Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803006627/tk6096sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803006627/tk6096Isup2.hkl |
CCDC reference: 209994
(I) was prepared using a procedure similar to a reported method (Wang et al., 1999). Yellow single crystals were obtained by recrystallization from a hot ethanol solution of the compound. IR (KBr): 3390 (s), 3260 (s), 1615 (s) cm−1. 1H NMR (DMSO-d6): δ 14.58 (1H, m), 8.89 (1H, m), 11.15 (1H, s), 7.02–7.98 (4H, s). Calculated for C9H7N3OS2: C 45.23, H2.68, N 17.50%; found: C 45.53, H 2.97, N 17.74%.
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.
C9H7N3OS2 | F(000) = 488 |
Mr = 237.30 | Dx = 1.502 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 6.587 (3) Å | Cell parameters from 662 reflections |
b = 13.723 (5) Å | θ = 3.1–26.0° |
c = 11.758 (5) Å | µ = 0.48 mm−1 |
β = 99.183 (6)° | T = 293 K |
V = 1049.2 (7) Å3 | Block, yellow |
Z = 4 | 0.30 × 0.25 × 0.20 mm |
Bruker SMART CCD area-detector diffractometer | 1822 independent reflections |
Radiation source: fine-focus sealed tube | 1440 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
ϕ and ω scans | θmax = 25.1°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Blessing, 1995; Sheldrick, 1996) | h = −4→7 |
Tmin = 0.841, Tmax = 0.890 | k = −14→16 |
2862 measured reflections | l = −12→14 |
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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.085 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0363P)2 + 0.2779P] where P = (Fo2 + 2Fc2)/3 |
1822 reflections | (Δ/σ)max < 0.001 |
137 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
C9H7N3OS2 | V = 1049.2 (7) Å3 |
Mr = 237.30 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 6.587 (3) Å | µ = 0.48 mm−1 |
b = 13.723 (5) Å | T = 293 K |
c = 11.758 (5) Å | 0.30 × 0.25 × 0.20 mm |
β = 99.183 (6)° |
Bruker SMART CCD area-detector diffractometer | 1822 independent reflections |
Absorption correction: multi-scan (SADABS; Blessing, 1995; Sheldrick, 1996) | 1440 reflections with I > 2σ(I) |
Tmin = 0.841, Tmax = 0.890 | Rint = 0.017 |
2862 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 0 restraints |
wR(F2) = 0.085 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.22 e Å−3 |
1822 reflections | Δρmin = −0.18 e Å−3 |
137 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 | 0.02404 (9) | 0.41301 (5) | 0.69266 (5) | 0.0463 (2) | |
S2 | −0.37268 (10) | 0.52545 (5) | 0.68937 (5) | 0.0553 (2) | |
N2 | −0.1020 (3) | 0.36578 (15) | 0.48081 (15) | 0.0490 (5) | |
N1 | 0.2126 (3) | 0.29468 (14) | 0.54584 (15) | 0.0451 (5) | |
N3 | −0.2447 (3) | 0.42387 (14) | 0.51818 (15) | 0.0467 (5) | |
H3A | −0.3548 | 0.4395 | 0.4721 | 0.056* | |
C6 | 0.5334 (3) | 0.21686 (16) | 0.61021 (17) | 0.0389 (5) | |
C5 | 0.6984 (4) | 0.20360 (16) | 0.70044 (19) | 0.0445 (6) | |
H5 | 0.6946 | 0.2334 | 0.7711 | 0.053* | |
C7 | 0.3638 (3) | 0.27793 (16) | 0.62733 (18) | 0.0413 (5) | |
H7 | 0.3632 | 0.3061 | 0.6992 | 0.050* | |
C8 | 0.0505 (4) | 0.35235 (16) | 0.56372 (17) | 0.0418 (6) | |
C9 | −0.2142 (3) | 0.45686 (16) | 0.62677 (18) | 0.0422 (5) | |
C1 | 0.5415 (4) | 0.16994 (19) | 0.50441 (19) | 0.0512 (6) | |
C4 | 0.8644 (4) | 0.14782 (18) | 0.6865 (2) | 0.0528 (6) | |
H4 | 0.9729 | 0.1402 | 0.7469 | 0.063* | |
O1 | 0.3886 (3) | 0.17983 (17) | 0.41334 (14) | 0.0781 (6) | |
H1 | 0.2950 | 0.2121 | 0.4326 | 0.117* | |
C3 | 0.8696 (5) | 0.10311 (19) | 0.5824 (2) | 0.0627 (8) | |
H3 | 0.9835 | 0.0658 | 0.5727 | 0.075* | |
C2 | 0.7088 (5) | 0.1126 (2) | 0.4918 (2) | 0.0665 (8) | |
H2 | 0.7134 | 0.0804 | 0.4226 | 0.080* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0449 (4) | 0.0553 (4) | 0.0351 (3) | 0.0079 (3) | −0.0048 (2) | −0.0032 (3) |
S2 | 0.0478 (4) | 0.0715 (5) | 0.0436 (3) | 0.0128 (3) | −0.0018 (3) | −0.0044 (3) |
N2 | 0.0479 (12) | 0.0623 (13) | 0.0345 (10) | 0.0063 (10) | −0.0005 (9) | 0.0006 (9) |
N1 | 0.0472 (12) | 0.0529 (12) | 0.0340 (10) | 0.0069 (10) | 0.0025 (9) | 0.0004 (8) |
N3 | 0.0418 (11) | 0.0608 (12) | 0.0342 (10) | 0.0058 (10) | −0.0040 (8) | 0.0020 (9) |
C6 | 0.0442 (13) | 0.0413 (12) | 0.0315 (11) | 0.0006 (10) | 0.0066 (10) | 0.0035 (9) |
C5 | 0.0513 (14) | 0.0470 (13) | 0.0339 (11) | 0.0025 (12) | 0.0032 (10) | 0.0028 (10) |
C7 | 0.0473 (14) | 0.0471 (13) | 0.0296 (11) | −0.0016 (11) | 0.0063 (10) | 0.0011 (9) |
C8 | 0.0460 (14) | 0.0476 (13) | 0.0304 (11) | −0.0014 (11) | 0.0017 (10) | 0.0029 (10) |
C9 | 0.0411 (13) | 0.0455 (13) | 0.0377 (12) | −0.0039 (11) | −0.0011 (10) | 0.0044 (10) |
C1 | 0.0621 (17) | 0.0565 (15) | 0.0335 (12) | 0.0081 (13) | 0.0030 (11) | 0.0002 (11) |
C4 | 0.0528 (15) | 0.0550 (15) | 0.0479 (14) | 0.0107 (13) | −0.0001 (11) | 0.0057 (12) |
O1 | 0.0837 (15) | 0.1076 (16) | 0.0364 (9) | 0.0337 (13) | −0.0111 (9) | −0.0168 (10) |
C3 | 0.0703 (19) | 0.0609 (17) | 0.0582 (16) | 0.0254 (15) | 0.0145 (14) | 0.0017 (13) |
C2 | 0.086 (2) | 0.0679 (18) | 0.0450 (14) | 0.0236 (16) | 0.0093 (14) | −0.0100 (13) |
S1—C9 | 1.743 (2) | C5—C4 | 1.366 (3) |
S1—C8 | 1.762 (2) | C5—H5 | 0.9300 |
S2—C9 | 1.662 (3) | C7—H7 | 0.9300 |
N2—C8 | 1.296 (3) | C1—O1 | 1.354 (3) |
N2—N3 | 1.358 (3) | C1—C2 | 1.382 (4) |
N1—C7 | 1.288 (3) | C4—C3 | 1.375 (3) |
N1—C8 | 1.372 (3) | C4—H4 | 0.9300 |
N3—C9 | 1.339 (3) | O1—H1 | 0.8200 |
N3—H3A | 0.8600 | C3—C2 | 1.383 (4) |
C6—C5 | 1.404 (3) | C3—H3 | 0.9300 |
C6—C1 | 1.409 (3) | C2—H2 | 0.9300 |
C6—C7 | 1.436 (3) | ||
C9—S1—C8 | 89.22 (11) | N1—C8—S1 | 126.19 (16) |
C8—N2—N3 | 109.48 (19) | N3—C9—S2 | 127.19 (17) |
C7—N1—C8 | 121.16 (19) | N3—C9—S1 | 107.13 (17) |
C9—N3—N2 | 120.04 (18) | S2—C9—S1 | 125.68 (13) |
C9—N3—H3A | 120.0 | O1—C1—C2 | 118.5 (2) |
N2—N3—H3A | 120.0 | O1—C1—C6 | 121.6 (2) |
C5—C6—C1 | 118.3 (2) | C2—C1—C6 | 119.9 (2) |
C5—C6—C7 | 119.69 (19) | C5—C4—C3 | 119.4 (2) |
C1—C6—C7 | 122.0 (2) | C5—C4—H4 | 120.3 |
C4—C5—C6 | 121.3 (2) | C3—C4—H4 | 120.3 |
C4—C5—H5 | 119.3 | C1—O1—H1 | 109.5 |
C6—C5—H5 | 119.3 | C4—C3—C2 | 121.3 (3) |
N1—C7—C6 | 121.8 (2) | C4—C3—H3 | 119.4 |
N1—C7—H7 | 119.1 | C2—C3—H3 | 119.4 |
C6—C7—H7 | 119.1 | C1—C2—C3 | 119.8 (2) |
N2—C8—N1 | 119.7 (2) | C1—C2—H2 | 120.1 |
N2—C8—S1 | 114.12 (18) | C3—C2—H2 | 120.1 |
C8—N2—N3—C9 | −0.4 (3) | N2—N3—C9—S1 | 1.2 (3) |
C1—C6—C5—C4 | 0.8 (3) | C8—S1—C9—N3 | −1.20 (17) |
C7—C6—C5—C4 | −178.5 (2) | C8—S1—C9—S2 | 178.05 (17) |
C8—N1—C7—C6 | 179.3 (2) | C5—C6—C1—O1 | −179.6 (2) |
C5—C6—C7—N1 | 177.7 (2) | C7—C6—C1—O1 | −0.3 (4) |
C1—C6—C7—N1 | −1.6 (3) | C5—C6—C1—C2 | 0.1 (4) |
N3—N2—C8—N1 | 179.24 (19) | C7—C6—C1—C2 | 179.4 (2) |
N3—N2—C8—S1 | −0.6 (3) | C6—C5—C4—C3 | −0.5 (4) |
C7—N1—C8—N2 | −178.2 (2) | C5—C4—C3—C2 | −0.8 (4) |
C7—N1—C8—S1 | 1.6 (3) | O1—C1—C2—C3 | 178.4 (3) |
C9—S1—C8—N2 | 1.12 (19) | C6—C1—C2—C3 | −1.3 (4) |
C9—S1—C8—N1 | −178.8 (2) | C4—C3—C2—C1 | 1.7 (5) |
N2—N3—C9—S2 | −178.03 (17) |
Experimental details
Crystal data | |
Chemical formula | C9H7N3OS2 |
Mr | 237.30 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 6.587 (3), 13.723 (5), 11.758 (5) |
β (°) | 99.183 (6) |
V (Å3) | 1049.2 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.48 |
Crystal size (mm) | 0.30 × 0.25 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Blessing, 1995; Sheldrick, 1996) |
Tmin, Tmax | 0.841, 0.890 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2862, 1822, 1440 |
Rint | 0.017 |
(sin θ/λ)max (Å−1) | 0.597 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.085, 1.06 |
No. of reflections | 1822 |
No. of parameters | 137 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.22, −0.18 |
Computer programs: SMART (Bruker, 1998), SMART, SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998), SHELXTL.
S1—C9 | 1.743 (2) | N1—C7 | 1.288 (3) |
S1—C8 | 1.762 (2) | N1—C8 | 1.372 (3) |
S2—C9 | 1.662 (3) | N3—C9 | 1.339 (3) |
N2—C8 | 1.296 (3) | C1—O1 | 1.354 (3) |
N2—N3 | 1.358 (3) | ||
C7—N1—C8 | 121.16 (19) | N1—C7—C6 | 121.8 (2) |
The biological versatility of compounds incorporating a thiadiazole ring is well known (Kumar et al., 1988; Yadav et al., 1989). In this connection, it was thought of interest to combine a Schiff base with a thiadiazole ring system. Thus, the synthesis and structure of a new compound, namely 5-[(2-hydroxyphenyl)methyleneamino]-1,3,4-thiadiazole-2(3H)-thione, (I), is reported.
The molecular structure of (I) (Fig. 1 and Table 1) has two approximately parallel fragments linked by an Schiff base, with the dihedral angle between the aromatic and thiadiazole rings being 1.0 (1)°. The C9—S2 bond length of 1.662 (3) Å is approximately 0.08 Å shorter than the C9—S1 bond length, confirming the presence of the thione. There is an O1—H···N1 intramolecular hydrogen-bonding interaction, so that the O···N separation is 2.614 (3) Å, with an O—H···N angle of 146°. Centrosymmetrically related molecules associate via N—H···Si contacts [H···S2i = 2.44° and N3···S2i = 3.291 (2) Å; symmetry code: (i) −1 − x, 1 − y, 1 − z]. There is also a C7—H···O1ii interaction with a C···Oii separation of 3.391 (3) Å [symmetry code: (ii) x, 1/2 − y, 1/2 + z].
Further work investigating the biological profile of (I) is in progress.