organic compounds
2-(2,4-Dichlorophenyl)-3-[5-(4-methoxyphenyl)-1,3,4-thiadiazol-2-yl]-1,3-thiazolidin-4-one
aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, No. 5 Xinmofan Road, Nanjing 210009, People's Republic of China
*Correspondence e-mail: rwan@njut.edu.cn
In the molecule of the title compound, C18H13Cl2N3O2S2, the thiazolidinone ring has an with the S atom displaced by 0.394 (3) Å from the plane of the other ring atoms. The thiadiazole ring is oriented at a dihedral angle of 7.40 (4)° with respect to the 4-methoxyphenyl ring. Intramolecular C—H⋯S, C—H⋯N and C—H⋯Cl hydrogen bonds result in the formation of two planar and two non-planar five-membered rings. The planar five-membered rings are oriented at a dihedral angle of 6.23 (3)°. The 2,4-dichlorophenyl ring is oriented at dihedral angles of 84.21 (4) and 83.55 (3)° with respect to the thiadiazole and 4-methoxyphenyl rings, respectively. In the intermolecular C—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers.
Related literature
For general background, see: Chen et al. (2000); Kidwai et al. (2000); Vicentini et al. (1998); Arun et al. (1999); Wasfy et al. (1996).
Experimental
Crystal data
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Refinement
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Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); 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/S1600536808008465/hk2442sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808008465/hk2442Isup2.hkl
N-(2,4-dichlorobenzylidene)-5-(4-methoxyphenyl)-1,3,4-thiadiazol -2-amine (5 mmol) and mercapto-acetic acid (5 mmol) were added in toluene (50 ml). The water was removed by distillation for 5 h. The reaction mixture was left to cool to room temperature, filtered, and the filter cake was crystallized from acetone to give pure compound (I) (m.p. 507-509 K). Crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an acetone solution.
H atoms were positioned geometrically, with C-H = 0.93, 0.98, 0.97 and 0.96 Å for aromatic, methine, methylene and methyl H, respectively, and constrained to ride on their parent atoms with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell
CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); 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).C18H13Cl2N3O2S2 | Z = 2 |
Mr = 438.33 | F(000) = 448 |
Triclinic, P1 | Dx = 1.578 Mg m−3 |
Hall symbol: -P 1 | Melting point = 507–509 K |
a = 7.1310 (14) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.1540 (16) Å | Cell parameters from 25 reflections |
c = 16.671 (3) Å | θ = 9–12° |
α = 93.19 (3)° | µ = 0.60 mm−1 |
β = 96.43 (3)° | T = 298 K |
γ = 105.89 (3)° | Block, colorless |
V = 922.7 (3) Å3 | 0.30 × 0.10 × 0.10 mm |
Enraf–Nonius CAD-4 diffractometer | 2228 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.084 |
Graphite monochromator | θmax = 25.2°, θmin = 1.2° |
ω/2θ scans | h = 0→8 |
Absorption correction: ψ scan (North et al., 1968) | k = −9→9 |
Tmin = 0.841, Tmax = 0.943 | l = −19→19 |
3606 measured reflections | 3 standard reflections every 200 reflections |
3315 independent reflections | intensity decay: none |
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)] = 0.067 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.211 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.1P)2 + 2P] where P = (Fo2 + 2Fc2)/3 |
3315 reflections | (Δ/σ)max < 0.001 |
244 parameters | Δρmax = 0.47 e Å−3 |
0 restraints | Δρmin = −0.61 e Å−3 |
C18H13Cl2N3O2S2 | γ = 105.89 (3)° |
Mr = 438.33 | V = 922.7 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.1310 (14) Å | Mo Kα radiation |
b = 8.1540 (16) Å | µ = 0.60 mm−1 |
c = 16.671 (3) Å | T = 298 K |
α = 93.19 (3)° | 0.30 × 0.10 × 0.10 mm |
β = 96.43 (3)° |
Enraf–Nonius CAD-4 diffractometer | 2228 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.084 |
Tmin = 0.841, Tmax = 0.943 | 3 standard reflections every 200 reflections |
3606 measured reflections | intensity decay: none |
3315 independent reflections |
R[F2 > 2σ(F2)] = 0.067 | 0 restraints |
wR(F2) = 0.211 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.47 e Å−3 |
3315 reflections | Δρmin = −0.61 e Å−3 |
244 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 > 2sigma(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 | 1.3375 (3) | 0.6645 (2) | 0.50289 (13) | 0.0801 (6) | |
Cl2 | 1.1228 (2) | 1.20318 (19) | 0.40205 (10) | 0.0606 (5) | |
S1 | 0.78625 (18) | 0.7174 (2) | 0.06058 (9) | 0.0492 (4) | |
S2 | 0.5812 (2) | 0.9562 (2) | 0.33166 (11) | 0.0659 (5) | |
O1 | 1.3277 (6) | 0.6538 (6) | −0.2389 (2) | 0.0616 (11) | |
O2 | 0.4564 (5) | 0.6490 (6) | 0.1380 (3) | 0.0653 (12) | |
N1 | 1.1375 (6) | 0.9039 (7) | 0.1050 (3) | 0.0535 (13) | |
N2 | 1.0345 (6) | 0.9262 (7) | 0.1690 (3) | 0.0557 (13) | |
N3 | 0.7229 (6) | 0.8433 (6) | 0.2094 (3) | 0.0488 (12) | |
C1 | 1.5346 (9) | 0.7003 (9) | −0.2423 (4) | 0.0677 (18) | |
H1B | 1.5586 | 0.6672 | −0.2955 | 0.102* | |
H1C | 1.5962 | 0.6431 | −0.2030 | 0.102* | |
H1D | 1.5880 | 0.8220 | −0.2306 | 0.102* | |
C2 | 1.2658 (8) | 0.6915 (7) | −0.1674 (3) | 0.0481 (13) | |
C3 | 1.0653 (8) | 0.6308 (9) | −0.1639 (4) | 0.0606 (17) | |
H3A | 0.9826 | 0.5675 | −0.2088 | 0.073* | |
C4 | 0.9884 (8) | 0.6632 (8) | −0.0956 (4) | 0.0556 (16) | |
H4A | 0.8538 | 0.6203 | −0.0944 | 0.067* | |
C5 | 1.1052 (7) | 0.7578 (7) | −0.0282 (3) | 0.0444 (13) | |
C6 | 1.3061 (8) | 0.8127 (8) | −0.0323 (4) | 0.0561 (16) | |
H6A | 1.3900 | 0.8721 | 0.0131 | 0.067* | |
C7 | 1.3842 (8) | 0.7822 (8) | −0.1009 (4) | 0.0556 (16) | |
H7A | 1.5189 | 0.8237 | −0.1021 | 0.067* | |
C8 | 1.0288 (7) | 0.8015 (7) | 0.0450 (3) | 0.0451 (13) | |
C9 | 0.8518 (7) | 0.8390 (7) | 0.1524 (3) | 0.0457 (13) | |
C10 | 0.5300 (7) | 0.7452 (8) | 0.1973 (4) | 0.0491 (14) | |
C11 | 0.4280 (9) | 0.7736 (9) | 0.2684 (4) | 0.0670 (18) | |
H11A | 0.4038 | 0.6734 | 0.2987 | 0.080* | |
H11B | 0.3025 | 0.7928 | 0.2499 | 0.080* | |
C12 | 0.7992 (7) | 0.9486 (7) | 0.2846 (3) | 0.0463 (13) | |
H12A | 0.8693 | 1.0643 | 0.2731 | 0.056* | |
C13 | 0.9363 (7) | 0.8774 (7) | 0.3396 (3) | 0.0414 (12) | |
C14 | 0.9118 (8) | 0.7054 (7) | 0.3390 (4) | 0.0501 (14) | |
H14A | 0.8099 | 0.6322 | 0.3033 | 0.060* | |
C15 | 1.0296 (8) | 0.6354 (7) | 0.3883 (4) | 0.0518 (14) | |
H15A | 1.0095 | 0.5175 | 0.3865 | 0.062* | |
C16 | 1.1798 (8) | 0.7468 (8) | 0.4411 (3) | 0.0473 (13) | |
C17 | 1.2064 (7) | 0.9194 (7) | 0.4448 (3) | 0.0464 (13) | |
H17A | 1.3064 | 0.9927 | 0.4813 | 0.056* | |
C18 | 1.0853 (7) | 0.9832 (7) | 0.3946 (3) | 0.0425 (12) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0617 (10) | 0.0839 (13) | 0.0961 (14) | 0.0270 (9) | −0.0084 (9) | 0.0253 (10) |
Cl2 | 0.0494 (8) | 0.0463 (8) | 0.0828 (11) | 0.0091 (6) | 0.0096 (7) | −0.0025 (7) |
S1 | 0.0242 (6) | 0.0653 (10) | 0.0511 (9) | 0.0018 (6) | 0.0043 (6) | 0.0040 (7) |
S2 | 0.0417 (8) | 0.0898 (13) | 0.0728 (11) | 0.0289 (8) | 0.0138 (8) | −0.0028 (9) |
O1 | 0.044 (2) | 0.072 (3) | 0.058 (3) | −0.001 (2) | 0.0138 (19) | −0.011 (2) |
O2 | 0.028 (2) | 0.088 (3) | 0.068 (3) | −0.001 (2) | 0.0030 (19) | −0.002 (3) |
N1 | 0.028 (2) | 0.076 (3) | 0.051 (3) | 0.004 (2) | 0.011 (2) | −0.005 (2) |
N2 | 0.030 (2) | 0.075 (3) | 0.054 (3) | 0.002 (2) | 0.008 (2) | −0.003 (3) |
N3 | 0.026 (2) | 0.072 (3) | 0.049 (3) | 0.012 (2) | 0.012 (2) | 0.007 (2) |
C1 | 0.045 (3) | 0.090 (5) | 0.071 (4) | 0.018 (3) | 0.026 (3) | 0.002 (4) |
C2 | 0.038 (3) | 0.049 (3) | 0.053 (3) | 0.004 (2) | 0.009 (3) | 0.006 (3) |
C3 | 0.033 (3) | 0.084 (5) | 0.053 (4) | 0.004 (3) | 0.000 (3) | −0.010 (3) |
C4 | 0.025 (3) | 0.076 (4) | 0.057 (4) | 0.003 (3) | −0.001 (2) | −0.002 (3) |
C5 | 0.029 (3) | 0.048 (3) | 0.052 (3) | 0.003 (2) | 0.004 (2) | 0.005 (3) |
C6 | 0.027 (3) | 0.076 (4) | 0.050 (3) | −0.005 (3) | 0.001 (2) | −0.009 (3) |
C7 | 0.029 (3) | 0.075 (4) | 0.055 (4) | 0.001 (3) | 0.009 (3) | 0.001 (3) |
C8 | 0.025 (2) | 0.052 (3) | 0.056 (3) | 0.004 (2) | 0.007 (2) | 0.011 (3) |
C9 | 0.030 (3) | 0.056 (3) | 0.052 (3) | 0.012 (2) | 0.007 (2) | 0.011 (3) |
C10 | 0.025 (3) | 0.061 (4) | 0.062 (4) | 0.010 (2) | 0.008 (3) | 0.012 (3) |
C11 | 0.039 (3) | 0.092 (5) | 0.072 (4) | 0.018 (3) | 0.020 (3) | 0.008 (4) |
C12 | 0.034 (3) | 0.054 (3) | 0.054 (3) | 0.015 (2) | 0.010 (2) | 0.006 (3) |
C13 | 0.028 (2) | 0.048 (3) | 0.049 (3) | 0.011 (2) | 0.011 (2) | 0.000 (2) |
C14 | 0.037 (3) | 0.052 (3) | 0.058 (4) | 0.009 (3) | 0.005 (3) | −0.003 (3) |
C15 | 0.041 (3) | 0.043 (3) | 0.071 (4) | 0.011 (3) | 0.014 (3) | 0.004 (3) |
C16 | 0.035 (3) | 0.058 (4) | 0.053 (3) | 0.016 (3) | 0.010 (2) | 0.011 (3) |
C17 | 0.028 (3) | 0.057 (4) | 0.050 (3) | 0.006 (2) | 0.006 (2) | 0.000 (3) |
C18 | 0.034 (3) | 0.042 (3) | 0.054 (3) | 0.010 (2) | 0.019 (2) | 0.003 (2) |
S1—C9 | 1.721 (6) | C4—C5 | 1.375 (8) |
S1—C8 | 1.732 (5) | C4—H4A | 0.9300 |
Cl1—C16 | 1.734 (6) | C5—C6 | 1.390 (7) |
O1—C2 | 1.366 (7) | C5—C8 | 1.456 (8) |
O1—C1 | 1.427 (7) | C6—C7 | 1.366 (8) |
N1—C8 | 1.295 (7) | C6—H6A | 0.9300 |
N1—N2 | 1.393 (6) | C7—H7A | 0.9300 |
C1—H1B | 0.9600 | C10—C11 | 1.498 (8) |
C1—H1C | 0.9600 | C11—H11A | 0.9700 |
C1—H1D | 0.9600 | C11—H11B | 0.9700 |
Cl2—C18 | 1.735 (5) | C12—C13 | 1.517 (7) |
S2—C11 | 1.788 (7) | C12—H12A | 0.9800 |
S2—C12 | 1.832 (5) | C13—C14 | 1.364 (8) |
O2—C10 | 1.200 (7) | C13—C18 | 1.381 (7) |
C2—C7 | 1.358 (8) | C14—C15 | 1.367 (8) |
C2—C3 | 1.388 (7) | C14—H14A | 0.9300 |
N2—C9 | 1.292 (7) | C15—C16 | 1.383 (8) |
N3—C10 | 1.375 (7) | C15—H15A | 0.9300 |
N3—C9 | 1.399 (7) | C16—C17 | 1.365 (8) |
N3—C12 | 1.441 (7) | C17—C18 | 1.360 (8) |
C3—C4 | 1.362 (8) | C17—H17A | 0.9300 |
C3—H3A | 0.9300 | ||
C9—S1—C8 | 86.0 (3) | N2—C9—S1 | 116.2 (4) |
C2—O1—C1 | 117.6 (5) | N3—C9—S1 | 124.3 (4) |
C8—N1—N2 | 113.1 (4) | O2—C10—N3 | 124.0 (5) |
O1—C1—H1B | 109.5 | O2—C10—C11 | 125.4 (5) |
O1—C1—H1C | 109.5 | N3—C10—C11 | 110.6 (5) |
H1B—C1—H1C | 109.5 | C10—C11—S2 | 108.7 (4) |
O1—C1—H1D | 109.5 | C10—C11—H11A | 110.0 |
H1B—C1—H1D | 109.5 | S2—C11—H11A | 110.0 |
H1C—C1—H1D | 109.5 | C10—C11—H11B | 110.0 |
C11—S2—C12 | 92.5 (3) | S2—C11—H11B | 110.0 |
C7—C2—O1 | 125.2 (5) | H11A—C11—H11B | 108.3 |
C7—C2—C3 | 118.7 (5) | N3—C12—C13 | 112.7 (4) |
O1—C2—C3 | 116.1 (5) | N3—C12—S2 | 104.8 (3) |
C9—N2—N1 | 110.6 (5) | C13—C12—S2 | 111.2 (4) |
C10—N3—C9 | 122.2 (5) | N3—C12—H12A | 109.3 |
C10—N3—C12 | 119.5 (4) | C13—C12—H12A | 109.3 |
C9—N3—C12 | 118.3 (4) | S2—C12—H12A | 109.3 |
C4—C3—C2 | 120.7 (5) | C14—C13—C18 | 117.3 (5) |
C4—C3—H3A | 119.7 | C14—C13—C12 | 121.2 (5) |
C2—C3—H3A | 119.7 | C18—C13—C12 | 121.5 (5) |
C3—C4—C5 | 121.5 (5) | C13—C14—C15 | 123.3 (5) |
C3—C4—H4A | 119.2 | C13—C14—H14A | 118.4 |
C5—C4—H4A | 119.2 | C15—C14—H14A | 118.4 |
C4—C5—C6 | 116.7 (5) | C14—C15—C16 | 117.3 (5) |
C4—C5—C8 | 123.5 (5) | C14—C15—H15A | 121.4 |
C6—C5—C8 | 119.8 (5) | C16—C15—H15A | 121.4 |
C7—C6—C5 | 122.1 (5) | C17—C16—C15 | 121.2 (5) |
C7—C6—H6A | 119.0 | C17—C16—Cl1 | 119.7 (4) |
C5—C6—H6A | 119.0 | C15—C16—Cl1 | 119.0 (5) |
C2—C7—C6 | 120.2 (5) | C18—C17—C16 | 119.4 (5) |
C2—C7—H7A | 119.9 | C18—C17—H17A | 120.3 |
C6—C7—H7A | 119.9 | C16—C17—H17A | 120.3 |
N1—C8—C5 | 122.9 (4) | C17—C18—C13 | 121.5 (5) |
N1—C8—S1 | 114.1 (4) | C17—C18—Cl2 | 117.8 (4) |
C5—C8—S1 | 123.0 (4) | C13—C18—Cl2 | 120.6 (4) |
N2—C9—N3 | 119.5 (5) | ||
C1—O1—C2—C7 | 5.7 (9) | C12—N3—C10—O2 | −177.0 (6) |
C1—O1—C2—C3 | −174.3 (6) | C9—N3—C10—C11 | 179.2 (5) |
C8—N1—N2—C9 | −0.6 (7) | C12—N3—C10—C11 | 2.1 (7) |
C7—C2—C3—C4 | 0.7 (10) | O2—C10—C11—S2 | −169.0 (5) |
O1—C2—C3—C4 | −179.3 (6) | N3—C10—C11—S2 | 12.0 (7) |
C2—C3—C4—C5 | 0.6 (10) | C12—S2—C11—C10 | −17.2 (5) |
C3—C4—C5—C6 | −2.5 (9) | C10—N3—C12—C13 | 106.6 (5) |
C3—C4—C5—C8 | 177.4 (6) | C9—N3—C12—C13 | −70.6 (6) |
C4—C5—C6—C7 | 3.2 (10) | C10—N3—C12—S2 | −14.5 (6) |
C8—C5—C6—C7 | −176.8 (6) | C9—N3—C12—S2 | 168.3 (4) |
O1—C2—C7—C6 | 179.9 (6) | C11—S2—C12—N3 | 17.6 (4) |
C3—C2—C7—C6 | −0.1 (10) | C11—S2—C12—C13 | −104.5 (4) |
C5—C6—C7—C2 | −1.9 (10) | N3—C12—C13—C14 | −31.0 (7) |
N2—N1—C8—C5 | −179.4 (5) | S2—C12—C13—C14 | 86.3 (6) |
N2—N1—C8—S1 | −0.9 (7) | N3—C12—C13—C18 | 151.9 (5) |
C4—C5—C8—N1 | −173.3 (6) | S2—C12—C13—C18 | −90.8 (5) |
C6—C5—C8—N1 | 6.6 (9) | C18—C13—C14—C15 | −1.7 (8) |
C4—C5—C8—S1 | 8.3 (8) | C12—C13—C14—C15 | −178.9 (5) |
C6—C5—C8—S1 | −171.8 (5) | C13—C14—C15—C16 | 0.1 (9) |
C9—S1—C8—N1 | 1.5 (5) | C14—C15—C16—C17 | 1.4 (8) |
C9—S1—C8—C5 | −179.9 (5) | C14—C15—C16—Cl1 | −178.2 (4) |
N1—N2—C9—N3 | 179.6 (5) | C15—C16—C17—C18 | −1.3 (8) |
N1—N2—C9—S1 | 1.8 (7) | Cl1—C16—C17—C18 | 178.3 (4) |
C10—N3—C9—N2 | −175.9 (5) | C16—C17—C18—C13 | −0.3 (8) |
C12—N3—C9—N2 | 1.1 (8) | C16—C17—C18—Cl2 | 179.4 (4) |
C10—N3—C9—S1 | 1.7 (8) | C14—C13—C18—C17 | 1.7 (8) |
C12—N3—C9—S1 | 178.7 (4) | C12—C13—C18—C17 | 179.0 (5) |
C8—S1—C9—N2 | −1.9 (5) | C14—C13—C18—Cl2 | −178.0 (4) |
C8—S1—C9—N3 | −179.6 (5) | C12—C13—C18—Cl2 | −0.7 (7) |
C9—N3—C10—O2 | 0.1 (9) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4A···S1 | 0.93 | 2.79 | 3.180 (7) | 106 |
C6—H6A···N1 | 0.93 | 2.55 | 2.856 (8) | 100 |
C12—H12A···Cl2 | 0.98 | 2.63 | 3.063 (5) | 107 |
C14—H14A···N3 | 0.93 | 2.54 | 2.863 (8) | 101 |
C14—H14A···O1i | 0.93 | 2.41 | 3.219 (7) | 146 |
Symmetry code: (i) −x+2, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C18H13Cl2N3O2S2 |
Mr | 438.33 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 7.1310 (14), 8.1540 (16), 16.671 (3) |
α, β, γ (°) | 93.19 (3), 96.43 (3), 105.89 (3) |
V (Å3) | 922.7 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.60 |
Crystal size (mm) | 0.30 × 0.10 × 0.10 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.841, 0.943 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3606, 3315, 2228 |
Rint | 0.084 |
(sin θ/λ)max (Å−1) | 0.599 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.067, 0.211, 1.02 |
No. of reflections | 3315 |
No. of parameters | 244 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.47, −0.61 |
Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4A···S1 | 0.93 | 2.79 | 3.180 (7) | 106 |
C6—H6A···N1 | 0.93 | 2.55 | 2.856 (8) | 100 |
C12—H12A···Cl2 | 0.98 | 2.63 | 3.063 (5) | 107 |
C14—H14A···N3 | 0.93 | 2.54 | 2.863 (8) | 101 |
C14—H14A···O1i | 0.93 | 2.41 | 3.219 (7) | 146 |
Symmetry code: (i) −x+2, −y+1, −z. |
Acknowledgements
The authors thank Professor Hua-Qin Wang of Nanjing University for carrying out the X-ray crystallographic analysis.
References
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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.
1,3,4-Thiadiazole derivatives containing the thiazolidinone unit are of great interest because of their chemical and pharmaceutical properties. Some derivatives have fungicidal activities and exhibit certain herbicidal activities (Chen et al., 2000; Kidwai et al., 2000; Vicentini et al., 1998). On the other hand, some of them show insecticidal activities (Arun et al., 1999; Wasfy et al., 1996). We report herein the crystal structure of the title compound, (I).
In the molecule of (I), (Fig. 1), rings A (C2-C7), B (S1/N1/N2/C8/C9) and D (C13-C18) are, of course, planar. The dihedral angles between them are A/B = 7.40 (4)°, A/D = 83.55 (3)° and B/D = 84.21 (4)°. So, rings A and B are nearly coplanar. Ring C (S2/N3/C10-C12) has envelope conformation with atom S2 displaced by 0.394 (3) Å from the plane of the other ring atoms. The intramolecular C-H···S, C-H···N and C-H···Cl hydrogen bonds (Table 1) result in the formation of two planar and two non-planar five-membered rings E (S1/C4/H4A/C5/C8), F (N1/C5/C6/H6A/C8) and G (N3/C12-C14/H14A), H (Cl2/C12/H12A/C13/C18). The dihedral angle between the planar rings E and F is E/F = 6.23 (3)°, and they are oriented with respect to the adjacent rings at dihedral angles of A/E = 3.26 (4)°, A/F = 4.55 (3)°, B/E = 5.03 (4)° and B/F = 7.27 (4)°. So, they are also nearly coplanar.
In the crystal structure, intermolecular C-H···O hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers (Fig. 2), in which they may be effective in the stabilization of the structure.