Acta Cryst. (2009). E65, o2977 [ doi:10.1107/S1600536809045450 ]
The molecular skeleton of the title molecule, C26H20N6S2, adopts a cis conformation with the two arms positioned on one side of the benzene ring plane. Intramolecular ![[pi]](/logos/entities/pi_rmgif.gif)
- interactions between the pyrimidine rings [centroid-centroid distance = 3.654 (2) Å] and between the pyridine rings [centroid-centroid distance = 3.775 (2) Å] help to set the molecular conformation; the pyrimidine rings, as well as the pyridine rings, are nearly parallel, forming dihedral angles of 4.12 (14) and 2.46 (14)°, respectively.
All solvents and chemicals were of analytical grade and were used without further purification. The title compound was prepared by similar procedure reported in the literature (Dong et al., 2008; 2009), To a solution of 4-(4-pyridinyl)pyrimidine-2-thiol (3.78 g, 20 mmol) and sodium hydroxide (0.80 g, 20 mmol) in dry ethanol (300 ml), 1,2-bis(bromomethyl)benzene (2.64 g, 10 mmol) in CCl4 (30 ml) was added. The mixture was stirred and refluxed for 8 h. After cooling, precipitates were filtered, washed in water and ethanol, and dried in vacuum. Anal. Calcd for C26H20N6S2: C, 64.98; H, 4.19; N, 17.49%. Found: C, 65.07; H, 4.52; N, 17.34%. Single crystals of ligang suitable for X-ray diffraction were grown from methanol solution by slow evaporation in air at room temperature.
All hydrogen atoms were geometrically positioned (C—H 0.93–0.97 Å) and refined as riding, with Uiso(H)=1.2Ueq(C).
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./cv2646fig1thm.gif)
| Fig. 1. The molecular structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme. |
| C26H20N6S2 | F(000) = 1000.0 |
| Mr = 480.62 | Dx = 1.404 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2yn | Cell parameters from 4903 reflections |
| a = 8.6078 (11) Å | θ = 2.2–27.0° |
| b = 27.102 (3) Å | µ = 0.26 mm−1 |
| c = 10.0282 (12) Å | T = 291 K |
| β = 103.661 (2)° | Block, pale yellow |
| V = 2273.3 (5) Å3 | 0.32 × 0.18 × 0.16 mm |
| Z = 4 |
| Bruker SMART CCD area-detector diffractometer | 4903 independent reflections |
| Radiation source: fine-focus sealed tube | 3067 reflections with I > 2σ(I) |
| graphite | Rint = 0.052 |
| φ and ω scans | θmax = 27.0°, θmin = 2.2° |
| Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −10→8 |
| Tmin = 0.917, Tmax = 0.966 | k = −34→31 |
| 13064 measured reflections | l = −12→12 |
| 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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.108 | H-atom parameters constrained |
| S = 0.90 | w = 1/[σ2(Fo2) + (0.0421P)2] where P = (Fo2 + 2Fc2)/3 |
| 4903 reflections | (Δ/σ)max = 0.001 |
| 307 parameters | Δρmax = 0.32 e Å−3 |
| 0 restraints | Δρmin = −0.22 e Å−3 |
| C26H20N6S2 | V = 2273.3 (5) Å3 |
| Mr = 480.62 | Z = 4 |
| Monoclinic, P21/n | Mo Kα radiation |
| a = 8.6078 (11) Å | µ = 0.26 mm−1 |
| b = 27.102 (3) Å | T = 291 K |
| c = 10.0282 (12) Å | 0.32 × 0.18 × 0.16 mm |
| β = 103.661 (2)° |
| Bruker SMART CCD area-detector diffractometer | 4903 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2000) | 3067 reflections with I > 2σ(I) |
| Tmin = 0.917, Tmax = 0.966 | Rint = 0.052 |
| 13064 measured reflections | θmax = 27.0° |
| R[F2 > 2σ(F2)] = 0.052 | H-atom parameters constrained |
| wR(F2) = 0.108 | Δρmax = 0.32 e Å−3 |
| S = 0.90 | Δρmin = −0.22 e Å−3 |
| 4903 reflections | Absolute structure: ? |
| 307 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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 | ||
| C1 | 0.7345 (3) | 0.22381 (8) | 0.8229 (2) | 0.0384 (5) | |
| C2 | 0.9748 (3) | 0.25202 (9) | 0.9324 (2) | 0.0494 (6) | |
| H2 | 1.0799 | 0.2469 | 0.9807 | 0.059* | |
| C3 | 0.9230 (3) | 0.29935 (8) | 0.9059 (2) | 0.0474 (6) | |
| H3 | 0.9909 | 0.3259 | 0.9351 | 0.057* | |
| C4 | 0.7668 (3) | 0.30680 (8) | 0.8343 (2) | 0.0411 (6) | |
| C5 | 0.6967 (3) | 0.35654 (8) | 0.8048 (2) | 0.0436 (6) | |
| C6 | 0.7521 (3) | 0.39620 (9) | 0.8867 (3) | 0.0623 (8) | |
| H6 | 0.8355 | 0.3922 | 0.9640 | 0.075* | |
| C7 | 0.6845 (4) | 0.44177 (10) | 0.8545 (3) | 0.0774 (9) | |
| H7 | 0.7240 | 0.4680 | 0.9125 | 0.093* | |
| C8 | 0.5126 (3) | 0.41215 (9) | 0.6685 (3) | 0.0690 (8) | |
| H8 | 0.4291 | 0.4172 | 0.5919 | 0.083* | |
| C9 | 0.5716 (3) | 0.36519 (8) | 0.6935 (3) | 0.0529 (7) | |
| H9 | 0.5275 | 0.3394 | 0.6357 | 0.063* | |
| C10 | 0.6875 (3) | 0.12421 (7) | 0.8693 (2) | 0.0472 (6) | |
| H10A | 0.7817 | 0.1124 | 0.8418 | 0.057* | |
| H10B | 0.7188 | 0.1342 | 0.9648 | 0.057* | |
| C11 | 0.5630 (3) | 0.08400 (8) | 0.8510 (2) | 0.0443 (6) | |
| C12 | 0.5488 (3) | 0.05264 (9) | 0.7392 (3) | 0.0592 (7) | |
| H12 | 0.6183 | 0.0560 | 0.6815 | 0.071* | |
| C13 | 0.4334 (4) | 0.01686 (9) | 0.7133 (3) | 0.0687 (8) | |
| H13 | 0.4248 | −0.0038 | 0.6379 | 0.082* | |
| C14 | 0.3317 (3) | 0.01133 (9) | 0.7966 (3) | 0.0660 (8) | |
| H14 | 0.2519 | −0.0126 | 0.7777 | 0.079* | |
| C15 | 0.3473 (3) | 0.04123 (8) | 0.9091 (3) | 0.0566 (7) | |
| H15 | 0.2794 | 0.0367 | 0.9677 | 0.068* | |
| C16 | 0.4617 (3) | 0.07813 (8) | 0.9376 (2) | 0.0446 (6) | |
| C17 | 0.4698 (3) | 0.11019 (7) | 1.0609 (2) | 0.0502 (6) | |
| H17A | 0.5805 | 0.1184 | 1.1017 | 0.060* | |
| H17B | 0.4283 | 0.0921 | 1.1285 | 0.060* | |
| C18 | 0.4950 (3) | 0.21357 (8) | 1.0767 (2) | 0.0380 (5) | |
| C19 | 0.7376 (3) | 0.24131 (9) | 1.1805 (2) | 0.0484 (6) | |
| H19 | 0.8442 | 0.2358 | 1.2238 | 0.058* | |
| C20 | 0.6847 (3) | 0.28872 (8) | 1.1637 (2) | 0.0446 (6) | |
| H20 | 0.7523 | 0.3151 | 1.1955 | 0.053* | |
| C21 | 0.5267 (3) | 0.29608 (8) | 1.0977 (2) | 0.0393 (5) | |
| C22 | 0.4562 (3) | 0.34572 (8) | 1.0709 (2) | 0.0399 (5) | |
| C23 | 0.5154 (3) | 0.38590 (9) | 1.1509 (3) | 0.0589 (7) | |
| H23 | 0.6024 | 0.3823 | 1.2253 | 0.071* | |
| C24 | 0.4452 (4) | 0.43133 (9) | 1.1201 (3) | 0.0701 (9) | |
| H24 | 0.4868 | 0.4579 | 1.1761 | 0.084* | |
| C25 | 0.3284 (3) | 0.35403 (8) | 0.9626 (2) | 0.0497 (6) | |
| H25 | 0.2835 | 0.3282 | 0.9052 | 0.060* | |
| C26 | 0.2679 (3) | 0.40072 (9) | 0.9402 (3) | 0.0597 (7) | |
| H26 | 0.1816 | 0.4054 | 0.8656 | 0.072* | |
| N1 | 0.8822 (2) | 0.21295 (7) | 0.89261 (18) | 0.0458 (5) | |
| N2 | 0.6713 (2) | 0.26820 (6) | 0.79073 (17) | 0.0405 (5) | |
| N3 | 0.5667 (3) | 0.45081 (8) | 0.7465 (3) | 0.0771 (8) | |
| N4 | 0.6443 (2) | 0.20240 (7) | 1.13813 (19) | 0.0463 (5) | |
| N5 | 0.4294 (2) | 0.25802 (6) | 1.05275 (17) | 0.0394 (5) | |
| N6 | 0.3221 (3) | 0.43947 (7) | 1.0157 (2) | 0.0640 (6) | |
| S1 | 0.60063 (8) | 0.17575 (2) | 0.76342 (6) | 0.04810 (19) | |
| S2 | 0.35623 (8) | 0.16649 (2) | 1.01669 (6) | 0.04634 (19) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0353 (14) | 0.0411 (13) | 0.0382 (13) | −0.0043 (11) | 0.0074 (11) | 0.0000 (10) |
| C2 | 0.0363 (16) | 0.0586 (16) | 0.0487 (15) | −0.0038 (12) | 0.0005 (12) | 0.0005 (12) |
| C3 | 0.0409 (16) | 0.0496 (15) | 0.0480 (15) | −0.0112 (12) | 0.0031 (12) | −0.0033 (11) |
| C4 | 0.0424 (15) | 0.0443 (13) | 0.0377 (13) | −0.0058 (12) | 0.0116 (11) | −0.0023 (10) |
| C5 | 0.0423 (16) | 0.0436 (14) | 0.0462 (14) | −0.0055 (11) | 0.0131 (12) | −0.0066 (11) |
| C6 | 0.068 (2) | 0.0518 (16) | 0.0583 (17) | −0.0030 (15) | −0.0019 (14) | −0.0126 (13) |
| C7 | 0.090 (3) | 0.0455 (17) | 0.086 (2) | −0.0035 (16) | −0.001 (2) | −0.0243 (15) |
| C8 | 0.063 (2) | 0.0504 (16) | 0.081 (2) | 0.0088 (14) | −0.0070 (16) | −0.0122 (15) |
| C9 | 0.0461 (17) | 0.0422 (14) | 0.0656 (17) | −0.0020 (12) | 0.0036 (14) | −0.0122 (12) |
| C10 | 0.0394 (15) | 0.0401 (13) | 0.0559 (15) | 0.0036 (11) | −0.0010 (12) | 0.0066 (11) |
| C11 | 0.0447 (16) | 0.0305 (12) | 0.0509 (15) | 0.0019 (11) | −0.0025 (12) | 0.0012 (11) |
| C12 | 0.064 (2) | 0.0480 (15) | 0.0640 (18) | −0.0002 (14) | 0.0131 (15) | −0.0030 (13) |
| C13 | 0.079 (2) | 0.0455 (16) | 0.072 (2) | −0.0027 (15) | −0.0014 (18) | −0.0151 (14) |
| C14 | 0.058 (2) | 0.0367 (15) | 0.094 (2) | −0.0075 (13) | −0.0005 (17) | −0.0006 (15) |
| C15 | 0.0512 (18) | 0.0380 (14) | 0.079 (2) | 0.0012 (12) | 0.0129 (15) | 0.0064 (13) |
| C16 | 0.0457 (16) | 0.0304 (12) | 0.0526 (15) | 0.0027 (11) | 0.0016 (12) | 0.0056 (11) |
| C17 | 0.0563 (17) | 0.0387 (13) | 0.0527 (16) | 0.0057 (12) | 0.0071 (13) | 0.0101 (11) |
| C18 | 0.0354 (15) | 0.0429 (13) | 0.0355 (13) | 0.0000 (11) | 0.0084 (11) | −0.0030 (10) |
| C19 | 0.0335 (15) | 0.0601 (16) | 0.0471 (15) | 0.0018 (13) | 0.0005 (12) | 0.0007 (12) |
| C20 | 0.0357 (15) | 0.0464 (14) | 0.0473 (14) | −0.0037 (11) | 0.0014 (12) | −0.0047 (11) |
| C21 | 0.0379 (14) | 0.0453 (13) | 0.0340 (13) | −0.0012 (11) | 0.0070 (11) | −0.0043 (10) |
| C22 | 0.0364 (14) | 0.0410 (13) | 0.0417 (13) | −0.0033 (11) | 0.0080 (11) | −0.0054 (10) |
| C23 | 0.0475 (17) | 0.0524 (16) | 0.0654 (18) | 0.0002 (13) | −0.0096 (14) | −0.0141 (13) |
| C24 | 0.065 (2) | 0.0455 (16) | 0.088 (2) | −0.0040 (14) | −0.0062 (17) | −0.0218 (14) |
| C25 | 0.0514 (17) | 0.0407 (14) | 0.0511 (15) | 0.0003 (12) | 0.0003 (13) | −0.0089 (11) |
| C26 | 0.0584 (19) | 0.0521 (16) | 0.0590 (17) | 0.0073 (14) | −0.0057 (14) | −0.0017 (13) |
| N1 | 0.0354 (13) | 0.0505 (12) | 0.0475 (12) | −0.0011 (10) | 0.0016 (10) | 0.0037 (9) |
| N2 | 0.0357 (12) | 0.0397 (11) | 0.0440 (11) | −0.0041 (9) | 0.0054 (9) | −0.0016 (9) |
| N3 | 0.079 (2) | 0.0508 (14) | 0.0889 (19) | 0.0089 (13) | −0.0057 (15) | −0.0148 (13) |
| N4 | 0.0392 (13) | 0.0472 (11) | 0.0494 (12) | 0.0050 (10) | 0.0041 (10) | 0.0038 (9) |
| N5 | 0.0350 (12) | 0.0394 (11) | 0.0420 (11) | 0.0016 (9) | 0.0053 (9) | −0.0027 (8) |
| N6 | 0.0645 (17) | 0.0434 (13) | 0.0754 (16) | 0.0052 (11) | −0.0007 (13) | −0.0055 (11) |
| S1 | 0.0409 (4) | 0.0417 (3) | 0.0538 (4) | −0.0057 (3) | −0.0044 (3) | 0.0051 (3) |
| S2 | 0.0425 (4) | 0.0402 (3) | 0.0539 (4) | −0.0003 (3) | 0.0067 (3) | −0.0024 (3) |
| C1—N2 | 1.328 (2) | C13—H13 | 0.9300 |
| C1—N1 | 1.331 (3) | C14—C15 | 1.369 (3) |
| C1—S1 | 1.748 (2) | C14—H14 | 0.9300 |
| C2—N1 | 1.329 (3) | C15—C16 | 1.385 (3) |
| C2—C3 | 1.364 (3) | C15—H15 | 0.9300 |
| C2—H2 | 0.9300 | C16—C17 | 1.500 (3) |
| C3—C4 | 1.381 (3) | C17—S2 | 1.810 (2) |
| C3—H3 | 0.9300 | C17—H17A | 0.9700 |
| C4—N2 | 1.338 (2) | C17—H17B | 0.9700 |
| C4—C5 | 1.478 (3) | C18—N4 | 1.323 (3) |
| C5—C6 | 1.369 (3) | C18—N5 | 1.328 (2) |
| C5—C9 | 1.375 (3) | C18—S2 | 1.754 (2) |
| C6—C7 | 1.371 (3) | C19—N4 | 1.333 (3) |
| C6—H6 | 0.9300 | C19—C20 | 1.360 (3) |
| C7—N3 | 1.320 (3) | C19—H19 | 0.9300 |
| C7—H7 | 0.9300 | C20—C21 | 1.379 (3) |
| C8—N3 | 1.324 (3) | C20—H20 | 0.9300 |
| C8—C9 | 1.372 (3) | C21—N5 | 1.339 (2) |
| C8—H8 | 0.9300 | C21—C22 | 1.474 (3) |
| C9—H9 | 0.9300 | C22—C25 | 1.369 (3) |
| C10—C11 | 1.509 (3) | C22—C23 | 1.377 (3) |
| C10—S1 | 1.807 (2) | C23—C24 | 1.374 (3) |
| C10—H10A | 0.9700 | C23—H23 | 0.9300 |
| C10—H10B | 0.9700 | C24—N6 | 1.321 (3) |
| C11—C16 | 1.377 (3) | C24—H24 | 0.9300 |
| C11—C12 | 1.389 (3) | C25—C26 | 1.367 (3) |
| C12—C13 | 1.368 (3) | C25—H25 | 0.9300 |
| C12—H12 | 0.9300 | C26—N6 | 1.314 (3) |
| C13—C14 | 1.354 (4) | C26—H26 | 0.9300 |
| N2—C1—N1 | 127.8 (2) | C14—C15—H15 | 119.2 |
| N2—C1—S1 | 113.12 (17) | C16—C15—H15 | 119.2 |
| N1—C1—S1 | 119.04 (17) | C11—C16—C15 | 118.6 (2) |
| N1—C2—C3 | 123.0 (2) | C11—C16—C17 | 122.7 (2) |
| N1—C2—H2 | 118.5 | C15—C16—C17 | 118.7 (2) |
| C3—C2—H2 | 118.5 | C16—C17—S2 | 111.68 (15) |
| C2—C3—C4 | 118.2 (2) | C16—C17—H17A | 109.3 |
| C2—C3—H3 | 120.9 | S2—C17—H17A | 109.3 |
| C4—C3—H3 | 120.9 | C16—C17—H17B | 109.3 |
| N2—C4—C3 | 120.2 (2) | S2—C17—H17B | 109.3 |
| N2—C4—C5 | 117.2 (2) | H17A—C17—H17B | 107.9 |
| C3—C4—C5 | 122.6 (2) | N4—C18—N5 | 128.1 (2) |
| C6—C5—C9 | 116.6 (2) | N4—C18—S2 | 120.10 (17) |
| C6—C5—C4 | 121.9 (2) | N5—C18—S2 | 111.83 (17) |
| C9—C5—C4 | 121.5 (2) | N4—C19—C20 | 123.3 (2) |
| C5—C6—C7 | 119.8 (2) | N4—C19—H19 | 118.4 |
| C5—C6—H6 | 120.1 | C20—C19—H19 | 118.4 |
| C7—C6—H6 | 120.1 | C19—C20—C21 | 117.4 (2) |
| N3—C7—C6 | 124.2 (2) | C19—C20—H20 | 121.3 |
| N3—C7—H7 | 117.9 | C21—C20—H20 | 121.3 |
| C6—C7—H7 | 117.9 | N5—C21—C20 | 121.2 (2) |
| N3—C8—C9 | 124.2 (2) | N5—C21—C22 | 116.3 (2) |
| N3—C8—H8 | 117.9 | C20—C21—C22 | 122.4 (2) |
| C9—C8—H8 | 117.9 | C25—C22—C23 | 116.7 (2) |
| C8—C9—C5 | 119.5 (2) | C25—C22—C21 | 120.9 (2) |
| C8—C9—H9 | 120.3 | C23—C22—C21 | 122.4 (2) |
| C5—C9—H9 | 120.3 | C24—C23—C22 | 119.7 (2) |
| C11—C10—S1 | 107.66 (15) | C24—C23—H23 | 120.1 |
| C11—C10—H10A | 110.2 | C22—C23—H23 | 120.1 |
| S1—C10—H10A | 110.2 | N6—C24—C23 | 123.7 (2) |
| C11—C10—H10B | 110.2 | N6—C24—H24 | 118.1 |
| S1—C10—H10B | 110.2 | C23—C24—H24 | 118.1 |
| H10A—C10—H10B | 108.5 | C26—C25—C22 | 119.1 (2) |
| C16—C11—C12 | 119.3 (2) | C26—C25—H25 | 120.4 |
| C16—C11—C10 | 122.9 (2) | C22—C25—H25 | 120.4 |
| C12—C11—C10 | 117.7 (2) | N6—C26—C25 | 125.1 (2) |
| C13—C12—C11 | 120.6 (3) | N6—C26—H26 | 117.4 |
| C13—C12—H12 | 119.7 | C25—C26—H26 | 117.4 |
| C11—C12—H12 | 119.7 | C2—N1—C1 | 114.35 (19) |
| C14—C13—C12 | 120.5 (3) | C1—N2—C4 | 116.4 (2) |
| C14—C13—H13 | 119.8 | C7—N3—C8 | 115.6 (2) |
| C12—C13—H13 | 119.8 | C18—N4—C19 | 114.42 (19) |
| C13—C14—C15 | 119.4 (3) | C18—N5—C21 | 115.62 (19) |
| C13—C14—H14 | 120.3 | C26—N6—C24 | 115.6 (2) |
| C15—C14—H14 | 120.3 | C1—S1—C10 | 103.16 (11) |
| C14—C15—C16 | 121.6 (3) | C18—S2—C17 | 104.16 (11) |
The authors are indebted to the National Natural Science Foundationof China (grant No. 20801011) for financial support.
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Remarkable attention has been paid to the rational design and assembly of new coordination polymers with heterocyclic thiolates or thioethers in recent years. In our previous work, we reported aserials dithioether ligands (Dong et al., 2008; 2009; Huang et al., 2007). As our continuing study, herein we report the molecular structure of the title compound - the newly synthesized ligand derived from 4-(4-pyridinyl)pyrimidine-2-thiol.
The molecular structure of the title compound is shown in Fig. 1. The molecule adopts a cis conformation with two arms positioned on one side of the benzene ring plane. It is noted that intramolecular π-π interactions between the pyrimidinyl rings [centroid-centroid distance of 3.654 (2) Å] and between the pyridinyl rings [centroid-centroid distance of 3.775 (2) Å] set the molecular conformation - the pyrimidinyl rings, as well as the pyridinyl ones, are nearly parallel forming dihedral angles of 4.12 (14)° and 2.46 (14)°, respectively.