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

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ISSN: 2056-9890

Benzyl N-[1-(furan-2-yl)ethyl­­idene]­hydrazine­carbodi­thio­ate

aDepartment of Chemistry, Universiti Putra Malaysia, 43400 UPM, Selangor, Malaysia, bChemical Crystallography, Chemistry Research Laboratory, 12 Mansfield Road, Oxford OX1 3TA, England, and cDepartment of Chemistry, Rajshahi University, Rajshahi 6205, Bangladesh
*Correspondence e-mail: teng.khoo@chem.ox.ac.uk

(Received 17 May 2005; accepted 1 July 2005; online 9 July 2005)

The title compound, C14H12N2S2O, contains a dithio­carbazate group. The phenyl ring is disordered and perpendicular [dihedral angle of 48.0 (3)°] to the rest of the mol­ecule, which is planar.

Comment

Dithio­carbazate derivatives have been widely studied and have great potential biological activity as anticancer and antimicrobial drugs (Bharti et al., 2000[Bharti, N., Maurya, M. R., Naqvi, F., Bhattacharya, A., Bhattacharya, S. & Azam, A. (2000). Eur. J. Med. Chem. 35, 481-486.]) and in radiopharmaceutical applications (Boschi et al., 2003[Boschi, A., Bolzati, C., Uccelli, L. & Duatti, A. (2003). Nucl. Med. Biol. 30, 381-387.]). This functional group is of particular inter­est because it is easily tuned by reaction with different aldehydes or ketones to give varied geometries for chelation to transition metals. In the structure of the title compound, (I)[link], we were inter­ested in studying the effect of introducing a furan ring to determine if it can also participate in chelation to a metal centre. The previously reported CdII complex of this ligand (Tarafder et al., 2002b[Tarafder, M. T. H., Khoo, T.-J., Crouse, K. A., Ali, A. M., Yamin, B. M.,& Fun, H.-K. (2002b). Polyhedron, 21, 2691-2698.]) indicated that it only forms a bis-chelating bidentate ligand without O coordination. The biological activity of the compound and its analytical characterization have also been reported (Tarafder et al., 2002a[Tarafder, M. T. H., Khoo, T.-J., Crouse, K. A., Ali, A. M., Yamin, B. M. & Fun, H.-K. (2002a). Polyhedron, 21, 2547-2554.]).

[Scheme 1]

Compound (I)[link] (Figs. 1[link]–3[link][link]) crystallizes in the unprotonated thione form with a C=S bond length of 1.664 (2) Å, which is slightly longer than that previously reported for a dithio­carbazate Schiff base [1.6503 (17) Å; Chan et al., 2003[Chan, M.-H. E., Crouse, K. A., Tarafder, M. T. H. & Yamin, B. M. (2003). Acta Cryst. E59, o628-629.]]. This is in accordance with other experimental characterizations, which indicate that this type of compound forms the thione tautomer in the solid state. The formation of the CdII complex occurs through coordination at the azomethane N atom and thiol­ate S atom (Tarafder et al., 2002b[Tarafder, M. T. H., Khoo, T.-J., Crouse, K. A., Ali, A. M., Yamin, B. M.,& Fun, H.-K. (2002b). Polyhedron, 21, 2691-2698.]) but does not show any bond-length change: N1—N2 = 1.381 (2) Å in (I)[link].

The mol­ecule crystallizes in the conformer in which the N1—N2 bond adopts a trans geometry with respect to C12=S2, while the S-benzyl group adopts a cis geometry. The furan and phenyl groups are cis to each other across N2/N1/C12/S1. The C13=N2 bond [1.289 (3) Å] is formed from the condensation reaction. The C14 methyl group is cis to the furyl O atom in this free ligand but transforms to trans upon chelation to CdII (Tarafder et al., 2002b[Tarafder, M. T. H., Khoo, T.-J., Crouse, K. A., Ali, A. M., Yamin, B. M.,& Fun, H.-K. (2002b). Polyhedron, 21, 2691-2698.]), even though the O atom does not coordinate to the metal centre. The S1—C12=S2 angle is maintained at 125.22 (12)° after coordination [125.22 (12)° in (I)].

[Figure 1]
Figure 1
The mol­ecular structure of (I)[link]. with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Both disorder components are shown. H atoms have been omitted.
[Figure 2]
Figure 2
A projection along the a axis of part of the packing of (I)[link], showing that the phenyl groups form a layer in the crystal structure. The alternative orientations of the phenyl C atoms are coloured red and blue.
[Figure 3]
Figure 3
A projection along the b axis of a section of the crystal structure of (I)[link]. The alternative orientations of the phenyl C atoms are coloured red and blue. Note that if alternate red and blue phenyl groups are selected in any layer, there are no short inter­molecular clashes.

Experimental

The Schiff base ligand was prepared according to the literature method of Tarafder et al. (2002a[Tarafder, M. T. H., Khoo, T.-J., Crouse, K. A., Ali, A. M., Yamin, B. M. & Fun, H.-K. (2002a). Polyhedron, 21, 2547-2554.]). S-Benzyl­dithio­carbazate (1.98 g, 0.1 mol) in absolute ethanol (40 ml) was added to an equimolar quantity of 2-furylmethyl­ketone in absolute ethanol (50 ml). The mixture was heated over a steam bath for 10 min and then cooled to 273 K in an ice bath. The Schiff base which precipitated was filtered, washed with cold ethanol and dried in vacuo over silica gel, giving a dark-orange product (yield 80%, m.p 406 K). Yellow single crystals of (I)[link], suitable for X-ray analysis, were obtained by slow evaporation of an ethanol solution over a period of three weeks.

Crystal data
  • C14H14N2OS2

  • Mr = 290.41

  • Monoclinic, P 21 /c

  • a = 4.7347 (1) Å

  • b = 32.6510 (7) Å

  • c = 9.3959 (2) Å

  • β = 109.0305 (9)°

  • V = 1373.15 (5) Å3

  • Z = 4

  • Dx = 1.405 Mg m−3

  • Mo Kα radiation

  • Cell parameters from 2559 reflections

  • θ = 5–27°

  • μ = 0.38 mm−1

  • T = 150 K

  • Block, yellow

  • 0.40 × 0.30 × 0.30 mm

Data collection
  • Nonius KappaCCD area-detector diffractometer

  • ω scans

  • Absorption correction: multi-scan(DENZO and SCALEPACK; Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.])Tmin = 0.89, Tmax = 0.89

  • 5121 measured reflections

  • 3055 independent reflections

  • 2036 reflections with I > 3σ(I)

  • Rint = 0.019

  • θmax = 27.5°

  • h = −6 → 6

  • k = −38 → 42

  • l = −12 → 12

Refinement
  • Refinement on F

  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.047

  • S = 1.09

  • 2036 reflections

  • 208 parameters

  • H-atom parameters constrained

  • Chebychev polynomial, with Ai coefficients 1.29, 0.798, 1.02

  • (Δ/σ)max < 0.001

  • Δρmax = 0.37 e Å−3

  • Δρmin = −0.27 e Å−3

Table 1
Selected geometric parameters (Å, °)[link]

C12—N1 1.343 (3)
C12—S1 1.749 (2)
C12—S2 1.664 (2)
C13—N2 1.289 (3)
C15—C16 1.344 (3)
C15—O1 1.374 (2)
C16—C17 1.423 (3)
C17—C18 1.330 (3)
C18—O1 1.364 (3)
N1—N2 1.381 (2)
N1—C12—S1 113.77 (15)
N1—C12—S2 121.00 (16)
S1—C12—S2 125.22 (12)
C14—C13—N2 125.2 (2)
C15—C13—N2 115.42 (18)
C12—N1—N2 119.35 (17)
C12—N1—H3 119.4
N1—N2—C13 116.37 (18)
C15—O1—C18 106.40 (16)
C11—S1—C12 101.75 (10)

The phenyl group was seen to be disordered. The site occupancy factors for the two orientations refined to 0.508 (4):0.492 (4), in close agreement with the value of 0.5:0.5 which would be required by strict alternation of the two orientations in each mol­ecular layer (Figs. 2[link] and 3[link]). All H atoms (including those of the disordered phenyl group) were located in a difference map, but those attached to C atoms were repositioned geometrically. All H atoms were initially refined with soft restraints on the bond lengths and angles to regularize their geometry (C—H in the range 0.93–98 and N—H = 0.85 Å) and isotropic atomic displacement parameters [Uiso(H) in the range 1.2–1.5 times Ueq of the parent atom], after which they were refined with riding constraints.

Data collection: COLLECT (Nonius, 2001[Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003[Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, C. K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.]); molecular graphics: CAMERON (Watkin et al., 1996[Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.]); software used to prepare material for publication: CRYSTALS.

Supporting information


Comment top

Dithiocarbazate derivatives have been widely studied and have great potential biological activity as anticancer and antimicrobial drugs (Bharti et al., 2000) and in radiopharmaceutical applications (Boschi et al., 2003). This moiety is of particular interest because it is easily tuned by reaction with different aldehydes or ketones to give varied geometries from chelation to transition metals. In the structure of the title compound, (I), we were interested in studying the presence of the furan ring to determine if it undergoes chelation to a metal centre. The previously reported CdII complex of this ligand (Tarafder et al., 2002b) indicated that it only forms a bis-chelated bidentate ligand without O coordination. The biological activity of the compound and its analytical characterization have also been reported (Tarafder et al., 2002a).

Compound (I) (Figs. 1–3) crystallizes in the unprotonated thione form with a CS bond length of 1.664 (2) Å, which is slightly longer than that previously reported for a dithiocarbazate Schiff base [1.6503 (17) Å; Chan et al., 2003]. This is in accordance with other experimental characterizations, which indicate that this type of compound forms the thione tautomer in the solid state. The formation of the CdII complex occurs through coordination at the azomethane N atom and thiolate S atom (Tarafder et al., 2002b) but does not show any bond-length change: N1—N2 = 1.381 (2) Å in (I).

The molecule crystallizes in the conformer in which the N1—N2 bond adopts a trans geometry with respect to C12S2, while the S-benzyl group adopts a cis geometry. The furan and phenyl groups are cis to each other across N2/N1/C12/S1. The C13N2 bond [1.289 (3) Å] is formed from the condensation reaction. The C14 methyl group is cis to the furyl O atom in this free ligand but transforms to trans upon chelation to CdII (Tarafder et al., 2002b), even though the O atom does not coordinate to the metal centre. The S1—C12S2 angle is maintained at 125.22 (12)° after coordination [125.22 (12)° in (I)].

Experimental top

The Schiff base ligand was prepared according to the literature method of Tarafder et al. (2002a). An equimolar of S-benzyldithiocarbazate (1.98 g, 0.1 mol) in absolute ethanol (40 ml) was added to an equimolar quantity of 2-furylmethylketone in absolute ethanol (50 ml). The mixture was heated over a steam bath for 10 min and then cooled to 273 K in an ice bath. The Schiff base which precipitated was filtered, washed with cold ethanol and dried in vacuo over silica gel, giving a dark-orange product (yield 80%, m.p 406 K). Yellow single crystals of (I), suitable for X-ray analysis, were obtained by slow evaporation of an ethanol solution after three weeks.

Refinement top

The phenyl group was seen to be disordered. The site occupancy factors for the two orientations refined to 0.508 (4):0.492 (4), in close agreement with the value of 0.5:0.5 which would be required by strict alternation of the two orientations in each molecular layer (Figs. 2 and 3). All H atoms (including those of the disordered phenyl group) were located in a difference map, but those attached to C atoms were repositioned geometrically. All H atoms were initially refined with soft restraints on the bond lengths and angles to regularize their geometry (C—H in the range 0.93–98 and N—H = 0.85 Å) and isotropic atomic displacement parameters [Uiso(H) in the range 1.2–1.5 times Ueq of the parent atom], after which they were refined with riding constraints.

Computing details top

Data collection: COLLECT (Nonius, 2001); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: CRYSTALS.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I). with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A projection along the a axis of part of the unit cell of (I), showing that the phenyl groups form a layer passing through the crystal structure. The alternative orientations of the phenyl C atoms are coloured red and blue.
[Figure 3] Fig. 3. A projection along the b axis of part of the unit cell of (I). The alternative orientations of the phenyl C atoms are coloured red and blue. Note that if alternate red and blue phenyl groups are selected in any layer, there are no short intermolecular clashes.
Benzyl N-[1-(furan-2-yl)ethylidene]hydrazinecarbodithioate top
Crystal data top
C14H14N2OS2Dx = 1.405 Mg m3
Mr = 290.41Melting point: 406 K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 4.7347 (1) ÅCell parameters from 2559 reflections
b = 32.6510 (7) Åθ = 5–27°
c = 9.3959 (2) ŵ = 0.38 mm1
β = 109.0305 (9)°T = 150 K
V = 1373.15 (5) Å3Block, yellow
Z = 40.40 × 0.30 × 0.30 mm
F(000) = 608
Data collection top
Nonius KappaCCD area-detector
diffractometer
2036 reflections with I > 3σ(I)
Graphite monochromatorRint = 0.019
ω scansθmax = 27.5°, θmin = 5.2°
Absorption correction: multi-scan
(DENZO and SCALEPACK; Otwinowski & Minor, 1997)
h = 66
Tmin = 0.89, Tmax = 0.89k = 3842
5121 measured reflectionsl = 1212
3055 independent reflections
Refinement top
Refinement on FPrimary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.047H-atom parameters constrained
S = 1.09 Chebychev polynomial, with Ai coefficients 1.29, 0.798, 1.02
2036 reflections(Δ/σ)max = 0.000357
208 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.27 e Å3
Crystal data top
C14H14N2OS2V = 1373.15 (5) Å3
Mr = 290.41Z = 4
Monoclinic, P21/cMo Kα radiation
a = 4.7347 (1) ŵ = 0.38 mm1
b = 32.6510 (7) ÅT = 150 K
c = 9.3959 (2) Å0.40 × 0.30 × 0.30 mm
β = 109.0305 (9)°
Data collection top
Nonius KappaCCD area-detector
diffractometer
3055 independent reflections
Absorption correction: multi-scan
(DENZO and SCALEPACK; Otwinowski & Minor, 1997)
2036 reflections with I > 3σ(I)
Tmin = 0.89, Tmax = 0.89Rint = 0.019
5121 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.047H-atom parameters constrained
S = 1.09Δρmax = 0.37 e Å3
2036 reflectionsΔρmin = 0.27 e Å3
208 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.4734 (5)0.27775 (7)0.3069 (2)0.0290
C20.3756 (10)0.25222 (14)0.1810 (5)0.02990.5079
C30.3952 (9)0.20941 (13)0.1950 (4)0.02490.5079
C40.6012 (10)0.25859 (14)0.4492 (5)0.03060.5079
C50.6238 (10)0.21637 (13)0.4617 (5)0.02750.5079
C60.7425 (10)0.26000 (13)0.3674 (5)0.02830.4921
C70.7646 (10)0.21747 (13)0.3807 (4)0.02480.4921
C80.2116 (10)0.25508 (14)0.2590 (5)0.02630.4921
C90.2317 (10)0.21287 (14)0.2720 (5)0.02720.4921
C100.5141 (4)0.19259 (6)0.3337 (2)0.0232
C110.5367 (5)0.14628 (6)0.3472 (2)0.0267
C120.4384 (5)0.07792 (6)0.4993 (2)0.0246
C130.1442 (5)0.06134 (6)0.7908 (2)0.0265
C140.1635 (7)0.01591 (7)0.8110 (3)0.0443
C150.0181 (5)0.08592 (6)0.8846 (2)0.0253
C160.0427 (5)0.12595 (7)0.8912 (2)0.0291
C170.1686 (5)0.13048 (7)1.0087 (3)0.0302
C180.1758 (6)0.09333 (7)1.0655 (3)0.0348
N10.3493 (4)0.05880 (5)0.6039 (2)0.0267
N20.2315 (4)0.08155 (6)0.69490 (19)0.0261
O10.0656 (4)0.06489 (5)0.99101 (19)0.0371
S10.39774 (13)0.131167 (15)0.49885 (6)0.0269
S20.57251 (14)0.051604 (17)0.38374 (7)0.0331
H10.46240.30710.29780.0439*
H20.41640.13380.25600.0358*
H30.36550.03300.61230.0360*
H40.36490.00660.82720.0867*
H60.10660.00780.89630.0868*
H90.24660.08721.14370.0520*
H820.03170.00270.72260.0868*
H830.23390.15461.04060.0412*
H840.73900.13800.36820.0359*
H850.00780.14670.83140.0400*
H610.92660.27730.40290.0284*0.4921
H710.96600.20460.42530.0250*0.4921
H410.67610.27590.54180.0329*0.5079
H510.71840.20320.56220.0281*0.5079
H810.01330.26890.21620.0266*0.4921
H910.04480.19610.23740.0281*0.4921
H210.28970.26470.07880.0293*0.5079
H310.32250.19160.10380.0256*0.5079
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0354 (12)0.0245 (10)0.0300 (10)0.0012 (8)0.0148 (9)0.0016 (8)
C20.030 (2)0.033 (2)0.025 (2)0.0038 (17)0.0062 (17)0.0059 (16)
C30.026 (2)0.029 (2)0.0213 (18)0.0073 (16)0.0103 (15)0.0039 (16)
C40.040 (2)0.029 (2)0.030 (2)0.0112 (18)0.0206 (19)0.0068 (17)
C50.032 (2)0.032 (2)0.0207 (18)0.0029 (17)0.0105 (16)0.0044 (16)
C60.034 (2)0.023 (2)0.028 (2)0.0084 (18)0.0102 (18)0.0001 (17)
C70.025 (2)0.031 (2)0.0196 (18)0.0014 (16)0.0079 (15)0.0007 (16)
C80.027 (2)0.031 (2)0.0225 (19)0.0066 (17)0.0090 (16)0.0020 (16)
C90.026 (2)0.033 (2)0.025 (2)0.0009 (17)0.0117 (16)0.0018 (17)
C100.0228 (10)0.0281 (10)0.0230 (10)0.0006 (7)0.0132 (8)0.0014 (8)
C110.0317 (11)0.0266 (10)0.0276 (10)0.0033 (8)0.0175 (8)0.0001 (8)
C120.0284 (11)0.0253 (10)0.0221 (9)0.0007 (8)0.0111 (8)0.0004 (8)
C130.0341 (11)0.0220 (10)0.0278 (10)0.0005 (8)0.0162 (9)0.0014 (8)
C140.079 (2)0.0241 (10)0.0492 (14)0.0063 (12)0.0478 (15)0.0040 (11)
C150.0305 (11)0.0251 (10)0.0255 (10)0.0008 (8)0.0163 (8)0.0018 (8)
C160.0389 (12)0.0242 (10)0.0286 (11)0.0002 (9)0.0173 (9)0.0014 (8)
C170.0349 (12)0.0282 (11)0.0321 (11)0.0003 (9)0.0171 (9)0.0071 (9)
C180.0500 (15)0.0332 (12)0.0324 (12)0.0014 (10)0.0286 (11)0.0040 (9)
N10.0387 (10)0.0211 (8)0.0262 (9)0.0006 (7)0.0187 (8)0.0002 (7)
N20.0316 (10)0.0261 (9)0.0254 (9)0.0016 (7)0.0160 (8)0.0013 (7)
O10.0643 (12)0.0247 (7)0.0383 (9)0.0020 (8)0.0387 (8)0.0028 (7)
S10.0364 (3)0.0234 (3)0.0279 (3)0.0033 (2)0.0199 (2)0.0022 (2)
S20.0526 (4)0.0242 (3)0.0346 (3)0.0005 (2)0.0310 (3)0.0020 (2)
Geometric parameters (Å, º) top
C1—C21.397 (5)C10—C111.518 (3)
C1—C41.421 (5)C11—S11.822 (2)
C1—H10.961C11—H20.951
C1—C61.345 (5)C11—H840.952
C1—C81.387 (5)C12—N11.343 (3)
C1—H10.961C12—S11.749 (2)
C2—C31.404 (6)C12—S21.664 (2)
C2—H211.000C13—C141.494 (3)
C3—C101.356 (5)C13—C151.456 (3)
C3—H311.000C13—N21.289 (3)
C4—C51.385 (6)C14—H40.964
C4—H411.000C14—H60.962
C5—C101.383 (5)C14—H820.962
C5—H511.000C15—C161.344 (3)
C6—C71.395 (6)C15—O11.374 (2)
C6—H611.000C16—C171.423 (3)
C7—C101.386 (5)C16—H850.928
C7—H711.000C17—C181.330 (3)
C8—C91.384 (6)C17—H830.930
C8—H811.000C18—O11.364 (3)
C9—C101.434 (5)C18—H90.924
C9—H911.000N1—N21.381 (2)
C10—C111.518 (3)N1—H30.848
C2—C1—C4117.1 (3)C10—C11—S1107.55 (14)
C2—C1—H1121.8C10—C11—H2110.2
C4—C1—H1121.1S1—C11—H2109.0
C6—C1—C8122.0 (3)C10—C11—H84109.8
C6—C1—H1118.9S1—C11—H84110.9
C8—C1—H1119.1H2—C11—H84109.4
C1—C2—C3121.4 (4)N1—C12—S1113.77 (15)
C1—C2—H21119.3N1—C12—S2121.00 (16)
C3—C2—H21119.3S1—C12—S2125.22 (12)
C2—C3—C10119.1 (3)C14—C13—C15119.37 (18)
C2—C3—H31120.4C14—C13—N2125.2 (2)
C10—C3—H31120.4C15—C13—N2115.42 (18)
C1—C4—C5121.0 (4)C13—C14—H4110.4
C1—C4—H41119.5C13—C14—H6110.8
C5—C4—H41119.5H4—C14—H6108.3
C4—C5—C10119.2 (4)C13—C14—H82109.8
C4—C5—H51120.4H4—C14—H82109.0
C10—C5—H51120.4H6—C14—H82108.5
C1—C6—C7120.0 (4)C13—C15—C16134.45 (19)
C1—C6—H61120.0C13—C15—O1115.96 (18)
C7—C6—H61120.0C16—C15—O1109.58 (18)
C6—C7—C10121.6 (4)C15—C16—C17106.70 (19)
C6—C7—H71119.2C15—C16—H85126.7
C10—C7—H71119.2C17—C16—H85126.6
C1—C8—C9118.3 (4)C16—C17—C18106.75 (19)
C1—C8—H81120.8C16—C17—H83127.3
C9—C8—H81120.8C18—C17—H83126.0
C8—C9—C10121.6 (4)C17—C18—O1110.56 (19)
C8—C9—H91119.2C17—C18—H9125.5
C10—C9—H91119.2O1—C18—H9124.0
C5—C10—C3122.0 (3)C12—N1—N2119.35 (17)
C5—C10—C11119.4 (2)C12—N1—H3119.4
C3—C10—C11118.7 (2)N2—N1—H3121.3
C9—C10—C7116.5 (3)N1—N2—C13116.37 (18)
C9—C10—C11121.7 (2)C15—O1—C18106.40 (16)
C7—C10—C11121.8 (2)C11—S1—C12101.75 (10)

Experimental details

Crystal data
Chemical formulaC14H14N2OS2
Mr290.41
Crystal system, space groupMonoclinic, P21/c
Temperature (K)150
a, b, c (Å)4.7347 (1), 32.6510 (7), 9.3959 (2)
β (°) 109.0305 (9)
V3)1373.15 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.38
Crystal size (mm)0.40 × 0.30 × 0.30
Data collection
DiffractometerNonius KappaCCD area-detector
diffractometer
Absorption correctionMulti-scan
(DENZO and SCALEPACK; Otwinowski & Minor, 1997)
Tmin, Tmax0.89, 0.89
No. of measured, independent and
observed [I > 3σ(I)] reflections
5121, 3055, 2036
Rint0.019
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.047, 1.09
No. of reflections2036
No. of parameters208
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.37, 0.27

Computer programs: COLLECT (Nonius, 2001), DENZO and SCALEPACK (Otwinowski & Minor, 1997), DENZO and SCALEPACK, SIR92 (Altomare et al., 1994), CRYSTALS (Betteridge et al., 2003), CAMERON (Watkin et al., 1996), CRYSTALS.

Selected geometric parameters (Å, º) top
C12—N11.343 (3)C15—O11.374 (2)
C12—S11.749 (2)C16—C171.423 (3)
C12—S21.664 (2)C17—C181.330 (3)
C13—N21.289 (3)C18—O11.364 (3)
C15—C161.344 (3)N1—N21.381 (2)
N1—C12—S1113.77 (15)C12—N1—N2119.35 (17)
N1—C12—S2121.00 (16)C12—N1—H3119.4
S1—C12—S2125.22 (12)N1—N2—C13116.37 (18)
C14—C13—N2125.2 (2)C15—O1—C18106.40 (16)
C15—C13—N2115.42 (18)C11—S1—C12101.75 (10)
 

Footnotes

Current address: Chemical Crystallography, Chemistry Research Laboratory, 12 Mansfield Road, Oxford OX1 3TA, England.

Acknowledgements

KTJ gratefully acknowledges MOSTI, Malaysia, for an attachment grant under an NSF scholarship, and the Chemical Crystallography Laboratory, University of Oxford, for instrumental facilities.

References

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First citationTarafder, M. T. H., Khoo, T.-J., Crouse, K. A., Ali, A. M., Yamin, B. M. & Fun, H.-K. (2002a). Polyhedron, 21, 2547–2554. Web of Science CSD CrossRef CAS
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