Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270102012994/fr1383sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270102012994/fr1383Isup2.hkl |
CCDC reference: 197349
Aerial oxidation of 4-aminothiophenol leads to the disulfide which co-crystallizes with the original thiophenol leading to yellow crystals of the 1:1 molecular complex.
H atoms on C atoms were refined using a riding model starting from idealized geometries, with Uiso(H) = 1.5Ueq(C). The positions of H atoms on N and S atoms were taken from a difference Fourier map and these H atoms were also refined as riding, with Uiso(H) = 1.2Ueq(N) or 1.5Ueq(S). We note that the geometry around the amino group N1 is pyramidal and this is in accord with previous observations in crystal structures of aromatic amines where the N-atom is a hydrogen bond acceptor (Allen et al., 1997). The maximum/minimum residual electron densities are located close to the S-atoms, obviously also influencing the position of the attached H1-atom.
Data collection: SMART (Bruker, 1997); cell refinement: SMART (Bruker, 1997); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL (Bruker, 2001); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL (Bruker, 2001).
C12H12N2S2·C6H7NS | F(000) = 784 |
Mr = 373.54 | Dx = 1.389 Mg m−3 |
Monoclinic, P21/n | Melting point: 200 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 15.210 (3) Å | Cell parameters from 5202 reflections |
b = 6.0099 (11) Å | θ = 2.7–28.3° |
c = 19.683 (4) Å | µ = 0.42 mm−1 |
β = 96.814 (3)° | T = 203 K |
V = 1786.6 (6) Å3 | Rod, yellow |
Z = 4 | 0.28 × 0.08 × 0.05 mm |
Bruker SMART CCD area-detector diffractometer | 4410 independent reflections |
Radiation source: fine-focus sealed tube | 3497 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.081 |
Detector resolution: 512 pixels mm-1 | θmax = 28.3°, θmin = 1.8° |
Hemi sphere data collection scans | h = −20→20 |
Absorption correction: empirical (using intensity measurements) (SADABS; Blessing, 1995) | k = 0→8 |
Tmin = 0.89, Tmax = 0.99 | l = −26→26 |
8776 measured reflections |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.128 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.07P)2 + 0.063P] where P = (Fo2 + 2Fc2)/3 |
4410 reflections | (Δ/σ)max = 0.001 |
217 parameters | Δρmax = 0.79 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
C12H12N2S2·C6H7NS | V = 1786.6 (6) Å3 |
Mr = 373.54 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 15.210 (3) Å | µ = 0.42 mm−1 |
b = 6.0099 (11) Å | T = 203 K |
c = 19.683 (4) Å | 0.28 × 0.08 × 0.05 mm |
β = 96.814 (3)° |
Bruker SMART CCD area-detector diffractometer | 4410 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS; Blessing, 1995) | 3497 reflections with I > 2σ(I) |
Tmin = 0.89, Tmax = 0.99 | Rint = 0.081 |
8776 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.128 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.79 e Å−3 |
4410 reflections | Δρmin = −0.25 e Å−3 |
217 parameters |
Experimental. Hemi sphere data collection with omega at 0.3 ° scan width, two runs with 740 frames, phi = 0, 270(°) and two runs with 436 frames, phi = 88, 180(°) Bruker SADABS program multi-scan V2.03 R·H. Blessing, Acta Cryst. (1995) A51 33–38 |
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 | ||
C1 | 0.15155 (11) | 0.5469 (2) | 0.15570 (8) | 0.0318 (3) | |
C2 | 0.14980 (12) | 0.3331 (3) | 0.18260 (8) | 0.0352 (3) | |
H2 | 0.0982 | 0.2805 | 0.1992 | 0.042* | |
C3 | 0.22339 (12) | 0.1968 (3) | 0.18514 (8) | 0.0353 (3) | |
H3 | 0.2213 | 0.0533 | 0.2039 | 0.042* | |
C4 | 0.30057 (11) | 0.2684 (2) | 0.16057 (7) | 0.0325 (3) | |
C5 | 0.30172 (11) | 0.4846 (2) | 0.13336 (8) | 0.0333 (3) | |
H5 | 0.3532 | 0.5372 | 0.1165 | 0.040* | |
C6 | 0.22851 (11) | 0.6204 (2) | 0.13103 (8) | 0.0329 (3) | |
H6 | 0.2306 | 0.7643 | 0.1126 | 0.039* | |
N1 | 0.37355 (11) | 0.1251 (2) | 0.15862 (7) | 0.0410 (3) | |
H1A | 0.4251 | 0.1947 | 0.1624 | 0.049* | |
H1B | 0.3794 | 0.0377 | 0.1900 | 0.049* | |
S1 | 0.06154 (3) | 0.73431 (7) | 0.15535 (2) | 0.04440 (15) | |
H1 | 0.0128 | 0.6495 | 0.1577 | 0.053* | |
C7 | 0.56318 (11) | 0.7629 (3) | 0.14613 (8) | 0.0330 (3) | |
C8 | 0.59837 (12) | 0.9756 (3) | 0.15723 (9) | 0.0382 (4) | |
H8 | 0.5989 | 1.0430 | 0.2004 | 0.046* | |
C9 | 0.63242 (13) | 1.0880 (3) | 0.10530 (9) | 0.0416 (4) | |
H9 | 0.6570 | 1.2303 | 0.1137 | 0.050* | |
C10 | 0.63100 (12) | 0.9935 (3) | 0.04024 (9) | 0.0395 (4) | |
C11 | 0.59223 (12) | 0.7840 (3) | 0.02866 (8) | 0.0397 (4) | |
H11 | 0.5883 | 0.7203 | −0.0152 | 0.048* | |
C12 | 0.55975 (12) | 0.6698 (3) | 0.08127 (8) | 0.0357 (3) | |
H12 | 0.5349 | 0.5277 | 0.0730 | 0.043* | |
C13 | 0.63360 (12) | 0.7444 (3) | 0.34511 (9) | 0.0373 (4) | |
C14 | 0.68407 (12) | 0.9354 (3) | 0.33891 (9) | 0.0422 (4) | |
H14 | 0.7122 | 0.9569 | 0.2994 | 0.051* | |
C15 | 0.69319 (13) | 1.0939 (3) | 0.38987 (9) | 0.0456 (4) | |
H15 | 0.7278 | 1.2212 | 0.3849 | 0.055* | |
C16 | 0.65152 (13) | 1.0673 (3) | 0.44909 (9) | 0.0437 (4) | |
C17 | 0.60226 (13) | 0.8734 (3) | 0.45598 (9) | 0.0421 (4) | |
H17 | 0.5750 | 0.8504 | 0.4958 | 0.050* | |
C18 | 0.59399 (12) | 0.7134 (3) | 0.40442 (9) | 0.0391 (4) | |
H18 | 0.5608 | 0.5839 | 0.4097 | 0.047* | |
N2 | 0.67105 (13) | 1.0968 (3) | −0.01082 (9) | 0.0563 (5) | |
H2A | 0.6769 | 1.2344 | −0.0034 | 0.068* | |
H2B | 0.6549 | 1.0549 | −0.0527 | 0.068* | |
N3 | 0.65603 (15) | 1.2320 (3) | 0.49806 (9) | 0.0587 (5) | |
H3A | 0.6964 | 1.3430 | 0.4973 | 0.070* | |
H3B | 0.6404 | 1.1878 | 0.5363 | 0.070* | |
S2 | 0.51935 (3) | 0.61204 (7) | 0.21176 (2) | 0.03839 (14) | |
S3 | 0.62695 (3) | 0.53320 (7) | 0.28168 (2) | 0.04368 (15) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0293 (8) | 0.0331 (7) | 0.0327 (7) | 0.0009 (6) | 0.0024 (6) | −0.0046 (5) |
C2 | 0.0336 (8) | 0.0372 (8) | 0.0359 (7) | −0.0072 (7) | 0.0079 (6) | −0.0040 (6) |
C3 | 0.0420 (9) | 0.0284 (7) | 0.0352 (7) | −0.0028 (6) | 0.0037 (6) | 0.0001 (6) |
C4 | 0.0340 (8) | 0.0337 (7) | 0.0290 (7) | 0.0018 (6) | −0.0001 (6) | −0.0010 (5) |
C5 | 0.0306 (8) | 0.0360 (7) | 0.0336 (7) | −0.0041 (6) | 0.0051 (6) | 0.0011 (6) |
C6 | 0.0358 (9) | 0.0285 (7) | 0.0341 (7) | −0.0034 (6) | 0.0027 (6) | 0.0008 (5) |
N1 | 0.0405 (9) | 0.0397 (7) | 0.0420 (7) | 0.0103 (6) | 0.0012 (6) | 0.0049 (6) |
S1 | 0.0337 (3) | 0.0427 (2) | 0.0563 (3) | 0.00621 (17) | 0.0033 (2) | −0.00657 (17) |
C7 | 0.0285 (8) | 0.0338 (7) | 0.0365 (8) | 0.0021 (6) | 0.0024 (6) | 0.0016 (6) |
C8 | 0.0400 (9) | 0.0335 (7) | 0.0397 (8) | 0.0038 (7) | −0.0013 (7) | −0.0045 (6) |
C9 | 0.0407 (10) | 0.0315 (8) | 0.0502 (9) | −0.0027 (7) | −0.0050 (7) | 0.0035 (6) |
C10 | 0.0329 (8) | 0.0412 (8) | 0.0431 (9) | −0.0011 (7) | −0.0008 (7) | 0.0092 (6) |
C11 | 0.0403 (10) | 0.0445 (9) | 0.0336 (8) | −0.0032 (7) | 0.0024 (7) | −0.0008 (6) |
C12 | 0.0334 (8) | 0.0341 (7) | 0.0393 (8) | −0.0038 (6) | 0.0028 (6) | −0.0022 (6) |
C13 | 0.0306 (8) | 0.0403 (8) | 0.0399 (8) | 0.0038 (7) | −0.0003 (6) | 0.0097 (6) |
C14 | 0.0297 (9) | 0.0520 (10) | 0.0437 (9) | −0.0028 (7) | −0.0008 (7) | 0.0169 (7) |
C15 | 0.0356 (9) | 0.0455 (9) | 0.0517 (10) | −0.0089 (8) | −0.0115 (8) | 0.0167 (7) |
C16 | 0.0447 (10) | 0.0405 (8) | 0.0412 (9) | −0.0016 (8) | −0.0136 (7) | 0.0089 (7) |
C17 | 0.0453 (10) | 0.0440 (9) | 0.0359 (8) | −0.0035 (8) | 0.0009 (7) | 0.0086 (6) |
C18 | 0.0384 (9) | 0.0365 (8) | 0.0413 (8) | −0.0032 (7) | −0.0002 (7) | 0.0098 (6) |
N2 | 0.0610 (12) | 0.0582 (10) | 0.0492 (9) | −0.0189 (9) | 0.0050 (8) | 0.0137 (7) |
N3 | 0.0787 (14) | 0.0454 (8) | 0.0468 (9) | −0.0104 (9) | −0.0136 (9) | 0.0052 (7) |
S2 | 0.0341 (2) | 0.0431 (2) | 0.0387 (2) | −0.00334 (16) | 0.00754 (16) | −0.00024 (15) |
S3 | 0.0456 (3) | 0.0420 (2) | 0.0437 (2) | 0.01216 (18) | 0.00654 (19) | 0.00776 (16) |
C1—C2 | 1.391 (2) | C10—N2 | 1.383 (2) |
C1—C6 | 1.391 (2) | C10—C11 | 1.397 (2) |
C1—S1 | 1.7721 (16) | C11—C12 | 1.382 (2) |
C2—C3 | 1.383 (2) | C11—H11 | 0.9400 |
C2—H2 | 0.9400 | C12—H12 | 0.9400 |
C3—C4 | 1.390 (3) | C13—C18 | 1.388 (3) |
C3—H3 | 0.9400 | C13—C14 | 1.394 (2) |
C4—C5 | 1.407 (2) | C13—S3 | 1.7749 (18) |
C4—N1 | 1.409 (2) | C14—C15 | 1.379 (3) |
C5—C6 | 1.377 (2) | C14—H14 | 0.9400 |
C5—H5 | 0.9400 | C15—C16 | 1.400 (3) |
C6—H6 | 0.9400 | C15—H15 | 0.9400 |
N1—H1A | 0.8841 | C16—N3 | 1.378 (2) |
N1—H1B | 0.8078 | C16—C17 | 1.401 (2) |
S1—H1 | 0.9051 | C17—C18 | 1.393 (3) |
C7—C12 | 1.389 (2) | C17—H17 | 0.9400 |
C7—C8 | 1.393 (2) | C18—H18 | 0.9400 |
C7—S2 | 1.7719 (17) | N2—H2A | 0.8427 |
C8—C9 | 1.377 (3) | N2—H2B | 0.8697 |
C8—H8 | 0.9400 | N3—H3A | 0.9074 |
C9—C10 | 1.399 (3) | N3—H3B | 0.8580 |
C9—H9 | 0.9400 | S2—S3 | 2.0645 (7) |
C2—C1—C6 | 118.73 (15) | C11—C10—C9 | 118.40 (16) |
C2—C1—S1 | 122.60 (13) | C12—C11—C10 | 120.45 (15) |
C6—C1—S1 | 118.60 (12) | C12—C11—H11 | 119.8 |
C3—C2—C1 | 120.59 (16) | C10—C11—H11 | 119.8 |
C3—C2—H2 | 119.6 | C11—C12—C7 | 120.73 (15) |
C1—C2—H2 | 119.8 | C11—C12—H12 | 119.6 |
C2—C3—C4 | 121.15 (14) | C7—C12—H12 | 119.6 |
C2—C3—H3 | 119.5 | C18—C13—C14 | 118.84 (16) |
C4—C3—H3 | 119.4 | C18—C13—S3 | 120.10 (13) |
C3—C4—C5 | 117.87 (15) | C14—C13—S3 | 120.88 (15) |
C3—C4—N1 | 121.40 (14) | C15—C14—C13 | 120.96 (18) |
C5—C4—N1 | 120.60 (16) | C15—C14—H14 | 119.4 |
C6—C5—C4 | 120.91 (16) | C13—C14—H14 | 119.7 |
C6—C5—H5 | 119.5 | C14—C15—C16 | 120.67 (16) |
C4—C5—H5 | 119.5 | C14—C15—H15 | 119.7 |
C5—C6—C1 | 120.74 (14) | C16—C15—H15 | 119.6 |
C5—C6—H6 | 119.6 | N3—C16—C15 | 120.69 (18) |
C1—C6—H6 | 119.6 | N3—C16—C17 | 120.86 (19) |
C4—N1—H1A | 113.7 | C15—C16—C17 | 118.41 (16) |
C4—N1—H1B | 113.1 | C18—C17—C16 | 120.45 (18) |
H1A—N1—H1B | 103.1 | C18—C17—H17 | 119.7 |
C1—S1—H1 | 106.2 | C16—C17—H17 | 119.8 |
C12—C7—C8 | 119.04 (15) | C13—C18—C17 | 120.64 (16) |
C12—C7—S2 | 119.19 (12) | C13—C18—H18 | 119.7 |
C8—C7—S2 | 121.73 (12) | C17—C18—H18 | 119.6 |
C9—C8—C7 | 120.35 (15) | C10—N2—H2A | 111.1 |
C9—C8—H8 | 119.7 | C10—N2—H2B | 117.4 |
C7—C8—H8 | 119.9 | H2A—N2—H2B | 117.5 |
C8—C9—C10 | 120.94 (15) | C16—N3—H3A | 119.6 |
C8—C9—H9 | 119.6 | C16—N3—H3B | 113.3 |
C10—C9—H9 | 119.5 | H3A—N3—H3B | 120.0 |
N2—C10—C11 | 119.99 (17) | C7—S2—S3 | 105.44 (6) |
N2—C10—C9 | 121.52 (16) | C13—S3—S2 | 106.22 (6) |
C6—C1—C2—C3 | 0.4 (2) | C8—C7—C12—C11 | 1.2 (3) |
S1—C1—C2—C3 | −176.48 (11) | S2—C7—C12—C11 | 179.14 (13) |
C1—C2—C3—C4 | −0.5 (2) | C18—C13—C14—C15 | −1.5 (2) |
C2—C3—C4—C5 | 0.4 (2) | S3—C13—C14—C15 | −176.47 (13) |
C2—C3—C4—N1 | −175.51 (14) | C13—C14—C15—C16 | −0.3 (3) |
C3—C4—C5—C6 | −0.2 (2) | C14—C15—C16—N3 | −175.91 (17) |
N1—C4—C5—C6 | 175.72 (14) | C14—C15—C16—C17 | 1.5 (3) |
C4—C5—C6—C1 | 0.1 (2) | N3—C16—C17—C18 | 176.38 (17) |
C2—C1—C6—C5 | −0.2 (2) | C15—C16—C17—C18 | −1.1 (3) |
S1—C1—C6—C5 | 176.78 (11) | C14—C13—C18—C17 | 1.9 (3) |
C12—C7—C8—C9 | −2.6 (2) | S3—C13—C18—C17 | 176.97 (13) |
S2—C7—C8—C9 | 179.61 (14) | C16—C17—C18—C13 | −0.7 (3) |
C7—C8—C9—C10 | 1.2 (3) | C12—C7—S2—S3 | 113.14 (13) |
C8—C9—C10—N2 | −174.90 (17) | C8—C7—S2—S3 | −69.02 (14) |
C8—C9—C10—C11 | 1.5 (3) | C18—C13—S3—S2 | 94.31 (14) |
N2—C10—C11—C12 | 173.65 (17) | C14—C13—S3—S2 | −90.74 (14) |
C9—C10—C11—C12 | −2.8 (3) | C7—S2—S3—C13 | 94.81 (8) |
C10—C11—C12—C7 | 1.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2B···N1i | 0.87 | 2.34 | 3.199 (2) | 168 |
N1—H1A···S2 | 0.88 | 2.99 | 3.7452 (16) | 144 |
N3—H3A···N2ii | 0.91 | 2.52 | 3.410 (3) | 168 |
C2—H2···S2iii | 0.94 | 2.84 | 3.7387 (18) | 162 |
S1—H1···Cg3iii | 0.90 | 2.89 | 3.7310 (12) | 155 |
N3—H3B···Cg1iv | 0.86 | 2.65 | 3.312 (2) | 135 |
C3—H3···Cg1iii | 0.94 | 2.88 | 3.544 (2) | 129 |
C15—H15···Cg2ii | 0.94 | 2.83 | 3.614 (2) | 142 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+3/2, y+1/2, −z+1/2; (iii) −x+1/2, y−1/2, −z+1/2; (iv) x−1/2, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C12H12N2S2·C6H7NS |
Mr | 373.54 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 203 |
a, b, c (Å) | 15.210 (3), 6.0099 (11), 19.683 (4) |
β (°) | 96.814 (3) |
V (Å3) | 1786.6 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.42 |
Crystal size (mm) | 0.28 × 0.08 × 0.05 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Empirical (using intensity measurements) (SADABS; Blessing, 1995) |
Tmin, Tmax | 0.89, 0.99 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8776, 4410, 3497 |
Rint | 0.081 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.128, 1.04 |
No. of reflections | 4410 |
No. of parameters | 217 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.79, −0.25 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 2000), SHELXTL (Bruker, 2001).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2B···N1i | 0.87 | 2.34 | 3.199 (2) | 168.3 |
N1—H1A···S2 | 0.88 | 2.99 | 3.7452 (16) | 144.1 |
N3—H3A···N2ii | 0.91 | 2.52 | 3.410 (3) | 168.0 |
C2—H2···S2iii | 0.94 | 2.84 | 3.7387 (18) | 161.6 |
S1—H1···Cg3iii | 0.90 | 2.889 | 3.7310 (12) | 155.3 |
N3—H3B···Cg1iv | 0.86 | 2.652 | 3.312 (2) | 134.7 |
C3—H3···Cg1iii | 0.94 | 2.875 | 3.544 (2) | 129.1 |
C15—H15···Cg2ii | 0.94 | 2.825 | 3.614 (2) | 142.1 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+3/2, y+1/2, −z+1/2; (iii) −x+1/2, y−1/2, −z+1/2; (iv) x−1/2, −y+1/2, z−1/2. |
Crystals of the title complex, (I), were obtained during an investigation of 4-aminothiophenol. Aerial oxidation of this compound leads to the disulfide, which co-crystallizes with the original thiophenol to give the 1:1 molecular complex. \sch
Complex (I) illustrates a situation wherein a crystal structure is stabilized by the interplay of strong as well as weak intermolecular interactions. The molecular geometry and numbering are given in Fig. 1. The S—S distance of 2.0645 (7) Å is normal and is comparable with the length of 2.074 (1) Å reported for bis(4-aminophenyl) disulfide (Vittal & Anjali, 1998). The C—S—S—C torsion angle in (I) is 94.8 (1)° [80.2 (1)° in bis(4-aminophenyl) disulfide]. Fig. 2 shows the packing diagram of (I) viewed down the [010] axis. The intermolecular interactions and geometrical parameters are listed in Table 1.
The structure of (I) is stabilized by a finite cooperative chain of N3—H3A···N2—H2B···N1—H1A···S2 hydrogen bonds in the ac plane. The weak C2—H2···S2 interaction is anticooperative with respect to the above set of interactions. Other anticooperative interactions, namely N3—H3B···π and C3—H3···π, are also seen. A weak C15—H15···π interaction exists between screw-related molecules.
Although the S—H group is considered to be one of the classical hydrogen-bonding groups, it does not form S—H···X interactions very often (Desiraju & Steiner, 1999; Allen et al., 1997; Steiner, 2000). In (I), there is a well characterized S—H···π interaction, which is uncommon. In the Cambridge Structural Database (CSD, Version 5.23; Allen & Kennard, 1993), there are only eight crystal structures [refcodes HIPMUO (Zhu-Ohlbach et al., 1998), SIZBAE (Bernardinelli et al., 1991), TASPOS (Slusarchyk et al., 1995), TAXMUA (Nishio et al., 1996), VOPBEH (Garbarczyk & Krolikowska, 1992), YOMWAY01 (Gibbs et al.,1995), and YULZOU and YULZUA (Sellmann et al., 1995)], containing 12 thiol groups, wherein such S—H···π interactions are seen. Not many crystal structures of aminothiols have been reported to date. The present structure is in contrast with that of 6-aminopyridine-1-thiol (Sabino et al., 2002), where N—H···N hydrogen bonds are preferentially formed. References were missing for all eight refcodes - please check carefully the citations added above and the references added to the list below.