2-Chloro­quinoxaline

Ng, S.W.

doi:10.1107/S1600536809003717

organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o455

doi:10.1107/S1600536809003717

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2-Chloroquinoxaline

Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 29 January 2009; accepted 29 January 2009; online 4 February 2009)

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 ); 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_r = 164.59
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.038
wR(F²) = 0.099
S = 1.03
1659 reflections
100 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −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 ).

Supporting information

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

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

checkCIF report

Related literature top

The title compound is the reagent for 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 top

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

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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).

Figures top

	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.

2-Chloroquinoxaline top

Crystal data top

C₈H₅ClN₂	F(000) = 336
M_r = 164.59	D_x = 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

Data collection top

Bruker SMART APEX diffractometer	1659 independent reflections
Radiation source: fine-focus sealed tube	1173 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
ω scans	θ_max = 27.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.916, T_max = 0.991	k = −4→4
6145 measured reflections	l = −27→27

Refinement top

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(F_o²) + (0.0465P)² + 0.1632P] where P = (F_o² + 2F_c²)/3
1659 reflections	(Δ/σ)_max = 0.001
100 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₈H₅ClN₂	V = 731.82 (3) Å³
M_r = 164.59	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.1299 (2) Å	µ = 0.44 mm⁻¹
b = 3.8082 (1) Å	T = 118 K
c = 21.0777 (6) Å	0.20 × 0.06 × 0.02 mm
β = 93.028 (2)°

Data collection top

Bruker SMART APEX diffractometer	1659 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1173 reflections with I > 2σ(I)
T_min = 0.916, T_max = 0.991	R_int = 0.048
6145 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 1.03	Δρ_max = 0.29 e Å⁻³
1659 reflections	Δρ_min = −0.30 e Å⁻³
100 parameters

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

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₈H₅ClN₂
M_r	164.59
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	118
a, b, c (Å)	9.1299 (2), 3.8082 (1), 21.0777 (6)
β (°)	93.028 (2)
V (Å³)	731.82 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.44
Crystal size (mm)	0.20 × 0.06 × 0.02

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.916, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	6145, 1659, 1173
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.099, 1.03
No. of reflections	1659
No. of parameters	100
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.30

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Acknowledgements

I thank the University of Malaya for supporting this study.

References

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