Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805028941/ob6582sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805028941/ob6582Isup2.hkl |
CCDC reference: 287683
1,3-Thiazolidine-2-thione (0.60 g, 5 mmol), prepared according to the procedure of Owen (1967), and triethylamine (0.62 g, 6 mmol) were dissolved in dichloromethane (15 ml) with stirring. Phenyl chloroformate (0.95 g, 6 mmol) was added dropwise to the mixture in an ice bath. The mixture was stirred at 273 K for 6 h and then dried in vacuo to give a yellow solid of (I) (1.15 g, yield 96.2%), which was then recrystallized from ethanol by slow evaporation to give yellow blocks (m.p. 386–388 K).
All H atoms were placed in idealized positions and allowed to ride on their parent atoms (C—H = 0.97 Å), with Uiso(H) = 1.2Ueq(C).
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1993); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.
Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids. |
C10H9NO2S2 | F(000) = 496.00 |
Mr = 239.31 | Dx = 1.445 Mg m−3 |
Monoclinic, P21/c | Melting point = 386–388 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.7107 Å |
a = 11.5465 (6) Å | Cell parameters from 7221 reflections |
b = 8.9066 (4) Å | θ = 2.3–27.4° |
c = 11.9102 (6) Å | µ = 0.46 mm−1 |
β = 116.112 (2)° | T = 293 K |
V = 1099.83 (10) Å3 | Block, yellow |
Z = 4 | 0.50 × 0.50 × 0.40 mm |
Rigaku R-AXIS RAPID diffractometer | 1537 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.027 |
ω scans | θmax = 27.4° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −14→14 |
Tmin = 0.772, Tmax = 0.831 | k = −11→11 |
9973 measured reflections | l = −15→15 |
2505 independent reflections |
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.068 | w = 4Fo2/[0.0101Fo2 + σ(Fo2)] |
wR(F2) = 0.220 | (Δ/σ)max = 0.004 |
S = 1.00 | Δρmax = 0.35 e Å−3 |
2505 reflections | Δρmin = −0.41 e Å−3 |
136 parameters |
C10H9NO2S2 | V = 1099.83 (10) Å3 |
Mr = 239.31 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.5465 (6) Å | µ = 0.46 mm−1 |
b = 8.9066 (4) Å | T = 293 K |
c = 11.9102 (6) Å | 0.50 × 0.50 × 0.40 mm |
β = 116.112 (2)° |
Rigaku R-AXIS RAPID diffractometer | 2505 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 1537 reflections with F2 > 2σ(F2) |
Tmin = 0.772, Tmax = 0.831 | Rint = 0.027 |
9973 measured reflections |
R[F2 > 2σ(F2)] = 0.068 | 136 parameters |
wR(F2) = 0.220 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.35 e Å−3 |
2505 reflections | Δρmin = −0.41 e Å−3 |
Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY |
Refinement. Refinement using reflections with F2 > 2.0 σ(F2). The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
S1 | −0.0244 (1) | 0.4486 (2) | 0.2170 (1) | 0.0803 (5) | |
S2 | −0.2445 (1) | 0.6318 (2) | 0.0616 (2) | 0.0939 (5) | |
O1 | 0.1860 (3) | 0.5967 (4) | 0.1794 (4) | 0.086 (1) | |
O2 | 0.1439 (3) | 0.8042 (3) | 0.0627 (3) | 0.0640 (9) | |
N1 | −0.0216 (3) | 0.6831 (3) | 0.0709 (3) | 0.0505 (8) | |
C1 | −0.2325 (5) | 0.787 (1) | −0.023 (1) | 0.087 (4) | |
C2 | −0.1068 (4) | 0.7922 (5) | −0.0237 (4) | 0.070 (1) | |
C3 | −0.0828 (4) | 0.5889 (4) | 0.1186 (4) | 0.053 (1) | |
C4 | 0.1123 (4) | 0.6845 (4) | 0.1113 (4) | 0.053 (1) | |
C5 | 0.2761 (4) | 0.8273 (4) | 0.0987 (4) | 0.058 (1) | |
C6 | 0.3241 (5) | 0.7911 (6) | 0.0150 (5) | 0.072 (1) | |
C7 | 0.4495 (6) | 0.8240 (7) | 0.0441 (7) | 0.098 (2) | |
C8 | 0.5264 (6) | 0.8924 (7) | 0.1558 (7) | 0.095 (2) | |
C9 | 0.4782 (6) | 0.9293 (7) | 0.2379 (6) | 0.092 (2) | |
C10 | 0.3510 (5) | 0.8942 (6) | 0.2106 (5) | 0.074 (1) | |
H1 | −0.2992 | 0.7797 | −0.1083 | 0.119* | |
H2 | −0.2445 | 0.8782 | 0.0150 | 0.121* | |
H3 | −0.0709 | 0.8925 | −0.0032 | 0.078* | |
H4 | −0.1153 | 0.7641 | −0.1056 | 0.078* | |
H5 | 0.2692 | 0.7423 | −0.0634 | 0.090* | |
H6 | 0.4843 | 0.7972 | −0.0139 | 0.126* | |
H7 | 0.6151 | 0.9168 | 0.1754 | 0.114* | |
H8 | 0.5323 | 0.9796 | 0.3157 | 0.099* | |
H9 | 0.3159 | 0.9175 | 0.2691 | 0.088* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0761 (9) | 0.088 (1) | 0.0751 (9) | 0.0046 (6) | 0.0322 (7) | 0.0344 (7) |
S2 | 0.0522 (7) | 0.0702 (9) | 0.144 (1) | 0.0000 (5) | 0.0293 (8) | 0.0166 (8) |
O1 | 0.053 (2) | 0.067 (2) | 0.116 (3) | 0.009 (1) | 0.018 (2) | 0.043 (2) |
O2 | 0.059 (2) | 0.066 (2) | 0.071 (2) | 0.012 (1) | 0.032 (1) | 0.024 (1) |
N1 | 0.050 (2) | 0.042 (2) | 0.050 (2) | 0.005 (1) | 0.014 (1) | 0.006 (1) |
C1 | 0.053 (3) | 0.068 (8) | 0.118 (1) | 0.009 (4) | 0.017 (5) | 0.045 (1) |
C2 | 0.065 (3) | 0.070 (3) | 0.060 (3) | 0.019 (2) | 0.015 (2) | 0.019 (2) |
C3 | 0.050 (2) | 0.050 (2) | 0.053 (2) | −0.003 (2) | 0.018 (2) | −0.008 (2) |
C4 | 0.051 (2) | 0.047 (2) | 0.055 (2) | 0.004 (2) | 0.017 (2) | 0.004 (2) |
C5 | 0.063 (2) | 0.046 (2) | 0.067 (3) | 0.002 (2) | 0.030 (2) | 0.012 (2) |
C6 | 0.068 (3) | 0.073 (3) | 0.084 (3) | −0.013 (2) | 0.043 (2) | −0.011 (2) |
C7 | 0.081 (4) | 0.112 (5) | 0.122 (5) | −0.019 (3) | 0.063 (4) | −0.011 (4) |
C8 | 0.071 (3) | 0.096 (4) | 0.117 (5) | −0.018 (3) | 0.041 (3) | 0.001 (4) |
C9 | 0.083 (4) | 0.085 (4) | 0.079 (4) | −0.015 (3) | 0.009 (3) | 0.003 (3) |
C10 | 0.084 (3) | 0.070 (3) | 0.066 (3) | 0.005 (2) | 0.030 (2) | 0.003 (2) |
S1—C3 | 1.641 (4) | C7—C8 | 1.375 (9) |
S2—C1 | 1.750 (8) | C8—C9 | 1.360 (9) |
S2—C3 | 1.725 (4) | C9—C10 | 1.393 (9) |
O1—C4 | 1.177 (5) | C1—H1 | 0.9700 |
O2—C4 | 1.338 (5) | C1—H2 | 0.9700 |
O2—C5 | 1.407 (5) | C2—H3 | 0.9700 |
N1—C2 | 1.485 (5) | C2—H4 | 0.9700 |
N1—C3 | 1.371 (6) | C6—H5 | 0.9700 |
N1—C4 | 1.403 (5) | C7—H6 | 0.9700 |
C1—C2 | 1.460 (9) | C8—H7 | 0.9700 |
C5—C6 | 1.376 (9) | C9—H8 | 0.9700 |
C5—C10 | 1.365 (6) | C10—H9 | 0.9700 |
C6—C7 | 1.364 (8) | H3—C2 | 0.9700 |
S1—C3—S2 | 118.9 (3) | S2—C1—H1 | 108.8806 |
S1—C3—N1 | 129.5 (3) | S2—C1—H2 | 109.2747 |
C3—S2—C1 | 93.2 (3) | N1—C2—H3 | 110.1758 |
S2—C1—C2 | 111.2 (5) | N1—C2—H4 | 109.5406 |
S2—C3—N1 | 111.5 (3) | H1—C1—C2 | 109.2151 |
O1—C4—N1 | 125.7 (4) | H2—C1—C2 | 108.8356 |
O1—C4—O2 | 125.1 (4) | C1—C2—H3 | 110.2497 |
O2—C4—N1 | 109.1 (3) | C1—C2—H4 | 109.7336 |
C5—O2—C4 | 116.8 (3) | H2—C1—H1 | 109.4601 |
O2—C5—C6 | 118.2 (4) | H4—C2—H3 | 109.4621 |
O2—C5—C10 | 119.9 (5) | C5—C6—H5 | 120.1531 |
C3—N1—C2 | 115.1 (3) | C5—C10—H9 | 120.5588 |
C4—N1—C2 | 121.1 (4) | H5—C6—C7 | 120.7284 |
N1—C2—C1 | 107.7 (6) | C6—C7—H6 | 119.5422 |
C4—N1—C3 | 123.7 (3) | H6—C7—C8 | 120.2747 |
C10—C5—C6 | 121.7 (5) | C7—C8—H7 | 119.7586 |
C5—C6—C7 | 119.1 (5) | C8—C9—H8 | 120.1307 |
C5—C10—C9 | 118.4 (6) | H7—C8—C9 | 119.7272 |
C6—C7—C8 | 120.2 (7) | C9—C10—H9 | 121.0211 |
C7—C8—C9 | 120.5 (6) | H8—C9—C10 | 119.8144 |
C8—C9—C10 | 120.1 (5) | ||
C3—S2—C1—C2 | 9.2 (7) | C2—N1—C4—O1 | −174.8 (4) |
C1—S2—C3—S1 | 177.1 (2) | C2—N1—C4—O2 | 6.9 (5) |
C1—S2—C3—N1 | −3.1 (3) | C3—N1—C4—O1 | 8.6 (7) |
C5—O2—C4—O1 | −1.4 (7) | C3—N1—C4—O2 | −169.7 (3) |
C5—O2—C4—N1 | 176.9 (3) | S2—C1—C2—N1 | −12.3 (9) |
C4—O2—C5—C6 | 103.7 (5) | O2—C5—C6—C7 | 174.7 (5) |
C4—O2—C5—C10 | −80.9 (5) | C10—C5—C6—C7 | −0.6 (7) |
C3—N1—C2—C1 | 10.5 (6) | O2—C5—C10—C9 | −173.6 (4) |
C4—N1—C2—C1 | −166.4 (6) | C6—C5—C10—C9 | 1.6 (7) |
C2—N1—C3—S1 | 175.9 (3) | C5—C6—C7—C8 | 0.1 (7) |
C2—N1—C3—S2 | −3.9 (4) | C6—C7—C8—C9 | 0 (1) |
C4—N1—C3—S1 | −7.3 (6) | C7—C8—C9—C10 | 1.7 (9) |
C4—N1—C3—S2 | 172.9 (3) | C8—C9—C10—C5 | −2.2 (8) |
Experimental details
Crystal data | |
Chemical formula | C10H9NO2S2 |
Mr | 239.31 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 11.5465 (6), 8.9066 (4), 11.9102 (6) |
β (°) | 116.112 (2) |
V (Å3) | 1099.83 (10) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.46 |
Crystal size (mm) | 0.50 × 0.50 × 0.40 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.772, 0.831 |
No. of measured, independent and observed [F2 > 2σ(F2)] reflections | 9973, 2505, 1537 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.648 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.068, 0.220, 1.00 |
No. of reflections | 2505 |
No. of parameters | 136 |
No. of restraints | ? |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.35, −0.41 |
Computer programs: PROCESS-AUTO (Rigaku, 1998), PROCESS-AUTO, CrystalStructure (Rigaku/MSC, 2004), SIR97 (Altomare et al., 1993), CRYSTALS (Betteridge et al., 2003), ORTEP-3 for Windows (Farrugia, 1997), CrystalStructure.
S1—C3 | 1.641 (4) | O2—C5 | 1.407 (5) |
S2—C1 | 1.750 (8) | N1—C2 | 1.485 (5) |
S2—C3 | 1.725 (4) | N1—C3 | 1.371 (6) |
O1—C4 | 1.177 (5) | N1—C4 | 1.403 (5) |
O2—C4 | 1.338 (5) | ||
S1—C3—S2 | 118.9 (3) | S2—C3—N1 | 111.5 (3) |
S1—C3—N1 | 129.5 (3) | C3—N1—C2 | 115.1 (3) |
C3—S2—C1 | 93.2 (3) | N1—C2—C1 | 107.7 (6) |
S2—C1—C2 | 111.2 (5) | ||
C1—S2—C3—N1 | −3.1 (3) | C2—N1—C3—S2 | −3.9 (4) |
C5—O2—C4—N1 | 176.9 (3) | C3—N1—C4—O1 | 8.6 (7) |
C4—O2—C5—C6 | 103.7 (5) |
1,3-Thiazolidine-2-thione derivatives have a high potential for biological activity, and these derivatives have been widely used in agrochemical fungicides (Takashi et al., 1997). In addition, 3-acyl-1,3-thiazolidine-2-thiones can be used as active amides for peptide synthesis (Li et al., 1981). In order to investigate the structure–activity and structure–properties relationships, a series of new 1,3-thiazolidine-2-thione derivatives has been synthesized in our laboratory. We report here the structure of the title compound, (I), as an early result in our study of this series of compounds.
The molecular structure of (I) is illustrated in Fig. 1. Selected bond lengths and angles are listed in Table 1. In solution, 1,3-thiazolidine-2-thione exists in tautomeric equilibrium with its thiol form (Atzei et al., 2001). However, only the thione form is observed in the crystal of (I).