2-Chloro-quinoxaline.

In the title compound, C(8)H(5)ClN(2), the planar mol-ecules are arranged with their Cl atoms in close contact [Cl⋯Cl = 3.808 (1) and 3.881 (1) Å], indicating weak Cl⋯Cl inter-actions, which give rise to a supra-molecular 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 ▶); Cuenca et al. (2008 ▶); Hassan et al. (2006 ▶); Rangisetty et al. (2001 ▶); Rizzo et al. (2002 ▶); Sugimoto et al. (2003 ▶).

Experimental

Crystal data

C8H5ClN2

M = 164.59

Monoclinic,

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 ▶) 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 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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 ▶).

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

C8H5ClN2	F(000) = 336
Mr = 164.59	Dx = 1.494 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1328 reflections
a = 9.1299 (2) Å	θ = 2.4–28.1°
b = 3.8082 (1) Å	µ = 0.44 mm−1
c = 21.0777 (6) Å	T = 118 K
β = 93.028 (2)°	Prism, colorless
V = 731.82 (3) Å3	0.20 × 0.06 × 0.02 mm
Z = 4

Bruker SMART APEX diffractometer	1659 independent reflections
Radiation source: fine-focus sealed tube	1173 reflections with I > 2σ(I)
graphite	Rint = 0.048
ω scans	θmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.916, Tmax = 0.991	k = −4→4
6145 measured reflections	l = −27→27

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0465P)2 + 0.1632P] where P = (Fo2 + 2Fc2)/3
1659 reflections	(Δ/σ)max = 0.001
100 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

	x	y	z	Uiso*/Ueq
Cl1	0.60849 (6)	0.47749 (15)	0.58158 (3)	0.03308 (19)
N1	0.88157 (18)	0.6668 (4)	0.57567 (8)	0.0202 (4)
N2	0.8977 (2)	0.9189 (4)	0.70202 (8)	0.0248 (4)
C1	0.7733 (2)	0.6552 (5)	0.61274 (10)	0.0219 (5)
C2	0.7783 (2)	0.7779 (6)	0.67617 (10)	0.0261 (5)
H2	0.6938	0.7575	0.7003	0.031*
C3	1.0163 (2)	0.9407 (5)	0.66453 (9)	0.0194 (4)
C4	1.1478 (2)	1.0934 (5)	0.68919 (10)	0.0231 (5)
H4	1.1540	1.1816	0.7314	0.028*
C5	1.2662 (2)	1.1150 (5)	0.65264 (10)	0.0250 (5)
H5	1.3549	1.2165	0.6696	0.030*
C6	1.2576 (2)	0.9872 (5)	0.58970 (10)	0.0254 (5)
H6	1.3408	1.0049	0.5646	0.030*
C7	1.1318 (2)	0.8385 (5)	0.56422 (10)	0.0214 (4)
H7	1.1275	0.7528	0.5218	0.026*
C8	1.0086 (2)	0.8132 (5)	0.60139 (9)	0.0179 (4)

	U11	U22	U33	U12	U13	U23
Cl1	0.0215 (3)	0.0305 (3)	0.0466 (4)	−0.0056 (2)	−0.0042 (2)	0.0009 (3)
N1	0.0187 (9)	0.0178 (8)	0.0239 (9)	0.0000 (7)	−0.0020 (7)	0.0008 (7)
N2	0.0286 (10)	0.0243 (9)	0.0219 (9)	0.0009 (8)	0.0049 (8)	0.0013 (7)
C1	0.0190 (10)	0.0185 (10)	0.0277 (11)	−0.0005 (8)	−0.0029 (9)	0.0043 (9)
C2	0.0252 (12)	0.0257 (11)	0.0278 (12)	0.0006 (9)	0.0067 (9)	0.0018 (10)
C3	0.0234 (10)	0.0148 (9)	0.0200 (10)	0.0022 (8)	0.0005 (8)	0.0027 (8)
C4	0.0316 (12)	0.0177 (10)	0.0194 (11)	−0.0007 (8)	−0.0047 (9)	−0.0008 (8)
C5	0.0247 (11)	0.0198 (10)	0.0296 (12)	−0.0018 (8)	−0.0066 (9)	0.0028 (9)
C6	0.0222 (11)	0.0232 (11)	0.0310 (12)	−0.0007 (9)	0.0032 (9)	0.0045 (10)
C7	0.0256 (11)	0.0192 (10)	0.0195 (10)	0.0028 (9)	0.0019 (8)	0.0000 (9)
C8	0.0188 (10)	0.0144 (9)	0.0201 (10)	0.0014 (8)	−0.0031 (8)	0.0028 (8)

Cl1—C1	1.746 (2)	C4—C5	1.363 (3)
N1—C1	1.293 (3)	C4—H4	0.9500
N1—C8	1.372 (2)	C5—C6	1.411 (3)
N2—C2	1.308 (3)	C5—H5	0.9500
N2—C3	1.376 (3)	C6—C7	1.365 (3)
C1—C2	1.415 (3)	C6—H6	0.9500
C2—H2	0.9500	C7—C8	1.408 (3)
C3—C4	1.409 (3)	C7—H7	0.9500
C3—C8	1.415 (3)
C1—N1—C8	115.61 (17)	C3—C4—H4	119.9
C2—N2—C3	116.68 (18)	C4—C5—C6	120.3 (2)
N1—C1—C2	124.93 (19)	C4—C5—H5	119.9
N1—C1—Cl1	117.21 (16)	C6—C5—H5	119.9
C2—C1—Cl1	117.87 (16)	C7—C6—C5	121.13 (19)
N2—C2—C1	120.92 (19)	C7—C6—H6	119.4
N2—C2—H2	119.5	C5—C6—H6	119.4
C1—C2—H2	119.5	C6—C7—C8	119.33 (19)
N2—C3—C4	119.62 (18)	C6—C7—H7	120.3
N2—C3—C8	121.21 (18)	C8—C7—H7	120.3
C4—C3—C8	119.18 (18)	N1—C8—C7	119.43 (18)
C5—C4—C3	120.18 (19)	N1—C8—C3	120.65 (18)
C5—C4—H4	119.9	C7—C8—C3	119.91 (18)
C8—N1—C1—C2	−0.5 (3)	C4—C5—C6—C7	−0.3 (3)
C8—N1—C1—Cl1	178.97 (14)	C5—C6—C7—C8	0.2 (3)
C3—N2—C2—C1	0.0 (3)	C1—N1—C8—C7	−179.61 (18)
N1—C1—C2—N2	0.6 (3)	C1—N1—C8—C3	0.0 (3)
Cl1—C1—C2—N2	−178.91 (16)	C6—C7—C8—N1	179.40 (18)
C2—N2—C3—C4	179.27 (19)	C6—C7—C8—C3	−0.2 (3)
C2—N2—C3—C8	−0.5 (3)	N2—C3—C8—N1	0.6 (3)
N2—C3—C4—C5	179.69 (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—C6	0.5 (3)	C4—C3—C8—C7	0.3 (3)