1,3-Bis[(3-chloro-pyrazin-2-yl)-oxy]benzene.

The asymmetric unit of the title compound, C14H8Cl2N4O2, contains one half-mol-ecule, the complete mol-ecule being generated by the operation of a twofold rotation axis. The Cl atom deviates significantly from the plane of the pyrazine ring [0.0215 (4) Å]. The central benzene ring makes a dihedral angle of 72.82 (7)° with the plane of the pyrazine ring.

Related literature

For applications of the pyrazine ring system in drug development, see: Du et al. (2009 ▶); Dubinina et al. (2006 ▶); Ellsworth et al. (2007 ▶); Mukaiyama et al. (2007 ▶). For background to the fluorescence properties of compounds related to the title compound, see: Kawai et al. (2001 ▶); Abdullah (2005 ▶). For a related structure, see: Nasir et al. (2010 ▶).

Experimental

Crystal data

C14H8Cl2N4O2

M = 335.14

Monoclinic,

a = 9.9618 (3) Å

b = 10.2196 (4) Å

c = 14.6010 (6) Å

β = 106.231 (2)°

V = 1427.22 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.47 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.873, T max = 0.912

6736 measured reflections

1781 independent reflections

1552 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.113

S = 1.00

1781 reflections

101 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.31 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: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681301129X/kp2450sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681301129X/kp2450Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681301129X/kp2450Isup3.cml

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

C14H8Cl2N4O2	F(000) = 680
Mr = 335.14	Dx = 1.560 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1781 reflections
a = 9.9618 (3) Å	θ = 2.9–28.4°
b = 10.2196 (4) Å	µ = 0.47 mm−1
c = 14.6010 (6) Å	T = 293 K
β = 106.231 (2)°	Block, colourless
V = 1427.22 (9) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker SMART APEXII area-detector diffractometer	1781 independent reflections
Radiation source: fine-focus sealed tube	1552 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
ω and φ scans	θmax = 28.4°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −13→13
Tmin = 0.873, Tmax = 0.912	k = −13→12
6736 measured reflections	l = −19→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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0685P)2 + 0.5533P] where P = (Fo2 + 2Fc2)/3
1781 reflections	(Δ/σ)max < 0.001
101 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

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 > 2sigma(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
C1	0.10770 (15)	0.37514 (13)	−0.02670 (10)	0.0461 (3)
C2	−0.07466 (18)	0.3213 (2)	−0.15100 (11)	0.0644 (4)
H2	−0.1203	0.3246	−0.2159	0.077*
C3	−0.13428 (17)	0.25363 (19)	−0.09216 (11)	0.0618 (4)
H3	−0.2196	0.2121	−0.1178	0.074*
C4	0.04654 (14)	0.30517 (13)	0.03426 (9)	0.0417 (3)
C5	0.05477 (14)	0.23121 (15)	0.18814 (9)	0.0454 (3)
C6	0.0000	0.3013 (2)	0.2500	0.0436 (4)
H6	0.0000	0.3923	0.2500	0.052*
C7	0.05777 (19)	0.09686 (17)	0.18801 (10)	0.0597 (4)
H7	0.0979	0.0516	0.1470	0.072*
C8	0.0000	0.0305 (2)	0.2500	0.0694 (7)
H8	0.0000	−0.0605	0.2500	0.083*
N1	0.04795 (16)	0.38337 (13)	−0.11809 (9)	0.0580 (3)
N2	−0.07257 (13)	0.24545 (13)	0.00221 (8)	0.0515 (3)
O1	0.11655 (11)	0.30189 (12)	0.12853 (7)	0.0537 (3)
Cl1	0.26460 (5)	0.45456 (4)	0.01959 (4)	0.06883 (19)

	U11	U22	U33	U12	U13	U23
C1	0.0581 (7)	0.0383 (6)	0.0511 (8)	0.0030 (5)	0.0308 (6)	−0.0006 (5)
C2	0.0681 (10)	0.0875 (12)	0.0390 (7)	0.0107 (9)	0.0175 (7)	0.0107 (7)
C3	0.0527 (8)	0.0885 (12)	0.0432 (8)	−0.0002 (8)	0.0121 (6)	0.0067 (7)
C4	0.0491 (6)	0.0447 (7)	0.0363 (6)	0.0042 (5)	0.0201 (5)	0.0004 (5)
C5	0.0493 (7)	0.0565 (8)	0.0298 (6)	−0.0035 (5)	0.0104 (5)	0.0000 (5)
C6	0.0461 (9)	0.0492 (10)	0.0340 (8)	0.000	0.0085 (7)	0.000
C7	0.0861 (11)	0.0587 (9)	0.0385 (7)	0.0055 (8)	0.0240 (7)	−0.0053 (6)
C8	0.119 (2)	0.0472 (12)	0.0468 (12)	0.000	0.0308 (13)	0.000
N1	0.0756 (8)	0.0596 (8)	0.0484 (7)	0.0084 (6)	0.0332 (6)	0.0117 (6)
N2	0.0489 (6)	0.0689 (8)	0.0387 (6)	−0.0036 (5)	0.0157 (5)	0.0063 (5)
O1	0.0553 (6)	0.0703 (7)	0.0374 (5)	−0.0130 (5)	0.0162 (4)	−0.0022 (4)
Cl1	0.0778 (3)	0.0608 (3)	0.0815 (4)	−0.02286 (19)	0.0447 (2)	−0.01437 (19)

C1—N1	1.303 (2)	C5—C7	1.373 (2)
C1—C4	1.4064 (18)	C5—C6	1.3789 (17)
C1—Cl1	1.7229 (15)	C5—O1	1.3991 (17)
C2—N1	1.340 (2)	C6—C5i	1.3789 (17)
C2—C3	1.362 (2)	C6—H6	0.9300
C2—H2	0.9300	C7—C8	1.379 (2)
C3—N2	1.345 (2)	C7—H7	0.9300
C3—H3	0.9300	C8—C7i	1.379 (2)
C4—N2	1.2996 (18)	C8—H8	0.9300
C4—O1	1.3584 (16)
N1—C1—C4	121.76 (14)	C6—C5—O1	117.57 (14)
N1—C1—Cl1	118.42 (11)	C5—C6—C5i	117.45 (19)
C4—C1—Cl1	119.81 (11)	C5—C6—H6	121.3
N1—C2—C3	121.90 (14)	C5i—C6—H6	121.3
N1—C2—H2	119.0	C5—C7—C8	118.51 (15)
C3—C2—H2	119.0	C5—C7—H7	120.7
N2—C3—C2	121.51 (15)	C8—C7—H7	120.7
N2—C3—H3	119.2	C7i—C8—C7	121.1 (2)
C2—C3—H3	119.2	C7i—C8—H8	119.4
N2—C4—O1	120.78 (11)	C7—C8—H8	119.4
N2—C4—C1	121.62 (12)	C1—N1—C2	116.50 (13)
O1—C4—C1	117.60 (12)	C4—N2—C3	116.71 (13)
C7—C5—C6	122.18 (14)	C4—O1—C5	116.90 (10)
C7—C5—O1	120.12 (13)
N1—C2—C3—N2	−0.1 (3)	C4—C1—N1—C2	−0.2 (2)
N1—C1—C4—N2	0.0 (2)	Cl1—C1—N1—C2	−179.30 (12)
Cl1—C1—C4—N2	179.08 (11)	C3—C2—N1—C1	0.3 (3)
N1—C1—C4—O1	179.94 (13)	O1—C4—N2—C3	−179.81 (14)
Cl1—C1—C4—O1	−0.95 (17)	C1—C4—N2—C3	0.2 (2)
C7—C5—C6—C5i	−1.04 (11)	C2—C3—N2—C4	−0.1 (3)
O1—C5—C6—C5i	−176.94 (13)	N2—C4—O1—C5	0.4 (2)
C6—C5—C7—C8	2.0 (2)	C1—C4—O1—C5	−179.61 (12)
O1—C5—C7—C8	177.84 (11)	C7—C5—O1—C4	75.09 (18)
C5—C7—C8—C7i	−0.99 (11)	C6—C5—O1—C4	−108.92 (13)