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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

1-(1,3-Benzo­thia­zol-2-yl)-3-benzoyl­thio­urea

aDepartment of Chemistry, Allama Iqbal Open University, Islamabad, Pakistan, bDepartment of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan, and cDepartment of Chemistry, Hong Kong Baptist University, Waterloo Road, Kowloon Tong, Hong Kong
*Correspondence e-mail: uzma_yunus@yahoo.com

(Received 5 November 2007; accepted 20 November 2007; online 6 December 2007)

The title compound, C15H11N3OS2, was synthesized from benzoyl thio­cyanate and 2-amino­benzothia­zole in dry acetone. The thio­urea group is in the thio­amide form. The mol­ecules are stabilized by two inter­molecular C—H⋯S and C—H⋯O hydrogen bonds. Intra­molecular N—H⋯O hydrogen bonding results in a pseudo-S(6) planar ring with dihedral angles of 11.23 and 11.91° with the benzothiazole ring system and the phenyl ring, respectively.

Related literature

For related literature see: Büyükgüngör et al. (2004[Büyükgüngör, O., Çalışkan, N., Davran, C. & Batı, H. (2004). Acta Cryst. E60, o1414-o1416.]); del Campo et al. (2002[Campo, R. del, Criado, J. J., García, E., Hermosa, M. R., Jiménez-Sánchez, A., Manzano, J. L., Monte, E., Rodríguez-Fernández, E. & Sanz, F. (2002). J. Inorg. Biochem. 89, 74-82.]); Chen et al. (2003[Chen, Z.-F., Tang, Y.-Z., Shi, S.-M., Wang, X.-W., Liang, H. & Yu, K.-B. (2003). Acta Cryst. E59, o1461-o1463.]); D'hooghe et al. (2005[D'hooghe, M., Waterinckx, A. & De Kimpe, N. (2005). J. Org. Chem. 70, 227-232.]); Koketsu & Ishihara (2006[Koketsu, M. & Ishihara, H. (2006). Curr. Org. Synth. 3, 439-455.]); Morales et al. (2000[Morales, A. D., Novoa de Armas, H., Blaton, N. M., Peeters, O. M., De Ranter, C. J., Márquez, H. & Pomés Hernández, R. (2000). Acta Cryst. C56, 503-504.]); Rodríguez-Fernández et al. (2005[Rodríguez-Fernández, E., Manzano, J. L., Benito, J. J., Hermosa, R., Monte, E. & Criado, J. J. (2005). J. Inorg. Biochem. 99, 1558-1572.]); Yamin & Hassan (2004[Yamin, B. M. & Hassan, I. N. (2004). Acta Cryst. E60, o2513-o2514.]); Yunus et al. (2007[Yunus, U., Tahir, M. K., Bhatti, M. H., Ali, S. & Helliwell, M. (2007). Acta Cryst. E63, o3690.]); Zeng et al. (2003[Zeng, R.-S., Zou, J.-P., Zhi, S.-J. & Shen, Q. (2003). Org. Lett. 5, 1657-1659.]).

[Scheme 1]

Experimental

Crystal data
  • C15H11N3OS2

  • Mr = 313.39

  • Monoclinic, P 2/c

  • a = 12.4402 (8) Å

  • b = 5.8608 (4) Å

  • c = 19.7240 (13) Å

  • β = 90.223 (1)°

  • V = 1438.06 (16) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.37 mm−1

  • T = 293 (2) K

  • 0.32 × 0.26 × 0.20 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1999[Bruker (1999). SMART (Version 5.0), SAINT (Version 6.02a), SADABS (Version 2.03) and SHELXTL (Version 5.1). Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.933, Tmax = 1.000 (expected range = 0.866–0.928)

  • 8487 measured reflections

  • 3508 independent reflections

  • 2724 reflections with I > 2σ(I)

  • Rint = 0.019

Refinement
  • R[F2 > 2σ(F2)] = 0.035

  • wR(F2) = 0.102

  • S = 1.04

  • 3508 reflections

  • 190 parameters

  • H-atom parameters constrained

  • Δρmax = 0.31 e Å−3

  • Δρmin = −0.26 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2B⋯O1 0.86 1.86 2.5878 (17) 142
C1—H1A⋯S2i 0.93 2.84 3.4017 (17) 120
C5—H5A⋯O1ii 0.93 2.57 3.470 (2) 162
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 1999[Bruker (1999). SMART (Version 5.0), SAINT (Version 6.02a), SADABS (Version 2.03) and SHELXTL (Version 5.1). Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1999[Bruker (1999). SMART (Version 5.0), SAINT (Version 6.02a), SADABS (Version 2.03) and SHELXTL (Version 5.1). Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: SHELXTL (Bruker, 1999[Bruker (1999). SMART (Version 5.0), SAINT (Version 6.02a), SADABS (Version 2.03) and SHELXTL (Version 5.1). Bruker AXS Inc., Madison, Wisconsin, USA.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Thiourea and its derivatives have found extensive applications in the fields of medicine, agriculture and analytical chemistry. They are known to exhibit a wide variety of biological activities such as antiviral, antibacterial, antifungal, antitubercular, herbicidal and insecticidal (Koketsu & Ishihara, 2006). Thioureas are also widely used as precursors or intermediates towards the syntheisis of a variety of heterocyclic compounds (Zeng et al.2003; D'hooghe, et al. 2005). Among thiourea derivatives acylthiourea with potential donor atoms (O and S) have been found to display remarkably rich coordination chemistry. Such coordination compounds of thiourea have been studied for different biological systems (Rodríguez-Fernández et al. 2005). In recent years some attention has also been paid for potential use of acylthioureas as highly selective reagents for the enrichment and separation of metal cations (del Campo et al. 2002). The condensation of acyl / aroyl thiocyanates with primary amine affords 1,3-disubstituted thioureas in excellent yield in a single step. However, our attempt to synthesize thiourea derivative by treating benzoyl thiocyanate with 2-aminothiazole resulted in a fused 1,3,5-triazine instead of the expected thiourea product (Yunus et al. 2007). This observation prompted us to explore the outcome of the reaction with 2-aminothiazole derivatives such as 2-aminobenzothiazole. The reaction of the benzoyl thiocyanate with 2-aminobenzothiazole yielded the title compound (I) which is reported here.

The title compound crystallizes in the thioamide form. The conformation of the molecule with respect to the carbonyl and thiocarbonyl part is nearly planar as reflected by the torsion angles O1—C7—N1—C8, C7—N1—C8—S2 and C7—N1—C8—N2 of -0.42(°), -179.58(°) and -0.06(°) respectively. The benzoyl and benzothiazole groups are trans and cis, respectively, to the S atom across the thiourea C—N bonds (Figure 1 and Table 1). The C8—S2 and C7—O1 bonds show a typical double bond character with bond lengths of 1.6578 (15) and 1.2179 (19) Å respectively, closely related to other thiourea derivatives (Yamin & Hassan, 2004). All of the C—N bonds of thiourea fragment C7—N1, C8—N1, C8—N2 and C9—N2 are in the range 1.3933 (19) - 1.338 (2) Å, intermediate between those expected for single and double C—N bonds (1.47 and 1.27 Å respectively). Among these C—N bonds the C7—N1 is the longest indicating Csp2-Nsp2 single bond while C8—N2 is the shortest bond with more double bond character. This further demonstrate that there is π conjugation only along S2—C8—N2 system but not along O1—C7—N1 and C7—N1—C8 as found in 1-(3-methoxybenzoyl)-3,3-diethylthiourea (Morales et al., 2000). The bond lengths in the benzothizole ring system are normal and agree with the corresponding values found in 2-(benzothiazole-2-yliminomethyl)-6-methoxyphenol and N,N-(2-benzothia-zole)(2-pyridylmethyl)amine (Büyükgüngör et al. 2004; Chen et al. 2003). The bond length C9—N2 is very close to the value determined for the 2-(benzothiazole-2-yliminomethyl)-6-methoxyphenol suggesting the existence of a delocalized double bond in the benzothiazole moiety (Büyükgüngör et al. 2004). All bond lengths and angles confirm the sp2 hybridization for all C and N atoms of the benzothiazole ring with all C—C and C—N bond lengths intermediate between single and double bonds. The benzothiazole ring bonded to N2 is essentially planar and inclined at an angle -11.23(°) with respect to the plane of thiourea moiety. Similarly the phenyl ring bonded to C7 is at an angle of 11.91(°) with respect to the plane formed by the thiourea moiety.

The molecule is further stabilized by intermolecular and intramolecular hydrogen bonding. There are two types of intermolecular C1—H1A···S2i and C5—H5A···O1ii [Symmetry codes: (i) -x, -y + 1, -z + 1; (ii) -x + 1, -y + 1, -z + 1] hydrogen bonds. The intramolecular N2—H2B···O1 hydrogen bond is also observed. As a result, a pseudo six membered (O1—C7—N1—C8—N2···H2B) ring is formed.

Related literature top

For related literature see: Büyükgüngör et al. (2004); del Campo et al. (2002); Chen et al. (2003); D'hooghe et al. (2005); Koketsu & Ishihara (2006); Morales et al. (2000); Rodríguez-Fernández et al. (2005); Yamin & Hassan (2004); Yunus et al. (2007); Zeng et al. (2003).

Experimental top

A mixture of ammonium thiocyanate (26 mmol) and benzoyl chloride (26 mmol) in dry acetone (60 ml) was stirred for 30 min. Then 2-aminobenzothiazole (26 mmol) was added and the reaction mixture was refluxed for 2 h. After cooling, the reaction mixture was poured in an acidified cold water. The resulting yellow solid was filtered and washed with cold acetone. The title compound (I) was obtained as suitable single crystals for X-Ray analysis after recrystallization of the solid from an 1:1 ethanol-dichloromethane mixture.

Refinement top

H atoms were placed in idealized positions and refined using a riding model approximation. Bond lengths were fixed to 0.86 (amine NH) or 0.93 Å (aromatic CH). Isotropic displacement parameters were fixed to Uiso(H) = 1.2Ueq(carrier atom).

Structure description top

Thiourea and its derivatives have found extensive applications in the fields of medicine, agriculture and analytical chemistry. They are known to exhibit a wide variety of biological activities such as antiviral, antibacterial, antifungal, antitubercular, herbicidal and insecticidal (Koketsu & Ishihara, 2006). Thioureas are also widely used as precursors or intermediates towards the syntheisis of a variety of heterocyclic compounds (Zeng et al.2003; D'hooghe, et al. 2005). Among thiourea derivatives acylthiourea with potential donor atoms (O and S) have been found to display remarkably rich coordination chemistry. Such coordination compounds of thiourea have been studied for different biological systems (Rodríguez-Fernández et al. 2005). In recent years some attention has also been paid for potential use of acylthioureas as highly selective reagents for the enrichment and separation of metal cations (del Campo et al. 2002). The condensation of acyl / aroyl thiocyanates with primary amine affords 1,3-disubstituted thioureas in excellent yield in a single step. However, our attempt to synthesize thiourea derivative by treating benzoyl thiocyanate with 2-aminothiazole resulted in a fused 1,3,5-triazine instead of the expected thiourea product (Yunus et al. 2007). This observation prompted us to explore the outcome of the reaction with 2-aminothiazole derivatives such as 2-aminobenzothiazole. The reaction of the benzoyl thiocyanate with 2-aminobenzothiazole yielded the title compound (I) which is reported here.

The title compound crystallizes in the thioamide form. The conformation of the molecule with respect to the carbonyl and thiocarbonyl part is nearly planar as reflected by the torsion angles O1—C7—N1—C8, C7—N1—C8—S2 and C7—N1—C8—N2 of -0.42(°), -179.58(°) and -0.06(°) respectively. The benzoyl and benzothiazole groups are trans and cis, respectively, to the S atom across the thiourea C—N bonds (Figure 1 and Table 1). The C8—S2 and C7—O1 bonds show a typical double bond character with bond lengths of 1.6578 (15) and 1.2179 (19) Å respectively, closely related to other thiourea derivatives (Yamin & Hassan, 2004). All of the C—N bonds of thiourea fragment C7—N1, C8—N1, C8—N2 and C9—N2 are in the range 1.3933 (19) - 1.338 (2) Å, intermediate between those expected for single and double C—N bonds (1.47 and 1.27 Å respectively). Among these C—N bonds the C7—N1 is the longest indicating Csp2-Nsp2 single bond while C8—N2 is the shortest bond with more double bond character. This further demonstrate that there is π conjugation only along S2—C8—N2 system but not along O1—C7—N1 and C7—N1—C8 as found in 1-(3-methoxybenzoyl)-3,3-diethylthiourea (Morales et al., 2000). The bond lengths in the benzothizole ring system are normal and agree with the corresponding values found in 2-(benzothiazole-2-yliminomethyl)-6-methoxyphenol and N,N-(2-benzothia-zole)(2-pyridylmethyl)amine (Büyükgüngör et al. 2004; Chen et al. 2003). The bond length C9—N2 is very close to the value determined for the 2-(benzothiazole-2-yliminomethyl)-6-methoxyphenol suggesting the existence of a delocalized double bond in the benzothiazole moiety (Büyükgüngör et al. 2004). All bond lengths and angles confirm the sp2 hybridization for all C and N atoms of the benzothiazole ring with all C—C and C—N bond lengths intermediate between single and double bonds. The benzothiazole ring bonded to N2 is essentially planar and inclined at an angle -11.23(°) with respect to the plane of thiourea moiety. Similarly the phenyl ring bonded to C7 is at an angle of 11.91(°) with respect to the plane formed by the thiourea moiety.

The molecule is further stabilized by intermolecular and intramolecular hydrogen bonding. There are two types of intermolecular C1—H1A···S2i and C5—H5A···O1ii [Symmetry codes: (i) -x, -y + 1, -z + 1; (ii) -x + 1, -y + 1, -z + 1] hydrogen bonds. The intramolecular N2—H2B···O1 hydrogen bond is also observed. As a result, a pseudo six membered (O1—C7—N1—C8—N2···H2B) ring is formed.

For related literature see: Büyükgüngör et al. (2004); del Campo et al. (2002); Chen et al. (2003); D'hooghe et al. (2005); Koketsu & Ishihara (2006); Morales et al. (2000); Rodríguez-Fernández et al. (2005); Yamin & Hassan (2004); Yunus et al. (2007); Zeng et al. (2003).

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL (Bruker, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
1-(1,3-Benzothiazol-2-yl)-3-benzoylthiourea top
Crystal data top
C15H11N3OS2F(000) = 648
Mr = 313.39Dx = 1.447 Mg m3
Monoclinic, P2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ycCell parameters from 8487 reflections
a = 12.4402 (8) Åθ = 2.6–28.3°
b = 5.8608 (4) ŵ = 0.37 mm1
c = 19.7240 (13) ÅT = 293 K
β = 90.223 (1)°Block, pale-yellow
V = 1438.06 (16) Å30.32 × 0.26 × 0.20 mm
Z = 4
Data collection top
Bruker SMART CCD
diffractometer
3508 independent reflections
Radiation source: fine-focus sealed tube2724 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
φ and ω scansθmax = 28.3°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 1999)
h = 1616
Tmin = 0.933, Tmax = 1.000k = 77
8487 measured reflectionsl = 1926
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)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0541P)2 + 0.2538P]
where P = (Fo2 + 2Fc2)/3
3508 reflections(Δ/σ)max < 0.001
190 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.26 e Å3
Crystal data top
C15H11N3OS2V = 1438.06 (16) Å3
Mr = 313.39Z = 4
Monoclinic, P2/cMo Kα radiation
a = 12.4402 (8) ŵ = 0.37 mm1
b = 5.8608 (4) ÅT = 293 K
c = 19.7240 (13) Å0.32 × 0.26 × 0.20 mm
β = 90.223 (1)°
Data collection top
Bruker SMART CCD
diffractometer
3508 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1999)
2724 reflections with I > 2σ(I)
Tmin = 0.933, Tmax = 1.000Rint = 0.019
8487 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0350 restraints
wR(F2) = 0.102H-atom parameters constrained
S = 1.04Δρmax = 0.31 e Å3
3508 reflectionsΔρmin = 0.26 e Å3
190 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.21573 (13)0.0594 (3)0.53895 (8)0.0416 (4)
H1A0.14800.07920.51970.050*
C20.23408 (16)0.1206 (3)0.58247 (9)0.0515 (4)
H2A0.17850.22030.59320.062*
C30.33485 (18)0.1525 (4)0.61000 (10)0.0602 (5)
H3A0.34730.27490.63900.072*
C40.41698 (17)0.0051 (4)0.59497 (11)0.0646 (5)
H4A0.48480.02800.61370.078*
C50.39901 (14)0.1779 (3)0.55189 (9)0.0529 (5)
H5A0.45470.27810.54190.063*
C60.29787 (12)0.2116 (3)0.52370 (8)0.0378 (3)
C70.28504 (12)0.4117 (3)0.47818 (8)0.0380 (3)
C80.14589 (12)0.6519 (3)0.42051 (8)0.0372 (3)
C90.22056 (12)0.9776 (3)0.35659 (7)0.0354 (3)
C100.29090 (13)1.2734 (3)0.30503 (8)0.0388 (3)
C110.36820 (14)1.4337 (3)0.28664 (9)0.0472 (4)
H11A0.43821.42250.30300.057*
C120.33920 (16)1.6082 (3)0.24397 (9)0.0517 (4)
H12A0.39021.71590.23130.062*
C130.23408 (17)1.6266 (3)0.21919 (9)0.0551 (5)
H13A0.21641.74500.18980.066*
C140.15669 (15)1.4723 (3)0.23769 (9)0.0514 (4)
H14A0.08671.48550.22140.062*
C150.18525 (13)1.2952 (3)0.28139 (8)0.0412 (4)
N10.18011 (10)0.4716 (2)0.46078 (7)0.0395 (3)
H1B0.13030.38610.47700.047*
N20.22510 (10)0.7819 (2)0.39602 (7)0.0385 (3)
H2B0.28890.73720.40640.046*
N30.30872 (10)1.0881 (2)0.34739 (7)0.0397 (3)
O10.36174 (9)0.5195 (2)0.45724 (6)0.0482 (3)
S10.10503 (3)1.08096 (8)0.31634 (2)0.04440 (13)
S20.01565 (3)0.69188 (9)0.40697 (2)0.05128 (15)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0415 (8)0.0417 (9)0.0415 (8)0.0026 (7)0.0017 (7)0.0018 (7)
C20.0636 (11)0.0424 (10)0.0486 (10)0.0033 (8)0.0075 (8)0.0042 (8)
C30.0734 (13)0.0535 (11)0.0536 (11)0.0096 (10)0.0028 (10)0.0161 (9)
C40.0549 (11)0.0708 (13)0.0680 (13)0.0098 (10)0.0134 (9)0.0184 (11)
C50.0423 (9)0.0610 (12)0.0553 (11)0.0008 (8)0.0066 (8)0.0146 (9)
C60.0389 (8)0.0385 (8)0.0362 (8)0.0038 (6)0.0000 (6)0.0004 (6)
C70.0358 (7)0.0394 (8)0.0388 (8)0.0009 (6)0.0025 (6)0.0003 (7)
C80.0360 (8)0.0391 (8)0.0366 (8)0.0027 (6)0.0012 (6)0.0027 (6)
C90.0359 (7)0.0363 (8)0.0339 (7)0.0054 (6)0.0023 (6)0.0005 (6)
C100.0422 (8)0.0398 (8)0.0343 (8)0.0048 (7)0.0034 (6)0.0000 (6)
C110.0471 (9)0.0494 (10)0.0451 (9)0.0003 (8)0.0056 (7)0.0020 (8)
C120.0631 (11)0.0460 (10)0.0460 (10)0.0016 (8)0.0126 (8)0.0040 (8)
C130.0740 (13)0.0474 (10)0.0441 (10)0.0154 (9)0.0092 (9)0.0106 (8)
C140.0511 (10)0.0554 (11)0.0476 (10)0.0141 (8)0.0005 (8)0.0088 (8)
C150.0442 (9)0.0414 (9)0.0381 (8)0.0061 (7)0.0022 (7)0.0018 (7)
N10.0324 (6)0.0398 (7)0.0461 (7)0.0007 (5)0.0018 (5)0.0073 (6)
N20.0323 (6)0.0392 (7)0.0441 (7)0.0031 (5)0.0024 (5)0.0046 (6)
N30.0380 (7)0.0413 (7)0.0399 (7)0.0021 (6)0.0018 (5)0.0030 (6)
O10.0351 (6)0.0515 (7)0.0581 (7)0.0035 (5)0.0043 (5)0.0143 (6)
S10.0367 (2)0.0473 (3)0.0491 (2)0.00442 (17)0.00595 (17)0.00779 (18)
S20.0328 (2)0.0624 (3)0.0586 (3)0.00376 (19)0.00173 (18)0.0142 (2)
Geometric parameters (Å, º) top
C1—C21.379 (2)C9—N31.287 (2)
C1—C61.390 (2)C9—N21.387 (2)
C1—H1A0.9300C9—S11.7476 (15)
C2—C31.377 (3)C10—N31.387 (2)
C2—H2A0.9300C10—C111.393 (2)
C3—C41.371 (3)C10—C151.399 (2)
C3—H3A0.9300C11—C121.372 (2)
C4—C51.386 (3)C11—H11A0.9300
C4—H4A0.9300C12—C131.398 (3)
C5—C61.388 (2)C12—H12A0.9300
C5—H5A0.9300C13—C141.371 (3)
C6—C71.486 (2)C13—H13A0.9300
C7—O11.2179 (19)C14—C151.395 (2)
C7—N11.3933 (19)C14—H14A0.9300
C8—N21.338 (2)C15—S11.7471 (17)
C8—N11.388 (2)N1—H1B0.8600
C8—S21.6578 (15)N2—H2B0.8600
C2—C1—C6120.37 (16)N3—C10—C11125.14 (15)
C2—C1—H1A119.8N3—C10—C15114.84 (14)
C6—C1—H1A119.8C11—C10—C15120.01 (15)
C3—C2—C1119.85 (18)C12—C11—C10118.83 (17)
C3—C2—H2A120.1C12—C11—H11A120.6
C1—C2—H2A120.1C10—C11—H11A120.6
C4—C3—C2120.47 (18)C11—C12—C13121.01 (18)
C4—C3—H3A119.8C11—C12—H12A119.5
C2—C3—H3A119.8C13—C12—H12A119.5
C3—C4—C5120.11 (18)C14—C13—C12120.85 (17)
C3—C4—H4A119.9C14—C13—H13A119.6
C5—C4—H4A119.9C12—C13—H13A119.6
C4—C5—C6119.95 (18)C13—C14—C15118.55 (17)
C4—C5—H5A120.0C13—C14—H14A120.7
C6—C5—H5A120.0C15—C14—H14A120.7
C5—C6—C1119.24 (15)C14—C15—C10120.72 (16)
C5—C6—C7116.71 (15)C14—C15—S1129.37 (14)
C1—C6—C7124.06 (14)C10—C15—S1109.89 (12)
O1—C7—N1121.35 (14)C8—N1—C7128.15 (13)
O1—C7—C6122.16 (14)C8—N1—H1B115.9
N1—C7—C6116.49 (14)C7—N1—H1B115.9
N2—C8—N1114.57 (13)C8—N2—C9130.20 (13)
N2—C8—S2125.60 (12)C8—N2—H2B114.9
N1—C8—S2119.83 (12)C9—N2—H2B114.9
N3—C9—N2117.53 (13)C9—N3—C10110.14 (13)
N3—C9—S1117.47 (12)C15—S1—C987.62 (7)
N2—C9—S1124.97 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···O10.861.862.5878 (17)142
C1—H1A···S2i0.932.843.4017 (17)120
C5—H5A···O1ii0.932.573.470 (2)162
Symmetry codes: (i) x, y+1, z+1; (ii) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC15H11N3OS2
Mr313.39
Crystal system, space groupMonoclinic, P2/c
Temperature (K)293
a, b, c (Å)12.4402 (8), 5.8608 (4), 19.7240 (13)
β (°) 90.223 (1)
V3)1438.06 (16)
Z4
Radiation typeMo Kα
µ (mm1)0.37
Crystal size (mm)0.32 × 0.26 × 0.20
Data collection
DiffractometerBruker SMART CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 1999)
Tmin, Tmax0.933, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
8487, 3508, 2724
Rint0.019
(sin θ/λ)max1)0.666
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.102, 1.04
No. of reflections3508
No. of parameters190
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.31, 0.26

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···O10.861.862.5878 (17)142
C1—H1A···S2i0.932.843.4017 (17)120
C5—H5A···O1ii0.932.573.470 (2)162
Symmetry codes: (i) x, y+1, z+1; (ii) x+1, y+1, z+1.
 

Acknowledgements

The authors gratefully acknowledge Allama Iqbal Open University, Islamabad, Pakistan, for providing research facilities.

References

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