Abstract
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
▶); Abdullah & Ng (2008 ▶). For N-(pyrazin-2-yl)-4-toluidine; see: Wan Saffiee et al. (2008b
▶).
Experimental
Crystal data
C10H8ClN3
M r = 205.64
Monoclinic,
a = 12.1257 (3) Å
b = 3.7944 (1) Å
c = 19.7242 (5) Å
β = 91.370 (2)°
V = 907.25 (4) Å3
Z = 4
Mo Kα radiation
μ = 0.38 mm−1
T = 100 (2) K
0.25 × 0.05 × 0.01 mm
Data collection
Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.912, T max = 0.996
7922 measured reflections
2073 independent reflections
1633 reflections with I > 2σ(I)
R int = 0.033
Refinement
R[F 2 > 2σ(F 2)] = 0.037
wR(F 2) = 0.128
S = 1.14
2073 reflections
131 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρmax = 0.39 e Å−3
Δρmin = −0.28 e Å−3
Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: 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 ▶).
Supplementary Material
Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808041172/tk2340sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536808041172/tk2340Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Table 1. Hydrogen-bond geometry (Å, °).
| 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) 
.
Acknowledgments
We thank the University of Malaya for supporting this study (FS205/2008 A).
supplementary crystallographic information
Experimental
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.
Refinement
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.
Figures
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.
Crystal data
| 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 |
Data collection
| 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
| 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 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| 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* |
Atomic displacement parameters (Å2)
| 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) |
Geometric parameters (Å, °)
| 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) |
Hydrogen-bond geometry (Å, °)
| 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.
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2340).
References
- Abdullah, Z. & Ng, S. W. (2008). Acta Cryst. E64, o2106. [DOI] [PMC free article] [PubMed]
- 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. [DOI] [PubMed]
- Wan Saffiee, W. A. M., Idris, A., Abdullah, Z., Aiyub, Z. & Ng, S. W. (2008a). Acta Cryst. E64, o2105. [DOI] [PMC free article] [PubMed]
- Wan Saffiee, W. A. M., Idris, A., Aiyub, Z., Abdullah, Z. & Ng, S. W. (2008b). Acta Cryst. E64, o2440. [DOI] [PMC free article] [PubMed]
- Westrip, S. P. (2009). publCIF In preparation.
Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808041172/tk2340sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536808041172/tk2340Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report