Acta Cryst. (2009). E65, o7 [ doi:10.1107/S1600536808040099 ]
In the title compound, C10H8N2O, the dihedral angle between the aromatic rings is 64.2 (1)° and the bridging C-O-C angle is 119.1 (1)°.
Phenol (0.94 g, 0.01 mol) was dissolved in a small volume of water containing sodium hydroxide (0.40 g, 0.01 mol). The mixture was heated to remove most of the water. This and 2-chloropyrazine (1.15 g, 0.01 mol) were heated for 5 h. The material was extracted with chloroform and the organic phase then dried over sodium sulfate. Evaporation of the solvent gave the crude product, which was recrystallized from chloroform.
The H atoms were placed in calculated positions (C—H = 0.95 Å) and refined as riding with Uiso(H) = 1.2Ueq(C).
Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).
![[Figure 1]](./hb2867fig1thm.gif)
| Fig. 1. The molecular structure of (I) at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. |
| C10H8N2O | F(000) = 360 |
| Mr = 172.18 | Dx = 1.335 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 739 reflections |
| a = 5.704 (1) Å | θ = 3.3–26.1° |
| b = 8.557 (2) Å | µ = 0.09 mm−1 |
| c = 17.595 (4) Å | T = 100 K |
| β = 94.382 (3)° | Irregular block, colorless |
| V = 856.4 (3) Å3 | 0.20 × 0.15 × 0.10 mm |
| Z = 4 |
| Bruker SMART APEX diffractometer | 1207 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.042 |
| graphite | θmax = 27.5°, θmin = 2.3° |
| ω scans | h = −6→7 |
| 4641 measured reflections | k = −11→10 |
| 1950 independent reflections | l = −22→21 |
| 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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.119 | H-atom parameters constrained |
| S = 0.97 | w = 1/[σ2(Fo2) + (0.0572P)2] where P = (Fo2 + 2Fc2)/3 |
| 1950 reflections | (Δ/σ)max = 0.001 |
| 118 parameters | Δρmax = 0.20 e Å−3 |
| 0 restraints | Δρmin = −0.27 e Å−3 |
| C10H8N2O | V = 856.4 (3) Å3 |
| Mr = 172.18 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 5.704 (1) Å | µ = 0.09 mm−1 |
| b = 8.557 (2) Å | T = 100 K |
| c = 17.595 (4) Å | 0.20 × 0.15 × 0.10 mm |
| β = 94.382 (3)° |
| Bruker SMART APEX diffractometer | 1207 reflections with I > 2σ(I) |
| 4641 measured reflections | Rint = 0.042 |
| 1950 independent reflections | θmax = 27.5° |
| R[F2 > 2σ(F2)] = 0.046 | H-atom parameters constrained |
| wR(F2) = 0.119 | Δρmax = 0.20 e Å−3 |
| S = 0.97 | Δρmin = −0.27 e Å−3 |
| 1950 reflections | Absolute structure: ? |
| 118 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
| x | y | z | Uiso*/Ueq | ||
| O1 | 0.0900 (2) | 0.70888 (14) | 0.45704 (7) | 0.0301 (3) | |
| N1 | 0.4770 (3) | 0.56153 (17) | 0.60955 (8) | 0.0281 (4) | |
| N2 | 0.4352 (3) | 0.81790 (16) | 0.51088 (8) | 0.0252 (4) | |
| C1 | 0.0879 (3) | 0.8138 (2) | 0.39557 (9) | 0.0244 (4) | |
| C2 | −0.1015 (3) | 0.9128 (2) | 0.38509 (10) | 0.0288 (4) | |
| H2 | −0.2208 | 0.9130 | 0.4199 | 0.035* | |
| C3 | −0.1150 (3) | 1.0127 (2) | 0.32238 (10) | 0.0320 (5) | |
| H3 | −0.2447 | 1.0819 | 0.3140 | 0.038* | |
| C4 | 0.0604 (3) | 1.0112 (2) | 0.27248 (10) | 0.0309 (5) | |
| H4 | 0.0520 | 1.0803 | 0.2301 | 0.037* | |
| C5 | 0.2481 (3) | 0.9097 (2) | 0.28386 (10) | 0.0298 (5) | |
| H5 | 0.3672 | 0.9086 | 0.2489 | 0.036* | |
| C6 | 0.2641 (3) | 0.8093 (2) | 0.34580 (9) | 0.0266 (4) | |
| H6 | 0.3927 | 0.7393 | 0.3539 | 0.032* | |
| C7 | 0.2816 (3) | 0.70451 (19) | 0.50838 (9) | 0.0225 (4) | |
| C8 | 0.2987 (3) | 0.5762 (2) | 0.55764 (10) | 0.0279 (4) | |
| H8 | 0.1799 | 0.4981 | 0.5537 | 0.033* | |
| C9 | 0.6367 (3) | 0.6767 (2) | 0.61232 (10) | 0.0275 (4) | |
| H9 | 0.7686 | 0.6707 | 0.6486 | 0.033* | |
| C10 | 0.6149 (3) | 0.8027 (2) | 0.56430 (9) | 0.0274 (4) | |
| H10 | 0.7311 | 0.8823 | 0.5690 | 0.033* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0285 (7) | 0.0309 (8) | 0.0299 (7) | −0.0092 (6) | −0.0033 (5) | 0.0105 (6) |
| N1 | 0.0356 (9) | 0.0253 (8) | 0.0237 (8) | −0.0023 (7) | 0.0037 (7) | 0.0021 (7) |
| N2 | 0.0304 (9) | 0.0229 (8) | 0.0222 (8) | −0.0055 (6) | 0.0020 (6) | 0.0000 (7) |
| C1 | 0.0279 (10) | 0.0230 (10) | 0.0215 (9) | −0.0088 (8) | −0.0028 (7) | 0.0039 (8) |
| C2 | 0.0233 (10) | 0.0323 (11) | 0.0307 (10) | −0.0049 (8) | 0.0021 (7) | 0.0031 (9) |
| C3 | 0.0267 (11) | 0.0321 (11) | 0.0362 (10) | −0.0007 (8) | −0.0041 (8) | 0.0044 (9) |
| C4 | 0.0338 (11) | 0.0344 (11) | 0.0237 (9) | −0.0062 (9) | −0.0037 (8) | 0.0068 (9) |
| C5 | 0.0316 (11) | 0.0368 (11) | 0.0209 (9) | −0.0056 (9) | 0.0011 (8) | −0.0027 (9) |
| C6 | 0.0280 (10) | 0.0256 (10) | 0.0255 (9) | −0.0014 (8) | −0.0020 (8) | −0.0032 (8) |
| C7 | 0.0253 (10) | 0.0224 (10) | 0.0203 (8) | −0.0029 (7) | 0.0043 (7) | −0.0007 (8) |
| C8 | 0.0319 (11) | 0.0246 (10) | 0.0274 (10) | −0.0060 (8) | 0.0048 (8) | 0.0015 (8) |
| C9 | 0.0315 (11) | 0.0287 (10) | 0.0219 (9) | −0.0001 (8) | −0.0011 (7) | 0.0005 (8) |
| C10 | 0.0295 (10) | 0.0287 (11) | 0.0238 (9) | −0.0076 (8) | 0.0003 (7) | −0.0011 (9) |
| O1—C7 | 1.364 (2) | C3—H3 | 0.9500 |
| O1—C1 | 1.4050 (19) | C4—C5 | 1.382 (3) |
| N1—C8 | 1.320 (2) | C4—H4 | 0.9500 |
| N1—C9 | 1.340 (2) | C5—C6 | 1.385 (2) |
| N2—C7 | 1.306 (2) | C5—H5 | 0.9500 |
| N2—C10 | 1.343 (2) | C6—H6 | 0.9500 |
| C1—C2 | 1.374 (3) | C7—C8 | 1.398 (2) |
| C1—C6 | 1.383 (2) | C8—H8 | 0.9500 |
| C2—C3 | 1.394 (2) | C9—C10 | 1.370 (2) |
| C2—H2 | 0.9500 | C9—H9 | 0.9500 |
| C3—C4 | 1.381 (3) | C10—H10 | 0.9500 |
| C7—O1—C1 | 119.11 (13) | C6—C5—H5 | 119.8 |
| C8—N1—C9 | 116.18 (15) | C1—C6—C5 | 118.29 (17) |
| C7—N2—C10 | 115.21 (15) | C1—C6—H6 | 120.9 |
| C2—C1—C6 | 122.28 (16) | C5—C6—H6 | 120.9 |
| C2—C1—O1 | 117.23 (15) | N2—C7—O1 | 120.23 (15) |
| C6—C1—O1 | 120.38 (16) | N2—C7—C8 | 123.24 (16) |
| C1—C2—C3 | 118.68 (17) | O1—C7—C8 | 116.52 (15) |
| C1—C2—H2 | 120.7 | N1—C8—C7 | 121.13 (16) |
| C3—C2—H2 | 120.7 | N1—C8—H8 | 119.4 |
| C4—C3—C2 | 119.90 (18) | C7—C8—H8 | 119.4 |
| C4—C3—H3 | 120.0 | N1—C9—C10 | 121.80 (16) |
| C2—C3—H3 | 120.0 | N1—C9—H9 | 119.1 |
| C3—C4—C5 | 120.36 (17) | C10—C9—H9 | 119.1 |
| C3—C4—H4 | 119.8 | N2—C10—C9 | 122.43 (17) |
| C5—C4—H4 | 119.8 | N2—C10—H10 | 118.8 |
| C4—C5—C6 | 120.49 (17) | C9—C10—H10 | 118.8 |
| C4—C5—H5 | 119.8 | ||
| C7—O1—C1—C2 | −126.78 (17) | C10—N2—C7—O1 | 179.05 (14) |
| C7—O1—C1—C6 | 56.9 (2) | C10—N2—C7—C8 | 0.5 (2) |
| C6—C1—C2—C3 | −0.5 (3) | C1—O1—C7—N2 | 15.5 (2) |
| O1—C1—C2—C3 | −176.75 (15) | C1—O1—C7—C8 | −165.92 (14) |
| C1—C2—C3—C4 | −0.2 (3) | C9—N1—C8—C7 | 0.6 (2) |
| C2—C3—C4—C5 | 0.8 (3) | N2—C7—C8—N1 | −1.1 (3) |
| C3—C4—C5—C6 | −0.7 (3) | O1—C7—C8—N1 | −179.72 (15) |
| C2—C1—C6—C5 | 0.6 (3) | C8—N1—C9—C10 | 0.4 (3) |
| O1—C1—C6—C5 | 176.75 (14) | C7—N2—C10—C9 | 0.5 (2) |
| C4—C5—C6—C1 | 0.0 (3) | N1—C9—C10—N2 | −1.0 (3) |
We thank the University of Malaya for supporting this study (grant No. FS358/2008 A).
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Hassan, N. D., Tajuddin, H. A., Abdullah, Z. & Ng, S. W. (2008). Acta Cryst. E64, o1820.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Wan Saffiee, W. A. M., Idris, A., Abdullah, Z., Aiyub, Z. & Ng, S. W. (2008). Acta Cryst. E64, o2105.
Westrip, S. P. (2008). publCIF. In preparation.
