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access4-Chloro-N-(pyrazin-2-yl)aniline
aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my
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.
Related literature
For the two polymorphs of N-(pyrazin-2-yl)aniline, see: Wan Saffiee et al. (2008a![[Wan Saffiee, W. A. M., Idris, A., Abdullah, Z., Aiyub, Z. & Ng, S. W. (2008a). Acta Cryst. E64, o2105.]](../../../../../../logos/arrows/e_arr.gif "Wan Saffiee, W. A. M., Idris, A., Abdullah, Z., Aiyub, Z. & Ng, S. W. (2008a). Acta Cryst. E64, o2105.")
); Abdullah & Ng (2008). For N-(pyrazin-2-yl)-4-toluidine; see: Wan Saffiee et al. (2008b).
![[Scheme 1]](tk2340scheme1.gif)
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; 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).
Supporting information
contains datablocks global, I. DOI: 10.1107/S1600536808041172/tk2340sup1.cif
Structure factors: contains datablock I. DOI: 10.1107/S1600536808041172/tk2340Isup2.hkl
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 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 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 monochromator | 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 |
| R[F2 > 2σ(F2)] = 0.037 | 1 restraint |
| wR(F2) = 0.128 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.14 | Δρmax = 0.39 e Å−3 |
| 2073 reflections | Δρmin = −0.28 e Å−3 |
| 131 parameters |
| 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 code: (i) −x+1, −y+1, −z+1. |
Experimental details
| Crystal data | |
| Chemical formula | C10H8ClN3 |
| Mr | 205.64 |
| Crystal system, space group | Monoclinic, P21/c |
| Temperature (K) | 100 |
| a, b, c (Å) | 12.1257 (3), 3.7944 (1), 19.7242 (5) |
| β (°) | 91.370 (2) |
| V (Å3) | 907.25 (4) |
| Z | 4 |
| Radiation type | Mo Kα |
| µ (mm−1) | 0.38 |
| Crystal size (mm) | 0.25 × 0.05 × 0.01 |
| Data collection | |
| Diffractometer | Bruker SMART APEX diffractometer |
| Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
| Tmin, Tmax | 0.912, 0.996 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 7922, 2073, 1633 |
| Rint | 0.033 |
| (sin θ/λ)max (Å−1) | 0.650 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.128, 1.14 |
| No. of reflections | 2073 |
| No. of parameters | 131 |
| No. of restraints | 1 |
| H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
| Δρmax, Δρmin (e Å−3) | 0.39, −0.28 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).
| 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 code: (i) −x+1, −y+1, −z+1. |
Acknowledgements
We thank the University of Malaya for supporting this study (FS205/2008 A).
References
Abdullah, Z. & Ng, S. W. (2008). Acta Cryst. E64, o2106. Web of Science CSD CrossRef IUCr Journals Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wan Saffiee, W. A. M., Idris, A., Abdullah, Z., Aiyub, Z. & Ng, S. W. (2008a). Acta Cryst. E64, o2105. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wan Saffiee, W. A. M., Idris, A., Aiyub, Z., Abdullah, Z. & Ng, S. W. (2008b). Acta Cryst. E64, o2440. Web of Science CSD CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar
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