6,7-Dichloro-3-(2,4-dichloro-benz-yl)-quinoxalin-2(1H)-one.

In the title compound, C(15)H(8)Cl(4)N(2)O, the quinoxaline ring system is almost planar, with a dihedral angle between the benzene and pyrazine rings of 3.1 (2)°. The 2,4-dichloro-phenyl ring is approximately perpendicular to the pyrazine ring, with a dihedral angle of 86.47 (13)° between them. The crystal packing features inter-molecular N-H⋯O hydrogen bonds and π-π stacking inter-actions, with centroid-centroid distances in the range 3.699 (3)-4.054 (3) Å.

Related literature

For the bioactivity of quinoxalin-2(1H)-one derivatives, see: Mensah-Osman et al. (2002 ▶); Perez et al. (2002 ▶); Quint et al. (2002 ▶); Seitz et al. (2002 ▶).

Experimental

Crystal data

C15H8Cl4N2O

M = 374.03

Triclinic,

a = 7.7150 (7) Å

b = 8.2058 (8) Å

c = 11.9722 (12) Å

α = 83.771 (1)°

β = 84.362 (1)°

γ = 84.298 (2)°

V = 746.79 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.79 mm−1

T = 298 K

0.16 × 0.09 × 0.05 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.884, T max = 0.961

3811 measured reflections

2590 independent reflections

1364 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.103

S = 1.01

2590 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.26 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681203098X/sj5253sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681203098X/sj5253Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681203098X/sj5253Isup3.cml

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

C15H8Cl4N2O	Z = 2
Mr = 374.03	F(000) = 376
Triclinic, P1	Dx = 1.663 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7150 (7) Å	Cell parameters from 742 reflections
b = 8.2058 (8) Å	θ = 2.9–26.1°
c = 11.9722 (12) Å	µ = 0.79 mm−1
α = 83.771 (1)°	T = 298 K
β = 84.362 (1)°	Prism, colorless
γ = 84.298 (2)°	0.16 × 0.09 × 0.05 mm
V = 746.79 (12) Å3

Bruker SMART CCD area-detector diffractometer	2590 independent reflections
Radiation source: fine-focus sealed tube	1364 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
φ and ω scans	θmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→5
Tmin = 0.884, Tmax = 0.961	k = −9→9
3811 measured reflections	l = −13→14

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0247P)2] where P = (Fo2 + 2Fc2)/3
2590 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Experimental. The data was obtained at Xuzhou Medical College collected by Jinpeng Zhang.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Cl1	0.77372 (19)	0.40780 (15)	0.26074 (9)	0.0645 (4)
Cl2	0.62590 (18)	0.18395 (14)	0.47312 (10)	0.0575 (4)
Cl3	0.4357 (2)	1.04383 (15)	0.75266 (10)	0.0745 (5)
Cl4	0.0594 (2)	0.7248 (2)	1.09562 (11)	0.0880 (5)
N1	0.8827 (5)	0.8183 (4)	0.5316 (3)	0.0447 (10)
H1	0.9289	0.8757	0.4739	0.054*
N2	0.7257 (5)	0.6358 (4)	0.7161 (3)	0.0431 (10)
O1	0.9408 (4)	1.0040 (4)	0.6487 (2)	0.0540 (9)
C1	0.8754 (6)	0.8778 (5)	0.6340 (3)	0.0406 (12)
C2	0.7819 (6)	0.7756 (5)	0.7279 (3)	0.0418 (12)
C3	0.7456 (6)	0.5778 (5)	0.6094 (3)	0.0374 (11)
C4	0.8206 (6)	0.6717 (5)	0.5149 (3)	0.0356 (11)
C5	0.8302 (6)	0.6185 (5)	0.4072 (3)	0.0416 (12)
H5	0.8779	0.6820	0.3448	0.050*
C6	0.7680 (6)	0.4710 (5)	0.3953 (3)	0.0420 (12)
C7	0.6994 (6)	0.3725 (5)	0.4901 (4)	0.0399 (11)
C8	0.6891 (6)	0.4266 (5)	0.5954 (3)	0.0419 (12)
H8	0.6440	0.3613	0.6578	0.050*
C9	0.7583 (7)	0.8441 (6)	0.8411 (3)	0.0584 (14)
H9A	0.8507	0.7934	0.8862	0.070*
H9B	0.7706	0.9614	0.8296	0.070*
C10	0.5845 (7)	0.8167 (5)	0.9056 (3)	0.0426 (12)
C11	0.4300 (8)	0.9005 (5)	0.8721 (3)	0.0507 (14)
C12	0.2672 (7)	0.8752 (5)	0.9292 (4)	0.0544 (14)
H12	0.1657	0.9328	0.9045	0.065*
C13	0.2608 (7)	0.7620 (6)	1.0233 (4)	0.0562 (14)
C14	0.4100 (7)	0.6797 (6)	1.0607 (4)	0.0549 (14)
H14	0.4037	0.6059	1.1253	0.066*
C15	0.5711 (7)	0.7057 (5)	1.0027 (3)	0.0517 (14)
H15	0.6717	0.6485	1.0288	0.062*

	U11	U22	U33	U12	U13	U23
Cl1	0.0842 (11)	0.0672 (9)	0.0442 (7)	−0.0149 (8)	0.0021 (7)	−0.0150 (6)
Cl2	0.0672 (10)	0.0447 (7)	0.0626 (8)	−0.0132 (7)	−0.0054 (7)	−0.0079 (6)
Cl3	0.1159 (14)	0.0603 (8)	0.0459 (7)	−0.0194 (9)	−0.0035 (8)	0.0086 (6)
Cl4	0.0741 (12)	0.1161 (13)	0.0705 (9)	−0.0285 (10)	0.0238 (8)	−0.0039 (8)
N1	0.059 (3)	0.042 (2)	0.031 (2)	−0.014 (2)	0.0130 (18)	0.0019 (17)
N2	0.050 (3)	0.050 (2)	0.030 (2)	−0.012 (2)	0.0019 (19)	−0.0031 (18)
O1	0.070 (3)	0.0498 (19)	0.0455 (18)	−0.0295 (19)	0.0063 (17)	−0.0050 (15)
C1	0.041 (3)	0.045 (3)	0.035 (3)	−0.009 (2)	0.001 (2)	0.001 (2)
C2	0.045 (3)	0.049 (3)	0.031 (2)	−0.012 (3)	0.003 (2)	−0.004 (2)
C3	0.039 (3)	0.037 (2)	0.035 (2)	−0.005 (2)	0.005 (2)	0.000 (2)
C4	0.034 (3)	0.032 (2)	0.038 (2)	−0.004 (2)	0.002 (2)	0.003 (2)
C5	0.049 (3)	0.038 (3)	0.035 (2)	−0.008 (2)	0.003 (2)	0.004 (2)
C6	0.039 (3)	0.049 (3)	0.038 (2)	−0.003 (2)	−0.003 (2)	−0.004 (2)
C7	0.041 (3)	0.032 (2)	0.046 (3)	−0.004 (2)	0.000 (2)	−0.005 (2)
C8	0.046 (3)	0.039 (3)	0.037 (3)	−0.009 (2)	0.004 (2)	0.007 (2)
C9	0.072 (4)	0.069 (3)	0.041 (3)	−0.036 (3)	0.002 (3)	−0.013 (2)
C10	0.057 (4)	0.043 (3)	0.032 (3)	−0.022 (3)	0.006 (3)	−0.009 (2)
C11	0.087 (5)	0.037 (3)	0.030 (3)	−0.014 (3)	−0.002 (3)	−0.004 (2)
C12	0.061 (4)	0.055 (3)	0.048 (3)	−0.011 (3)	0.003 (3)	−0.013 (3)
C13	0.068 (4)	0.056 (3)	0.046 (3)	−0.018 (3)	0.014 (3)	−0.017 (3)
C14	0.069 (4)	0.060 (3)	0.037 (3)	−0.024 (3)	0.007 (3)	−0.003 (2)
C15	0.067 (4)	0.053 (3)	0.036 (3)	−0.012 (3)	−0.001 (3)	−0.004 (2)

Cl1—C6	1.740 (4)	C5—H5	0.9300
Cl2—C7	1.738 (4)	C6—C7	1.411 (5)
Cl3—C11	1.750 (4)	C7—C8	1.374 (5)
Cl4—C13	1.740 (5)	C8—H8	0.9300
N1—C1	1.362 (5)	C9—C10	1.505 (6)
N1—C4	1.380 (5)	C9—H9A	0.9700
N1—H1	0.8600	C9—H9B	0.9700
N2—C2	1.292 (5)	C10—C11	1.388 (6)
N2—C3	1.401 (5)	C10—C15	1.399 (5)
O1—C1	1.233 (5)	C11—C12	1.393 (6)
C1—C2	1.498 (5)	C12—C13	1.380 (6)
C2—C9	1.511 (5)	C12—H12	0.9300
C3—C8	1.387 (5)	C13—C14	1.365 (6)
C3—C4	1.407 (5)	C14—C15	1.386 (6)
C4—C5	1.398 (5)	C14—H14	0.9300
C5—C6	1.371 (5)	C15—H15	0.9300
C1—N1—C4	124.0 (3)	C7—C8—H8	119.8
C1—N1—H1	118.0	C3—C8—H8	119.8
C4—N1—H1	118.0	C10—C9—C2	113.7 (4)
C2—N2—C3	119.1 (3)	C10—C9—H9A	108.8
O1—C1—N1	123.2 (4)	C2—C9—H9A	108.8
O1—C1—C2	122.7 (4)	C10—C9—H9B	108.8
N1—C1—C2	114.1 (4)	C2—C9—H9B	108.8
N2—C2—C1	123.6 (4)	H9A—C9—H9B	107.7
N2—C2—C9	120.6 (4)	C11—C10—C15	116.8 (4)
C1—C2—C9	115.8 (4)	C11—C10—C9	121.7 (4)
C8—C3—N2	120.0 (3)	C15—C10—C9	121.5 (5)
C8—C3—C4	119.0 (4)	C10—C11—C12	122.8 (4)
N2—C3—C4	121.0 (4)	C10—C11—Cl3	119.6 (4)
N1—C4—C5	121.1 (3)	C12—C11—Cl3	117.5 (4)
N1—C4—C3	118.0 (3)	C13—C12—C11	118.1 (5)
C5—C4—C3	120.9 (4)	C13—C12—H12	121.0
C6—C5—C4	118.8 (4)	C11—C12—H12	121.0
C6—C5—H5	120.6	C14—C13—C12	120.9 (5)
C4—C5—H5	120.6	C14—C13—Cl4	119.6 (4)
C5—C6—C7	120.7 (4)	C12—C13—Cl4	119.4 (5)
C5—C6—Cl1	118.8 (3)	C13—C14—C15	120.3 (5)
C7—C6—Cl1	120.4 (3)	C13—C14—H14	119.8
C8—C7—C6	119.9 (4)	C15—C14—H14	119.8
C8—C7—Cl2	120.2 (3)	C14—C15—C10	121.0 (5)
C6—C7—Cl2	119.9 (3)	C14—C15—H15	119.5
C7—C8—C3	120.5 (4)	C10—C15—H15	119.5
C4—N1—C1—O1	175.5 (4)	Cl1—C6—C7—Cl2	1.9 (5)
C4—N1—C1—C2	−4.0 (6)	C6—C7—C8—C3	0.1 (7)
C3—N2—C2—C1	−2.8 (7)	Cl2—C7—C8—C3	−179.2 (3)
C3—N2—C2—C9	178.4 (4)	N2—C3—C8—C7	176.5 (4)
O1—C1—C2—N2	−173.8 (5)	C4—C3—C8—C7	−2.8 (7)
N1—C1—C2—N2	5.7 (7)	N2—C2—C9—C10	−39.4 (6)
O1—C1—C2—C9	5.1 (7)	C1—C2—C9—C10	141.7 (4)
N1—C1—C2—C9	−175.4 (4)	C2—C9—C10—C11	−70.7 (6)
C2—N2—C3—C8	178.8 (4)	C2—C9—C10—C15	109.5 (5)
C2—N2—C3—C4	−2.0 (6)	C15—C10—C11—C12	−1.5 (7)
C1—N1—C4—C5	179.2 (4)	C9—C10—C11—C12	178.8 (4)
C1—N1—C4—C3	−0.2 (7)	C15—C10—C11—Cl3	179.1 (3)
C8—C3—C4—N1	−177.2 (4)	C9—C10—C11—Cl3	−0.7 (6)
N2—C3—C4—N1	3.5 (6)	C10—C11—C12—C13	0.3 (7)
C8—C3—C4—C5	3.4 (7)	Cl3—C11—C12—C13	179.8 (3)
N2—C3—C4—C5	−175.9 (4)	C11—C12—C13—C14	1.2 (7)
N1—C4—C5—C6	179.4 (4)	C11—C12—C13—Cl4	−179.1 (3)
C3—C4—C5—C6	−1.2 (7)	C12—C13—C14—C15	−1.6 (8)
C4—C5—C6—C7	−1.5 (7)	Cl4—C13—C14—C15	178.7 (3)
C4—C5—C6—Cl1	178.0 (3)	C13—C14—C15—C10	0.3 (7)
C5—C6—C7—C8	2.1 (7)	C11—C10—C15—C14	1.1 (6)
Cl1—C6—C7—C8	−177.4 (3)	C9—C10—C15—C14	−179.1 (4)
C5—C6—C7—Cl2	−178.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	1.93	2.789 (4)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	1.93	2.789 (4)	173

Symmetry code: (i) .