Acta Cryst. (2009). E65, o2103 [ doi:10.1107/S1600536809030530 ]
The molecule of the title compound, C10H12N2O, is approximately planar, with an r.m.s. deviation of 0.072 Å from the mean plane for the non-H atoms. It was synthesized from 2-acetylpyridine and N,N-dimethylformamide dimethyl acetal in a one-step reaction.
A mixture of 2-acetylpyridine(10 mmol) and N,N-dimethylformamide-dimethyl acetal(40 ml) was refluxed for four hours. After concentration in vacuo, recrystallization of the orange residue from ethanol afforded yellow blocks of (I). Anal. Calc. for C10H12N2O: C 68.10, H 6.81, N 15.89%; Found: C 68.02, H 6.63, N 15.79%.
All H atoms were geometrically positioned (C—H = 0.93–0.97Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus (Bruker, 2004); 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).
![[Figure 1]](./hb5023fig1thm.gif)
| Fig. 1. The molecular structure of (I), drawn with 30% probability displacement ellipsoids for the non-hydrogen atoms. |
| C10H12N2O | F(000) = 376 |
| Mr = 176.22 | Dx = 1.223 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2yn | Cell parameters from 1775 reflections |
| a = 5.6670 (11) Å | θ = 1.8–25.5° |
| b = 23.117 (5) Å | µ = 0.08 mm−1 |
| c = 7.6880 (15) Å | T = 295 K |
| β = 108.17 (3)° | Block, yellow |
| V = 956.9 (3) Å3 | 0.12 × 0.10 × 0.08 mm |
| Z = 4 |
| Bruker APEXII CCD diffractometer | 1775 independent reflections |
| Radiation source: fine-focus sealed tube | 1403 reflections with I > 2σ(I) |
| graphite | Rint = 0.027 |
| φ and ω scans | θmax = 25.5°, θmin = 1.8° |
| Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −6→6 |
| Tmin = 0.990, Tmax = 0.994 | k = −27→28 |
| 7131 measured reflections | l = −9→9 |
| 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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.143 | H-atom parameters not refined |
| S = 1.00 | w = 1/[σ2(Fo2) + (0.087P)2 + 0.1213P] where P = (Fo2 + 2Fc2)/3 |
| 1775 reflections | (Δ/σ)max < 0.001 |
| 121 parameters | Δρmax = 0.18 e Å−3 |
| 0 restraints | Δρmin = −0.15 e Å−3 |
| C10H12N2O | V = 956.9 (3) Å3 |
| Mr = 176.22 | Z = 4 |
| Monoclinic, P21/n | Mo Kα radiation |
| a = 5.6670 (11) Å | µ = 0.08 mm−1 |
| b = 23.117 (5) Å | T = 295 K |
| c = 7.6880 (15) Å | 0.12 × 0.10 × 0.08 mm |
| β = 108.17 (3)° |
| Bruker APEXII CCD diffractometer | 1775 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2004) | 1403 reflections with I > 2σ(I) |
| Tmin = 0.990, Tmax = 0.994 | Rint = 0.027 |
| 7131 measured reflections | θmax = 25.5° |
| R[F2 > 2σ(F2)] = 0.047 | H-atom parameters not refined |
| wR(F2) = 0.143 | Δρmax = 0.18 e Å−3 |
| S = 1.00 | Δρmin = −0.15 e Å−3 |
| 1775 reflections | Absolute structure: ? |
| 121 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 | 0.3675 (4) | 0.01987 (8) | −0.3188 (3) | 0.0664 (6) | |
| H1A | 0.2562 | −0.0080 | −0.2945 | 0.100* | |
| H1B | 0.5232 | 0.0016 | −0.3092 | 0.100* | |
| H1C | 0.2964 | 0.0351 | −0.4401 | 0.100* | |
| C2 | 0.5845 (4) | 0.11075 (9) | −0.1969 (3) | 0.0674 (6) | |
| H2A | 0.5072 | 0.1481 | −0.2079 | 0.101* | |
| H2B | 0.6385 | 0.1038 | −0.3017 | 0.101* | |
| H2C | 0.7251 | 0.1096 | −0.0879 | 0.101* | |
| C3 | 0.2893 (3) | 0.06861 (7) | −0.0630 (2) | 0.0456 (4) | |
| H3 | 0.1843 | 0.0377 | −0.0633 | 0.055* | |
| C4 | 0.3024 (3) | 0.11046 (7) | 0.0648 (2) | 0.0464 (4) | |
| H4 | 0.4006 | 0.1430 | 0.0703 | 0.056* | |
| C5 | 0.1648 (3) | 0.10380 (7) | 0.1890 (2) | 0.0445 (4) | |
| C6 | 0.1719 (3) | 0.15207 (6) | 0.3237 (2) | 0.0423 (4) | |
| C7 | 0.0089 (3) | 0.15063 (8) | 0.4258 (2) | 0.0533 (5) | |
| H7 | −0.1038 | 0.1204 | 0.4118 | 0.064* | |
| C8 | 0.0165 (4) | 0.19467 (9) | 0.5484 (2) | 0.0615 (5) | |
| H8 | −0.0916 | 0.1947 | 0.6179 | 0.074* | |
| C9 | 0.1851 (4) | 0.23816 (8) | 0.5661 (2) | 0.0608 (5) | |
| H9 | 0.1951 | 0.2682 | 0.6484 | 0.073* | |
| C10 | 0.3406 (4) | 0.23655 (8) | 0.4592 (2) | 0.0584 (5) | |
| H10 | 0.4549 | 0.2664 | 0.4720 | 0.070* | |
| N1 | 0.4076 (3) | 0.06659 (6) | −0.18682 (18) | 0.0500 (4) | |
| N2 | 0.3368 (3) | 0.19482 (6) | 0.33867 (18) | 0.0505 (4) | |
| O1 | 0.0370 (3) | 0.06092 (5) | 0.19576 (18) | 0.0657 (4) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0977 (16) | 0.0551 (11) | 0.0587 (11) | 0.0089 (10) | 0.0423 (11) | −0.0012 (9) |
| C2 | 0.0611 (12) | 0.0857 (14) | 0.0628 (12) | −0.0074 (10) | 0.0303 (10) | 0.0026 (10) |
| C3 | 0.0508 (9) | 0.0462 (9) | 0.0432 (9) | 0.0036 (7) | 0.0197 (7) | 0.0052 (7) |
| C4 | 0.0487 (9) | 0.0464 (9) | 0.0466 (9) | −0.0007 (7) | 0.0185 (7) | −0.0010 (7) |
| C5 | 0.0491 (9) | 0.0431 (9) | 0.0427 (9) | 0.0008 (7) | 0.0164 (7) | 0.0007 (7) |
| C6 | 0.0457 (9) | 0.0423 (9) | 0.0387 (8) | 0.0060 (7) | 0.0128 (7) | 0.0034 (6) |
| C7 | 0.0541 (10) | 0.0571 (11) | 0.0531 (10) | 0.0016 (8) | 0.0232 (8) | −0.0037 (8) |
| C8 | 0.0649 (12) | 0.0701 (13) | 0.0560 (11) | 0.0110 (10) | 0.0284 (9) | −0.0077 (9) |
| C9 | 0.0763 (13) | 0.0555 (11) | 0.0482 (10) | 0.0122 (9) | 0.0161 (9) | −0.0103 (8) |
| C10 | 0.0730 (12) | 0.0476 (10) | 0.0519 (10) | −0.0048 (9) | 0.0158 (9) | −0.0051 (8) |
| N1 | 0.0591 (9) | 0.0520 (8) | 0.0462 (8) | 0.0031 (6) | 0.0271 (7) | 0.0023 (6) |
| N2 | 0.0581 (9) | 0.0476 (8) | 0.0466 (8) | −0.0037 (7) | 0.0178 (7) | −0.0031 (6) |
| O1 | 0.0896 (10) | 0.0554 (8) | 0.0676 (9) | −0.0208 (7) | 0.0472 (8) | −0.0144 (6) |
| C1—N1 | 1.451 (2) | C5—O1 | 1.2384 (18) |
| C1—H1A | 0.9600 | C5—C6 | 1.514 (2) |
| C1—H1B | 0.9600 | C6—N2 | 1.340 (2) |
| C1—H1C | 0.9600 | C6—C7 | 1.386 (2) |
| C2—N1 | 1.450 (2) | C7—C8 | 1.379 (2) |
| C2—H2A | 0.9600 | C7—H7 | 0.9300 |
| C2—H2B | 0.9600 | C8—C9 | 1.364 (3) |
| C2—H2C | 0.9600 | C8—H8 | 0.9300 |
| C3—N1 | 1.325 (2) | C9—C10 | 1.380 (3) |
| C3—C4 | 1.364 (2) | C9—H9 | 0.9300 |
| C3—H3 | 0.9300 | C10—N2 | 1.333 (2) |
| C4—C5 | 1.417 (2) | C10—H10 | 0.9300 |
| C4—H4 | 0.9300 | ||
| N1—C1—H1A | 109.5 | C4—C5—C6 | 118.57 (14) |
| N1—C1—H1B | 109.5 | N2—C6—C7 | 122.61 (15) |
| H1A—C1—H1B | 109.5 | N2—C6—C5 | 118.10 (14) |
| N1—C1—H1C | 109.5 | C7—C6—C5 | 119.29 (15) |
| H1A—C1—H1C | 109.5 | C8—C7—C6 | 119.01 (17) |
| H1B—C1—H1C | 109.5 | C8—C7—H7 | 120.5 |
| N1—C2—H2A | 109.5 | C6—C7—H7 | 120.5 |
| N1—C2—H2B | 109.5 | C9—C8—C7 | 118.94 (17) |
| H2A—C2—H2B | 109.5 | C9—C8—H8 | 120.5 |
| N1—C2—H2C | 109.5 | C7—C8—H8 | 120.5 |
| H2A—C2—H2C | 109.5 | C8—C9—C10 | 118.55 (16) |
| H2B—C2—H2C | 109.5 | C8—C9—H9 | 120.7 |
| N1—C3—C4 | 128.04 (15) | C10—C9—H9 | 120.7 |
| N1—C3—H3 | 116.0 | N2—C10—C9 | 123.96 (17) |
| C4—C3—H3 | 116.0 | N2—C10—H10 | 118.0 |
| C3—C4—C5 | 119.39 (15) | C9—C10—H10 | 118.0 |
| C3—C4—H4 | 120.3 | C3—N1—C2 | 121.81 (14) |
| C5—C4—H4 | 120.3 | C3—N1—C1 | 121.65 (15) |
| O1—C5—C4 | 124.55 (15) | C2—N1—C1 | 116.54 (14) |
| O1—C5—C6 | 116.87 (14) | C10—N2—C6 | 116.93 (15) |
The authors acknowledge financial support from the Science Foundation of Beihua University.
Bruker (2004). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Kida, N., Hikita, M., Kashima, I., Okubo, M., Itoi, M., Enomoto, M., Kato, K., Takata, M. & Kojima, N. (2009). J. Am. Chem. Soc. 131, 212–220
Liu, Y., Turner, D. B., Singh, T. N., Angeles-Boza, A. M., Chouai, A., Dunbar, K. R. & Turro, C. (2009). J. Am. Chem. Soc. 131, 26–27
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Zhang, X., Dou, J., Wei, P., Li, D., Li, B., Shi, C. & Hu, B. (2009). Inorg. Chim. Acta, 362, 3325–3332
Derives of heteroaromatic ligands have proven to be extremely popular amongst coordination chemists for a wide range of applications because of their ease of synthesis, ease of functionalization, and the steric protection which they afford to metal centres (Zhang et al.; Liu et al.; Kida et al.). Here, we report the synthesis and structure of the title compound, (I).
As shown in Fig. 1, non-hydrogen atoms including the pyridine ring, N,N-Dimethylamino, and prop-2-en-1-one are coplanar with Rms deviation of fitted atoms being 0.0724 Å. The title compound is synthesized from 2-acetylpyridine and N,N-dimethylformamide-dimethyl acetal by one step.