3-Benzyl-4-ethyl-1H-1,2,4-triazole-5(4H)-thione

Karczmarzyk, Z.; Pitucha, M.; Wysocki, W.; Pachuta-Stec, A.; Stańczuk, A.

doi:10.1107/S1600536812051276

organic compounds

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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Pages o155-o156

doi:10.1107/S1600536812051276

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3-Benzyl-4-ethyl-1H-1,2,4-triazole-5(4H)-thione

Zbigniew Karczmarzyk,^a ^* Monika Pitucha,^b Waldemar Wysocki,^a Anna Pachuta-Stec ^b and Andrzej Stańczuk ^a

^aDepartment of Chemistry, Siedlce University, ul. 3 Maja 54, 08-110 Siedlce, Poland, and ^bDepartment of Organic Chemistry, Faculty of Pharmacy with Division of Medical Analytics, Medical University, ul. Chodźki 4A, 20-093 Lublin, Poland
^*Correspondence e-mail: kar@uph.edu.pl

(Received 6 November 2012; accepted 19 December 2012; online 4 January 2013)

The title compound, C₁₁H₁₃N₃S, exists in the 5-thioxo tautomeric form. The benzene ring exhibits disorder with a refined ratio of 0.77 (2):0.23 (2) for components A and B with a common bridgehead C atom. The 1,2,4-triazole ring is essentially planar, with a maximum deviation of 0.002 (3) Å for the benzyl-substituted C atom, and forms dihedral angles of 88.94 (18) and 86.56 (49)° with the benzene rings of components A and B, respectively. The angle between the plane of the ethyl chain and the mean plane of 1,2,4-triazole ring is 88.55 (15)° and this conformation is stabilized by an intramolecular C—H⋯S contact. In the crystal, pairs of N—H⋯S hydrogen bonds link molecules into inversion dimers. π–π interactions are observed between the triazole and benzene rings, with centroid–centroid separations of 3.547 (4) and 3.544 (12) Å for components A and B, and slippages of 0.49 (6) and 0.58 (15) Å, respectively.

Related literature

For background information on 1,2,4-triazole-5-thiones, see: Saadeh et al. (2010 ); Akhtar et al. (2008 ); Al-Omar et al. (2010 ). For their biological activity, see: Pitucha et al. (2010 ). For the synthesis, see: Dobosz & Pachuta-Stec (1996 ). For related structures, see: Karczmarzyk et al. (2012 ); Kruszynski et al. (2007 ); Siwek et al. (2008 ). For graph-set motifs, see Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₁H₁₃N₃S
M_r = 219.30
Monoclinic, P 2₁ /c
a = 7.3731 (5) Å
b = 8.9408 (19) Å
c = 16.9936 (8) Å
β = 91.892 (4)°
V = 1119.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 296 K
0.55 × 0.20 × 0.20 mm

Data collection

Kuma KM-4 four-circle diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.834, T_max = 0.852
3392 measured reflections
3289 independent reflections
1385 reflections with I > 2σ(I)
R_int = 0.039
2 standard reflections every 100 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.156
S = 0.98
3289 reflections
187 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7B⋯S6	0.97	2.85	3.204 (3)	103
N1—H1⋯S6ⁱ	0.86 (3)	2.46 (3)	3.303 (3)	167 (3)
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: KM4B8 (Gałdecki et al., 1996 $[Gałdecki, Z., Kowalski, A., Kucharczyk, D. & Uszyński, L. (1996). KM4B8. Kuma Diffraction, Wrocław, Poland.]$ ); cell refinement: KM4B8; data reduction: DATAPROC (Gałdecki et al., 1995 $[Gałdecki, Z., Kowalski, A. & Uszyński, L. (1995). DATAPROC. Kuma Diffraction, Wrocław, Poland.]$ ); 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 ); software used to prepare material for publication: SHELXL97 and WinGX (Farrugia, 2012).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812051276/fy2077sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812051276/fy2077Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812051276/fy2077Isup3.cml

checkCIF report

Comment top

The 1,2,4-triazole-5-thiones were found to have significant antimicrobial action (Saadeh et al., 2010; Akhtar et al., 2008; Al-Omar et al., 2010). The title compound, (I), belongs to 3- and 4-substituted derivatives of 1,2,4-triazole-5-thiones with potential antituberculosis activity against mycobacterium strains of Mycobacterium smegmatis, Mycobacterium phlei and Mycobacterium H37Ra (Pitucha et al., 2010).

The X-ray analysis of the title compound revealed that this compound exists as the 5-thioxo tautomer in the crystalline state. The molecular geometry of (I) is very similar to that observed in the related structures of ethyl 2-(3-methyl-5-sulfanylidene-4,5-dihydro-1H-1,2,4-triazol-4-yl)acetate (Karczmarzyk et al., 2012), 2-(3-methyl-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-4-yl)acetic acid (Kruszynski et al., 2007) and 4-[3-(2-methyl-furan-3-yl)-5-thioxo-1,2,4-triazol-4-yl]acetic acid (Siwek et al., 2008). The 1,2,4-triazole ring is planar to within 0.002 (3) Å. The benzene ring exhibits disorder giving two components A and B with a common bridgehead C atom. The benzyl group adopts a cis-gauche conformation in respect to 1,2,4-triazole ring with the torsion angles N2—C3—C9—C10 and C3—C9—C10—C11A for benzene ring A and C3—C9—C10—C11B for benzene ring B of 25.1 (5), -102.9 (9) and -105 (4)°, respectively. The plane of the ethyl chain is positioned almost perpendicular to the mean plane of the 1,2,4-triazole ring with the dihedral angle of 88.55 (15)°. This conformation is stabilized by the C7—H71···S6 intramolecular hydrogen bond specified as S(5) in graph set notation (Bernstein et al., 1995).

In the crystal structure (Fig. 2), inversion-related molecules of (I) form molecular dimers designated as R²₂(8) rings via N1—H1···S6 intermolecular hydrogen bonds. Moreover, the π-electron systems of the pairs of triazole and benzene rings belonging to the molecules related by 2₁ axis overlap each other, with centroid-to-centroid separation of 3.547 (4) Å for ring A and 3.544 (12) Å for ring B between the triazole ring at (x, y, z) and benzene rings at (-x, y+1/2, -z+1/2) and benzene rings at (x, y, z) and triazole ring at (-x, y-1/2, -z+1/2). The angle between overlapping planes is 6.6 (3)° for A and 5.0 (10)° for B and the slippage is 0.490 (58) and 0.575 (147) Å for rings A and B, respectively.

Related literature top

For background information on 1,2,4-triazole-5-thiones, see: Saadeh et al. (2010); Akhtar et al. (2008); Al-Omar et al. (2010). For their biological activity, see: Pitucha et al. (2010). For the synthesis, see: Dobosz & Pachuta-Stec (1996). For related structures, see: Karczmarzyk et al. (2012); Kruszynski et al. ( 2007); Siwek et al. (2008). For graph-set motifs, see Bernstein et al. (1995).

Experimental top

The title compound, (I), was prepared by the cyclization reaction of 1-benzyl-4-ethylthiosemicarbazide in alkaline medium according to the metod described by Dobosz & Pachuta-Stec (1996). Crystals uitable for X-ray diffraction analysis were grown by slow evaporation of ethanol solution.

Computing details top

Data collection: KM4B8 (Gałdecki et al., 1996); cell refinement: KM4B8 (Gałdecki et al., 1996); data reduction: DATAPROC (Gałdecki et al., 1995); 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); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and WinGX (Farrugia, 2012).

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. A view of the molecular packing in (I).

3-Benzyl-4-ethyl-1H-1,2,4-triazole-5(4H)-thione top

Crystal data top

C₁₁H₁₃N₃S	F(000) = 464
M_r = 219.30	D_x = 1.301 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 425 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.3731 (5) Å	Cell parameters from 67 reflections
b = 8.9408 (19) Å	θ = 3.6–11.2°
c = 16.9936 (8) Å	µ = 0.26 mm⁻¹
β = 91.892 (4)°	T = 296 K
V = 1119.6 (3) Å³	Prism, colourless
Z = 4	0.55 × 0.20 × 0.20 mm

Data collection top

Kuma KM-4 four-circle diffractometer	1385 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.039
Graphite monochromator	θ_max = 30.1°, θ_min = 2.4°
ω–2θ scans	h = −10→10
Absorption correction: ψ scan (North et al., 1968)	k = 0→12
T_min = 0.834, T_max = 0.852	l = 0→23
3392 measured reflections	2 standard reflections every 100 reflections
3289 independent reflections	intensity decay: 1%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.156	w = 1/[σ²(F_o²) + (0.062P)² + 0.2203P] where P = (F_o² + 2F_c²)/3
S = 0.98	(Δ/σ)_max < 0.001
3289 reflections	Δρ_max = 0.23 e Å⁻³
187 parameters	Δρ_min = −0.20 e Å⁻³
6 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.012 (3)

Crystal data top

C₁₁H₁₃N₃S	V = 1119.6 (3) Å³
M_r = 219.30	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.3731 (5) Å	µ = 0.26 mm⁻¹
b = 8.9408 (19) Å	T = 296 K
c = 16.9936 (8) Å	0.55 × 0.20 × 0.20 mm
β = 91.892 (4)°

Data collection top

Kuma KM-4 four-circle diffractometer	1385 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.039
T_min = 0.834, T_max = 0.852	2 standard reflections every 100 reflections
3392 measured reflections	intensity decay: 1%
3289 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	6 restraints
wR(F²) = 0.156	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	Δρ_max = 0.23 e Å⁻³
3289 reflections	Δρ_min = −0.20 e Å⁻³
187 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
S6	−0.22230 (10)	0.33538 (8)	0.53097 (4)	0.0567 (3)
N1	0.0496 (3)	0.3323 (3)	0.42647 (13)	0.0473 (6)
H1	0.101 (4)	0.412 (4)	0.4446 (18)	0.071*
N2	0.1063 (3)	0.2595 (3)	0.36067 (13)	0.0525 (6)
N4	−0.1519 (3)	0.1693 (2)	0.40086 (12)	0.0445 (5)
C3	−0.0184 (4)	0.1613 (3)	0.34683 (16)	0.0516 (7)
C5	−0.1070 (3)	0.2807 (3)	0.45287 (15)	0.0412 (6)
C7	−0.3151 (4)	0.0780 (3)	0.40482 (17)	0.0563 (8)
H7A	−0.3527	0.0466	0.3521	0.084*
H7B	−0.4122	0.1375	0.4259	0.084*
C8	−0.2841 (5)	−0.0576 (4)	0.4557 (2)	0.0776 (11)
H8A	−0.2561	−0.0268	0.5088	0.116*
H8B	−0.1847	−0.1146	0.4362	0.116*
H8C	−0.3917	−0.1182	0.4545	0.116*
C9	−0.0260 (4)	0.0531 (4)	0.2795 (2)	0.0834 (12)
H91	−0.1034	0.0942	0.2376	0.125*
H92	−0.0813	−0.0391	0.2969	0.125*
C10	0.1561 (3)	0.0173 (3)	0.24685 (16)	0.0456 (6)
C11A	0.1986 (18)	0.0849 (15)	0.1776 (6)	0.0499 (18)	0.77 (2)
H11A	0.1175	0.1531	0.1547	0.075*	0.77 (2)
C12A	0.3582 (15)	0.0546 (11)	0.1410 (6)	0.062 (2)	0.77 (2)
H12A	0.3837	0.1027	0.0941	0.093*	0.77 (2)
C13A	0.4806 (9)	−0.0468 (11)	0.1733 (7)	0.066 (2)	0.77 (2)
H13A	0.5890	−0.0673	0.1490	0.100*	0.77 (2)
C14A	0.4388 (12)	−0.1159 (11)	0.2417 (7)	0.071 (3)	0.77 (2)
H14A	0.5179	−0.1870	0.2633	0.107*	0.77 (2)
C15A	0.2833 (14)	−0.0828 (10)	0.2790 (5)	0.068 (2)	0.77 (2)
H15A	0.2613	−0.1279	0.3270	0.102*	0.77 (2)
C11B	0.240 (5)	0.060 (6)	0.179 (2)	0.069 (11)	0.23 (2)
H11B	0.1873	0.1316	0.1463	0.103*	0.23 (2)
C12B	0.403 (3)	−0.004 (4)	0.1598 (16)	0.052 (8)	0.23 (2)
H12B	0.4608	0.0185	0.1134	0.077*	0.23 (2)
C13B	0.475 (3)	−0.104 (4)	0.214 (2)	0.074 (12)	0.23 (2)
H13B	0.5909	−0.1414	0.2053	0.112*	0.23 (2)
C14B	0.391 (3)	−0.154 (3)	0.280 (2)	0.072 (7)	0.23 (2)
H14B	0.4437	−0.2272	0.3126	0.108*	0.23 (2)
C15B	0.225 (3)	−0.093 (3)	0.2963 (16)	0.053 (6)	0.23 (2)
H15B	0.1608	−0.1244	0.3395	0.079*	0.23 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S6	0.0669 (5)	0.0494 (4)	0.0553 (4)	−0.0142 (4)	0.0264 (3)	−0.0107 (4)
N1	0.0485 (13)	0.0404 (12)	0.0538 (13)	−0.0110 (11)	0.0150 (10)	−0.0100 (11)
N2	0.0480 (13)	0.0527 (13)	0.0577 (15)	−0.0092 (11)	0.0180 (11)	−0.0129 (12)
N4	0.0407 (11)	0.0443 (12)	0.0491 (12)	−0.0089 (10)	0.0113 (9)	−0.0094 (11)
C3	0.0438 (14)	0.0560 (16)	0.0558 (16)	−0.0092 (14)	0.0160 (12)	−0.0166 (14)
C5	0.0429 (14)	0.0345 (12)	0.0465 (15)	−0.0038 (11)	0.0069 (11)	0.0005 (11)
C7	0.0447 (15)	0.0585 (18)	0.0665 (19)	−0.0148 (14)	0.0138 (13)	−0.0140 (15)
C8	0.080 (2)	0.0522 (18)	0.102 (3)	−0.0176 (17)	0.031 (2)	−0.0055 (18)
C9	0.0629 (19)	0.101 (3)	0.089 (2)	−0.0244 (19)	0.0288 (17)	−0.054 (2)
C10	0.0451 (15)	0.0458 (15)	0.0465 (15)	−0.0063 (12)	0.0078 (12)	−0.0113 (13)
C11A	0.052 (4)	0.043 (4)	0.055 (4)	0.004 (3)	0.006 (3)	−0.004 (2)
C12A	0.062 (5)	0.063 (5)	0.062 (4)	0.001 (3)	0.024 (3)	−0.004 (3)
C13A	0.043 (4)	0.077 (5)	0.080 (5)	0.008 (3)	0.014 (4)	−0.027 (4)
C14A	0.063 (6)	0.063 (5)	0.087 (8)	0.018 (4)	−0.015 (5)	0.002 (4)
C15A	0.091 (6)	0.063 (4)	0.050 (4)	−0.020 (5)	−0.003 (4)	0.007 (3)
C11B	0.054 (19)	0.06 (2)	0.09 (2)	0.006 (12)	−0.022 (13)	−0.003 (13)
C12B	0.032 (14)	0.07 (2)	0.052 (16)	−0.003 (12)	0.015 (12)	−0.019 (14)
C13B	0.051 (12)	0.10 (2)	0.07 (2)	−0.041 (13)	0.029 (13)	−0.041 (18)
C14B	0.074 (15)	0.049 (11)	0.094 (19)	0.016 (10)	−0.004 (13)	0.003 (11)
C15B	0.033 (10)	0.059 (12)	0.067 (15)	0.008 (9)	0.003 (7)	0.008 (8)

Geometric parameters (Å, º) top

S6—C5	1.673 (3)	C10—C11B	1.379 (5)
N1—C5	1.335 (3)	C10—C15A	1.394 (7)
N1—N2	1.371 (3)	C11A—C12A	1.376 (9)
N1—H1	0.86 (3)	C11A—H11A	0.9300
N2—C3	1.288 (3)	C12A—C13A	1.381 (10)
N4—C5	1.365 (3)	C12A—H12A	0.9300
N4—C3	1.370 (3)	C13A—C14A	1.360 (11)
N4—C7	1.457 (3)	C13A—H13A	0.9300
C3—C9	1.498 (4)	C14A—C15A	1.361 (9)
C7—C8	1.502 (4)	C14A—H14A	0.9300
C7—H7A	0.9700	C15A—H15A	0.9300
C7—H7B	0.9700	C11B—C12B	1.380 (5)
C8—H8A	0.9600	C11B—H11B	0.9300
C8—H8B	0.9600	C12B—C13B	1.379 (5)
C8—H8C	0.9600	C12B—H12B	0.9300
C9—C10	1.504 (4)	C13B—C14B	1.377 (5)
C9—H91	0.9700	C13B—H13B	0.9300
C9—H92	0.9700	C14B—C15B	1.379 (5)
C10—C11A	1.369 (6)	C14B—H14B	0.9300
C10—C15B	1.379 (5)	C15B—H15B	0.9300

C5—N1—N2	113.6 (2)	C15B—C10—C9	103.9 (10)
C5—N1—H1	123 (2)	C11B—C10—C9	133.0 (12)
N2—N1—H1	123 (2)	C15A—C10—C9	126.1 (5)
C3—N2—N1	103.7 (2)	C10—C11A—C12A	121.7 (8)
C5—N4—C3	107.9 (2)	C10—C11A—H11A	119.2
C5—N4—C7	124.2 (2)	C12A—C11A—H11A	119.2
C3—N4—C7	127.9 (2)	C11A—C12A—C13A	120.5 (9)
N2—C3—N4	111.5 (2)	C11A—C12A—H12A	119.8
N2—C3—C9	126.0 (2)	C13A—C12A—H12A	119.8
N4—C3—C9	122.4 (2)	C14A—C13A—C12A	118.3 (8)
N1—C5—N4	103.2 (2)	C14A—C13A—H13A	120.8
N1—C5—S6	129.3 (2)	C12A—C13A—H13A	120.8
N4—C5—S6	127.47 (18)	C13A—C14A—C15A	121.1 (7)
N4—C7—C8	111.6 (2)	C13A—C14A—H14A	119.4
N4—C7—H7A	109.3	C15A—C14A—H14A	119.4
C8—C7—H7A	109.3	C14A—C15A—C10	121.6 (5)
N4—C7—H7B	109.3	C14A—C15A—H15A	119.2
C8—C7—H7B	109.3	C10—C15A—H15A	119.2
H7A—C7—H7B	108.0	C10—C11B—C12B	120.3 (17)
C7—C8—H8A	109.5	C10—C11B—H11B	119.8
C7—C8—H8B	109.5	C12B—C11B—H11B	119.8
H8A—C8—H8B	109.5	C13B—C12B—C11B	115 (2)
C7—C8—H8C	109.5	C13B—C12B—H12B	122.3
H8A—C8—H8C	109.5	C11B—C12B—H12B	122.3
H8B—C8—H8C	109.5	C14B—C13B—C12B	126 (2)
C3—C9—C10	114.1 (3)	C14B—C13B—H13B	117.2
C3—C9—H91	108.7	C12B—C13B—H13B	117.2
C10—C9—H91	108.7	C13B—C14B—C15B	117 (2)
C3—C9—H92	108.7	C13B—C14B—H14B	121.3
C10—C9—H92	108.7	C15B—C14B—H14B	121.3
H91—C9—H92	107.6	C14B—C15B—C10	118.3 (15)
C15B—C10—C11B	122.5 (12)	C14B—C15B—H15B	120.8
C11A—C10—C15A	116.8 (5)	C10—C15B—H15B	120.8
C11A—C10—C9	117.1 (5)

C5—N1—N2—C3	−0.1 (3)	C3—C9—C10—C11B	−105 (4)
N1—N2—C3—N4	0.3 (3)	C3—C9—C10—C15A	79.6 (7)
N1—N2—C3—C9	178.3 (3)	C15A—C10—C11A—C12A	0.7 (18)
C5—N4—C3—N2	−0.3 (3)	C9—C10—C11A—C12A	−177.0 (11)
C7—N4—C3—N2	179.7 (3)	C10—C11A—C12A—C13A	0 (2)
C5—N4—C3—C9	−178.5 (3)	C11A—C12A—C13A—C14A	0.4 (17)
C7—N4—C3—C9	1.6 (5)	C12A—C13A—C14A—C15A	−2.2 (16)
N2—N1—C5—N4	−0.1 (3)	C13A—C14A—C15A—C10	3.3 (16)
N2—N1—C5—S6	179.3 (2)	C11A—C10—C15A—C14A	−2.5 (14)
C3—N4—C5—N1	0.2 (3)	C9—C10—C15A—C14A	175.0 (7)
C7—N4—C5—N1	−179.8 (2)	C15B—C10—C11B—C12B	−2 (7)
C3—N4—C5—S6	−179.2 (2)	C9—C10—C11B—C12B	−173 (3)
C7—N4—C5—S6	0.8 (4)	C10—C11B—C12B—C13B	−3 (7)
C5—N4—C7—C8	−88.5 (3)	C11B—C12B—C13B—C14B	7 (5)
C3—N4—C7—C8	91.4 (3)	C12B—C13B—C14B—C15B	−4 (5)
N2—C3—C9—C10	25.1 (5)	C13B—C14B—C15B—C10	−2 (5)
N4—C3—C9—C10	−157.0 (3)	C11B—C10—C15B—C14B	5 (5)
C3—C9—C10—C11A	−102.9 (9)	C9—C10—C15B—C14B	178 (3)
C3—C9—C10—C15B	83.1 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···S6	0.97	2.85	3.204 (3)	103
N1—H1···S6ⁱ	0.86 (3)	2.46 (3)	3.303 (3)	167 (3)

Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₃N₃S
M_r	219.30
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	7.3731 (5), 8.9408 (19), 16.9936 (8)
β (°)	91.892 (4)
V (Å³)	1119.6 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.55 × 0.20 × 0.20

Data collection
Diffractometer	Kuma KM-4 four-circle diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.834, 0.852
No. of measured, independent and observed [I > 2σ(I)] reflections	3392, 3289, 1385
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.706

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.156, 0.98
No. of reflections	3289
No. of parameters	187
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.20

Computer programs: KM4B8 (Gałdecki et al., 1996), DATAPROC (Gałdecki et al., 1995), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), SHELXL97 (Sheldrick, 2008) and WinGX (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···S6	0.97	2.85	3.204 (3)	103
N1—H1···S6ⁱ	0.86 (3)	2.46 (3)	3.303 (3)	167 (3)

Symmetry code: (i) −x, −y+1, −z+1.

References

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Volume 69| Part 2| February 2013| Pages o155-o156

doi:10.1107/S1600536812051276

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