Acta Cryst. (2008). E64, o973 [ doi:10.1107/S1600536808009550 ]
In the title compound, C14H10N6, the pyridine and tetrazole rings are nearly coplanar and are twisted from each other by a dihedral angle of only 0.86 (9)°. The benzene ring makes a dihedral angle of 70.55 (6)° with the tetrazole ring.
4-((5-(pyridin-3-yl)-2H-tetrazol-2-yl)methyl)benzonitrile (3 mmol) was dissolved in ethanol (20 ml) and evaporated in the air affording colorless block crystals of this compound suitable for X-ray analysis were obtained.
All H atoms were fixed geometrically and treated as riding with C–H = 0.93 Å (aromatic) and 0.97 Å (methylene) with Uiso(H) =1.2Ueq(C).
Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
![[Figure 1]](./dn2333fig1thm.gif)
| Fig. 1. A view of the title compound with the atomic numbering scheme. Displacement ellipsoids were drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii. |
| C14H10N6 | Z = 2 |
| Mr = 262.28 | F000 = 272 |
| Triclinic, P1 | Dx = 1.382 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation λ = 0.71073 Å |
| a = 8.0452 (16) Å | Cell parameters from 2882 reflections |
| b = 8.7081 (17) Å | θ = 3.4–27.5º |
| c = 10.171 (2) Å | µ = 0.09 mm−1 |
| α = 94.61 (3)º | T = 293 (2) K |
| β = 104.95 (3)º | Block, colourless |
| γ = 111.11 (3)º | 0.4 × 0.35 × 0.35 mm |
| V = 630.3 (3) Å3 |
| Rigaku Mercury2 diffractometer | 2882 independent reflections |
| Radiation source: fine-focus sealed tube | 2063 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.035 |
| Detector resolution: 13.6612 pixels mm-1 | θmax = 27.5º |
| T = 293(2) K | θmin = 3.4º |
| ω scans | h = −10→10 |
| Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | k = −11→11 |
| Tmin = 0.962, Tmax = 0.968 | l = −13→13 |
| 6638 measured reflections |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.049 | H-atom parameters constrained |
| wR(F2) = 0.123 | w = 1/[σ2(Fo2) + (0.0473P)2 + 0.0983P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.04 | (Δ/σ)max < 0.001 |
| 2882 reflections | Δρmax = 0.17 e Å−3 |
| 181 parameters | Δρmin = −0.20 e Å−3 |
| Primary atom site location: structure-invariant direct methods | Extinction correction: none |
| C14H10N6 | γ = 111.11 (3)º |
| Mr = 262.28 | V = 630.3 (3) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 8.0452 (16) Å | Mo Kα |
| b = 8.7081 (17) Å | µ = 0.09 mm−1 |
| c = 10.171 (2) Å | T = 293 (2) K |
| α = 94.61 (3)º | 0.4 × 0.35 × 0.35 mm |
| β = 104.95 (3)º |
| Rigaku Mercury2 diffractometer | 2882 independent reflections |
| Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | 2063 reflections with I > 2σ(I) |
| Tmin = 0.962, Tmax = 0.968 | Rint = 0.035 |
| 6638 measured reflections |
| R[F2 > 2σ(F2)] = 0.049 | 181 parameters |
| wR(F2) = 0.123 | H-atom parameters constrained |
| S = 1.04 | Δρmax = 0.17 e Å−3 |
| 2882 reflections | Δρmin = −0.20 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 | 0.1058 (3) | −0.1591 (2) | 0.5558 (2) | 0.0572 (5) | |
| H1 | 0.0253 | −0.2512 | 0.5801 | 0.069* | |
| C2 | 0.2506 (3) | −0.0395 (2) | 0.65976 (19) | 0.0573 (5) | |
| H2 | 0.2661 | −0.0497 | 0.7520 | 0.069* | |
| C3 | 0.3732 (2) | 0.0965 (2) | 0.62507 (17) | 0.0492 (4) | |
| H3 | 0.4736 | 0.1790 | 0.6936 | 0.059* | |
| C4 | 0.3447 (2) | 0.10834 (19) | 0.48717 (15) | 0.0379 (3) | |
| C5 | 0.1926 (2) | −0.0186 (2) | 0.39132 (18) | 0.0503 (4) | |
| H5 | 0.1717 | −0.0109 | 0.2983 | 0.060* | |
| C6 | 0.4708 (2) | 0.24879 (19) | 0.44434 (15) | 0.0389 (4) | |
| C7 | 0.6451 (3) | 0.4856 (2) | 0.2136 (2) | 0.0558 (5) | |
| H7A | 0.7176 | 0.6053 | 0.2454 | 0.067* | |
| H7B | 0.5309 | 0.4698 | 0.1420 | 0.067* | |
| C8 | 0.7564 (2) | 0.4087 (2) | 0.15309 (17) | 0.0443 (4) | |
| C9 | 0.9485 (2) | 0.4701 (2) | 0.21250 (18) | 0.0493 (4) | |
| H9 | 1.0070 | 0.5578 | 0.2888 | 0.059* | |
| C10 | 1.0544 (2) | 0.4029 (2) | 0.16004 (17) | 0.0474 (4) | |
| H10 | 1.1835 | 0.4445 | 0.2011 | 0.057* | |
| C11 | 0.9677 (2) | 0.2733 (2) | 0.04600 (16) | 0.0417 (4) | |
| C12 | 0.7746 (2) | 0.2088 (2) | −0.01356 (17) | 0.0513 (4) | |
| H12 | 0.7162 | 0.1201 | −0.0892 | 0.062* | |
| C13 | 0.6696 (2) | 0.2767 (2) | 0.03990 (18) | 0.0523 (4) | |
| H13 | 0.5403 | 0.2340 | 0.0000 | 0.063* | |
| C14 | 1.0826 (2) | 0.2107 (2) | −0.01146 (17) | 0.0490 (4) | |
| N1 | 0.0737 (2) | −0.15148 (18) | 0.42275 (17) | 0.0583 (4) | |
| N2 | 0.45326 (18) | 0.26697 (17) | 0.31385 (13) | 0.0448 (3) | |
| N3 | 0.59763 (19) | 0.41048 (17) | 0.32955 (14) | 0.0455 (3) | |
| N4 | 0.6996 (2) | 0.47768 (19) | 0.45939 (16) | 0.0551 (4) | |
| N5 | 0.61961 (19) | 0.37565 (18) | 0.53498 (14) | 0.0514 (4) | |
| N6 | 1.1781 (2) | 0.1676 (2) | −0.05615 (16) | 0.0654 (5) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0591 (11) | 0.0495 (10) | 0.0713 (13) | 0.0216 (9) | 0.0306 (10) | 0.0206 (9) |
| C2 | 0.0666 (12) | 0.0641 (12) | 0.0495 (10) | 0.0281 (10) | 0.0255 (9) | 0.0203 (9) |
| C3 | 0.0496 (10) | 0.0522 (10) | 0.0430 (9) | 0.0188 (8) | 0.0125 (8) | 0.0065 (7) |
| C4 | 0.0371 (8) | 0.0419 (8) | 0.0386 (8) | 0.0188 (7) | 0.0144 (7) | 0.0053 (6) |
| C5 | 0.0526 (10) | 0.0491 (10) | 0.0444 (9) | 0.0150 (8) | 0.0159 (8) | 0.0054 (7) |
| C6 | 0.0354 (8) | 0.0438 (9) | 0.0394 (8) | 0.0169 (7) | 0.0140 (7) | 0.0029 (7) |
| C7 | 0.0618 (11) | 0.0595 (11) | 0.0698 (12) | 0.0333 (10) | 0.0402 (10) | 0.0299 (9) |
| C8 | 0.0468 (9) | 0.0490 (9) | 0.0487 (9) | 0.0224 (8) | 0.0255 (8) | 0.0201 (8) |
| C9 | 0.0491 (10) | 0.0486 (10) | 0.0475 (9) | 0.0146 (8) | 0.0186 (8) | 0.0044 (8) |
| C10 | 0.0364 (8) | 0.0534 (10) | 0.0496 (9) | 0.0144 (8) | 0.0144 (8) | 0.0074 (8) |
| C11 | 0.0406 (9) | 0.0491 (9) | 0.0384 (8) | 0.0182 (7) | 0.0154 (7) | 0.0109 (7) |
| C12 | 0.0438 (9) | 0.0598 (11) | 0.0427 (9) | 0.0165 (8) | 0.0093 (8) | 0.0009 (8) |
| C13 | 0.0371 (9) | 0.0664 (11) | 0.0541 (10) | 0.0197 (8) | 0.0157 (8) | 0.0137 (9) |
| C14 | 0.0450 (9) | 0.0571 (10) | 0.0426 (9) | 0.0189 (8) | 0.0125 (8) | 0.0064 (8) |
| N1 | 0.0565 (9) | 0.0442 (8) | 0.0663 (10) | 0.0107 (7) | 0.0201 (8) | 0.0074 (7) |
| N2 | 0.0430 (8) | 0.0487 (8) | 0.0437 (8) | 0.0157 (6) | 0.0188 (6) | 0.0089 (6) |
| N3 | 0.0428 (8) | 0.0474 (8) | 0.0531 (8) | 0.0184 (7) | 0.0246 (7) | 0.0121 (7) |
| N4 | 0.0447 (8) | 0.0538 (9) | 0.0591 (9) | 0.0095 (7) | 0.0194 (7) | 0.0059 (7) |
| N5 | 0.0437 (8) | 0.0523 (8) | 0.0502 (8) | 0.0097 (7) | 0.0162 (7) | 0.0055 (7) |
| N6 | 0.0581 (10) | 0.0839 (12) | 0.0611 (10) | 0.0351 (9) | 0.0227 (8) | 0.0040 (9) |
| C1—N1 | 1.322 (2) | C7—H7B | 0.9700 |
| C1—C2 | 1.369 (3) | C8—C9 | 1.382 (2) |
| C1—H1 | 0.9300 | C8—C13 | 1.389 (3) |
| C2—C3 | 1.381 (3) | C9—C10 | 1.377 (2) |
| C2—H2 | 0.9300 | C9—H9 | 0.9300 |
| C3—C4 | 1.380 (2) | C10—C11 | 1.383 (2) |
| C3—H3 | 0.9300 | C10—H10 | 0.9300 |
| C4—C5 | 1.381 (2) | C11—C12 | 1.389 (2) |
| C4—C6 | 1.461 (2) | C11—C14 | 1.443 (2) |
| C5—N1 | 1.332 (2) | C12—C13 | 1.380 (2) |
| C5—H5 | 0.9300 | C12—H12 | 0.9300 |
| C6—N2 | 1.3265 (19) | C13—H13 | 0.9300 |
| C6—N5 | 1.348 (2) | C14—N6 | 1.140 (2) |
| C7—N3 | 1.464 (2) | N2—N3 | 1.3277 (19) |
| C7—C8 | 1.509 (2) | N3—N4 | 1.315 (2) |
| C7—H7A | 0.9700 | N4—N5 | 1.322 (2) |
| N1—C1—C2 | 123.89 (17) | C9—C8—C7 | 119.23 (16) |
| N1—C1—H1 | 118.1 | C13—C8—C7 | 121.38 (16) |
| C2—C1—H1 | 118.1 | C10—C9—C8 | 120.79 (16) |
| C1—C2—C3 | 118.73 (17) | C10—C9—H9 | 119.6 |
| C1—C2—H2 | 120.6 | C8—C9—H9 | 119.6 |
| C3—C2—H2 | 120.6 | C9—C10—C11 | 119.63 (15) |
| C4—C3—C2 | 119.00 (17) | C9—C10—H10 | 120.2 |
| C4—C3—H3 | 120.5 | C11—C10—H10 | 120.2 |
| C2—C3—H3 | 120.5 | C10—C11—C12 | 120.21 (15) |
| C3—C4—C5 | 117.22 (15) | C10—C11—C14 | 118.62 (15) |
| C3—C4—C6 | 121.38 (15) | C12—C11—C14 | 121.14 (15) |
| C5—C4—C6 | 121.40 (14) | C13—C12—C11 | 119.73 (16) |
| N1—C5—C4 | 124.61 (16) | C13—C12—H12 | 120.1 |
| N1—C5—H5 | 117.7 | C11—C12—H12 | 120.1 |
| C4—C5—H5 | 117.7 | C12—C13—C8 | 120.24 (16) |
| N2—C6—N5 | 112.35 (14) | C12—C13—H13 | 119.9 |
| N2—C6—C4 | 124.60 (14) | C8—C13—H13 | 119.9 |
| N5—C6—C4 | 123.05 (14) | N6—C14—C11 | 177.31 (19) |
| N3—C7—C8 | 111.58 (13) | C1—N1—C5 | 116.53 (16) |
| N3—C7—H7A | 109.3 | C6—N2—N3 | 101.60 (13) |
| C8—C7—H7A | 109.3 | N4—N3—N2 | 114.04 (13) |
| N3—C7—H7B | 109.3 | N4—N3—C7 | 122.32 (15) |
| C8—C7—H7B | 109.3 | N2—N3—C7 | 123.60 (15) |
| H7A—C7—H7B | 108.0 | N3—N4—N5 | 106.02 (13) |
| C9—C8—C13 | 119.38 (16) | N4—N5—C6 | 105.98 (13) |
This work was supported by a Start-up Grant from Southeast University to Professor Ren-Gen Xiong.
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In the past five years, we have focused on the chemistry of tetrazole derivatives because of their multiple coordination modes as ligands to metal ions and for the construction of novel metal-organic frameworks (Wang et al., 2005; Xiong et al., 2002). We report here the crystal structure of the title compound, 4-((5-(pyridin-3-yl)-2H-tetrazol-2-yl)methyl)benzonitrile.
There are three rings in the title compound (Fig. 1). The pyridine and tetrazole rings are nearly coplanar and are twisted from each other by a dihedral angle of only 0.86 (0.09) °.The benzene ring makes a dihedral angle of 70.55 (0.06) ° with the tetrazole ring owing to the methylene bridge which forces the two rings to be twisted twisted from each other. In the pyridine ring, the C1=N1 and C5=N1 bond distance of 1.322 and 1.332Å conforms to the value for a C=N double bond, while the C14—N6 bond length of 1.140 Å conforms to the value for a C≡N bond. The bond distances and bond angles of the tetrazole rings are within the usual ranges (Wang et al., 2005; Arp et al., 2000; Hu et al., 2007).