Acta Cryst. (2009). E65, o113 [ doi:10.1107/S1600536808041172 ]
In the title compound, C10H8ClN3, the dihedral angle between the aromatic rings is 43.0 (1)° and the bridging C-N-C angle is 128.19 (16)°. The amino N atom of one molecule forms a hydrogen bond to the 1-N atom of an adjacent pyrazinyl ring, generating an inversion dimer.
2-Chloropyrazine (1.15 g, 10 mmol) and 4-chloroaniline (1.28 g, 10 mmol) were mixed with ethanol (2 ml) and the mixture heated at 423–433 K for 3 h. The product was dissolved in water and the solution extracted with ether. The ether phase was dried over sodium sulfate; the evaporation of the solvent gave well shaped crystals along with some unidentified brown material.
Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2Ueq(C).
The amino H-atom was located in a difference Fourier map, and was refined with a distance restraint of N–H 0.88±0.01 Å; its temperature factor was freely refined.
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, 2009).
![[Figure 1]](./tk2340fig1thm.gif)
| Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of hydrogen-bonded dimeric structure of C10H8ClN3 at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. Hydrogen bonds are shown as red dashed lines. |
| C10H8ClN3 | F(000) = 424 |
| Mr = 205.64 | Dx = 1.506 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 2160 reflections |
| a = 12.1257 (3) Å | θ = 2.6–28.1° |
| b = 3.7944 (1) Å | µ = 0.38 mm−1 |
| c = 19.7242 (5) Å | T = 100 K |
| β = 91.370 (2)° | Plate, yellow |
| V = 907.25 (4) Å3 | 0.25 × 0.05 × 0.01 mm |
| Z = 4 |
| Bruker SMART APEX diffractometer | 2073 independent reflections |
| Radiation source: fine-focus sealed tube | 1633 reflections with I > 2σ(I) |
| graphite | Rint = 0.033 |
| ω scans | θmax = 27.5°, θmin = 1.7° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −15→15 |
| Tmin = 0.912, Tmax = 0.996 | k = −4→4 |
| 7922 measured reflections | l = −25→24 |
| 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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.128 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.14 | w = 1/[σ2(Fo2) + (0.0761P)2 + 0.0551P] where P = (Fo2 + 2Fc2)/3 |
| 2073 reflections | (Δ/σ)max = 0.001 |
| 131 parameters | Δρmax = 0.39 e Å−3 |
| 1 restraint | Δρmin = −0.28 e Å−3 |
| C10H8ClN3 | V = 907.25 (4) Å3 |
| Mr = 205.64 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 12.1257 (3) Å | µ = 0.38 mm−1 |
| b = 3.7944 (1) Å | T = 100 K |
| c = 19.7242 (5) Å | 0.25 × 0.05 × 0.01 mm |
| β = 91.370 (2)° |
| Bruker SMART APEX diffractometer | 2073 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1633 reflections with I > 2σ(I) |
| Tmin = 0.912, Tmax = 0.996 | Rint = 0.033 |
| 7922 measured reflections | θmax = 27.5° |
| R[F2 > 2σ(F2)] = 0.037 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.128 | Δρmax = 0.39 e Å−3 |
| S = 1.14 | Δρmin = −0.28 e Å−3 |
| 2073 reflections | Absolute structure: ? |
| 131 parameters | Flack parameter: ? |
| 1 restraint | Rogers parameter: ? |
| x | y | z | Uiso*/Ueq | ||
| Cl1 | 1.04801 (4) | −0.07942 (15) | 0.36089 (3) | 0.0269 (2) | |
| N1 | 0.59098 (13) | 0.2944 (5) | 0.43167 (8) | 0.0173 (4) | |
| H1 | 0.5832 (19) | 0.359 (6) | 0.4742 (6) | 0.019 (6)* | |
| N2 | 0.40848 (13) | 0.4535 (5) | 0.42294 (8) | 0.0152 (4) | |
| N3 | 0.39085 (14) | 0.1755 (5) | 0.29204 (8) | 0.0182 (4) | |
| C1 | 0.69716 (16) | 0.1986 (5) | 0.41131 (10) | 0.0147 (4) | |
| C2 | 0.76584 (16) | 0.0278 (5) | 0.45861 (10) | 0.0165 (4) | |
| H2 | 0.7381 | −0.0315 | 0.5018 | 0.020* | |
| C3 | 0.87334 (16) | −0.0565 (5) | 0.44384 (10) | 0.0181 (4) | |
| H3 | 0.9196 | −0.1710 | 0.4766 | 0.022* | |
| C4 | 0.91273 (16) | 0.0283 (5) | 0.38059 (11) | 0.0173 (4) | |
| C5 | 0.84635 (16) | 0.1980 (5) | 0.33265 (10) | 0.0176 (4) | |
| H5 | 0.8745 | 0.2545 | 0.2894 | 0.021* | |
| C6 | 0.73893 (16) | 0.2849 (5) | 0.34796 (10) | 0.0155 (4) | |
| H6 | 0.6935 | 0.4033 | 0.3154 | 0.019* | |
| C7 | 0.49564 (16) | 0.3053 (5) | 0.39334 (9) | 0.0141 (4) | |
| C8 | 0.48498 (16) | 0.1632 (5) | 0.32725 (10) | 0.0159 (4) | |
| H8 | 0.5473 | 0.0556 | 0.3075 | 0.019* | |
| C9 | 0.30456 (17) | 0.3280 (6) | 0.32195 (10) | 0.0185 (4) | |
| H9 | 0.2360 | 0.3451 | 0.2979 | 0.022* | |
| C10 | 0.31373 (16) | 0.4595 (5) | 0.38676 (10) | 0.0168 (4) | |
| H10 | 0.2503 | 0.5588 | 0.4067 | 0.020* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1 | 0.0139 (3) | 0.0324 (3) | 0.0346 (3) | 0.0038 (2) | 0.0035 (2) | −0.0016 (2) |
| N1 | 0.0157 (8) | 0.0266 (9) | 0.0096 (8) | 0.0025 (7) | 0.0006 (6) | −0.0028 (7) |
| N2 | 0.0154 (8) | 0.0179 (8) | 0.0124 (8) | 0.0017 (6) | 0.0004 (6) | 0.0011 (6) |
| N3 | 0.0190 (9) | 0.0222 (9) | 0.0134 (8) | −0.0051 (7) | −0.0009 (6) | 0.0010 (7) |
| C1 | 0.0134 (9) | 0.0158 (9) | 0.0148 (9) | −0.0009 (7) | −0.0007 (7) | −0.0024 (7) |
| C2 | 0.0194 (10) | 0.0181 (10) | 0.0121 (9) | −0.0008 (8) | −0.0014 (7) | 0.0000 (7) |
| C3 | 0.0180 (10) | 0.0168 (10) | 0.0192 (10) | 0.0019 (8) | −0.0039 (8) | 0.0009 (8) |
| C4 | 0.0121 (9) | 0.0178 (10) | 0.0219 (10) | −0.0001 (7) | 0.0004 (7) | −0.0040 (8) |
| C5 | 0.0177 (10) | 0.0203 (10) | 0.0148 (9) | −0.0034 (8) | 0.0028 (7) | −0.0018 (8) |
| C6 | 0.0155 (9) | 0.0166 (9) | 0.0142 (9) | −0.0008 (7) | −0.0017 (7) | 0.0005 (7) |
| C7 | 0.0143 (9) | 0.0154 (9) | 0.0125 (9) | −0.0014 (7) | 0.0003 (7) | 0.0020 (7) |
| C8 | 0.0164 (10) | 0.0186 (10) | 0.0129 (9) | −0.0012 (8) | 0.0024 (7) | −0.0008 (8) |
| C9 | 0.0154 (10) | 0.0236 (10) | 0.0163 (10) | −0.0025 (8) | −0.0018 (7) | 0.0045 (8) |
| C10 | 0.0145 (9) | 0.0192 (10) | 0.0167 (10) | 0.0008 (8) | 0.0013 (7) | 0.0026 (8) |
| Cl1—C4 | 1.743 (2) | C3—C4 | 1.385 (3) |
| N1—C7 | 1.367 (2) | C3—H3 | 0.9500 |
| N1—C1 | 1.406 (2) | C4—C5 | 1.386 (3) |
| N1—H1 | 0.881 (10) | C5—C6 | 1.384 (3) |
| N2—C10 | 1.338 (2) | C5—H5 | 0.9500 |
| N2—C7 | 1.343 (2) | C6—H6 | 0.9500 |
| N3—C8 | 1.323 (3) | C7—C8 | 1.414 (3) |
| N3—C9 | 1.344 (3) | C8—H8 | 0.9500 |
| C1—C2 | 1.395 (3) | C9—C10 | 1.374 (3) |
| C1—C6 | 1.398 (3) | C9—H9 | 0.9500 |
| C2—C3 | 1.380 (3) | C10—H10 | 0.9500 |
| C2—H2 | 0.9500 | ||
| C7—N1—C1 | 128.19 (16) | C6—C5—H5 | 120.1 |
| C7—N1—H1 | 114.2 (15) | C4—C5—H5 | 120.1 |
| C1—N1—H1 | 117.6 (15) | C5—C6—C1 | 120.14 (18) |
| C10—N2—C7 | 116.74 (16) | C5—C6—H6 | 119.9 |
| C8—N3—C9 | 117.11 (17) | C1—C6—H6 | 119.9 |
| C2—C1—C6 | 118.89 (18) | N2—C7—N1 | 115.87 (17) |
| C2—C1—N1 | 117.73 (17) | N2—C7—C8 | 120.33 (17) |
| C6—C1—N1 | 123.26 (17) | N1—C7—C8 | 123.78 (18) |
| C3—C2—C1 | 121.21 (18) | N3—C8—C7 | 121.97 (18) |
| C3—C2—H2 | 119.4 | N3—C8—H8 | 119.0 |
| C1—C2—H2 | 119.4 | C7—C8—H8 | 119.0 |
| C2—C3—C4 | 118.96 (18) | N3—C9—C10 | 121.19 (19) |
| C2—C3—H3 | 120.5 | N3—C9—H9 | 119.4 |
| C4—C3—H3 | 120.5 | C10—C9—H9 | 119.4 |
| C3—C4—C5 | 121.05 (18) | N2—C10—C9 | 122.63 (18) |
| C3—C4—Cl1 | 119.53 (16) | N2—C10—H10 | 118.7 |
| C5—C4—Cl1 | 119.42 (16) | C9—C10—H10 | 118.7 |
| C6—C5—C4 | 119.75 (19) | ||
| C7—N1—C1—C2 | −146.4 (2) | N1—C1—C6—C5 | 176.58 (18) |
| C7—N1—C1—C6 | 37.6 (3) | C10—N2—C7—N1 | −178.56 (17) |
| C6—C1—C2—C3 | −0.1 (3) | C10—N2—C7—C8 | −0.4 (3) |
| N1—C1—C2—C3 | −176.21 (19) | C1—N1—C7—N2 | −171.00 (19) |
| C1—C2—C3—C4 | −0.5 (3) | C1—N1—C7—C8 | 10.9 (3) |
| C2—C3—C4—C5 | 0.6 (3) | C9—N3—C8—C7 | −0.4 (3) |
| C2—C3—C4—Cl1 | −179.50 (16) | N2—C7—C8—N3 | 1.2 (3) |
| C3—C4—C5—C6 | 0.0 (3) | N1—C7—C8—N3 | 179.22 (19) |
| Cl1—C4—C5—C6 | −179.91 (15) | C8—N3—C9—C10 | −1.1 (3) |
| C4—C5—C6—C1 | −0.6 (3) | C7—N2—C10—C9 | −1.1 (3) |
| C2—C1—C6—C5 | 0.7 (3) | N3—C9—C10—N2 | 1.9 (3) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1···N2i | 0.88 (1) | 2.15 (1) | 3.023 (2) | 171 (2) |
| Symmetry codes: (i) −x+1, −y+1, −z+1. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1···N2i | 0.88 (1) | 2.15 (1) | 3.023 (2) | 171 (2) |
| Symmetry codes: (i) −x+1, −y+1, −z+1. |
Abdullah, Z. & Ng, S. W. (2008). Acta Cryst. E64, o2106.
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Wan Saffiee, W. A. M., Idris, A., Abdullah, Z., Aiyub, Z. & Ng, S. W. (2008a). Acta Cryst. E64, o2105.
Wan Saffiee, W. A. M., Idris, A., Aiyub, Z., Abdullah, Z. & Ng, S. W. (2008b). Acta Cryst. E64, o2440.
Westrip, S. P. (2009). publCIF. In preparation.
