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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 69| Part 5| May 2013| Page o697
https://doi.org/10.1107/S1600536813009501

4-Benzyl-3-(thio­phen-2-yl)-4,5-di­hydro-1H-1,2,4-triazole-5-thione

Mona M. Al-Shehri,a Ali A. El-Emam,a‡ Nasser R. El-Brollosy,a Seik Weng Ngb,c and Edward R. T. Tiekinkb*

aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
*Correspondence e-mail: Edward.Tiekink@gmail.com

(Received 8 April 2013; accepted 8 April 2013; online 13 April 2013)

In the title compound, C13H11N3S2, the triazole and thio­phene rings are coplanar [dihedral angle = 6.22 (13)°]. By contrast, the phenyl ring is perpendicular to the triazole ring [dihedral angle = 85.58 (13)°], so that the mol­ecule has an L-shape. The thio­phene S atom is syn with the ring imine N atom. In the crystal, eight-membered {⋯HNCS}2 synthons form between centrosymmetrically related mol­ecules, leading to dimeric aggregates that are connected into a supra­molecular layer parallel to (101) by π–π inter­actions between centrosymmetrically related triazole rings [centroid–centroid distance = 3.6091 (15) Å] and C—H⋯π inter­actions.

Related literature

For the pharmacological properties (anti-inflammatory, anti-microbial and anti-cancer) of 1,2,4-triazole derivatives, see: El-Emam & Ibrahim (1991[El-Emam, A. A. & Ibrahim, T. M. (1991). Arzneim. Forsch. Drug. Res. 41, 1260-1264.]); Navidpour et al. (2006[Navidpour, L., Shafaroodi, H., Abdi, K., Amini, M., Ghahremani, M. H., Dehpour, A. R. & Shafiee, A. (2006). Bioorg. Med. Chem. 14, 2507-2517.]); Kumar et al. (2010[Kumar, G. V. S., Rajendraprasad, Y., Mallikarjuna, B. P., Chandrashekar, S. M. & Kistayya, C. (2010). Eur. J. Med. Chem. 45, 2063-2074.]); Wang et al. (2011[Wang, L., Tseng, W., Wu, T., Kaneko, K., Takayama, H., Kimura, M., Yange, W., Wu, J. B., Juang, S. & Wong, F. F. (2011). Bioorg. Med. Chem. Lett. 21, 5358-5362.]). For a related structure, see: Zareef et al. (2008[Zareef, M., Iqbal, R. & Parvez, M. (2008). Acta Cryst. E64, o952-o953.]).

[Scheme 1]

Experimental

Crystal data

  • C13H11N3S2

  • Mr = 273.37

  • Monoclinic, P 21 /n

  • a = 13.422 (2) Å

  • b = 6.1670 (7) Å

  • c = 16.596 (2) Å

  • β = 111.972 (15)°

  • V = 1273.9 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.40 mm−1

  • T = 295 K

  • 0.30 × 0.05 × 0.05 mm
Data collection

  • Agilent SuperNova Dual diffractometer with an Atlas detector

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.806, Tmax = 1.000

  • 6460 measured reflections

  • 2937 independent reflections

  • 2088 reflections with I > 2σ(I)

  • Rint = 0.036
Refinement

  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.109

  • S = 1.02

  • 2937 reflections

  • 167 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.24 e Å−3

  • Δρmin = −0.27 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C8–C13 ring.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H2⋯S2i 0.88 (1) 2.43 (1) 3.297 (2) 169 (2)
C13—H13⋯Cg1ii 0.93 2.94 3.636 (3) 133
Symmetry codes: (i) -x+1, -y, -z+1; (ii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536813009501/hg5308sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813009501/hg5308Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813009501/hg5308Isup3.cml

checkCIF report


Comment top

In continuation of research into the chemical and pharmacological properties of 1,2,4-triazole derivatives (El-Emam & Ibrahim, 1991; Navidpour et al., 2006; Kumar et al., 2010; Wang et al., 2011), we describe herein the X-ray crystal structure determination of the title compound, (I).

In (I), Fig. 1, the triazole ring is plane (r.m.s. deviation = 0.008 Å) and the thione-S2 atom lies 0.030 (1) Å out of the plane. The thiophene ring is co-planar with the triazole ring [dihedral angle = 6.22 (13)°] and the latter forms a dihedral of 85.58 (13)° with the phenyl ring. The thiophene-S1 atom is syn with the ring imine-N2 atom. Overall, the molecule has the shape of the letter L. A similar conformation was found in the analogous furanyl compound for which two molecules comprise the asymmetric unit and which was characterized as an hydrate (Zareef et al., 2008).

In the crystal packing, centrosymmetrically related molecules aggregate into dimers via N—H···S hydrogen bonds that lead to eight-membered {···HNCS}2 synthons, Table 1. The dimers are connected into rows along the b axis by π—π interactions between centrosymmetrically related triazole rings [inter-centroid distance = 3.6091 (15) Å for symmetry operation: 1 - x, 1 - y, 1 - z]. Projecting out on either side of the row are the phenyl groups that inter-digitate with translationally related rows to enable the formation of edge-to-face C—H···π interactions, Table 1, that result in a supramolecular layer parallel to (1 0 1), Fig. 2. Layers stack with no specific interactions between them, Fig. 3.

Related literature top

For the pharmacological properties (anti-inflammatory, anti-microbial and anti-cancer) of 1,2,4-triazole derivatives, see: El-Emam & Ibrahim (1991); Navidpour et al. (2006); Kumar et al. (2010); Wang et al. (2011). For a related structure, see: Zareef et al. (2008).

Experimental top

A mixture of thiophene-2-carbohydrazide (1.42 g, 0.01 mol), benzyl isothiocyanate (1.49 g, 0.01 mol), in ethanol (10 ml) was heated under reflux with stirring for 1 h after which the solvent was distilled off in vacuo. Aqueous sodium hydroxide solution (10%, 15 ml) was added to the residue and the mixture was heated under reflux for 2 h then filtered hot. On cooling, the mixture was acidified with hydrochloric acid and the precipitated crude product was filtered, washed with water, dried and crystallized from aqueous ethanol to yield 2.32 g (85%) of the title compound as colourless crystals. M.pt: 515–517 K. Single crystals suitable for X-ray analysis were obtained by slow evaporation of its CHCl3:EtOH (1:1; 10 ml) solution at room temperature. 1H NMR (DMSO-d6, 500.13 MHz): δ 5.51 (s, 2H, CH2), 7.13–7.14 (m, 3H, Ar—H), 7.27–7.40 (m, 4H, Ar—H & thiophene-H), 7.77 (d, 1H, thiophene-H, J = 4.0 Hz), 14.21 (s, 1H, SH, thiol tautomer). 13C NMR (DMSO-d6, 125.76 MHz): δ 46.74 (CH2), 126.15, 126.33, 127.51, 128.19, 128.72, 128.86, 129.90, 135.40 (Ar—C & thiophene-C), 146.31 (triazole C-3), 168.31 (triazole C-5).

Refinement top

The C-bound H-atoms were placed in calculated positions [C—H = 0.93 to 0.97 Å, Uiso(H) = 1.2Ueq(C)] and were included in the refinement in the riding model approximation. The N-bound H-atom was refined with the distance restraint N—H = 0.88±0.01 Å.

Structure description top

In continuation of research into the chemical and pharmacological properties of 1,2,4-triazole derivatives (El-Emam & Ibrahim, 1991; Navidpour et al., 2006; Kumar et al., 2010; Wang et al., 2011), we describe herein the X-ray crystal structure determination of the title compound, (I).

In (I), Fig. 1, the triazole ring is plane (r.m.s. deviation = 0.008 Å) and the thione-S2 atom lies 0.030 (1) Å out of the plane. The thiophene ring is co-planar with the triazole ring [dihedral angle = 6.22 (13)°] and the latter forms a dihedral of 85.58 (13)° with the phenyl ring. The thiophene-S1 atom is syn with the ring imine-N2 atom. Overall, the molecule has the shape of the letter L. A similar conformation was found in the analogous furanyl compound for which two molecules comprise the asymmetric unit and which was characterized as an hydrate (Zareef et al., 2008).

In the crystal packing, centrosymmetrically related molecules aggregate into dimers via N—H···S hydrogen bonds that lead to eight-membered {···HNCS}2 synthons, Table 1. The dimers are connected into rows along the b axis by π—π interactions between centrosymmetrically related triazole rings [inter-centroid distance = 3.6091 (15) Å for symmetry operation: 1 - x, 1 - y, 1 - z]. Projecting out on either side of the row are the phenyl groups that inter-digitate with translationally related rows to enable the formation of edge-to-face C—H···π interactions, Table 1, that result in a supramolecular layer parallel to (1 0 1), Fig. 2. Layers stack with no specific interactions between them, Fig. 3.

For the pharmacological properties (anti-inflammatory, anti-microbial and anti-cancer) of 1,2,4-triazole derivatives, see: El-Emam & Ibrahim (1991); Navidpour et al. (2006); Kumar et al. (2010); Wang et al. (2011). For a related structure, see: Zareef et al. (2008).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 35% probability level.
[Figure 2] Fig. 2. A view of the supramolecular layer in (I), which is sustained by N—H···S hydrogen bonds as well as by π—π and C—H···π interactions shown as orange, blue and purple dashed lines, respectively.
[Figure 3] Fig. 3. View of the unit-cell contents in projection down the b axis of (I), highlighting the stacking of layers. The N—H···S hydrogen bonds as well as by π—π and C—H···π interactions shown as orange, blue and purple dashed lines, respectively.
4-Benzyl-3-(thiophen-2-yl)-4,5-dihydro-1H-1,2,4-triazole-5-thione top
Crystal data top
C13H11N3S2F(000) = 568
Mr = 273.37Dx = 1.425 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1615 reflections
a = 13.422 (2) Åθ = 3.0–27.5°
b = 6.1670 (7) ŵ = 0.40 mm−1
c = 16.596 (2) ÅT = 295 K
β = 111.972 (15)°Prism, colourless
V = 1273.9 (3) Å30.30 × 0.05 × 0.05 mm
Z = 4
Data collection top
Agilent SuperNova Dual
diffractometer with an Atlas detector		2937 independent reflections
Radiation source: SuperNova (Mo) X-ray Source2088 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.036
Detector resolution: 10.4041 pixels mm-1θmax = 27.6°, θmin = 3.3°
ω scanh = −12→17
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2011)		k = −8→5
Tmin = 0.806, Tmax = 1.000l = −21→19
6460 measured reflections
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0415P)2 + 0.2539P]
where P = (Fo2 + 2Fc2)/3
2937 reflections(Δ/σ)max < 0.001
167 parametersΔρmax = 0.24 e Å−3
1 restraintΔρmin = −0.27 e Å−3
Crystal data top
C13H11N3S2V = 1273.9 (3) Å3
Mr = 273.37Z = 4
Monoclinic, P21/nMo Kα radiation
a = 13.422 (2) ŵ = 0.40 mm−1
b = 6.1670 (7) ÅT = 295 K
c = 16.596 (2) Å0.30 × 0.05 × 0.05 mm
β = 111.972 (15)°
Data collection top
Agilent SuperNova Dual
diffractometer with an Atlas detector		2937 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2011)		2088 reflections with I > 2σ(I)
Tmin = 0.806, Tmax = 1.000Rint = 0.036
6460 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0451 restraint
wR(F2) = 0.109H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.24 e Å−3
2937 reflectionsΔρmin = −0.27 e Å−3
167 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
S10.21756 (5)0.78528 (13)0.30574 (4)0.0548 (2)
S20.47823 (5)0.12218 (10)0.62298 (3)0.03891 (18)
N10.34574 (15)0.4060 (3)0.39839 (11)0.0395 (5)
N20.40554 (15)0.2515 (3)0.45408 (12)0.0383 (5)
H20.4302 (18)0.138 (3)0.4349 (15)0.052 (8)*
N30.35676 (13)0.4651 (3)0.53331 (10)0.0304 (4)
C10.14130 (18)0.9997 (4)0.31144 (16)0.0475 (6)
H10.10541.09040.26480.057*
C20.1387 (2)1.0233 (4)0.39097 (16)0.0492 (6)
H2A0.10081.13300.40540.059*
C30.19944 (19)0.8647 (4)0.45051 (14)0.0426 (6)
H30.20540.85740.50810.051*
C40.24840 (16)0.7233 (4)0.41373 (13)0.0346 (5)
C50.31583 (17)0.5357 (4)0.44809 (13)0.0323 (5)
C60.41379 (16)0.2783 (3)0.53621 (13)0.0315 (5)
C70.34971 (17)0.5686 (4)0.61041 (13)0.0344 (5)
H7A0.35860.72380.60650.041*
H7B0.40850.51680.66140.041*
C80.24552 (17)0.5271 (4)0.62246 (12)0.0344 (5)
C90.1871 (2)0.3419 (5)0.59316 (17)0.0534 (7)
H90.21100.23910.56350.064*
C100.0931 (2)0.3049 (5)0.6069 (2)0.0708 (9)
H100.05400.17870.58630.085*
C110.0579 (2)0.4550 (6)0.65120 (19)0.0665 (8)
H11−0.00560.43160.66020.080*
C120.1160 (2)0.6383 (5)0.68195 (17)0.0595 (8)
H120.09280.73870.71290.071*
C130.2092 (2)0.6763 (4)0.66753 (15)0.0474 (6)
H130.24790.80290.68820.057*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0569 (4)0.0694 (5)0.0403 (3)0.0206 (4)0.0206 (3)0.0166 (3)
S20.0448 (3)0.0349 (3)0.0365 (3)0.0064 (3)0.0146 (2)0.0030 (3)
N10.0467 (11)0.0384 (11)0.0365 (10)0.0075 (9)0.0190 (8)0.0045 (9)
N20.0453 (11)0.0369 (11)0.0369 (10)0.0088 (9)0.0204 (9)0.0021 (9)
N30.0335 (9)0.0279 (9)0.0318 (9)0.0017 (8)0.0145 (7)−0.0002 (8)
C10.0385 (13)0.0476 (15)0.0501 (14)0.0047 (12)0.0095 (10)0.0177 (12)
C20.0478 (14)0.0404 (14)0.0561 (15)0.0098 (12)0.0155 (12)0.0040 (12)
C30.0500 (14)0.0378 (13)0.0386 (12)0.0104 (12)0.0148 (10)0.0046 (11)
C40.0328 (11)0.0346 (12)0.0355 (11)−0.0007 (10)0.0117 (9)0.0036 (10)
C50.0345 (11)0.0308 (11)0.0313 (10)−0.0024 (10)0.0120 (9)0.0009 (10)
C60.0309 (11)0.0301 (11)0.0355 (11)−0.0029 (9)0.0148 (9)−0.0015 (9)
C70.0371 (12)0.0337 (12)0.0314 (10)0.0001 (10)0.0116 (9)−0.0031 (9)
C80.0371 (12)0.0363 (12)0.0307 (10)0.0035 (10)0.0137 (9)0.0008 (10)
C90.0547 (16)0.0503 (16)0.0651 (16)−0.0097 (13)0.0339 (13)−0.0164 (13)
C100.0595 (18)0.073 (2)0.092 (2)−0.0239 (17)0.0418 (17)−0.0182 (19)
C110.0493 (16)0.089 (2)0.0722 (18)0.0006 (17)0.0350 (14)0.0030 (18)
C120.0588 (17)0.073 (2)0.0550 (15)0.0159 (16)0.0313 (13)−0.0069 (15)
C130.0531 (15)0.0455 (15)0.0458 (13)0.0023 (12)0.0211 (11)−0.0120 (12)
Geometric parameters (Å, º) top
S1—C11.696 (3)C4—C51.448 (3)
S1—C41.725 (2)C7—C81.507 (3)
S2—C61.678 (2)C7—H7A0.9700
N1—C51.315 (3)C7—H7B0.9700
N1—N21.361 (3)C8—C91.368 (3)
N2—C61.336 (3)C8—C131.384 (3)
N2—H20.881 (10)C9—C101.382 (4)
N3—C61.374 (3)C9—H90.9300
N3—C51.382 (2)C10—C111.372 (4)
N3—C71.464 (2)C10—H100.9300
C1—C21.341 (3)C11—C121.359 (4)
C1—H10.9300C11—H110.9300
C2—C31.412 (3)C12—C131.379 (4)
C2—H2A0.9300C12—H120.9300
C3—C41.366 (3)C13—H130.9300
C3—H30.9300
C1—S1—C491.71 (11)N3—C6—S2127.78 (15)
C5—N1—N2103.94 (17)N3—C7—C8114.11 (17)
C6—N2—N1114.13 (18)N3—C7—H7A108.7
C6—N2—H2124.6 (16)C8—C7—H7A108.7
N1—N2—H2121.0 (16)N3—C7—H7B108.7
C6—N3—C5107.63 (16)C8—C7—H7B108.7
C6—N3—C7123.51 (17)H7A—C7—H7B107.6
C5—N3—C7128.77 (18)C9—C8—C13118.4 (2)
C2—C1—S1112.20 (18)C9—C8—C7122.1 (2)
C2—C1—H1123.9C13—C8—C7119.4 (2)
S1—C1—H1123.9C8—C9—C10121.1 (3)
C1—C2—C3113.1 (2)C8—C9—H9119.5
C1—C2—H2A123.4C10—C9—H9119.5
C3—C2—H2A123.4C11—C10—C9119.7 (3)
C4—C3—C2112.2 (2)C11—C10—H10120.1
C4—C3—H3123.9C9—C10—H10120.1
C2—C3—H3123.9C12—C11—C10119.9 (3)
C3—C4—C5131.97 (19)C12—C11—H11120.1
C3—C4—S1110.76 (16)C10—C11—H11120.1
C5—C4—S1117.24 (16)C11—C12—C13120.4 (3)
N1—C5—N3110.66 (19)C11—C12—H12119.8
N1—C5—C4122.11 (18)C13—C12—H12119.8
N3—C5—C4127.23 (19)C12—C13—C8120.4 (3)
N2—C6—N3103.62 (17)C12—C13—H13119.8
N2—C6—S2128.59 (17)C8—C13—H13119.8
C5—N1—N2—C60.3 (3)N1—N2—C6—N3−1.0 (2)
C4—S1—C1—C2−0.2 (2)N1—N2—C6—S2178.98 (16)
S1—C1—C2—C3−0.2 (3)C5—N3—C6—N21.3 (2)
C1—C2—C3—C40.7 (3)C7—N3—C6—N2−175.41 (18)
C2—C3—C4—C5−178.7 (2)C5—N3—C6—S2−178.73 (16)
C2—C3—C4—S1−0.8 (3)C7—N3—C6—S24.6 (3)
C1—S1—C4—C30.61 (19)C6—N3—C7—C8−102.1 (2)
C1—S1—C4—C5178.87 (18)C5—N3—C7—C881.9 (3)
N2—N1—C5—N30.5 (2)N3—C7—C8—C929.0 (3)
N2—N1—C5—C4−179.08 (19)N3—C7—C8—C13−153.6 (2)
C6—N3—C5—N1−1.2 (2)C13—C8—C9—C100.9 (4)
C7—N3—C5—N1175.28 (19)C7—C8—C9—C10178.3 (2)
C6—N3—C5—C4178.4 (2)C8—C9—C10—C11−0.5 (5)
C7—N3—C5—C4−5.1 (3)C9—C10—C11—C12−0.6 (5)
C3—C4—C5—N1172.4 (2)C10—C11—C12—C131.2 (5)
S1—C4—C5—N1−5.4 (3)C11—C12—C13—C8−0.8 (4)
C3—C4—C5—N3−7.2 (4)C9—C8—C13—C12−0.3 (3)
S1—C4—C5—N3175.03 (17)C7—C8—C13—C12−177.8 (2)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C8–C13 ring.
D—H···AD—HH···AD···AD—H···A
N2—H2···S2i0.88 (1)2.43 (1)3.297 (2)169 (2)
C13—H13···Cg1ii0.932.943.636 (3)133
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1/2, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formulaC13H11N3S2
Mr273.37
Crystal system, space groupMonoclinic, P21/n
Temperature (K)295
a, b, c (Å)13.422 (2), 6.1670 (7), 16.596 (2)
β (°) 111.972 (15)
V (Å3)1273.9 (3)
Z4
Radiation typeMo Kα
µ (mm−1)0.40
Crystal size (mm)0.30 × 0.05 × 0.05
Data collection
DiffractometerAgilent SuperNova Dual
diffractometer with an Atlas detector
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2011)
Tmin, Tmax0.806, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections		6460, 2937, 2088
Rint0.036
(sin θ/λ)max (Å−1)0.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.109, 1.02
No. of reflections2937
No. of parameters167
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.24, −0.27

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C8–C13 ring.
D—H···AD—HH···AD···AD—H···A
N2—H2···S2i0.881 (10)2.429 (11)3.297 (2)169 (2)
C13—H13···Cg1ii0.932.943.636 (3)133
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1/2, y+1/2, −z+3/2.
 

Footnotes

‡Additional correspondence author, e-mail: elemam5@hotmail.com.

Acknowledgements

The financial support of the Deanship of Scientific Research and the Research Center for Female Scientific and Medical Colleges, King Saud University, is greatly appreciated. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/03).

References

First citationAgilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.  Google Scholar
 First citationBrandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationEl-Emam, A. A. & Ibrahim, T. M. (1991). Arzneim. Forsch. Drug. Res. 41, 1260–1264.  CAS Google Scholar
 First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationKumar, G. V. S., Rajendraprasad, Y., Mallikarjuna, B. P., Chandrashekar, S. M. & Kistayya, C. (2010). Eur. J. Med. Chem. 45, 2063–2074.  PubMed Google Scholar
 First citationNavidpour, L., Shafaroodi, H., Abdi, K., Amini, M., Ghahremani, M. H., Dehpour, A. R. & Shafiee, A. (2006). Bioorg. Med. Chem. 14, 2507–2517.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWang, L., Tseng, W., Wu, T., Kaneko, K., Takayama, H., Kimura, M., Yange, W., Wu, J. B., Juang, S. & Wong, F. F. (2011). Bioorg. Med. Chem. Lett. 21, 5358–5362.  Web of Science CrossRef CAS PubMed Google Scholar
 First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationZareef, M., Iqbal, R. & Parvez, M. (2008). Acta Cryst. E64, o952–o953.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar

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.

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ISSN: 2056-9890
Volume 69| Part 5| May 2013| Page o697
https://doi.org/10.1107/S1600536813009501
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