 | 178.40 (14) | N3—C17—C18—C19 | −175.06 (15) |
N2—C6—C7—N3 | 169.72 (14) | C22—C17—C18—C23 | −179.14 (17) |
C5—C6—C7—N3 | −11.6 (2) | N3—C17—C18—C23 | 6.0 (2) |
N2—C6—C7—C9 | −12.7 (2) | C15—C14—C13—C12 | 0.7 (3) |
C5—C6—C7—C9 | 165.96 (16) | C15—C10—C11—C12 | 2.1 (2) |
N2—C2—C3—C4 | 0.3 (2) | N1—C10—C11—C12 | −171.07 (15) |
C1—C2—C3—C4 | 179.40 (15) | C14—C13—C12—C11 | −0.8 (3) |
N2—C6—C5—C4 | −0.6 (2) | C10—C11—C12—C13 | −0.5 (3) |
C7—C6—C5—C4 | −179.19 (15) | C21—C20—C19—C18 | −0.4 (3) |
C1—N1—C10—C11 | −93.60 (19) | C17—C18—C19—C20 | 0.4 (3) |
C1—N1—C10—C15 | 93.31 (19) | C23—C18—C19—C20 | 179.31 (19) |
C7—N3—C17—C22 | 68.2 (2) | C19—C20—C21—C22 | 0.3 (3) |
C7—N3—C17—C18 | −117.05 (18) | C17—C22—C21—C20 | −0.1 (3) |
Experimental details
Crystal data | |
Chemical formula | C23H23N3 |
Mr | 341.44 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 193 |
a, b, c (Å) | 12.966 (3), 11.304 (2), 14.767 (3) |
β (°) | 115.62 (3) |
V (Å3) | 1951.6 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.56 × 0.41 × 0.36 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.960, 0.972 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18526, 4435, 2804 |
Rint | 0.037 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.157, 1.06 |
No. of reflections | 4435 |
No. of parameters | 235 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.22, −0.16 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Acknowledgements
This work was supported by the National Natural Science Foundation of China (grant Nos. 20771030 and 20671025), the Youthful Foundation of Heilongjiang Province of China (grant No. QC06C029) and the Research Fund for the Doctoral Program of Higher Education (grant No. 20070213005).
References
Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fan, R. Q., Zhu, D. S., Mu, Y., Li, G. H., Yang, Y. L., Su, Q. & Feng, S. H. (2004). Eur. J. Inorg. Chem. pp. 4891–4897. Web of Science CSD CrossRef Google Scholar
Huang, Y.-B., Ma, X.-L., Zheng, S.-N., Chen, J.-X. & Wei, C.-X. (2006). Acta Cryst. E62, o3044–o3045. Web of Science CSD CrossRef IUCr Journals Google Scholar
Mentes, A., Fawcett, J. & Kemmitt, R. D. W. (2001). Acta Cryst. E57, o424–o425. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tang, C. W. & Vanslyke, S. A. (1987). Appl. Phys. Lett. 51, 913–915. CrossRef CAS Web of Science Google Scholar
Wang, S. N. (2001). Coord. Chem. Rev. 215, 79–98. Web of Science CrossRef CAS Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Luminescent coordination compounds based on pyridine-type ligands have attracted intensive attention due to their potential application in areas of sensor technologies and electro-luminescent devices (Tang & Vanslyke, 1987; Wang, 2001). In order to explore potential luminescent complexes of this type, we prepared a series of bis(iminoalkyl)pyridine ligands by the condensation reaction of 2,6-diacetylpyridine with the corresponding aniline in methanol (Fan et al., 2004). It is still challenging to design and rationally synthesize ligands with unique structures and functions. In this regard, we report herein the synthesis and crystal structure of the title compound.
The molecule of the title compound (Fig. 1) possesses an approximate Cs symmetry about a plane bisecting the pyridine ring. The pyridine ring is coplanar with the two imino groups, which show typical C═N double bond character (1.2606 (18) and 1.2674 (19) Å for N1═C1 and N3═C7, respectively). These values are in good agreement with those observed in 2,6-bis[1-(phenylimino)ethyl]pyridine (1.266 (4) Å; Mentes et al., 2001) and in 2,6-bis[1-(2,6-dimethylphenylimino)ethyl]pyridine (1.265 (2) and 1.271 (2) Å; Huang et al., 2006). The dihedral angles between the C10–C15 and C17–C22 benzene rings and the pyridine ring are 89.68 (5) and 53.62 (6)°, respectively. The crystal packing (Fig. 2) is stabilized only by van der Waals interactions.