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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 12| December 2011| Page o3437
https://doi.org/10.1107/S1600536811049877

(E)-5-[(3-Eth­­oxy-2-hy­dr­oxy­benzyl­­idene)amino]-1,3,4-thia­diazole-2(3H)-thione

Hadi Kargara* and Reza Kiab,c

aDepartment of Chemistry, Payame Noor University, PO BOX 19395-3697 Tehran, Iran, bX-ray Crystallography Lab., Plasma Physics Research Center, Science and Research Branch, Islamic Azad University, Tehran, Iran, and cDepartment of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran
*Correspondence e-mail: hkargar@pnu.ac.ir

(Received 19 November 2011; accepted 21 November 2011; online 25 November 2011)

In the title compound, C11H11N3O2S2, the dihedral angle between the benzene ring and the five-membered ring is 6.85 (9)°. An intra­molecular O—H⋯N hydrogen bond makes an S(6) ring motif. In the crystal, mol­ecules are linked through bifurcated N—H⋯(O,O) hydrogen bonds with R12(5) ring motifs, forming chains along the b axis. A short C⋯S contact [3.3189 (19) Å], which is shorter than the sum of the van der Waals radii of these atoms (3.50 Å), occurs in the structure. The crystal structure is further stabilized by C—H⋯N hydrogen bonding and π–π inter­actions [centroid–centroid distance = 3.7649 (12) Å].

Related literature

For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For the biological versatility of thione ligands, see, for example: Kumar et al. (1988[Kumar, R., Giri S. & Nizamuddin (1988). J. Indian Chem. Soc. 65, 572-573.]); Yadav et al. (1989[Yadav, L. D. S., Shukla, K. N. & Singh, H. (1989). Indian J. Chem. Sect. B, 28, 78-80.]). For related structures, see: Zhang (2003[Zhang, Y.-X. (2003). Acta Cryst. E59, o581-o582.]); Kargar et al., (2011[Kargar, H., Kia, R. & Tahir, M. N. (2011). Acta Cryst. E67, o3311.]). For van der Waals radii, see: Bondi (1964[Bondi, A. (1964). J. Phys. Chem. 68, 441-451.]).

[Scheme 1]

Experimental

Crystal data

  • C11H11N3O2S2

  • Mr = 281.35

  • Monoclinic, P 21 /c

  • a = 8.925 (1) Å

  • b = 11.3664 (14) Å

  • c = 12.8945 (16) Å

  • β = 99.352 (9)°

  • V = 1290.7 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.41 mm−1

  • T = 291 K

  • 0.25 × 0.22 × 0.15 mm
Data collection

  • Stoe IPDS 2T Image Plate diffractometer

  • Absorption correction: multi-scan [MULABS (Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) in PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.])] Tmin = 0.905, Tmax = 0.941

  • 10227 measured reflections

  • 3461 independent reflections

  • 2376 reflections with I > 2σ(I)

  • Rint = 0.036
Refinement

  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.103

  • S = 1.00

  • 3461 reflections

  • 164 parameters

  • H-atom parameters constrained

  • Δρmax = 0.24 e Å−3

  • Δρmin = −0.30 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1⋯N1 0.87 1.81 2.5924 (19) 150
N3—H3⋯O1i 0.83 2.15 2.841 (2) 141
N3—H3⋯O2i 0.83 2.47 3.160 (2) 142
C3—H3A⋯N2ii 0.93 2.60 3.312 (3) 133
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: X-AREA (Stoe & Cie, 2009[Stoe & Cie (2009). X-AREA. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811049877/ff2044sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811049877/ff2044Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811049877/ff2044Isup3.cml

checkCIF report


Comment top

The biological versatility of compounds incorporating a thiadiazole ring is well known (Kumar et al., 1988; Yadav et al., 1989).

The asymmetric unit of the title compound, Fig. 1, comprises a thione-Schiff base ligand. The bond lengths (Allen et al., 1987) and angles are within the normal ranges and are comparable to the related structures (Zhang, 2003; Kargar et al., 2011).

The dihedral angle between the benzene ring and the five-membered ring is 6.85 (9)°. The intramolecular O—H···N hydrogen bond makes S22(6) ring motif (Bernstein et al.,1995). In the crystal packing molecules are linked together through bifurcated N—H···O hydrogen bonds with R21(5) ring motifs (Bernstein et al.,1995), forming one-dimensional extended chains along the b axis. The interesting feature of the crystal structure is the short C7···S2 contact [3.3189 (19)Å; (i) 2 - x, 1/2 + y, 1/2 - z], which is shorter than the sum of the van der Waals radii of these atoms [3.50Å]. The crystal structure is further stabilized by the intermolecular C—H···N hydrogen bonds and π-π interaction [Cg1···Cg2i = 3.7649 (12)Å, (i) 1 - x, 1 - y, -z; Cg1 and Cg2 are centroids of S(1)/C(8)/N(2)/N(3)/C(9) and C1–C6 rings, respectively].

Related literature top

For standard bond lengths, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the biological versatility of thione ligands, see, for example: Kumar et al. (1988); Yadav et al. (1989). For related structures, see: Zhang (2003); Kargar et al., (2011). For van der Waals radii, see: Bondi (1964).

Experimental top

The title compound was synthesized by adding 3-ethoxy-salicylaldehyde (1 mmol) to a solution of 5-aminothiophene-2-thiol (1 mmol) in ethanol (30 ml). The mixture was refluxed with stirring for half an hour. The resultant solution was filtered. Yellow single crystals of the title compound suitable for X-ray structure determination were recrystallized from ethanol by slow evaporation of the solvents at room temperature over several days.

Refinement top

All hydrogen atoms were positioned geometrically with C—H = 0.93–0.97 Å and included in a riding model approximation with Uiso (H) = 1.2 or 1.5 Ueq (C). A rotating group model was applied to the methyl group.

Structure description top

The biological versatility of compounds incorporating a thiadiazole ring is well known (Kumar et al., 1988; Yadav et al., 1989).

The asymmetric unit of the title compound, Fig. 1, comprises a thione-Schiff base ligand. The bond lengths (Allen et al., 1987) and angles are within the normal ranges and are comparable to the related structures (Zhang, 2003; Kargar et al., 2011).

The dihedral angle between the benzene ring and the five-membered ring is 6.85 (9)°. The intramolecular O—H···N hydrogen bond makes S22(6) ring motif (Bernstein et al.,1995). In the crystal packing molecules are linked together through bifurcated N—H···O hydrogen bonds with R21(5) ring motifs (Bernstein et al.,1995), forming one-dimensional extended chains along the b axis. The interesting feature of the crystal structure is the short C7···S2 contact [3.3189 (19)Å; (i) 2 - x, 1/2 + y, 1/2 - z], which is shorter than the sum of the van der Waals radii of these atoms [3.50Å]. The crystal structure is further stabilized by the intermolecular C—H···N hydrogen bonds and π-π interaction [Cg1···Cg2i = 3.7649 (12)Å, (i) 1 - x, 1 - y, -z; Cg1 and Cg2 are centroids of S(1)/C(8)/N(2)/N(3)/C(9) and C1–C6 rings, respectively].

For standard bond lengths, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the biological versatility of thione ligands, see, for example: Kumar et al. (1988); Yadav et al. (1989). For related structures, see: Zhang (2003); Kargar et al., (2011). For van der Waals radii, see: Bondi (1964).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2009); cell refinement: X-AREA (Stoe & Cie, 2009); data reduction: X-AREA (Stoe & Cie, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The ORTEP plot of the title compound, showing 40% probability displacement ellipsoids and the atomic numbering. The dashed lines show the intermolecular interaction.
[Figure 2] Fig. 2. The packing diagram of the title compound viewed down the c-axis showing linkning of molecules through the intermolecular N—H···O hydrogen bonds, forming one-dimensional extended chains along the b-axis. The dashed lines show the intermolecular interactions.
(E)-5-[(3-Ethoxy-2-hydroxybenzylidene)amino]-1,3,4-thiadiazole- 2(3H)-thione top
Crystal data top
C11H11N3O2S2F(000) = 584
Mr = 281.35Dx = 1.448 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8153 reflections
a = 8.925 (1) Åθ = 1.8–29.6°
b = 11.3664 (14) ŵ = 0.41 mm−1
c = 12.8945 (16) ÅT = 291 K
β = 99.352 (9)°Block, yellow
V = 1290.7 (3) Å30.25 × 0.22 × 0.15 mm
Z = 4
Data collection top
Stoe IPDS 2T Image Plate
diffractometer		3461 independent reflections
Radiation source: fine-focus sealed tube2376 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
φ and ω scansθmax = 29.2°, θmin = 2.3°
Absorption correction: multi-scan
[MULABS (Blessing, 1995) in PLATON (Spek, 2009)]		h = −12→12
Tmin = 0.905, Tmax = 0.941k = −15→15
10227 measured reflectionsl = −15→17
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0529P)2]
where P = (Fo2 + 2Fc2)/3
3461 reflections(Δ/σ)max = 0.001
164 parametersΔρmax = 0.24 e Å−3
0 restraintsΔρmin = −0.30 e Å−3
Crystal data top
C11H11N3O2S2V = 1290.7 (3) Å3
Mr = 281.35Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.925 (1) ŵ = 0.41 mm−1
b = 11.3664 (14) ÅT = 291 K
c = 12.8945 (16) Å0.25 × 0.22 × 0.15 mm
β = 99.352 (9)°
Data collection top
Stoe IPDS 2T Image Plate
diffractometer		3461 independent reflections
Absorption correction: multi-scan
[MULABS (Blessing, 1995) in PLATON (Spek, 2009)]		2376 reflections with I > 2σ(I)
Tmin = 0.905, Tmax = 0.941Rint = 0.036
10227 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.103H-atom parameters constrained
S = 1.00Δρmax = 0.24 e Å−3
3461 reflectionsΔρmin = −0.30 e Å−3
164 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.87646 (6)0.66233 (4)0.17887 (4)0.04681 (15)
S20.95905 (7)0.83877 (5)0.35481 (6)0.0674 (2)
O10.46721 (15)0.31614 (11)0.07089 (10)0.0420 (3)
H10.51380.37430.10560.063*
O20.37731 (16)0.13586 (11)−0.04539 (11)0.0464 (3)
N10.66203 (16)0.48422 (12)0.12047 (11)0.0343 (3)
N20.65853 (18)0.59227 (13)0.27073 (13)0.0431 (4)
N30.73429 (19)0.68024 (13)0.32832 (13)0.0459 (4)
H30.70410.70480.38200.055*
C10.54149 (19)0.29557 (15)−0.01085 (12)0.0324 (4)
C20.4937 (2)0.19863 (15)−0.07513 (14)0.0364 (4)
C30.5647 (3)0.17501 (17)−0.16015 (15)0.0473 (5)
H3A0.53430.1104−0.20260.057*
C40.6810 (3)0.2464 (2)−0.18320 (17)0.0564 (6)
H4A0.72740.2295−0.24100.068*
C50.7277 (2)0.34171 (19)−0.12110 (16)0.0481 (5)
H5A0.80460.3900−0.13760.058*
C60.6600 (2)0.36673 (15)−0.03266 (13)0.0348 (4)
C70.7168 (2)0.46283 (15)0.03607 (14)0.0355 (4)
H7A0.79430.51000.01900.043*
C80.72069 (18)0.57225 (14)0.18892 (13)0.0327 (4)
C90.8533 (2)0.73096 (16)0.29585 (15)0.0410 (4)
C100.3216 (3)0.03555 (18)−0.10841 (18)0.0571 (6)
H10A0.3994−0.0246−0.10400.069*
H10B0.29310.0585−0.18140.069*
C110.1864 (3)−0.0103 (2)−0.0663 (2)0.0802 (8)
H11A0.1507−0.0808−0.10320.120*
H11B0.10730.0479−0.07590.120*
H11C0.2143−0.02730.00720.120*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0386 (3)0.0513 (3)0.0539 (3)−0.0096 (2)0.0173 (2)−0.0106 (2)
S20.0545 (3)0.0618 (4)0.0836 (5)−0.0179 (3)0.0043 (3)−0.0267 (3)
O10.0520 (8)0.0428 (7)0.0348 (7)−0.0101 (6)0.0177 (6)−0.0064 (5)
O20.0550 (8)0.0394 (7)0.0444 (8)−0.0097 (6)0.0067 (6)−0.0034 (6)
N10.0360 (8)0.0322 (7)0.0349 (8)0.0024 (6)0.0061 (6)−0.0007 (6)
N20.0478 (9)0.0386 (8)0.0459 (9)−0.0094 (7)0.0163 (7)−0.0090 (7)
N30.0511 (10)0.0440 (8)0.0460 (9)−0.0089 (7)0.0174 (8)−0.0154 (7)
C10.0367 (9)0.0349 (8)0.0261 (8)0.0069 (7)0.0062 (7)0.0013 (6)
C20.0406 (9)0.0347 (8)0.0322 (9)0.0042 (7)0.0011 (7)0.0025 (7)
C30.0592 (12)0.0446 (10)0.0378 (10)0.0063 (9)0.0066 (9)−0.0100 (8)
C40.0604 (13)0.0683 (14)0.0451 (12)0.0048 (11)0.0221 (10)−0.0173 (10)
C50.0426 (10)0.0616 (12)0.0438 (11)−0.0024 (9)0.0182 (9)−0.0077 (9)
C60.0349 (9)0.0398 (9)0.0301 (8)0.0054 (7)0.0065 (7)−0.0012 (7)
C70.0310 (9)0.0384 (9)0.0372 (9)0.0012 (7)0.0062 (7)0.0019 (7)
C80.0323 (8)0.0297 (8)0.0369 (9)0.0020 (7)0.0077 (7)0.0006 (7)
C90.0359 (9)0.0380 (9)0.0478 (11)0.0030 (8)0.0031 (8)−0.0062 (8)
C100.0692 (15)0.0437 (11)0.0527 (13)−0.0090 (10)−0.0070 (11)−0.0053 (9)
C110.0754 (18)0.0700 (16)0.090 (2)−0.0320 (14)−0.0014 (15)−0.0004 (14)
Geometric parameters (Å, º) top
S1—C91.7400 (19)C2—C31.379 (3)
S1—C81.7483 (17)C3—C41.387 (3)
S2—C91.6544 (19)C3—H3A0.9300
O1—C11.354 (2)C4—C51.371 (3)
O1—H10.8659C4—H4A0.9300
O2—C21.365 (2)C5—C61.404 (3)
O2—C101.441 (2)C5—H5A0.9300
N1—C71.287 (2)C6—C71.446 (2)
N1—C81.380 (2)C7—H7A0.9300
N2—C81.290 (2)C10—C111.495 (3)
N2—N31.358 (2)C10—H10A0.9700
N3—C91.335 (2)C10—H10B0.9700
N3—H30.8311C11—H11A0.9600
C1—C61.396 (2)C11—H11B0.9600
C1—C21.403 (2)C11—H11C0.9600
C9—S1—C889.45 (9)C1—C6—C7121.06 (15)
C1—O1—H1106.2C5—C6—C7119.78 (17)
C2—O2—C10117.63 (16)N1—C7—C6121.18 (16)
C7—N1—C8121.41 (15)N1—C7—H7A119.4
C8—N2—N3109.58 (15)C6—C7—H7A119.4
C9—N3—N2119.82 (15)N2—C8—N1118.84 (15)
C9—N3—H3119.9N2—C8—S1114.22 (13)
N2—N3—H3120.2N1—C8—S1126.94 (13)
O1—C1—C6122.67 (15)N3—C9—S2126.83 (15)
O1—C1—C2117.08 (15)N3—C9—S1106.92 (13)
C6—C1—C2120.25 (16)S2—C9—S1126.25 (12)
O2—C2—C3126.19 (16)O2—C10—C11107.2 (2)
O2—C2—C1114.63 (15)O2—C10—H10A110.3
C3—C2—C1119.18 (17)C11—C10—H10A110.3
C2—C3—C4120.87 (18)O2—C10—H10B110.3
C2—C3—H3A119.6C11—C10—H10B110.3
C4—C3—H3A119.6H10A—C10—H10B108.5
C5—C4—C3120.29 (18)C10—C11—H11A109.5
C5—C4—H4A119.9C10—C11—H11B109.5
C3—C4—H4A119.9H11A—C11—H11B109.5
C4—C5—C6120.27 (19)C10—C11—H11C109.5
C4—C5—H5A119.9H11A—C11—H11C109.5
C6—C5—H5A119.9H11B—C11—H11C109.5
C1—C6—C5119.12 (16)
C8—N2—N3—C90.1 (3)C4—C5—C6—C7175.99 (19)
C10—O2—C2—C3−0.4 (3)C8—N1—C7—C6176.85 (15)
C10—O2—C2—C1179.53 (16)C1—C6—C7—N11.4 (3)
O1—C1—C2—O2−0.7 (2)C5—C6—C7—N1−176.53 (17)
C6—C1—C2—O2179.79 (15)N3—N2—C8—N1178.96 (15)
O1—C1—C2—C3179.21 (16)N3—N2—C8—S1−0.3 (2)
C6—C1—C2—C3−0.3 (3)C7—N1—C8—N2177.93 (17)
O2—C2—C3—C4179.21 (19)C7—N1—C8—S1−2.9 (2)
C1—C2—C3—C4−0.7 (3)C9—S1—C8—N20.27 (15)
C2—C3—C4—C50.3 (3)C9—S1—C8—N1−178.89 (16)
C3—C4—C5—C61.0 (3)N2—N3—C9—S2179.90 (14)
O1—C1—C6—C5−177.84 (16)N2—N3—C9—S10.1 (2)
C2—C1—C6—C51.6 (3)C8—S1—C9—N3−0.18 (14)
O1—C1—C6—C74.2 (3)C8—S1—C9—S2179.99 (14)
C2—C1—C6—C7−176.35 (15)C2—O2—C10—C11−174.57 (18)
C4—C5—C6—C1−2.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.871.812.5924 (19)150
N3—H3···O1i0.832.152.841 (2)141
N3—H3···O2i0.832.473.160 (2)142
C3—H3A···N2ii0.932.603.312 (3)133
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formulaC11H11N3O2S2
Mr281.35
Crystal system, space groupMonoclinic, P21/c
Temperature (K)291
a, b, c (Å)8.925 (1), 11.3664 (14), 12.8945 (16)
β (°) 99.352 (9)
V (Å3)1290.7 (3)
Z4
Radiation typeMo Kα
µ (mm−1)0.41
Crystal size (mm)0.25 × 0.22 × 0.15
Data collection
DiffractometerStoe IPDS 2T Image Plate
Absorption correctionMulti-scan
[MULABS (Blessing, 1995) in PLATON (Spek, 2009)]
Tmin, Tmax0.905, 0.941
No. of measured, independent and
observed [I > 2σ(I)] reflections		10227, 3461, 2376
Rint0.036
(sin θ/λ)max (Å−1)0.686
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.103, 1.00
No. of reflections3461
No. of parameters164
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.24, −0.30

Computer programs: X-AREA (Stoe & Cie, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.871.812.5924 (19)150
N3—H3···O1i0.832.152.841 (2)141
N3—H3···O2i0.832.473.160 (2)142
C3—H3A···N2ii0.932.603.312 (3)133
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x, −y+1/2, z−1/2.
 

Acknowledgements

HK thanks PNU for financial support.

References

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ISSN: 2056-9890
Volume 67| Part 12| December 2011| Page o3437
https://doi.org/10.1107/S1600536811049877
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