2-(4-Bromo-phen-yl)quinoxaline.

In the title compound, C(14)H(9)BrN(2), the benzene and quinoxaline rings are almost coplanar [r.m.s. deviation = 0.0285 (3) Å and dihedral angle = 2.1 (2)°].

Related literature

For the synthesis of quinoxaline derivatives, see: Raw et al. (2003 ▶); Bhosale et al. (2005 ▶). For their applications, see: Brock et al. (1999 ▶); Seitz et al. (2002 ▶); He et al. (2003 ▶). For typical bond lengths in a related structure, see: Rong et al. (2006 ▶).

Experimental

Crystal data

C14H9BrN2

M = 285.14

Monoclinic,

a = 13.959 (3) Å

b = 5.9031 (12) Å

c = 14.497 (3) Å

β = 109.53 (3)°

V = 1125.9 (4) Å3

Z = 4

Mo Kα radiation

μ = 3.63 mm−1

T = 153 K

0.20 × 0.18 × 0.10 mm

Data collection

Rigaku MM-OO7/Saturn 70 CCD area-detector diffractometer

Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T min = 0.531, T max = 0.713

8910 measured reflections

2683 independent reflections

1763 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.075

S = 0.96

2683 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.76 e Å−3

Δρmin = −0.69 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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 datablocks global, I. DOI: 10.1107/S160053681001723X/zs2039sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681001723X/zs2039Isup2.hkl

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

C14H9BrN2	F(000) = 568
Mr = 285.14	Dx = 1.682 Mg m−3
Monoclinic, P21/c	Melting point: 418 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 13.959 (3) Å	Cell parameters from 3221 reflections
b = 5.9031 (12) Å	θ = 2.9–27.9°
c = 14.497 (3) Å	µ = 3.63 mm−1
β = 109.53 (3)°	T = 153 K
V = 1125.9 (4) Å3	Prism, colorless
Z = 4	0.20 × 0.18 × 0.10 mm

Rigaku Model name? CCD area-detector diffractometer	2683 independent reflections
Radiation source: rotating anode	1763 reflections with I > 2σ(I)
multilayer	Rint = 0.052
Detector resolution: 7.31 pixels mm-1	θmax = 27.9°, θmin = 2.9°
φ and ω scans	h = −18→11
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	k = −7→7
Tmin = 0.531, Tmax = 0.713	l = −19→19
8910 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032	H-atom parameters constrained
wR(F2) = 0.075	w = 1/[σ2(Fo2) + (0.0337P)2] where P = (Fo2 + 2Fc2)/3
S = 0.96	(Δ/σ)max = 0.001
2683 reflections	Δρmax = 0.76 e Å−3
155 parameters	Δρmin = −0.69 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0540 (17)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
Br1	0.460263 (18)	1.10538 (4)	0.33474 (2)	0.03213 (13)
N1	−0.12149 (15)	0.6560 (3)	0.02060 (15)	0.0218 (5)
N2	−0.05847 (15)	1.0700 (3)	0.12055 (14)	0.0169 (4)
C1	0.00712 (17)	0.9095 (4)	0.11986 (16)	0.0150 (5)
C2	−0.02653 (17)	0.7012 (4)	0.07034 (17)	0.0210 (6)
H2	0.0229	0.5882	0.0736	0.025*
C3	−0.19054 (16)	0.8203 (4)	0.02054 (16)	0.0160 (5)
C4	−0.29514 (17)	0.7808 (4)	−0.02863 (17)	0.0204 (6)
H4	−0.3168	0.6436	−0.0636	0.024*
C5	−0.36496 (18)	0.9398 (4)	−0.02576 (17)	0.0213 (6)
H5	−0.4352	0.9126	−0.0588	0.026*
C6	−0.33379 (19)	1.1438 (4)	0.02573 (18)	0.0229 (6)
H6	−0.3833	1.2523	0.0279	0.028*
C7	−0.23291 (17)	1.1877 (4)	0.07274 (17)	0.0176 (5)
H7	−0.2126	1.3275	0.1060	0.021*
C8	−0.15888 (16)	1.0252 (4)	0.07190 (15)	0.0150 (5)
C9	0.11683 (17)	0.9532 (4)	0.17107 (16)	0.0157 (5)
C10	0.19145 (17)	0.7987 (4)	0.16884 (17)	0.0186 (5)
H10	0.1721	0.6609	0.1337	0.022*
C11	0.29343 (17)	0.8427 (4)	0.21702 (18)	0.0206 (6)
H11	0.3437	0.7360	0.2152	0.025*
C12	0.32117 (17)	1.0434 (4)	0.26773 (17)	0.0186 (5)
C13	0.24914 (17)	1.2017 (4)	0.27042 (17)	0.0196 (5)
H13	0.2692	1.3406	0.3045	0.023*
C14	0.14782 (18)	1.1554 (4)	0.22297 (16)	0.0186 (5)
H14	0.0980	1.2627	0.2255	0.022*

	U11	U22	U33	U12	U13	U23
Br1	0.01429 (15)	0.0399 (2)	0.03931 (19)	−0.00711 (11)	0.00519 (12)	−0.00733 (13)
N1	0.0176 (11)	0.0191 (10)	0.0248 (11)	0.0017 (8)	0.0021 (9)	−0.0045 (9)
N2	0.0157 (10)	0.0175 (10)	0.0176 (9)	0.0015 (8)	0.0054 (9)	−0.0003 (8)
C1	0.0153 (11)	0.0153 (12)	0.0148 (11)	0.0002 (9)	0.0058 (10)	0.0002 (9)
C2	0.0158 (12)	0.0198 (12)	0.0246 (13)	0.0035 (10)	0.0029 (11)	−0.0052 (11)
C3	0.0148 (12)	0.0172 (11)	0.0147 (11)	0.0002 (9)	0.0031 (10)	0.0018 (9)
C4	0.0188 (13)	0.0194 (12)	0.0193 (11)	−0.0026 (10)	0.0015 (11)	0.0002 (10)
C5	0.0115 (12)	0.0273 (14)	0.0216 (12)	0.0004 (9)	0.0009 (10)	0.0039 (10)
C6	0.0248 (14)	0.0213 (13)	0.0234 (13)	0.0085 (11)	0.0090 (12)	0.0048 (10)
C7	0.0188 (12)	0.0135 (11)	0.0209 (12)	0.0022 (10)	0.0070 (11)	0.0018 (10)
C8	0.0149 (12)	0.0165 (12)	0.0141 (11)	−0.0005 (9)	0.0053 (10)	0.0022 (9)
C9	0.0149 (12)	0.0169 (12)	0.0151 (11)	−0.0009 (9)	0.0048 (10)	0.0013 (9)
C10	0.0173 (12)	0.0158 (11)	0.0227 (12)	−0.0020 (10)	0.0068 (10)	−0.0043 (10)
C11	0.0156 (12)	0.0210 (13)	0.0268 (13)	0.0021 (10)	0.0090 (11)	−0.0011 (10)
C12	0.0124 (11)	0.0229 (13)	0.0198 (12)	−0.0047 (9)	0.0045 (10)	0.0007 (10)
C13	0.0212 (13)	0.0171 (11)	0.0203 (12)	−0.0051 (10)	0.0068 (11)	−0.0018 (10)
C14	0.0182 (12)	0.0200 (13)	0.0172 (11)	0.0029 (10)	0.0055 (11)	−0.0018 (10)

Br1—C12	1.894 (2)	C6—C7	1.369 (3)
N1—C2	1.307 (3)	C6—H6	0.9500
N1—C3	1.367 (3)	C7—C8	1.413 (3)
N2—C1	1.320 (3)	C7—H7	0.9500
N2—C8	1.368 (3)	C9—C10	1.393 (3)
C1—C2	1.422 (3)	C9—C14	1.400 (3)
C1—C9	1.484 (3)	C10—C11	1.385 (3)
C2—H2	0.9500	C10—H10	0.9500
C3—C8	1.411 (3)	C11—C12	1.379 (3)
C3—C4	1.414 (3)	C11—H11	0.9500
C4—C5	1.364 (3)	C12—C13	1.383 (3)
C4—H4	0.9500	C13—C14	1.378 (3)
C5—C6	1.407 (3)	C13—H13	0.9500
C5—H5	0.9500	C14—H14	0.9500
C2—N1—C3	116.11 (19)	C8—C7—H7	120.0
C1—N2—C8	116.82 (18)	N2—C8—C3	121.6 (2)
N2—C1—C2	120.8 (2)	N2—C8—C7	119.4 (2)
N2—C1—C9	118.30 (19)	C3—C8—C7	119.0 (2)
C2—C1—C9	120.9 (2)	C10—C9—C14	118.1 (2)
N1—C2—C1	123.9 (2)	C10—C9—C1	121.96 (19)
N1—C2—H2	118.0	C14—C9—C1	119.9 (2)
C1—C2—H2	118.0	C11—C10—C9	121.1 (2)
N1—C3—C8	120.74 (19)	C11—C10—H10	119.5
N1—C3—C4	119.5 (2)	C9—C10—H10	119.5
C8—C3—C4	119.7 (2)	C12—C11—C10	119.2 (2)
C5—C4—C3	119.9 (2)	C12—C11—H11	120.4
C5—C4—H4	120.0	C10—C11—H11	120.4
C3—C4—H4	120.0	C11—C12—C13	121.2 (2)
C4—C5—C6	120.5 (2)	C11—C12—Br1	119.76 (18)
C4—C5—H5	119.7	C13—C12—Br1	119.03 (17)
C6—C5—H5	119.7	C14—C13—C12	119.1 (2)
C7—C6—C5	120.7 (2)	C14—C13—H13	120.4
C7—C6—H6	119.7	C12—C13—H13	120.4
C5—C6—H6	119.7	C13—C14—C9	121.3 (2)
C6—C7—C8	120.1 (2)	C13—C14—H14	119.4
C6—C7—H7	120.0	C9—C14—H14	119.4
C8—N2—C1—C2	0.1 (3)	C4—C3—C8—C7	−0.2 (3)
C8—N2—C1—C9	179.40 (19)	C6—C7—C8—N2	−179.0 (2)
C3—N1—C2—C1	−2.1 (3)	C6—C7—C8—C3	1.2 (3)
N2—C1—C2—N1	2.2 (4)	N2—C1—C9—C10	−176.0 (2)
C9—C1—C2—N1	−177.1 (2)	C2—C1—C9—C10	3.3 (4)
C2—N1—C3—C8	0.0 (3)	N2—C1—C9—C14	3.5 (3)
C2—N1—C3—C4	−177.7 (2)	C2—C1—C9—C14	−177.2 (2)
N1—C3—C4—C5	177.3 (2)	C14—C9—C10—C11	0.4 (4)
C8—C3—C4—C5	−0.4 (3)	C1—C9—C10—C11	179.9 (2)
C3—C4—C5—C6	0.1 (4)	C9—C10—C11—C12	−0.2 (4)
C4—C5—C6—C7	0.8 (4)	C10—C11—C12—C13	−0.6 (4)
C5—C6—C7—C8	−1.5 (4)	C10—C11—C12—Br1	179.59 (19)
C1—N2—C8—C3	−2.2 (3)	C11—C12—C13—C14	1.2 (4)
C1—N2—C8—C7	178.0 (2)	Br1—C12—C13—C14	−179.02 (17)
N1—C3—C8—N2	2.2 (3)	C12—C13—C14—C9	−1.0 (4)
C4—C3—C8—N2	179.9 (2)	C10—C9—C14—C13	0.2 (4)
N1—C3—C8—C7	−177.9 (2)	C1—C9—C14—C13	−179.4 (2)