PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 March 1; 65(Pt 3): o455.
Published online 2009 February 4. doi:  10.1107/S1600536809003717
PMCID: PMC2968544

2-Chloro­quinoxaline

Abstract

In the title compound, C8H5ClN2, the planar mol­ecules are arranged with their Cl atoms in close contact [Cl(...)Cl = 3.808 (1) and 3.881 (1) Å], indicating weak Cl(...)Cl inter­actions, which give rise to a supra­molecular chain.

Related literature

The title compound is a reagent in the synthesis of chloro­quinoxaline sulfamide, which is active against human cancers. For the synthesis of other phamaceutically active derivatives through conventional and other synthetic routes, see: Bhattacharjee et al. (2008 [triangle]); Cuenca et al. (2008 [triangle]); Hassan et al. (2006 [triangle]); Rangisetty et al. (2001 [triangle]); Rizzo et al. (2002 [triangle]); Sugimoto et al. (2003 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o455-scheme1.jpg

Experimental

Crystal data

  • C8H5ClN2
  • M r = 164.59
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o455-efi1.jpg
  • a = 9.1299 (2) Å
  • b = 3.8082 (1) Å
  • c = 21.0777 (6) Å
  • β = 93.028 (2)°
  • V = 731.82 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.44 mm−1
  • T = 118 (2) K
  • 0.20 × 0.06 × 0.02 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.916, T max = 0.991
  • 6145 measured reflections
  • 1659 independent reflections
  • 1173 reflections with I > 2σ(I)
  • R int = 0.048

Refinement

  • R[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.099
  • S = 1.03
  • 1659 reflections
  • 100 parameters
  • H-atom parameters constrained
  • Δρmax = 0.29 e Å−3
  • Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809003717/tk2366sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809003717/tk2366Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

I thank the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

The compound was returned unchanged in an attempt at coupling it wih benzoquinone. Crystals were obtained from recrystallization from a chloroform/ether mixture.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.93 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C).

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of C8H5ClN2; ellipsoids are drawn at the 70% probability level and H atoms of arbitrary radius.
Fig. 2.
Chain structure in C8H5ClN2; the Cl···Cl contacts are shown as dashed bonds.

Crystal data

C8H5ClN2F(000) = 336
Mr = 164.59Dx = 1.494 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1328 reflections
a = 9.1299 (2) Åθ = 2.4–28.1°
b = 3.8082 (1) ŵ = 0.44 mm1
c = 21.0777 (6) ÅT = 118 K
β = 93.028 (2)°Prism, colorless
V = 731.82 (3) Å30.20 × 0.06 × 0.02 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer1659 independent reflections
Radiation source: fine-focus sealed tube1173 reflections with I > 2σ(I)
graphiteRint = 0.048
ω scansθmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −11→11
Tmin = 0.916, Tmax = 0.991k = −4→4
6145 measured reflectionsl = −27→27

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0465P)2 + 0.1632P] where P = (Fo2 + 2Fc2)/3
1659 reflections(Δ/σ)max = 0.001
100 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = −0.30 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Cl10.60849 (6)0.47749 (15)0.58158 (3)0.03308 (19)
N10.88157 (18)0.6668 (4)0.57567 (8)0.0202 (4)
N20.8977 (2)0.9189 (4)0.70202 (8)0.0248 (4)
C10.7733 (2)0.6552 (5)0.61274 (10)0.0219 (5)
C20.7783 (2)0.7779 (6)0.67617 (10)0.0261 (5)
H20.69380.75750.70030.031*
C31.0163 (2)0.9407 (5)0.66453 (9)0.0194 (4)
C41.1478 (2)1.0934 (5)0.68919 (10)0.0231 (5)
H41.15401.18160.73140.028*
C51.2662 (2)1.1150 (5)0.65264 (10)0.0250 (5)
H51.35491.21650.66960.030*
C61.2576 (2)0.9872 (5)0.58970 (10)0.0254 (5)
H61.34081.00490.56460.030*
C71.1318 (2)0.8385 (5)0.56422 (10)0.0214 (4)
H71.12750.75280.52180.026*
C81.0086 (2)0.8132 (5)0.60139 (9)0.0179 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0215 (3)0.0305 (3)0.0466 (4)−0.0056 (2)−0.0042 (2)0.0009 (3)
N10.0187 (9)0.0178 (8)0.0239 (9)0.0000 (7)−0.0020 (7)0.0008 (7)
N20.0286 (10)0.0243 (9)0.0219 (9)0.0009 (8)0.0049 (8)0.0013 (7)
C10.0190 (10)0.0185 (10)0.0277 (11)−0.0005 (8)−0.0029 (9)0.0043 (9)
C20.0252 (12)0.0257 (11)0.0278 (12)0.0006 (9)0.0067 (9)0.0018 (10)
C30.0234 (10)0.0148 (9)0.0200 (10)0.0022 (8)0.0005 (8)0.0027 (8)
C40.0316 (12)0.0177 (10)0.0194 (11)−0.0007 (8)−0.0047 (9)−0.0008 (8)
C50.0247 (11)0.0198 (10)0.0296 (12)−0.0018 (8)−0.0066 (9)0.0028 (9)
C60.0222 (11)0.0232 (11)0.0310 (12)−0.0007 (9)0.0032 (9)0.0045 (10)
C70.0256 (11)0.0192 (10)0.0195 (10)0.0028 (9)0.0019 (8)0.0000 (9)
C80.0188 (10)0.0144 (9)0.0201 (10)0.0014 (8)−0.0031 (8)0.0028 (8)

Geometric parameters (Å, °)

Cl1—C11.746 (2)C4—C51.363 (3)
N1—C11.293 (3)C4—H40.9500
N1—C81.372 (2)C5—C61.411 (3)
N2—C21.308 (3)C5—H50.9500
N2—C31.376 (3)C6—C71.365 (3)
C1—C21.415 (3)C6—H60.9500
C2—H20.9500C7—C81.408 (3)
C3—C41.409 (3)C7—H70.9500
C3—C81.415 (3)
C1—N1—C8115.61 (17)C3—C4—H4119.9
C2—N2—C3116.68 (18)C4—C5—C6120.3 (2)
N1—C1—C2124.93 (19)C4—C5—H5119.9
N1—C1—Cl1117.21 (16)C6—C5—H5119.9
C2—C1—Cl1117.87 (16)C7—C6—C5121.13 (19)
N2—C2—C1120.92 (19)C7—C6—H6119.4
N2—C2—H2119.5C5—C6—H6119.4
C1—C2—H2119.5C6—C7—C8119.33 (19)
N2—C3—C4119.62 (18)C6—C7—H7120.3
N2—C3—C8121.21 (18)C8—C7—H7120.3
C4—C3—C8119.18 (18)N1—C8—C7119.43 (18)
C5—C4—C3120.18 (19)N1—C8—C3120.65 (18)
C5—C4—H4119.9C7—C8—C3119.91 (18)
C8—N1—C1—C2−0.5 (3)C4—C5—C6—C7−0.3 (3)
C8—N1—C1—Cl1178.97 (14)C5—C6—C7—C80.2 (3)
C3—N2—C2—C10.0 (3)C1—N1—C8—C7−179.61 (18)
N1—C1—C2—N20.6 (3)C1—N1—C8—C30.0 (3)
Cl1—C1—C2—N2−178.91 (16)C6—C7—C8—N1179.40 (18)
C2—N2—C3—C4179.27 (19)C6—C7—C8—C3−0.2 (3)
C2—N2—C3—C8−0.5 (3)N2—C3—C8—N10.6 (3)
N2—C3—C4—C5179.69 (18)C4—C3—C8—N1−179.22 (18)
C8—C3—C4—C5−0.5 (3)N2—C3—C8—C7−179.87 (17)
C3—C4—C5—C60.5 (3)C4—C3—C8—C70.3 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2366).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bhattacharjee, G., Sondhi, S. M., Dinodia, M. & Mishra, S. K. (2008). Ind. J. Chem. Technol.15, 72–74.
  • Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Cuenca, A., Perez, S., Yepez, A., Paredes, L., Montecinos, L., Llovera, L. & Rodriguez, C. (2008). J. Heterocycl. Chem.45, 1199–1201.
  • Hassan, S. Y., Khattab, S. N., Bekhit, A. A. & Amer, A. (2006). Bioorg. Med. Chem. Lett.16, 1753–1756. [PubMed]
  • Rangisetty, J. B., Gupta, C. N. V. H. B., Prasad, A. L., Srinivas, P., Sridhar, N., Parimoo, P. & Veeranjaneyulu, A. (2001). J. Pharm. Pharmacol.53, 1409–1413. [PubMed]
  • Rizzo, A., Campos, G., Alvarez, A. & Cuenca, A. (2002). Synth. Commun.32, 813–817.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Sugimoto, O., Yamada, S. & Tanji, K. (2003). J. Org. Chem.68, 2054–2057. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography