Acta Cryst. (2007). E63, o3042 [ doi:10.1107/S1600536807023203 ]
In the crystal structure of the title compound, C11H10N4, molecules form dimers , which form a zigzag pattern in the crystal. The hydrogen-bond network can be described by graph-set notation as R22(14).
The chemical synthesis of the title compound was performed by analogy to procedures described previously (Popp, 1989). Generally, the compound was recrystallized from methanol/water. The 2-Pyridylhydrazone crystal was grown by slow evaporation from methanol solution.
Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalStructure (Molecular Structure Corporation & Rigaku, 2005); program(s) used to solve structure: SIR88 (Burla et al., 1989 Reference OK?); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); software used to prepare material for publication: CrystalStructure.
![[Figure 1]](./sg2161fig1thm.gif)
| Fig. 1. A view of I with the atomic numbering scheme. Displacement ellipsoids are drawn at the 40% probability level. |
![[Figure 2]](./sg2161fig2thm.gif)
| Fig. 2. Projection of crystal lattice molecular packing of (I) along OX axis. |
![[Figure 3]](./sg2161fig3thm.gif)
| Fig. 3. Projection of crystal lattice molecular packing of (I) along OY axis. |
| C11H10N4 | F(000) = 416.00 |
| Mr = 198.23 | Dx = 1.325 Mg m−3 |
| Monoclinic, P21/n | Melting point: 449 K |
| Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71070 Å |
| a = 10.896 (5) Å | Cell parameters from 1851 reflections |
| b = 4.0270 (17) Å | θ = 3.2–30.0° |
| c = 22.710 (9) Å | µ = 0.09 mm−1 |
| β = 94.304 (8)° | T = 293 K |
| V = 993.6 (7) Å3 | Prism, colorless |
| Z = 4 | 0.40 × 0.30 × 0.10 mm |
| Rigaku Saturn diffractometer | 2273 reflections with F2 > 2σ(F2) |
| Detector resolution: 7.31 pixels mm-1 | Rint = 0.037 |
| ω scans | θmax = 30.4° |
| Absorption correction: multi-scan Jacobson (1998) | h = −14→14 |
| Tmin = 0.892, Tmax = 0.992 | k = −3→5 |
| 9025 measured reflections | l = −32→31 |
| 3614 independent reflections |
| Refinement on F | Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979) 88.1628 106.9210 44.1569 |
| R[F2 > 2σ(F2)] = 0.045 | (Δ/σ)max = 0.006 |
| wR(F2) = 0.048 | Δρmax = 0.66 e Å−3 |
| S = 0.97 | Δρmin = −0.52 e Å−3 |
| 3614 reflections | Extinction correction: Larson (1970) Crystallographic Computing eq. 22 |
| 177 parameters | Extinction coefficient: 41 (21) |
| All H-atom parameters refined |
| C11H10N4 | V = 993.6 (7) Å3 |
| Mr = 198.23 | Z = 4 |
| Monoclinic, P21/n | Mo Kα radiation |
| a = 10.896 (5) Å | µ = 0.09 mm−1 |
| b = 4.0270 (17) Å | T = 293 K |
| c = 22.710 (9) Å | 0.40 × 0.30 × 0.10 mm |
| β = 94.304 (8)° |
| Rigaku Saturn diffractometer | 3614 independent reflections |
| Absorption correction: multi-scan Jacobson (1998) | 2273 reflections with F2 > 2σ(F2) |
| Tmin = 0.892, Tmax = 0.992 | Rint = 0.037 |
| 9025 measured reflections | θmax = 30.4° |
| R[F2 > 2σ(F2)] = 0.045 | All H-atom parameters refined |
| wR(F2) = 0.048 | Δρmax = 0.66 e Å−3 |
| S = 0.97 | Δρmin = −0.52 e Å−3 |
| 3614 reflections | Absolute structure: ? |
| 177 parameters | Flack parameter: ? |
| ? restraints | Rogers parameter: ? |
Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY |
Refinement. Refinement using reflections with F2 > 3.0 σ(F2). The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
| x | y | z | Uiso*/Ueq | ||
| N1 | 0.58600 (12) | 0.1829 (3) | 0.62487 (5) | 0.0552 (4) | |
| N2 | 0.57422 (12) | 0.2776 (3) | 0.56706 (5) | 0.0583 (4) | |
| N3 | 0.64083 (11) | 0.2790 (3) | 0.47412 (5) | 0.0573 (4) | |
| N4 | 0.39775 (16) | 0.1814 (4) | 0.80823 (6) | 0.0817 (6) | |
| C1 | 0.49701 (17) | 0.2595 (4) | 0.65614 (6) | 0.0565 (5) | |
| C2 | 0.50216 (14) | 0.1730 (4) | 0.71847 (6) | 0.0508 (5) | |
| C3 | 0.60286 (18) | 0.0237 (4) | 0.74843 (6) | 0.0572 (5) | |
| C4 | 0.6002 (2) | −0.0391 (4) | 0.80754 (8) | 0.0679 (6) | |
| C5 | 0.4975 (2) | 0.0415 (5) | 0.83536 (9) | 0.0752 (7) | |
| C6 | 0.40282 (18) | 0.2461 (5) | 0.75060 (8) | 0.0685 (6) | |
| C7 | 0.66146 (14) | 0.1757 (4) | 0.53006 (6) | 0.0501 (5) | |
| C8 | 0.76185 (16) | −0.0184 (4) | 0.54956 (8) | 0.0579 (5) | |
| C9 | 0.84375 (19) | −0.1077 (4) | 0.50947 (9) | 0.0680 (6) | |
| C10 | 0.82507 (18) | −0.0028 (4) | 0.45175 (8) | 0.0669 (6) | |
| C11 | 0.72443 (17) | 0.1861 (4) | 0.43666 (8) | 0.0614 (6) | |
| H1 | 0.4229 (13) | 0.386 (3) | 0.6392 (5) | 0.059 (4)* | |
| H2 | 0.4999 (17) | 0.419 (4) | 0.5523 (7) | 0.101 (6)* | |
| H3 | 0.6766 (12) | −0.036 (3) | 0.7269 (5) | 0.058 (4)* | |
| H4 | 0.6726 (14) | −0.133 (4) | 0.8288 (6) | 0.075 (5)* | |
| H5 | 0.4973 (14) | 0.002 (4) | 0.8809 (7) | 0.092 (5)* | |
| H6 | 0.3308 (14) | 0.349 (3) | 0.7279 (6) | 0.078 (5)* | |
| H8 | 0.7715 (12) | −0.100 (3) | 0.5907 (6) | 0.061 (4)* | |
| H9 | 0.9192 (14) | −0.251 (4) | 0.5233 (6) | 0.078 (5)* | |
| H10 | 0.8840 (13) | −0.067 (3) | 0.4231 (6) | 0.069 (4)* | |
| H11 | 0.7058 (13) | 0.271 (3) | 0.3930 (6) | 0.071 (4)* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| N1 | 0.0598 (9) | 0.0669 (10) | 0.0390 (7) | −0.0061 (7) | 0.0043 (6) | 0.0036 (6) |
| N2 | 0.0522 (9) | 0.0841 (11) | 0.0390 (7) | 0.0041 (8) | 0.0049 (7) | 0.0107 (7) |
| N3 | 0.0558 (8) | 0.0752 (10) | 0.0411 (7) | −0.0023 (7) | 0.0056 (6) | 0.0025 (7) |
| N4 | 0.0849 (12) | 0.1059 (13) | 0.0575 (10) | −0.0055 (10) | 0.0267 (9) | 0.0024 (9) |
| C1 | 0.0503 (11) | 0.0746 (14) | 0.0447 (10) | 0.0025 (10) | 0.0046 (8) | 0.0070 (9) |
| C2 | 0.0500 (10) | 0.0583 (11) | 0.0445 (8) | −0.0014 (8) | 0.0070 (8) | 0.0002 (8) |
| C3 | 0.0602 (11) | 0.0648 (12) | 0.0472 (10) | −0.0018 (10) | 0.0072 (9) | 0.0035 (9) |
| C4 | 0.0756 (14) | 0.0746 (13) | 0.0529 (12) | −0.0008 (11) | −0.0003 (11) | 0.0077 (10) |
| C5 | 0.0966 (17) | 0.0823 (15) | 0.0478 (11) | −0.0209 (13) | 0.0121 (12) | 0.0046 (11) |
| C6 | 0.0600 (12) | 0.0914 (16) | 0.0552 (11) | 0.0032 (11) | 0.0129 (10) | 0.0052 (11) |
| C7 | 0.0486 (10) | 0.0576 (11) | 0.0445 (9) | −0.0085 (9) | 0.0056 (8) | −0.0009 (8) |
| C8 | 0.0608 (12) | 0.0626 (12) | 0.0499 (10) | −0.0022 (9) | 0.0026 (9) | 0.0042 (10) |
| C9 | 0.0669 (13) | 0.0690 (14) | 0.0688 (13) | 0.0071 (10) | 0.0104 (10) | 0.0033 (10) |
| C10 | 0.0723 (14) | 0.0683 (13) | 0.0626 (11) | 0.0054 (11) | 0.0224 (10) | −0.0035 (10) |
| C11 | 0.0668 (12) | 0.0700 (13) | 0.0483 (10) | −0.0022 (10) | 0.0107 (9) | −0.0009 (9) |
| N1—N2 | 1.3640 (16) | C8—C9 | 1.370 (2) |
| N1—C1 | 1.282 (2) | C9—C10 | 1.378 (2) |
| N2—C7 | 1.378 (2) | C10—C11 | 1.357 (2) |
| N3—C7 | 1.3396 (19) | N2—H2 | 1.026 (18) |
| N3—C11 | 1.345 (2) | C1—H1 | 1.007 (14) |
| N4—C5 | 1.334 (2) | C3—H3 | 1.001 (14) |
| N4—C6 | 1.340 (2) | C4—H4 | 0.971 (15) |
| C1—C2 | 1.455 (2) | C5—H5 | 1.048 (17) |
| C2—C3 | 1.384 (2) | C6—H6 | 0.996 (15) |
| C2—C6 | 1.382 (2) | C8—H8 | 0.988 (14) |
| C3—C4 | 1.368 (2) | C9—H9 | 1.034 (16) |
| C4—C5 | 1.364 (3) | C10—H10 | 0.981 (15) |
| C7—C8 | 1.390 (2) | C11—H11 | 1.054 (14) |
| N2—N1—C1 | 116.45 (13) | C7—N2—H2 | 122.0 (9) |
| N1—N2—C7 | 118.97 (13) | N1—C1—H1 | 122.0 (8) |
| C7—N3—C11 | 116.11 (13) | C2—C1—H1 | 117.6 (8) |
| C5—N4—C6 | 116.20 (18) | C2—C3—H3 | 120.0 (7) |
| N1—C1—C2 | 120.39 (15) | C4—C3—H3 | 120.8 (7) |
| C1—C2—C3 | 123.61 (15) | C3—C4—H4 | 118.9 (9) |
| C1—C2—C6 | 119.24 (15) | C5—C4—H4 | 121.8 (9) |
| C3—C2—C6 | 117.15 (15) | N4—C5—H5 | 117.3 (8) |
| C2—C3—C4 | 119.20 (17) | C4—C5—H5 | 119.0 (8) |
| C3—C4—C5 | 119.28 (19) | N4—C6—H6 | 119.8 (9) |
| N4—C5—C4 | 123.69 (18) | C2—C6—H6 | 115.7 (9) |
| N4—C6—C2 | 124.47 (17) | C7—C8—H8 | 120.8 (8) |
| N2—C7—N3 | 114.31 (13) | C9—C8—H8 | 120.9 (8) |
| N2—C7—C8 | 122.40 (14) | C8—C9—H9 | 119.2 (8) |
| N3—C7—C8 | 123.29 (15) | C10—C9—H9 | 121.1 (8) |
| C7—C8—C9 | 118.19 (16) | C9—C10—H10 | 119.5 (8) |
| C8—C9—C10 | 119.65 (18) | C11—C10—H10 | 122.4 (8) |
| C9—C10—C11 | 118.10 (18) | N3—C11—H11 | 114.5 (8) |
| N3—C11—C10 | 124.66 (16) | C10—C11—H11 | 120.9 (8) |
| N1—N2—H2 | 119.0 (9) | ||
| N2—N1—C1—C2 | −179.10 (14) | C1—C2—C3—C4 | 178.10 (17) |
| C1—N1—N2—C7 | −174.09 (15) | C1—C2—C6—N4 | −179.27 (17) |
| N1—N2—C7—N3 | 179.33 (13) | C3—C2—C6—N4 | −0.2 (2) |
| N1—N2—C7—C8 | −0.5 (2) | C6—C2—C3—C4 | −1.0 (2) |
| C7—N3—C11—C10 | 0.5 (2) | C2—C3—C4—C5 | 1.2 (2) |
| C11—N3—C7—N2 | 179.64 (14) | C3—C4—C5—N4 | −0.2 (3) |
| C11—N3—C7—C8 | −0.5 (2) | N2—C7—C8—C9 | 179.95 (14) |
| C5—N4—C6—C2 | 1.1 (2) | N3—C7—C8—C9 | 0.1 (2) |
| C6—N4—C5—C4 | −0.8 (3) | C7—C8—C9—C10 | 0.4 (2) |
| N1—C1—C2—C3 | 3.7 (2) | C8—C9—C10—C11 | −0.4 (2) |
| N1—C1—C2—C6 | −177.31 (16) | C9—C10—C11—N3 | −0.1 (2) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N2—H2···N3i | 1.026 (18) | 2.012 (18) | 3.0371 (18) | 176.5 (13) |
| Symmetry codes: (i) −x+1, −y+1, −z+1. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N2—H2···N3i | 1.026 (18) | 2.012 (18) | 3.0371 (18) | 176.5 (13) |
| Symmetry codes: (i) −x+1, −y+1, −z+1. |
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
Burla, M. C., Camalli, M., Cascarano, G., Giacovazzo, C., Polidori, G., Spagna, R. & Viterbo, D. (1989). J. Appl. Cryst. 22, 389–393.
Cory, J. G., Downes, D. L., Cory, A. H., Schaper, K.-J. & Seydel, J. K. (1994). Anticancer Res. 14, 875–880.
Etter, M. C. (1990). Acc. Chem. Res. 23, 120–126.
Jacobson, R. (1998). Private communication
Molecular Structure Corporation & Rigaku (2005). CrystalClear and CrystalStructure. Single Crystal Structure Analysis Software. Rigaku/MSC, 9009 New Trails Drive, The Woodlands, TX, USA 77381-5209. Rigaku, 3-9-12 Akishima, Tokyo 196-8666, Japan.
Popp, F. D. (1989). Eur. J. Med. Chem. 24, 313–316.
Seydel, J. K., Schaper, K.-J. & Rüsch-Gerdes, S. (1994). Immunobiology, 191, 569–577.
Watkin, D. J., Prout, C. K., Carruthers, J. R. & Betteridge, P. W. (1996). CRYSTALS Issue 10, Chemical Crystallography Laboratory, Oxford, UK.
2-Pyridylhydrazone (2-pyridinylhydrazone 3-Pyridinecarboxaldehyde, I) belongs to the class of heterocyclic hydrazones, which have an anti-tuberculosis activity (Cory et al., 1994; Seydel et al., 1994). These compounds show some inhibitory activity towards ribonucleotide reductase and anticonvulsant activity as well (Popp, 1989). Crystal structure of (I) has not been solved before. Therefore the aim of the work was to fill this gap. A view of molecule (I) with the atomic numbering is presented in Fig 1. The parameters of the hydrogen bond geometry are shown in Table 1. The bond lengths are within the normal range of such bonds (Allen et al., 1987). The conformational state of the molecule in the crystal structure can be characterized in the following way. The torsion angle N1—C1—C2—C3, which characterizes the orientation of the one pyridine fragment Py1 [N4—C6–C2—C3—C4—C5] with respect to bridge group (C1—N1—N2), is 3.5 (2) °. At other side, he torsion angle C8—C7—N2—N1, which describes the orientation of the second pyridine ring Py2 [N3—C7–C8—C9—C10—C11] with respect to the bridge group, is 0.9 (2) °. The torsion angle C2–C1—N1—N2, which characterize a planarity of bridge group, is 178.86 (13) °. The pyridine fragments are rotated relatively o each other by 8.2 (2)°. The molecular packing architecture is shown in Figs. 2 & 3. The molecules of (I) form dimers by hydrogen bonds N2—H2···N3. The hydrogen-bond network can be described by the graph-set assignment introduced by Etter (1990) as R22(14). The dimers are packed in cups where interact to each other by van-der-Waals forces.