organic compounds
2,2′-[o-Phenylenebis(methylenethio)]bis(pyridine N-oxide)
aCollege of Environmental and Energy Engineering, Beijing University of Technology, Beijing 100022, People's Republic of China
*Correspondence e-mail: xieyabo@bjut.edu.cn
In the title compound, C18H16N2O2S2, the benzene ring makes dihedral angles of 7.41 and 86.59° with the two outer pyridine N-oxygen rings. Two short intramolecular C—H⋯S contacts occur. The crystal packing is stabilized by C—H⋯O hydrogen bonds, C—H⋯π interactions and weak π–π staking interactions [centroid–centroid distance 3.7596 (7) Å].
Related literature
For a related stucture, see: Han et al. (2005). For thioether compounds, see: Xie et al. (2005).
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: SMART (Bruker, 1998); cell SAINT (Bruker, 1998); data reduction: SAINT; 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.
Supporting information
10.1107/S160053680902073X/at2798sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053680902073X/at2798Isup2.hkl
2-Mercaptopyridine N-oxide (1.2719 g, 10.00 mmol) was added to a stirred solution of KOH (0.6091 g, 10.85 mmol) in ethanol (50 ml). After 30 min, o-xylylene dibromide (1.3206 g, 5.00 mmol) was added and the mixture was heated to 343 K for 6 h with vigorous stirring. The mixture was cooled to room temperature and the precipitate was filtered off and washed with ethanol and water, giving a white powder in 66.0% yield. Then, a solution of the powder in CHCl3/CH3CN with a molar ratio of 1:1 was filtered. Slow diffusion of ether into the filtrate yielded colourless prism crystals.
The H atoms H6A and H6B of the C6 atom were found from a difference Fourier map and refined freely. The rest H atoms were fixed geometrically with C—H = 0.93-0.97 Å and treated as riding with Uiso(H) = 1.2Ueq(C).
Data collection: SMART (Bruker, 1998); cell
SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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 (Sheldrick, 2008).Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level for non-hydrogen atoms. |
C18H16N2O2S2 | F(000) = 744 |
Mr = 356.47 | Dx = 1.470 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 9866 reflections |
a = 7.5075 (15) Å | θ = 2.0–27.9° |
b = 17.810 (4) Å | µ = 0.34 mm−1 |
c = 12.480 (3) Å | T = 293 K |
β = 105.20 (3)° | Prism, colourless |
V = 1610.3 (7) Å3 | 0.34 × 0.28 × 0.16 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 3145 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.017 |
Graphite monochromator | θmax = 27.9°, θmin = 2.0° |
ω scans | h = −8→9 |
9681 measured reflections | k = −17→23 |
3782 independent reflections | l = −15→16 |
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)] = 0.030 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.083 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0371P)2 + 0.5053P] where P = (Fo2 + 2Fc2)/3 |
3782 reflections | (Δ/σ)max < 0.001 |
225 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C18H16N2O2S2 | V = 1610.3 (7) Å3 |
Mr = 356.47 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.5075 (15) Å | µ = 0.34 mm−1 |
b = 17.810 (4) Å | T = 293 K |
c = 12.480 (3) Å | 0.34 × 0.28 × 0.16 mm |
β = 105.20 (3)° |
Bruker SMART CCD area-detector diffractometer | 3145 reflections with I > 2σ(I) |
9681 measured reflections | Rint = 0.017 |
3782 independent reflections |
R[F2 > 2σ(F2)] = 0.030 | 0 restraints |
wR(F2) = 0.083 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.25 e Å−3 |
3782 reflections | Δρmin = −0.20 e Å−3 |
225 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 | ||
S1 | 0.17377 (5) | 0.17901 (2) | 0.34399 (3) | 0.03675 (11) | |
S2 | −0.30419 (5) | −0.03050 (2) | −0.04963 (3) | 0.03289 (10) | |
C7 | −0.00609 (19) | 0.04497 (8) | 0.25080 (11) | 0.0304 (3) | |
N1 | −0.47078 (17) | −0.01887 (7) | −0.25627 (10) | 0.0350 (3) | |
O1 | −0.48428 (16) | −0.09127 (6) | −0.24087 (9) | 0.0458 (3) | |
C14 | −0.38096 (18) | 0.02425 (8) | −0.16810 (11) | 0.0308 (3) | |
C6 | 0.0423 (2) | 0.12465 (8) | 0.22786 (12) | 0.0335 (3) | |
C1 | 0.0008 (2) | 0.20710 (8) | 0.40531 (11) | 0.0324 (3) | |
C12 | −0.11785 (18) | 0.00251 (8) | 0.16387 (11) | 0.0301 (3) | |
C15 | −0.3632 (2) | 0.10057 (9) | −0.18273 (13) | 0.0397 (3) | |
H15A | −0.3009 | 0.1304 | −0.1235 | 0.048* | |
N2 | 0.06622 (19) | 0.25129 (7) | 0.49662 (10) | 0.0402 (3) | |
C2 | −0.1847 (2) | 0.18976 (9) | 0.37257 (13) | 0.0388 (3) | |
H2A | −0.2299 | 0.1592 | 0.3111 | 0.047* | |
C11 | −0.1519 (2) | −0.07213 (9) | 0.18381 (13) | 0.0421 (4) | |
H11A | −0.2260 | −0.1007 | 0.1270 | 0.051* | |
C13 | −0.19734 (19) | 0.03928 (8) | 0.05228 (11) | 0.0318 (3) | |
H13A | −0.0999 | 0.0646 | 0.0285 | 0.038* | |
H13B | −0.2883 | 0.0765 | 0.0587 | 0.038* | |
O2 | 0.24350 (18) | 0.26652 (7) | 0.52668 (10) | 0.0570 (3) | |
C8 | 0.0643 (2) | 0.01115 (9) | 0.35310 (12) | 0.0402 (3) | |
H8A | 0.1367 | 0.0392 | 0.4112 | 0.048* | |
C9 | 0.0293 (3) | −0.06342 (10) | 0.37091 (14) | 0.0500 (4) | |
H9A | 0.0787 | −0.0852 | 0.4401 | 0.060* | |
C18 | −0.5444 (2) | 0.01241 (10) | −0.35676 (13) | 0.0456 (4) | |
H18A | −0.6060 | −0.0178 | −0.4157 | 0.055* | |
C5 | −0.0505 (3) | 0.27874 (9) | 0.55340 (14) | 0.0536 (5) | |
H5A | −0.0048 | 0.3091 | 0.6151 | 0.064* | |
C3 | −0.3033 (3) | 0.21749 (10) | 0.43040 (16) | 0.0511 (4) | |
H3A | −0.4284 | 0.2060 | 0.4084 | 0.061* | |
C17 | −0.5296 (3) | 0.08746 (11) | −0.37289 (14) | 0.0527 (4) | |
H17A | −0.5807 | 0.1085 | −0.4424 | 0.063* | |
C16 | −0.4379 (3) | 0.13227 (10) | −0.28521 (14) | 0.0507 (4) | |
H16A | −0.4269 | 0.1836 | −0.2955 | 0.061* | |
C10 | −0.0783 (3) | −0.10491 (10) | 0.28622 (14) | 0.0512 (4) | |
H10A | −0.1019 | −0.1552 | 0.2975 | 0.061* | |
C4 | −0.2338 (3) | 0.26248 (10) | 0.52122 (17) | 0.0584 (5) | |
H4A | −0.3125 | 0.2819 | 0.5608 | 0.070* | |
H6A | 0.125 (2) | 0.1237 (9) | 0.1798 (14) | 0.042 (4)* | |
H6B | −0.062 (2) | 0.1528 (10) | 0.1903 (14) | 0.043 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.03174 (19) | 0.0384 (2) | 0.0364 (2) | −0.00423 (14) | 0.00247 (14) | −0.00293 (15) |
S2 | 0.03698 (19) | 0.03129 (19) | 0.02808 (18) | 0.00011 (14) | 0.00442 (14) | −0.00330 (13) |
C7 | 0.0319 (7) | 0.0324 (7) | 0.0271 (7) | 0.0032 (5) | 0.0081 (5) | −0.0001 (5) |
N1 | 0.0348 (6) | 0.0363 (7) | 0.0308 (6) | −0.0028 (5) | 0.0034 (5) | −0.0047 (5) |
O1 | 0.0547 (7) | 0.0324 (6) | 0.0443 (6) | −0.0074 (5) | 0.0022 (5) | −0.0070 (5) |
C14 | 0.0285 (7) | 0.0351 (7) | 0.0271 (7) | −0.0009 (5) | 0.0044 (5) | −0.0038 (5) |
C6 | 0.0403 (8) | 0.0321 (7) | 0.0267 (7) | 0.0001 (6) | 0.0064 (6) | −0.0010 (5) |
C1 | 0.0395 (8) | 0.0268 (7) | 0.0277 (7) | −0.0026 (6) | 0.0033 (6) | −0.0006 (5) |
C12 | 0.0308 (7) | 0.0320 (7) | 0.0276 (7) | 0.0021 (5) | 0.0078 (5) | −0.0003 (5) |
C15 | 0.0450 (9) | 0.0357 (8) | 0.0354 (8) | −0.0046 (6) | 0.0054 (6) | −0.0039 (6) |
N2 | 0.0555 (8) | 0.0280 (6) | 0.0312 (6) | −0.0053 (6) | 0.0009 (6) | −0.0017 (5) |
C2 | 0.0385 (8) | 0.0371 (8) | 0.0390 (8) | −0.0029 (6) | 0.0069 (6) | −0.0036 (6) |
C11 | 0.0507 (9) | 0.0357 (8) | 0.0365 (8) | −0.0049 (7) | 0.0053 (7) | 0.0004 (6) |
C13 | 0.0333 (7) | 0.0323 (7) | 0.0271 (7) | −0.0009 (5) | 0.0031 (5) | −0.0019 (5) |
O2 | 0.0580 (8) | 0.0494 (7) | 0.0497 (7) | −0.0150 (6) | −0.0107 (6) | −0.0095 (6) |
C8 | 0.0462 (9) | 0.0415 (8) | 0.0283 (7) | 0.0008 (7) | 0.0015 (6) | 0.0019 (6) |
C9 | 0.0655 (11) | 0.0444 (9) | 0.0351 (9) | 0.0038 (8) | 0.0046 (8) | 0.0130 (7) |
C18 | 0.0472 (9) | 0.0530 (10) | 0.0289 (8) | −0.0032 (8) | −0.0037 (6) | −0.0035 (7) |
C5 | 0.0920 (15) | 0.0324 (8) | 0.0374 (9) | 0.0016 (9) | 0.0186 (9) | −0.0065 (7) |
C3 | 0.0484 (10) | 0.0446 (9) | 0.0644 (12) | 0.0024 (8) | 0.0223 (9) | 0.0019 (8) |
C17 | 0.0617 (11) | 0.0541 (11) | 0.0348 (9) | −0.0003 (9) | −0.0004 (7) | 0.0086 (7) |
C16 | 0.0653 (11) | 0.0380 (9) | 0.0447 (10) | −0.0039 (8) | 0.0071 (8) | 0.0055 (7) |
C10 | 0.0695 (12) | 0.0348 (8) | 0.0467 (10) | −0.0019 (8) | 0.0104 (8) | 0.0093 (7) |
C4 | 0.0828 (14) | 0.0410 (10) | 0.0630 (12) | 0.0088 (9) | 0.0398 (11) | −0.0010 (8) |
S1—C1 | 1.7442 (15) | C2—C3 | 1.376 (2) |
S1—C6 | 1.8061 (15) | C2—H2A | 0.9300 |
S2—C14 | 1.7384 (15) | C11—C10 | 1.382 (2) |
S2—C13 | 1.8084 (14) | C11—H11A | 0.9300 |
C7—C8 | 1.385 (2) | C13—H13A | 0.9700 |
C7—C12 | 1.4055 (19) | C13—H13B | 0.9700 |
C7—C6 | 1.511 (2) | C8—C9 | 1.383 (2) |
N1—O1 | 1.3116 (16) | C8—H8A | 0.9300 |
N1—C18 | 1.351 (2) | C9—C10 | 1.367 (2) |
N1—C14 | 1.3660 (17) | C9—H9A | 0.9300 |
C14—C15 | 1.383 (2) | C18—C17 | 1.361 (3) |
C6—H6A | 0.971 (17) | C18—H18A | 0.9300 |
C6—H6B | 0.942 (18) | C5—C4 | 1.360 (3) |
C1—N2 | 1.3658 (18) | C5—H5A | 0.9300 |
C1—C2 | 1.380 (2) | C3—C4 | 1.374 (3) |
C12—C11 | 1.389 (2) | C3—H3A | 0.9300 |
C12—C13 | 1.5128 (19) | C17—C16 | 1.383 (2) |
C15—C16 | 1.376 (2) | C17—H17A | 0.9300 |
C15—H15A | 0.9300 | C16—H16A | 0.9300 |
N2—O2 | 1.3130 (18) | C10—H10A | 0.9300 |
N2—C5 | 1.355 (2) | C4—H4A | 0.9300 |
C1—S1—C6 | 101.12 (7) | C12—C11—H11A | 119.3 |
C14—S2—C13 | 101.52 (7) | C12—C13—S2 | 110.19 (10) |
C8—C7—C12 | 118.93 (13) | C12—C13—H13A | 109.6 |
C8—C7—C6 | 122.05 (13) | S2—C13—H13A | 109.6 |
C12—C7—C6 | 118.93 (12) | C12—C13—H13B | 109.6 |
O1—N1—C18 | 120.85 (12) | S2—C13—H13B | 109.6 |
O1—N1—C14 | 118.39 (12) | H13A—C13—H13B | 108.1 |
C18—N1—C14 | 120.76 (13) | C9—C8—C7 | 121.54 (14) |
N1—C14—C15 | 119.39 (13) | C9—C8—H8A | 119.2 |
N1—C14—S2 | 110.69 (10) | C7—C8—H8A | 119.2 |
C15—C14—S2 | 129.92 (11) | C10—C9—C8 | 119.57 (15) |
C7—C6—S1 | 117.35 (10) | C10—C9—H9A | 120.2 |
C7—C6—H6A | 109.0 (10) | C8—C9—H9A | 120.2 |
S1—C6—H6A | 101.6 (10) | N1—C18—C17 | 120.86 (15) |
C7—C6—H6B | 112.7 (10) | N1—C18—H18A | 119.6 |
S1—C6—H6B | 108.7 (10) | C17—C18—H18A | 119.6 |
H6A—C6—H6B | 106.4 (14) | N2—C5—C4 | 120.81 (16) |
N2—C1—C2 | 119.34 (14) | N2—C5—H5A | 119.6 |
N2—C1—S1 | 112.67 (11) | C4—C5—H5A | 119.6 |
C2—C1—S1 | 127.99 (12) | C4—C3—C2 | 118.96 (17) |
C11—C12—C7 | 118.52 (13) | C4—C3—H3A | 120.5 |
C11—C12—C13 | 122.19 (13) | C2—C3—H3A | 120.5 |
C7—C12—C13 | 119.29 (12) | C18—C17—C16 | 119.52 (16) |
C16—C15—C14 | 119.74 (14) | C18—C17—H17A | 120.2 |
C16—C15—H15A | 120.1 | C16—C17—H17A | 120.2 |
C14—C15—H15A | 120.1 | C15—C16—C17 | 119.72 (16) |
O2—N2—C5 | 121.49 (14) | C15—C16—H16A | 120.1 |
O2—N2—C1 | 118.23 (13) | C17—C16—H16A | 120.1 |
C5—N2—C1 | 120.27 (14) | C9—C10—C11 | 119.92 (15) |
C3—C2—C1 | 120.38 (15) | C9—C10—H10A | 120.0 |
C3—C2—H2A | 119.8 | C11—C10—H10A | 120.0 |
C1—C2—H2A | 119.8 | C5—C4—C3 | 120.23 (17) |
C10—C11—C12 | 121.50 (15) | C5—C4—H4A | 119.9 |
C10—C11—H11A | 119.3 | C3—C4—H4A | 119.9 |
O1—N1—C14—C15 | 179.24 (13) | S1—C1—C2—C3 | −179.40 (13) |
C18—N1—C14—C15 | −1.0 (2) | C7—C12—C11—C10 | −0.2 (2) |
O1—N1—C14—S2 | −0.70 (16) | C13—C12—C11—C10 | 180.00 (15) |
C18—N1—C14—S2 | 179.09 (12) | C11—C12—C13—S2 | −9.11 (17) |
C13—S2—C14—N1 | −178.90 (10) | C7—C12—C13—S2 | 171.08 (10) |
C13—S2—C14—C15 | 1.17 (16) | C14—S2—C13—C12 | −179.41 (9) |
C8—C7—C6—S1 | −7.41 (19) | C12—C7—C8—C9 | 1.0 (2) |
C12—C7—C6—S1 | 176.13 (10) | C6—C7—C8—C9 | −175.47 (15) |
C1—S1—C6—C7 | −80.37 (12) | C7—C8—C9—C10 | −0.5 (3) |
C6—S1—C1—N2 | −178.97 (10) | O1—N1—C18—C17 | −179.67 (16) |
C6—S1—C1—C2 | 1.27 (15) | C14—N1—C18—C17 | 0.5 (2) |
C8—C7—C12—C11 | −0.6 (2) | O2—N2—C5—C4 | 179.98 (16) |
C6—C7—C12—C11 | 175.95 (13) | C1—N2—C5—C4 | 0.5 (2) |
C8—C7—C12—C13 | 179.20 (13) | C1—C2—C3—C4 | −0.1 (3) |
C6—C7—C12—C13 | −4.23 (19) | N1—C18—C17—C16 | 0.0 (3) |
N1—C14—C15—C16 | 0.8 (2) | C14—C15—C16—C17 | −0.3 (3) |
S2—C14—C15—C16 | −179.24 (13) | C18—C17—C16—C15 | −0.1 (3) |
C2—C1—N2—O2 | 179.46 (13) | C8—C9—C10—C11 | −0.3 (3) |
S1—C1—N2—O2 | −0.33 (17) | C12—C11—C10—C9 | 0.7 (3) |
C2—C1—N2—C5 | −1.0 (2) | N2—C5—C4—C3 | 0.2 (3) |
S1—C1—N2—C5 | 179.20 (12) | C2—C3—C4—C5 | −0.4 (3) |
N2—C1—C2—C3 | 0.9 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2A···O1i | 0.93 | 2.42 | 3.133 (2) | 134 |
C5—H5A···O1ii | 0.93 | 2.38 | 3.253 (2) | 155 |
C8—H8A···S1 | 0.93 | 2.67 | 3.1105 (18) | 110 |
C11—H11A···S2 | 0.93 | 2.47 | 2.9322 (18) | 111 |
C15—H15A···O2iii | 0.93 | 2.58 | 3.461 (2) | 158 |
C9—H9A···Cg2iv | 0.93 | 2.90 | 3.645 (2) | 138 |
Symmetry codes: (i) −x−1, −y, −z; (ii) −x−1/2, y+1/2, −z+1/2; (iii) x−1/2, −y+1/2, z−1/2; (iv) −x, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C18H16N2O2S2 |
Mr | 356.47 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 7.5075 (15), 17.810 (4), 12.480 (3) |
β (°) | 105.20 (3) |
V (Å3) | 1610.3 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.34 |
Crystal size (mm) | 0.34 × 0.28 × 0.16 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9681, 3782, 3145 |
Rint | 0.017 |
(sin θ/λ)max (Å−1) | 0.658 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.030, 0.083, 1.02 |
No. of reflections | 3782 |
No. of parameters | 225 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.25, −0.20 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2A···O1i | 0.9300 | 2.4200 | 3.133 (2) | 134.00 |
C5—H5A···O1ii | 0.9300 | 2.3800 | 3.253 (2) | 155.00 |
C8—H8A···S1 | 0.9300 | 2.6700 | 3.1105 (18) | 110.00 |
C11—H11A···S2 | 0.9300 | 2.4700 | 2.9322 (18) | 111.00 |
C15—H15A···O2iii | 0.9300 | 2.5800 | 3.461 (2) | 158.00 |
C9—H9A···Cg2iv | 0.93 | 2.90 | 3.645 (2) | 138 |
Symmetry codes: (i) −x−1, −y, −z; (ii) −x−1/2, y+1/2, −z+1/2; (iii) x−1/2, −y+1/2, z−1/2; (iv) −x, −y, −z+1. |
Acknowledgements
This work was supported Beijing Municipal Natural Science Foundation (grant No. 2082004).
References
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Thioether-type ligands are attracting great attention as the conformational freedom, flexible multidentate bridging ligands (Xie et al., 2005). In continuation of the structural study of thioether-type ligands (Han et al., 2005), herein, we report the crystal sructure of the title compound.
The title compound (Fig. 1) was obtained by the reaction of 2-mercaptopyridine N-oxide and o-xylylene dibromide. In the asymmetric unit, the central benzene ring makes dihedral angles of 7.44 and 86.52° with the two outer pyridine N-oxygen rings and the crystal packing is stabilized by C—H···O and C—H..S hydrogen bonding, C—H···π interactions (Table 1) and weak π-π staking interactions [centroid-to-centroid distance 3.7596 (7) Å].