1,4-Bis(3-chloro-pyrazin-2-yl-oxy)benzene.

In the title compound, C14H8Cl2N4O2, the pyrazine rings are orthogonal to the benzene ring, making dihedral angles of 88.42 (8) and 89.22 (8)°. The Cl atoms attached to the pyrazine rings deviate by -0.0597 (5) and 0.0009 (5) Å from the ring plane. The crystal structure features C-H⋯N hydrogen bonds.

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 a related structure, see: Nasir et al. (2010 ▶).

Experimental

Crystal data

C14H8Cl2N4O2

M = 335.14

Monoclinic,

a = 11.083 (2) Å

b = 10.0452 (17) Å

c = 12.846 (2) Å

β = 105.681 (6)°

V = 1376.9 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.48 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 = 0.869, T max = 0.909

12550 measured reflections

3461 independent reflections

2835 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.092

S = 1.04

3461 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.26 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 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813007824/pv2624sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813007824/pv2624Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813007824/pv2624Isup3.cml

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

C14H8Cl2N4O2	F(000) = 680
Mr = 335.14	Dx = 1.617 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3461 reflections
a = 11.083 (2) Å	θ = 1.9–28.5°
b = 10.0452 (17) Å	µ = 0.48 mm−1
c = 12.846 (2) Å	T = 293 K
β = 105.681 (6)°	Block, colourless
V = 1376.9 (4) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker SMART APEXII area-detector diffractometer	3461 independent reflections
Radiation source: fine-focus sealed tube	2835 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
ω and φ scans	θmax = 28.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −14→14
Tmin = 0.869, Tmax = 0.909	k = −13→12
12550 measured reflections	l = −17→17

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0434P)2 + 0.4056P] where P = (Fo2 + 2Fc2)/3
3461 reflections	(Δ/σ)max = 0.001
199 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.26 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	0.22254 (14)	1.32153 (13)	1.02506 (11)	0.0359 (3)
C2	0.01581 (16)	1.31228 (17)	1.00820 (14)	0.0480 (4)
H2	−0.0583	1.3530	1.0117	0.058*
C3	0.01374 (15)	1.18158 (17)	0.97786 (13)	0.0453 (4)
H3	−0.0615	1.1350	0.9632	0.054*
C4	0.22027 (13)	1.18857 (13)	0.99072 (11)	0.0352 (3)
C5	0.32330 (13)	1.00672 (13)	0.93800 (13)	0.0387 (3)
C6	0.30055 (14)	0.99296 (15)	0.82880 (14)	0.0431 (3)
H6	0.2838	1.0671	0.7838	0.052*
C7	0.30274 (15)	0.86655 (15)	0.78589 (14)	0.0436 (3)
H7	0.2868	0.8545	0.7116	0.052*
C8	0.32871 (13)	0.75997 (13)	0.85454 (13)	0.0386 (3)
C9	0.35300 (17)	0.77452 (16)	0.96402 (14)	0.0494 (4)
H9	0.3712	0.7007	1.0092	0.059*
C10	0.35021 (17)	0.90062 (16)	1.00675 (15)	0.0495 (4)
H10	0.3664	0.9128	1.0810	0.059*
C11	0.24232 (12)	0.55046 (13)	0.79327 (11)	0.0333 (3)
C12	0.26134 (13)	0.41769 (14)	0.76895 (11)	0.0348 (3)
C13	0.05687 (15)	0.37541 (16)	0.74872 (13)	0.0447 (4)
H13	−0.0108	0.3171	0.7325	0.054*
C14	0.03882 (14)	0.50456 (16)	0.77375 (13)	0.0437 (3)
H14	−0.0409	0.5318	0.7752	0.052*
O1	0.32804 (10)	1.13575 (10)	0.98142 (10)	0.0464 (3)
O2	0.34166 (10)	0.63330 (10)	0.81253 (10)	0.0475 (3)
Cl1	0.36216 (4)	1.40754 (4)	1.05877 (4)	0.05003 (12)
Cl2	0.40796 (4)	0.36482 (4)	0.76640 (4)	0.05393 (13)
N1	0.12198 (14)	1.38253 (13)	1.03283 (11)	0.0445 (3)
N2	0.11690 (12)	1.11893 (12)	0.96874 (11)	0.0418 (3)
N3	0.13237 (11)	0.59329 (12)	0.79629 (11)	0.0397 (3)
N4	0.17015 (13)	0.33116 (12)	0.74704 (11)	0.0430 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0523 (8)	0.0232 (6)	0.0317 (7)	0.0015 (6)	0.0104 (6)	−0.0007 (5)
C2	0.0536 (9)	0.0444 (9)	0.0482 (9)	0.0148 (7)	0.0173 (7)	−0.0002 (7)
C3	0.0455 (8)	0.0433 (9)	0.0490 (9)	0.0019 (7)	0.0158 (7)	−0.0011 (7)
C4	0.0440 (7)	0.0246 (6)	0.0371 (7)	0.0019 (5)	0.0111 (6)	−0.0030 (5)
C5	0.0363 (7)	0.0233 (6)	0.0580 (9)	−0.0015 (5)	0.0153 (6)	−0.0111 (6)
C6	0.0485 (8)	0.0272 (7)	0.0546 (9)	−0.0001 (6)	0.0155 (7)	−0.0004 (6)
C7	0.0495 (8)	0.0351 (8)	0.0481 (9)	−0.0036 (6)	0.0163 (7)	−0.0082 (7)
C8	0.0340 (6)	0.0234 (6)	0.0604 (9)	−0.0027 (5)	0.0163 (6)	−0.0116 (6)
C9	0.0643 (10)	0.0274 (7)	0.0568 (10)	0.0043 (7)	0.0171 (8)	0.0004 (7)
C10	0.0648 (10)	0.0356 (8)	0.0478 (9)	0.0022 (7)	0.0149 (8)	−0.0073 (7)
C11	0.0384 (7)	0.0253 (6)	0.0359 (7)	−0.0015 (5)	0.0096 (5)	−0.0044 (5)
C12	0.0435 (7)	0.0268 (7)	0.0332 (7)	0.0020 (5)	0.0088 (6)	−0.0041 (5)
C13	0.0495 (8)	0.0409 (8)	0.0424 (8)	−0.0151 (7)	0.0101 (7)	−0.0062 (6)
C14	0.0374 (7)	0.0441 (8)	0.0486 (9)	−0.0045 (6)	0.0099 (6)	−0.0037 (7)
O1	0.0423 (5)	0.0261 (5)	0.0716 (8)	−0.0031 (4)	0.0168 (5)	−0.0173 (5)
O2	0.0401 (5)	0.0271 (5)	0.0798 (8)	−0.0047 (4)	0.0238 (5)	−0.0206 (5)
Cl1	0.0611 (2)	0.02891 (19)	0.0576 (3)	−0.00820 (16)	0.01178 (19)	−0.00849 (16)
Cl2	0.0508 (2)	0.0412 (2)	0.0695 (3)	0.01017 (16)	0.01584 (19)	−0.01644 (19)
N1	0.0605 (8)	0.0315 (6)	0.0420 (7)	0.0106 (6)	0.0146 (6)	−0.0013 (5)
N2	0.0452 (7)	0.0310 (6)	0.0507 (8)	−0.0008 (5)	0.0154 (6)	−0.0063 (5)
N3	0.0380 (6)	0.0306 (6)	0.0504 (7)	0.0005 (5)	0.0116 (5)	−0.0049 (5)
N4	0.0569 (8)	0.0293 (6)	0.0413 (7)	−0.0071 (5)	0.0107 (6)	−0.0073 (5)

C1—N1	1.2991 (19)	C7—H7	0.9300
C1—C4	1.4047 (19)	C8—C9	1.366 (2)
C1—Cl1	1.7224 (16)	C8—O2	1.4046 (16)
C2—N1	1.335 (2)	C9—C10	1.384 (2)
C2—C3	1.368 (2)	C9—H9	0.9300
C2—H2	0.9300	C10—H10	0.9300
C3—N2	1.3377 (19)	C11—N3	1.3028 (18)
C3—H3	0.9300	C11—O2	1.3486 (16)
C4—N2	1.3065 (19)	C11—C12	1.3987 (19)
C4—O1	1.3415 (17)	C12—N4	1.3048 (19)
C5—C10	1.365 (2)	C12—Cl2	1.7184 (15)
C5—C6	1.364 (2)	C13—N4	1.337 (2)
C5—O1	1.4063 (16)	C13—C14	1.364 (2)
C6—C7	1.387 (2)	C13—H13	0.9300
C6—H6	0.9300	C14—N3	1.3383 (19)
C7—C8	1.367 (2)	C14—H14	0.9300
N1—C1—C4	121.98 (14)	C8—C9—C10	119.13 (15)
N1—C1—Cl1	118.38 (11)	C8—C9—H9	120.4
C4—C1—Cl1	119.64 (11)	C10—C9—H9	120.4
N1—C2—C3	121.38 (15)	C5—C10—C9	118.84 (16)
N1—C2—H2	119.3	C5—C10—H10	120.6
C3—C2—H2	119.3	C9—C10—H10	120.6
N2—C3—C2	121.84 (15)	N3—C11—O2	120.97 (12)
N2—C3—H3	119.1	N3—C11—C12	121.34 (13)
C2—C3—H3	119.1	O2—C11—C12	117.68 (12)
N2—C4—O1	121.26 (12)	N4—C12—C11	121.92 (13)
N2—C4—C1	121.15 (13)	N4—C12—Cl2	118.13 (11)
O1—C4—C1	117.60 (13)	C11—C12—Cl2	119.96 (11)
C10—C5—C6	122.27 (13)	N4—C13—C14	121.20 (14)
C10—C5—O1	119.01 (15)	N4—C13—H13	119.4
C6—C5—O1	118.56 (14)	C14—C13—H13	119.4
C5—C6—C7	118.91 (15)	N3—C14—C13	121.99 (14)
C5—C6—H6	120.5	N3—C14—H14	119.0
C7—C6—H6	120.5	C13—C14—H14	119.0
C8—C7—C6	118.93 (15)	C4—O1—C5	117.46 (11)
C8—C7—H7	120.5	C11—O2—C8	117.80 (11)
C6—C7—H7	120.5	C1—N1—C2	116.88 (13)
C9—C8—C7	121.91 (13)	C4—N2—C3	116.72 (13)
C9—C8—O2	118.70 (14)	C11—N3—C14	116.74 (12)
C7—C8—O2	119.15 (14)	C12—N4—C13	116.80 (13)
N1—C2—C3—N2	−1.7 (3)	N2—C4—O1—C5	5.5 (2)
N1—C1—C4—N2	−2.5 (2)	C1—C4—O1—C5	−174.53 (13)
Cl1—C1—C4—N2	177.22 (12)	C10—C5—O1—C4	−95.31 (18)
N1—C1—C4—O1	177.57 (14)	C6—C5—O1—C4	89.25 (17)
Cl1—C1—C4—O1	−2.73 (19)	N3—C11—O2—C8	11.1 (2)
C10—C5—C6—C7	1.1 (2)	C12—C11—O2—C8	−169.49 (14)
O1—C5—C6—C7	176.40 (13)	C9—C8—O2—C11	86.67 (18)
C5—C6—C7—C8	−0.6 (2)	C7—C8—O2—C11	−98.82 (17)
C6—C7—C8—C9	−0.3 (2)	C4—C1—N1—C2	1.0 (2)
C6—C7—C8—O2	−174.58 (13)	Cl1—C1—N1—C2	−178.69 (12)
C7—C8—C9—C10	0.6 (2)	C3—C2—N1—C1	1.0 (2)
O2—C8—C9—C10	174.91 (14)	O1—C4—N2—C3	−178.35 (14)
C6—C5—C10—C9	−0.8 (2)	C1—C4—N2—C3	1.7 (2)
O1—C5—C10—C9	−176.08 (15)	C2—C3—N2—C4	0.3 (2)
C8—C9—C10—C5	0.0 (3)	O2—C11—N3—C14	178.56 (14)
N3—C11—C12—N4	0.8 (2)	C12—C11—N3—C14	−0.8 (2)
O2—C11—C12—N4	−178.58 (14)	C13—C14—N3—C11	0.0 (2)
N3—C11—C12—Cl2	−179.68 (11)	C11—C12—N4—C13	0.1 (2)
O2—C11—C12—Cl2	0.94 (19)	Cl2—C12—N4—C13	−179.44 (11)
N4—C13—C14—N3	0.9 (3)	C14—C13—N4—C12	−0.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···N3i	0.93	2.60	3.480 (2)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯N3i	0.93	2.60	3.480 (2)	159

Symmetry code: (i) .