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organic compounds
1,3,5-Tris(6-chloropyrazin-2-yloxy)benzene
aSchool of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China
*Correspondence e-mail: yugp2005@yahoo.com.cn
In the title compound, C18H9Cl3N6O3, 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 and by a weak π–π stacking interaction 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
|
Data collection: SMART (Bruker, 2001); cell 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.
Supporting information
https://doi.org/10.1107/S160053680706360X/fj2085sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053680706360X/fj2085Isup2.hkl
A flask was charged with 1.26 g (10 mmol) of 1,3,5-trihydroxybenzene, 4.47 g (30 mmol) of 2,6-dichloropyrazine and 3.18 g (30 mmol) of sodium carbonate, followed by addition of 50 ml of dried MeCN. The resultant mixture was refluxed over night. On cooling, the reaction mixture was filtered and the filtrate was portioned between 150 ml of water and 200 ml of dichloromethane. The organic phase was washed with brine, dried over sodium sulfate and evaporated on a rotary evaporator to furnish the crude product as a residue, which was chromatographed on silica gel to afford the pure product as colorless prisms. Crystals suitable for X-ray diffraction were obtained via slow evaporation of a solution of the title compound in ethyl acetate.
All H atoms were placed in calculated positions, with C—H = 0.93 Å, and included in the final cycles of
using a riding model, with Uiso(H) = 1.2 times Ueq(C).Pyrazine derivatives were shown to display antimycobacterial (Seitz et al., 2002) and potential antimalarial (Temple et al., 1970) activities. The title compound was prepared for the screening of these bioactivities. We report here the
of (I).In (I) (Fig. 1), all bond lengths and angles are normal and in a good agreement with those reported previously (Carter & Boer, 1974). The dihedral angles between benzene ring (C1—C6) and three Pyrazine rings (C7—C10/N1/N2; C11—C14/N3/N4; C15—C18/N5/N6) are 72.67 (2), 60.73 (3) and 77.74 (2)°, respectively. The crystal packing is stabilized by weak π–π stacking interactions and proved by the shorter distance Cg1···Cg1ii of 3.487 (2) Å, where Cg1 is a centroid of Pyrazine ring (C11—C14/N3/N4) [symmetry code:(ii) –X,1-Y,2-Z].
For related literatures see: Carter & Boer (1974); Seitz et al. (2002); Temple et al. (1970).
Data collection: SMART (Bruker, 2001); cell
SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL (Sheldrick, 2001); molecular graphics: SHELXTL (Sheldrick, 2001); software used to prepare material for publication: SHELXTL and local programs. ![]() | Fig. 1. View of the title compound (I), with displacement ellipsoids drawn at the 40% probability level. |
C18H9Cl3N6O3 | Z = 2 |
Mr = 463.66 | F(000) = 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 = 2.8–23.1° |
c = 11.039 (3) Å | µ = 0.51 mm−1 |
α = 72.768 (3)° | T = 298 K |
β = 68.308 (3)° | Prism, colorless |
γ = 69.342 (3)° | 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) |
Graphite monochromator | Rint = 0.017 |
φ and ω scans | θmax = 25.0°, θmin = 2.0° |
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 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.108 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0537P)2 + 0.2339P] where P = (Fo2 + 2Fc2)/3 |
3375 reflections | (Δ/σ)max = 0.001 |
271 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.39 e Å−3 |
C18H9Cl3N6O3 | γ = 69.342 (3)° |
Mr = 463.66 | V = 972.0 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.680 (2) Å | Mo Kα radiation |
b = 10.658 (2) Å | µ = 0.51 mm−1 |
c = 11.039 (3) Å | T = 298 K |
α = 72.768 (3)° | 0.58 × 0.31 × 0.30 mm |
β = 68.308 (3)° |
Bruker SMART CCD area-detector diffractometer | 3375 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | 2797 reflections with I > 2σ(I) |
Tmin = 0.758, Tmax = 0.863 | Rint = 0.017 |
4925 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.108 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.22 e Å−3 |
3375 reflections | Δρmin = −0.39 e Å−3 |
271 parameters |
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) |
Experimental details
Crystal data | |
Chemical formula | C18H9Cl3N6O3 |
Mr | 463.66 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 9.680 (2), 10.658 (2), 11.039 (3) |
α, β, γ (°) | 72.768 (3), 68.308 (3), 69.342 (3) |
V (Å3) | 972.0 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.51 |
Crystal size (mm) | 0.58 × 0.31 × 0.30 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2004) |
Tmin, Tmax | 0.758, 0.863 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4925, 3375, 2797 |
Rint | 0.017 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.108, 1.04 |
No. of reflections | 3375 |
No. of parameters | 271 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.22, −0.39 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2001), SHELXTL and local programs.
References
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Carter, D. R. & Boer, F. P. (1974). J. Chem. Soc. Perkin Trans. 2, pp. 1841–1844. CrossRef Google Scholar
Seitz, L. E., Suling, W. J. & Reynolds, R. C. (2002). J. Med. Chem. 45, 5604–5606. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2001). SHELXTL. Version 5.0. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany. Google Scholar
Temple, C. Jr, Rose, J. D. & Montgomery, J. A. (1970). J. Med. Chem. 13, 1234–1235. CrossRef CAS PubMed Web of Science Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Pyrazine derivatives were shown to display antimycobacterial (Seitz et al., 2002) and potential antimalarial (Temple et al., 1970) activities. The title compound was prepared for the screening of these bioactivities. We report here the crystal structure of (I).
In (I) (Fig. 1), all bond lengths and angles are normal and in a good agreement with those reported previously (Carter & Boer, 1974). The dihedral angles between benzene ring (C1—C6) and three Pyrazine rings (C7—C10/N1/N2; C11—C14/N3/N4; C15—C18/N5/N6) are 72.67 (2), 60.73 (3) and 77.74 (2)°, respectively. The crystal packing is stabilized by weak π–π stacking interactions and van der Waals forces, proved by the shorter distance Cg1···Cg1ii of 3.487 (2) Å, where Cg1 is a centroid of Pyrazine ring (C11—C14/N3/N4) [symmetry code:(ii) –X,1-Y,2-Z].