1,3,5-Tris(6-chloro-pyrazin-2-yl-oxy)benzene.

In the title compound, C(18)H(9)Cl(3)N(6)O(3), all bond lengths and angles are normal. The dihedral angles between the benzene ring and the three pyrazine rings are 72.67 (2), 60.73 (3) and 77.74 (2)°. The crystal packing is stabilized by van der Waals forces and by a weak π-π stacking inter-action between pyrazine rings, with a centroid-centroid distance of 3.487 (2) Å.

Related literature

For related literatures see: Carter & Boer (1974 ▶); Seitz et al. (2002 ▶); Temple et al. (1970 ▶).

Experimental

Crystal data

C18H9Cl3N6O3

M = 463.66

Triclinic,

a = 9.680 (2) Å

b = 10.658 (2) Å

c = 11.039 (3) Å

α = 72.768 (3)°

β = 68.308 (3)°

γ = 69.342 (3)°

V = 972.0 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.51 mm−1

T = 298 (2) K

0.58 × 0.31 × 0.30 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.758, T max = 0.863

4925 measured reflections

3375 independent reflections

2797 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.108

S = 1.04

3375 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.39 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2001 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680706360X/fj2085sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680706360X/fj2085Isup2.hkl

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

C18H9Cl3N6O3	Z = 2
Mr = 463.66	F000 = 468
Triclinic, P1	Dx = 1.584 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 9.680 (2) Å	Cell parameters from 1699 reflections
b = 10.658 (2) Å	θ = 2.8–23.1º
c = 11.039 (3) Å	µ = 0.51 mm−1
α = 72.768 (3)º	T = 298 (2) K
β = 68.308 (3)º	Prism, colorless
γ = 69.342 (3)º	0.58 × 0.31 × 0.30 mm
V = 972.0 (4) Å3

Bruker SMART CCD area-detector diffractometer	3375 independent reflections
Radiation source: fine-focus sealed tube	2797 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.017
T = 298(2) K	θmax = 25.0º
φ and ω scans	θmin = 2.0º
Absorption correction: multi-scan(SADABS; Sheldrick, 2004)	h = −9→11
Tmin = 0.758, Tmax = 0.863	k = −12→12
4925 measured reflections	l = −13→12

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)] = 0.041	H-atom parameters constrained
wR(F2) = 0.108	w = 1/[σ2(Fo2) + (0.0537P)2 + 0.2339P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
3375 reflections	Δρmax = 0.22 e Å−3
271 parameters	Δρmin = −0.39 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.04661 (7)	0.67966 (7)	0.44208 (6)	0.0642 (2)
Cl2	0.43548 (9)	1.27994 (7)	−0.59901 (7)	0.0772 (2)
Cl3	0.32169 (10)	1.47146 (8)	0.07383 (9)	0.0893 (3)
O1	0.43622 (16)	0.85408 (15)	0.05573 (15)	0.0530 (4)
O2	0.1867 (2)	0.93858 (16)	−0.27062 (15)	0.0616 (4)
O3	−0.01216 (16)	1.23869 (14)	0.03280 (16)	0.0513 (4)
N1	−0.1102 (3)	1.4653 (2)	0.2505 (2)	0.0743 (6)
N2	0.4938 (2)	0.6220 (2)	0.3517 (2)	0.0701 (6)
N3	0.2331 (3)	1.0283 (2)	−0.6181 (2)	0.0672 (6)
N4	0.1437 (2)	1.34503 (17)	0.05891 (17)	0.0469 (4)
N5	0.3057 (2)	1.09657 (17)	−0.42807 (17)	0.0459 (4)
N6	0.25692 (18)	0.76867 (16)	0.23874 (16)	0.0409 (4)
C1	0.0239 (4)	1.4929 (3)	0.2147 (3)	0.0718 (8)
H1B	0.0338	1.5541	0.2539	0.086*
C2	0.3070 (3)	1.1226 (3)	−0.6499 (2)	0.0600 (6)
H2B	0.3358	1.1674	−0.7377	0.072*
C3	−0.1181 (3)	1.3782 (3)	0.1916 (2)	0.0610 (6)
H3B	−0.2104	1.3560	0.2147	0.073*
C4	0.5191 (3)	0.7021 (3)	0.2337 (2)	0.0626 (7)
H4B	0.6188	0.7094	0.1867	0.075*
C5	0.1484 (3)	1.4320 (2)	0.1203 (2)	0.0542 (6)
C6	0.1940 (3)	0.9688 (3)	−0.4911 (2)	0.0602 (6)
H6B	0.1415	0.9025	−0.4643	0.072*
C7	0.3414 (2)	1.1549 (2)	−0.5553 (2)	0.0488 (5)
C8	0.2308 (3)	1.0047 (2)	−0.3975 (2)	0.0470 (5)
C9	0.3493 (3)	0.6156 (2)	0.4159 (2)	0.0540 (6)
H9A	0.3264	0.5614	0.5000	0.065*
C10	0.2025 (3)	0.9832 (2)	−0.1693 (2)	0.0467 (5)
C11	0.3125 (2)	0.8988 (2)	−0.1081 (2)	0.0467 (5)
H11A	0.3812	0.8202	−0.1386	0.056*
C12	0.2348 (2)	0.68880 (19)	0.3581 (2)	0.0407 (5)
C13	0.3169 (2)	0.9348 (2)	−0.0002 (2)	0.0421 (5)
C14	0.0097 (2)	1.3191 (2)	0.0952 (2)	0.0440 (5)
C15	0.1076 (2)	1.12977 (19)	−0.0168 (2)	0.0403 (5)
C16	0.2156 (2)	1.0492 (2)	0.0488 (2)	0.0409 (4)
H16A	0.2196	1.0713	0.1226	0.049*
C17	0.0996 (2)	1.0992 (2)	−0.1265 (2)	0.0444 (5)
H17A	0.0268	1.1553	−0.1699	0.053*
C18	0.3995 (2)	0.77556 (19)	0.1787 (2)	0.0419 (5)

	U11	U22	U33	U12	U13	U23
Cl1	0.0539 (3)	0.0787 (4)	0.0503 (4)	−0.0223 (3)	−0.0150 (3)	0.0057 (3)
Cl2	0.1024 (5)	0.0756 (4)	0.0561 (4)	−0.0460 (4)	−0.0100 (4)	−0.0072 (3)
Cl3	0.0920 (5)	0.0802 (5)	0.1186 (7)	−0.0405 (4)	−0.0433 (5)	−0.0155 (4)
O1	0.0408 (8)	0.0582 (9)	0.0452 (9)	−0.0084 (7)	−0.0133 (7)	0.0055 (7)
O2	0.0966 (13)	0.0628 (10)	0.0390 (9)	−0.0401 (9)	−0.0227 (8)	−0.0036 (7)
O3	0.0463 (8)	0.0467 (8)	0.0619 (10)	−0.0073 (6)	−0.0212 (7)	−0.0118 (7)
N1	0.0842 (17)	0.0791 (15)	0.0478 (13)	−0.0113 (13)	−0.0091 (11)	−0.0225 (11)
N2	0.0501 (12)	0.0856 (15)	0.0539 (13)	−0.0002 (10)	−0.0244 (10)	0.0053 (11)
N3	0.0846 (15)	0.0855 (15)	0.0436 (12)	−0.0288 (12)	−0.0243 (11)	−0.0158 (11)
N4	0.0521 (10)	0.0416 (9)	0.0439 (10)	−0.0120 (8)	−0.0150 (8)	−0.0040 (8)
N5	0.0531 (10)	0.0477 (10)	0.0367 (10)	−0.0103 (8)	−0.0156 (8)	−0.0090 (8)
N6	0.0451 (10)	0.0397 (9)	0.0361 (9)	−0.0061 (7)	−0.0174 (8)	−0.0044 (7)
C1	0.105 (2)	0.0596 (15)	0.0553 (16)	−0.0137 (15)	−0.0331 (16)	−0.0168 (13)
C2	0.0684 (15)	0.0727 (16)	0.0363 (12)	−0.0164 (13)	−0.0167 (11)	−0.0086 (11)
C3	0.0580 (14)	0.0666 (15)	0.0427 (13)	−0.0117 (12)	−0.0069 (11)	−0.0049 (12)
C4	0.0421 (12)	0.0782 (16)	0.0521 (15)	−0.0057 (11)	−0.0173 (11)	0.0003 (12)
C5	0.0693 (15)	0.0441 (12)	0.0515 (14)	−0.0153 (11)	−0.0271 (12)	−0.0008 (10)
C6	0.0758 (16)	0.0650 (14)	0.0508 (15)	−0.0256 (13)	−0.0228 (12)	−0.0137 (12)
C7	0.0502 (12)	0.0509 (12)	0.0394 (12)	−0.0091 (10)	−0.0103 (9)	−0.0097 (10)
C8	0.0562 (12)	0.0474 (12)	0.0385 (12)	−0.0122 (10)	−0.0172 (10)	−0.0080 (9)
C9	0.0569 (14)	0.0536 (12)	0.0395 (12)	−0.0016 (10)	−0.0201 (10)	−0.0010 (10)
C10	0.0627 (13)	0.0500 (12)	0.0312 (11)	−0.0271 (10)	−0.0145 (10)	0.0016 (9)
C11	0.0499 (12)	0.0434 (11)	0.0393 (12)	−0.0156 (9)	−0.0046 (9)	−0.0049 (9)
C12	0.0454 (11)	0.0378 (10)	0.0363 (11)	−0.0049 (8)	−0.0156 (9)	−0.0067 (8)
C13	0.0395 (10)	0.0442 (11)	0.0357 (11)	−0.0132 (8)	−0.0114 (9)	0.0045 (9)
C14	0.0487 (12)	0.0385 (10)	0.0361 (11)	−0.0070 (9)	−0.0142 (9)	0.0012 (8)
C15	0.0423 (11)	0.0369 (10)	0.0390 (11)	−0.0141 (8)	−0.0114 (9)	−0.0004 (8)
C16	0.0450 (11)	0.0460 (11)	0.0325 (10)	−0.0157 (9)	−0.0140 (9)	−0.0017 (8)
C17	0.0537 (12)	0.0446 (11)	0.0379 (11)	−0.0208 (10)	−0.0214 (10)	0.0070 (9)
C18	0.0429 (11)	0.0400 (10)	0.0395 (11)	−0.0049 (8)	−0.0158 (9)	−0.0060 (9)

Cl1—C12	1.735 (2)	C1—C5	1.371 (4)
Cl2—C7	1.728 (2)	C1—H1B	0.9300
Cl3—C5	1.729 (3)	C2—C7	1.367 (3)
O1—C18	1.360 (2)	C2—H2B	0.9300
O1—C13	1.402 (2)	C3—C14	1.390 (3)
O2—C8	1.351 (3)	C3—H3B	0.9300
O2—C10	1.411 (3)	C4—C18	1.386 (3)
O3—C14	1.357 (3)	C4—H4B	0.9300
O3—C15	1.396 (2)	C6—C8	1.394 (3)
N1—C3	1.317 (3)	C6—H6B	0.9300
N1—C1	1.323 (4)	C9—C12	1.364 (3)
N2—C4	1.319 (3)	C9—H9A	0.9300
N2—C9	1.330 (3)	C10—C17	1.369 (3)
N3—C2	1.326 (3)	C10—C11	1.377 (3)
N3—C6	1.326 (3)	C11—C13	1.374 (3)
N4—C14	1.312 (3)	C11—H11A	0.9300
N4—C5	1.320 (3)	C13—C16	1.377 (3)
N5—C8	1.312 (3)	C15—C17	1.379 (3)
N5—C7	1.325 (3)	C15—C16	1.382 (3)
N6—C18	1.310 (3)	C16—H16A	0.9300
N6—C12	1.328 (2)	C17—H17A	0.9300
C18—O1—C13	118.64 (15)	O2—C8—C6	116.6 (2)
C8—O2—C10	118.93 (16)	N2—C9—C12	119.8 (2)
C14—O3—C15	121.38 (16)	N2—C9—H9A	120.1
C3—N1—C1	117.2 (2)	C12—C9—H9A	120.1
C4—N2—C9	117.46 (19)	C17—C10—C11	122.6 (2)
C2—N3—C6	116.8 (2)	C17—C10—O2	119.58 (19)
C14—N4—C5	115.09 (19)	C11—C10—O2	117.48 (19)
C8—N5—C7	114.59 (18)	C13—C11—C10	117.54 (19)
C18—N6—C12	114.85 (16)	C13—C11—H11A	121.2
N1—C1—C5	120.6 (2)	C10—C11—H11A	121.2
N1—C1—H1B	119.7	N6—C12—C9	124.2 (2)
C5—C1—H1B	119.7	N6—C12—Cl1	116.16 (14)
N3—C2—C7	120.9 (2)	C9—C12—Cl1	119.64 (17)
N3—C2—H2B	119.6	C11—C13—C16	122.78 (18)
C7—C2—H2B	119.6	C11—C13—O1	117.27 (18)
N1—C3—C14	120.9 (2)	C16—C13—O1	119.85 (19)
N1—C3—H3B	119.6	N4—C14—O3	120.43 (19)
C14—C3—H3B	119.6	N4—C14—C3	122.7 (2)
N2—C4—C18	121.0 (2)	O3—C14—C3	116.8 (2)
N2—C4—H4B	119.5	C17—C15—C16	122.55 (19)
C18—C4—H4B	119.5	C17—C15—O3	115.06 (17)
N4—C5—C1	123.6 (2)	C16—C15—O3	121.97 (19)
N4—C5—Cl3	116.79 (18)	C13—C16—C15	116.97 (19)
C1—C5—Cl3	119.6 (2)	C13—C16—H16A	121.5
N3—C6—C8	120.7 (2)	C15—C16—H16A	121.5
N3—C6—H6B	119.6	C10—C17—C15	117.57 (19)
C8—C6—H6B	119.6	C10—C17—H17A	121.2
N5—C7—C2	124.0 (2)	C15—C17—H17A	121.2
N5—C7—Cl2	116.06 (17)	N6—C18—O1	120.19 (17)
C2—C7—Cl2	119.97 (18)	N6—C18—C4	122.7 (2)
N5—C8—O2	120.29 (18)	O1—C18—C4	117.13 (19)
N5—C8—C6	123.1 (2)
C3—N1—C1—C5	−0.2 (4)	N2—C9—C12—Cl1	179.78 (19)
C6—N3—C2—C7	0.5 (4)	C10—C11—C13—C16	1.0 (3)
C1—N1—C3—C14	−0.4 (4)	C10—C11—C13—O1	−175.44 (17)
C9—N2—C4—C18	−0.6 (4)	C18—O1—C13—C11	−111.4 (2)
C14—N4—C5—C1	−0.4 (3)	C18—O1—C13—C16	72.1 (2)
C14—N4—C5—Cl3	−178.98 (14)	C5—N4—C14—O3	175.50 (17)
N1—C1—C5—N4	0.7 (4)	C5—N4—C14—C3	−0.2 (3)
N1—C1—C5—Cl3	179.2 (2)	C15—O3—C14—N4	33.3 (3)
C2—N3—C6—C8	−0.4 (4)	C15—O3—C14—C3	−150.69 (19)
C8—N5—C7—C2	−1.0 (3)	N1—C3—C14—N4	0.7 (3)
C8—N5—C7—Cl2	178.31 (15)	N1—C3—C14—O3	−175.2 (2)
N3—C2—C7—N5	0.2 (4)	C14—O3—C15—C17	−150.15 (18)
N3—C2—C7—Cl2	−179.10 (19)	C14—O3—C15—C16	37.0 (3)
C7—N5—C8—O2	−179.47 (19)	C11—C13—C16—C15	−0.8 (3)
C7—N5—C8—C6	1.1 (3)	O1—C13—C16—C15	175.49 (16)
C10—O2—C8—N5	8.9 (3)	C17—C15—C16—C13	−0.1 (3)
C10—O2—C8—C6	−171.7 (2)	O3—C15—C16—C13	172.23 (17)
N3—C6—C8—N5	−0.5 (4)	C11—C10—C17—C15	−0.6 (3)
N3—C6—C8—O2	−179.9 (2)	O2—C10—C17—C15	172.20 (17)
C4—N2—C9—C12	1.0 (4)	C16—C15—C17—C10	0.8 (3)
C8—O2—C10—C17	76.1 (3)	O3—C15—C17—C10	−172.01 (17)
C8—O2—C10—C11	−110.8 (2)	C12—N6—C18—O1	179.91 (17)
C17—C10—C11—C13	−0.2 (3)	C12—N6—C18—C4	1.8 (3)
O2—C10—C11—C13	−173.20 (17)	C13—O1—C18—N6	4.8 (3)
C18—N6—C12—C9	−1.4 (3)	C13—O1—C18—C4	−177.0 (2)
C18—N6—C12—Cl1	178.83 (14)	N2—C4—C18—N6	−0.9 (4)
N2—C9—C12—N6	0.0 (3)	N2—C4—C18—O1	−179.0 (2)