Acta Cryst. (2009). E65, o2104 [ doi:10.1107/S1600536809030542 ]
The title compound, C10H12N2O, is approximately planar, the r.m.s. deviation of the non-H atoms from the mean plane being 0.099 Å.
A mixture of 4-acetylpyridine(10 mmol) and N,N-dimethylformamide-dimethyl acetal(40 ml) was refluxed for four hours. After concentration invacuo, 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 68.05, H 6.69, N 15.81%.
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]](./hb5024fig1thm.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 = 1.217 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2yn | Cell parameters from 1784 reflections |
| a = 5.6300 (11) Å | θ = 1.8–25.5° |
| b = 22.850 (5) Å | µ = 0.08 mm−1 |
| c = 7.8400 (16) Å | T = 294 K |
| β = 107.57 (3)° | Block, yellow |
| V = 961.5 (3) Å3 | 0.12 × 0.10 × 0.08 mm |
| Z = 4 |
| Bruker APEXII CCD diffractometer | 1784 independent reflections |
| Radiation source: fine-focus sealed tube | 1503 reflections with I > 2σ(I) |
| graphite | Rint = 0.022 |
| 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→26 |
| 5177 measured reflections | l = −7→9 |
| 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)] = 0.040 | H-atom parameters not refined |
| wR(F2) = 0.137 | w = 1/[σ2(Fo2) + (0.092P)2 + 0.1151P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.00 | (Δ/σ)max = 0.001 |
| 1784 reflections | Δρmax = 0.20 e Å−3 |
| 121 parameters | Δρmin = −0.12 e Å−3 |
| 0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.016 (6) |
| C10H12N2O | V = 961.5 (3) Å3 |
| Mr = 176.22 | Z = 4 |
| Monoclinic, P21/n | Mo Kα radiation |
| a = 5.6300 (11) Å | µ = 0.08 mm−1 |
| b = 22.850 (5) Å | T = 294 K |
| c = 7.8400 (16) Å | 0.12 × 0.10 × 0.08 mm |
| β = 107.57 (3)° |
| Bruker APEXII CCD diffractometer | 1784 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2004) | 1503 reflections with I > 2σ(I) |
| Tmin = 0.990, Tmax = 0.994 | Rint = 0.022 |
| 5177 measured reflections | θmax = 25.5° |
| R[F2 > 2σ(F2)] = 0.040 | H-atom parameters not refined |
| wR(F2) = 0.137 | Δρmax = 0.20 e Å−3 |
| S = 1.00 | Δρmin = −0.12 e Å−3 |
| 1784 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 | 0.8254 (2) | 0.15312 (5) | 0.68372 (16) | 0.0403 (3) | |
| C2 | 0.6652 (3) | 0.20055 (6) | 0.65592 (17) | 0.0451 (4) | |
| H2 | 0.5490 | 0.2036 | 0.7183 | 0.054* | |
| C3 | 0.6795 (3) | 0.24329 (7) | 0.5346 (2) | 0.0541 (4) | |
| H3 | 0.5698 | 0.2747 | 0.5180 | 0.065* | |
| C4 | 0.9907 (3) | 0.19670 (8) | 0.4672 (2) | 0.0634 (5) | |
| H4 | 1.1040 | 0.1947 | 0.4022 | 0.076* | |
| C5 | 0.9919 (3) | 0.15168 (7) | 0.5851 (2) | 0.0533 (4) | |
| H5 | 1.1034 | 0.1208 | 0.5980 | 0.064* | |
| C6 | 0.8303 (2) | 0.10391 (6) | 0.81421 (18) | 0.0441 (4) | |
| C7 | 0.6972 (2) | 0.11110 (6) | 0.94016 (18) | 0.0452 (4) | |
| H7 | 0.6012 | 0.1444 | 0.9377 | 0.054* | |
| C8 | 0.7118 (3) | 0.06832 (6) | 1.06560 (18) | 0.0453 (4) | |
| H8 | 0.8147 | 0.0367 | 1.0632 | 0.054* | |
| C9 | 0.4227 (3) | 0.11224 (8) | 1.2011 (2) | 0.0668 (5) | |
| H9A | 0.5085 | 0.1490 | 1.2271 | 0.100* | |
| H9B | 0.3519 | 0.1028 | 1.2948 | 0.100* | |
| H9C | 0.2924 | 0.1150 | 1.0894 | 0.100* | |
| C10 | 0.6374 (3) | 0.01980 (7) | 1.3199 (2) | 0.0641 (5) | |
| H10A | 0.7505 | −0.0083 | 1.2966 | 0.096* | |
| H10B | 0.4815 | 0.0011 | 1.3112 | 0.096* | |
| H10C | 0.7069 | 0.0355 | 1.4380 | 0.096* | |
| N1 | 0.8397 (3) | 0.24245 (6) | 0.44017 (18) | 0.0617 (4) | |
| N2 | 0.5966 (2) | 0.06690 (5) | 1.18924 (16) | 0.0494 (4) | |
| O1 | 0.9520 (2) | 0.05981 (5) | 0.80351 (16) | 0.0677 (4) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0414 (7) | 0.0407 (7) | 0.0388 (7) | −0.0052 (5) | 0.0120 (5) | −0.0024 (5) |
| C2 | 0.0477 (7) | 0.0453 (8) | 0.0433 (7) | −0.0010 (6) | 0.0153 (6) | −0.0018 (6) |
| C3 | 0.0581 (9) | 0.0476 (8) | 0.0541 (9) | 0.0035 (6) | 0.0131 (7) | 0.0068 (6) |
| C4 | 0.0583 (9) | 0.0715 (11) | 0.0699 (10) | 0.0001 (8) | 0.0337 (8) | 0.0178 (8) |
| C5 | 0.0500 (8) | 0.0541 (9) | 0.0623 (9) | 0.0035 (6) | 0.0268 (7) | 0.0092 (7) |
| C6 | 0.0480 (7) | 0.0410 (7) | 0.0460 (7) | 0.0005 (5) | 0.0184 (6) | 0.0004 (6) |
| C7 | 0.0498 (7) | 0.0429 (7) | 0.0467 (7) | 0.0020 (6) | 0.0202 (6) | 0.0009 (5) |
| C8 | 0.0499 (8) | 0.0442 (8) | 0.0460 (8) | −0.0016 (6) | 0.0210 (6) | −0.0037 (6) |
| C9 | 0.0651 (10) | 0.0810 (12) | 0.0631 (10) | 0.0146 (8) | 0.0326 (8) | 0.0008 (8) |
| C10 | 0.0914 (12) | 0.0553 (9) | 0.0583 (9) | −0.0050 (8) | 0.0415 (9) | 0.0036 (7) |
| N1 | 0.0633 (8) | 0.0598 (8) | 0.0646 (8) | −0.0018 (6) | 0.0232 (7) | 0.0176 (6) |
| N2 | 0.0576 (7) | 0.0507 (7) | 0.0476 (7) | 0.0002 (5) | 0.0274 (6) | 0.0012 (5) |
| O1 | 0.0928 (9) | 0.0519 (7) | 0.0772 (8) | 0.0237 (6) | 0.0538 (7) | 0.0171 (5) |
| C1—C2 | 1.3846 (18) | C7—C8 | 1.3713 (19) |
| C1—C5 | 1.3842 (19) | C7—H7 | 0.9300 |
| C1—C6 | 1.5148 (18) | C8—N2 | 1.3193 (17) |
| C2—C3 | 1.382 (2) | C8—H8 | 0.9300 |
| C2—H2 | 0.9300 | C9—N2 | 1.4476 (19) |
| C3—N1 | 1.329 (2) | C9—H9A | 0.9600 |
| C3—H3 | 0.9300 | C9—H9B | 0.9600 |
| C4—N1 | 1.323 (2) | C9—H9C | 0.9600 |
| C4—C5 | 1.382 (2) | C10—N2 | 1.4555 (19) |
| C4—H4 | 0.9300 | C10—H10A | 0.9600 |
| C5—H5 | 0.9300 | C10—H10B | 0.9600 |
| C6—O1 | 1.2357 (16) | C10—H10C | 0.9600 |
| C6—C7 | 1.4180 (18) | ||
| C2—C1—C5 | 116.72 (12) | C6—C7—H7 | 120.4 |
| C2—C1—C6 | 124.44 (12) | N2—C8—C7 | 127.45 (13) |
| C5—C1—C6 | 118.84 (12) | N2—C8—H8 | 116.3 |
| C1—C2—C3 | 119.39 (13) | C7—C8—H8 | 116.3 |
| C1—C2—H2 | 120.3 | N2—C9—H9A | 109.5 |
| C3—C2—H2 | 120.3 | N2—C9—H9B | 109.5 |
| N1—C3—C2 | 124.31 (14) | H9A—C9—H9B | 109.5 |
| N1—C3—H3 | 117.8 | N2—C9—H9C | 109.5 |
| C2—C3—H3 | 117.8 | H9A—C9—H9C | 109.5 |
| N1—C4—C5 | 124.67 (14) | H9B—C9—H9C | 109.5 |
| N1—C4—H4 | 117.7 | N2—C10—H10A | 109.5 |
| C5—C4—H4 | 117.7 | N2—C10—H10B | 109.5 |
| C4—C5—C1 | 119.24 (14) | H10A—C10—H10B | 109.5 |
| C4—C5—H5 | 120.4 | N2—C10—H10C | 109.5 |
| C1—C5—H5 | 120.4 | H10A—C10—H10C | 109.5 |
| O1—C6—C7 | 124.21 (12) | H10B—C10—H10C | 109.5 |
| O1—C6—C1 | 117.19 (12) | C4—N1—C3 | 115.67 (13) |
| C7—C6—C1 | 118.60 (11) | C8—N2—C9 | 121.45 (12) |
| C8—C7—C6 | 119.15 (12) | C8—N2—C10 | 121.81 (13) |
| C8—C7—H7 | 120.4 | C9—N2—C10 | 116.74 (12) |
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.
Ni, L., Zhao, J.-L. & Wei, H. (2009). Acta Cryst. E65, o0000. [HB5023]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
As part of our ongoing studies of heteroaromatic compounds (Ni et al., 2009), we now 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 the r.m.s deviation of the fitted atoms being 0.099 Å.