N-[(4-Amino-5-sulfanyl-idene-4,5-dihydro-1H-1,2,4-triazol-3-yl)meth-yl]-4-methyl-benzamide.

In the title compound, C(11)H(13)N(5)OS, the dihedral angle between the triazole ring and the benzene ring is 84.21 (7)°. The amino group adopts a pyramidal configuration. An intra-molecular N-H⋯O hydrogen bond stabilizes the mol-ecular structure and generates an S(8) ring. In the crystal, mol-ecules are linked by inter-molecular N-H⋯O, N-H⋯S, N-H⋯N and C-H⋯S hydrogen bonds into layers lying parallel to the bc plane. The crystal structure is further stabilized by aromatic π-π stacking inter-actions [centroid-centroid distance = 3.3330 (7) Å].

Related literature

For applications of 1,2,4-triazole derivatives, see: Demirbas et al. (2002 ▶, 2004 ▶); Tozkoparan et al. (2000 ▶); Turan-Zitouni et al. (1999 ▶); Kritsanida et al. (2002 ▶); Holla et al. (2002 ▶); Foroumadi et al. (2003 ▶); Isloor et al. (2009 ▶); Shujuan et al. (2004 ▶); Verreck et al. (2003 ▶); Clemons et al. (2004 ▶). For related structures, see: Fun et al. (2009 ▶). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C11H13N5OS

M = 263.32

Monoclinic,

a = 14.8148 (1) Å

b = 8.6702 (1) Å

c = 9.8534 (1) Å

β = 104.923 (1)°

V = 1222.96 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 100 K

0.30 × 0.27 × 0.11 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.926, T max = 0.972

15018 measured reflections

3555 independent reflections

3142 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.093

S = 1.07

3555 reflections

180 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.44 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810035014/hb5629sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035014/hb5629Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C11H13N5OS	F(000) = 552
Mr = 263.32	Dx = 1.430 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6908 reflections
a = 14.8148 (1) Å	θ = 2.8–32.6°
b = 8.6702 (1) Å	µ = 0.26 mm−1
c = 9.8534 (1) Å	T = 100 K
β = 104.923 (1)°	Block, colourless
V = 1222.96 (2) Å3	0.30 × 0.27 × 0.11 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	3555 independent reflections
Radiation source: fine-focus sealed tube	3142 reflections with I > 2σ(I)
graphite	Rint = 0.023
φ and ω scans	θmax = 30.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −20→20
Tmin = 0.926, Tmax = 0.972	k = −12→11
15018 measured reflections	l = −13→13

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0404P)2 + 0.7537P] where P = (Fo2 + 2Fc2)/3
3555 reflections	(Δ/σ)max = 0.001
180 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

	x	y	z	Uiso*/Ueq
S1	0.10394 (2)	0.62450 (3)	0.66661 (3)	0.01567 (9)
O1	0.25236 (6)	1.16404 (11)	0.93553 (9)	0.01636 (19)
N1	0.22250 (7)	1.27102 (12)	0.71802 (11)	0.0132 (2)
N2	0.10834 (7)	1.02977 (12)	0.49330 (11)	0.0126 (2)
N3	0.10360 (7)	0.87126 (12)	0.49292 (11)	0.0123 (2)
N4	0.10800 (7)	0.93784 (11)	0.70210 (10)	0.01071 (19)
N5	0.10633 (8)	0.92596 (13)	0.84341 (11)	0.0144 (2)
C1	0.44707 (9)	1.19963 (16)	0.96321 (14)	0.0194 (3)
H1A	0.4293	1.1194	1.0134	0.023*
C2	0.54098 (10)	1.23546 (18)	0.98378 (16)	0.0242 (3)
H2A	0.5857	1.1781	1.0474	0.029*
C3	0.56933 (10)	1.35571 (18)	0.91096 (15)	0.0244 (3)
C4	0.50110 (10)	1.44261 (18)	0.81922 (15)	0.0244 (3)
H4A	0.5188	1.5258	0.7724	0.029*
C5	0.40675 (9)	1.40711 (16)	0.79637 (14)	0.0196 (3)
H5A	0.3620	1.4655	0.7338	0.024*
C6	0.37934 (9)	1.28382 (14)	0.86742 (13)	0.0147 (2)
C7	0.27951 (8)	1.23533 (14)	0.84421 (13)	0.0130 (2)
C8	0.12391 (8)	1.22850 (13)	0.67896 (13)	0.0126 (2)
H8A	0.0896	1.2996	0.6084	0.015*
H8B	0.0990	1.2362	0.7606	0.015*
C9	0.11102 (8)	1.06742 (13)	0.62240 (12)	0.0110 (2)
C10	0.10403 (8)	0.81094 (13)	0.61801 (12)	0.0115 (2)
C11	0.67179 (11)	1.3904 (2)	0.9308 (2)	0.0371 (4)
H11A	0.7038	1.3810	1.0284	0.056*
H11B	0.6789	1.4936	0.8996	0.056*
H11C	0.6978	1.3188	0.8769	0.056*
H1N1	0.2453 (12)	1.299 (2)	0.6521 (18)	0.020 (4)*
H1N3	0.1054 (13)	0.822 (2)	0.419 (2)	0.031 (5)*
H1N5	0.1532 (13)	0.975 (2)	0.8901 (19)	0.025 (5)*
H2N5	0.0541 (12)	0.970 (2)	0.8501 (17)	0.016 (4)*

	U11	U22	U33	U12	U13	U23
S1	0.02516 (17)	0.00896 (14)	0.01334 (15)	−0.00100 (11)	0.00578 (12)	−0.00009 (10)
O1	0.0186 (4)	0.0182 (4)	0.0122 (4)	−0.0036 (3)	0.0038 (3)	0.0004 (3)
N1	0.0147 (5)	0.0127 (5)	0.0120 (5)	−0.0028 (4)	0.0030 (4)	0.0000 (4)
N2	0.0135 (5)	0.0108 (4)	0.0127 (5)	−0.0002 (4)	0.0020 (4)	0.0006 (4)
N3	0.0154 (5)	0.0106 (4)	0.0112 (5)	0.0000 (4)	0.0039 (4)	−0.0009 (4)
N4	0.0127 (4)	0.0094 (4)	0.0094 (4)	−0.0003 (3)	0.0018 (3)	0.0000 (3)
N5	0.0197 (5)	0.0143 (5)	0.0098 (5)	−0.0010 (4)	0.0046 (4)	−0.0009 (4)
C1	0.0188 (6)	0.0188 (6)	0.0193 (6)	−0.0019 (5)	0.0023 (5)	−0.0002 (5)
C2	0.0160 (6)	0.0269 (7)	0.0259 (7)	0.0013 (5)	−0.0014 (5)	−0.0030 (6)
C3	0.0165 (6)	0.0337 (8)	0.0237 (7)	−0.0067 (5)	0.0063 (5)	−0.0097 (6)
C4	0.0233 (7)	0.0312 (7)	0.0192 (7)	−0.0125 (6)	0.0063 (5)	−0.0019 (5)
C5	0.0203 (6)	0.0221 (6)	0.0155 (6)	−0.0047 (5)	0.0026 (5)	0.0016 (5)
C6	0.0150 (5)	0.0155 (5)	0.0138 (5)	−0.0019 (4)	0.0038 (4)	−0.0025 (4)
C7	0.0153 (5)	0.0105 (5)	0.0132 (5)	−0.0002 (4)	0.0034 (4)	−0.0018 (4)
C8	0.0130 (5)	0.0100 (5)	0.0143 (5)	0.0006 (4)	0.0024 (4)	−0.0006 (4)
C9	0.0106 (5)	0.0097 (5)	0.0121 (5)	0.0004 (4)	0.0016 (4)	0.0015 (4)
C10	0.0114 (5)	0.0112 (5)	0.0114 (5)	0.0007 (4)	0.0019 (4)	−0.0001 (4)
C11	0.0182 (7)	0.0538 (11)	0.0405 (10)	−0.0117 (7)	0.0099 (7)	−0.0131 (8)

S1—C10	1.6860 (12)	C1—H1A	0.9300
O1—C7	1.2409 (15)	C2—C3	1.390 (2)
N1—C7	1.3469 (16)	C2—H2A	0.9300
N1—C8	1.4587 (15)	C3—C4	1.391 (2)
N1—H1N1	0.843 (18)	C3—C11	1.510 (2)
N2—C9	1.3040 (15)	C4—C5	1.3919 (19)
N2—N3	1.3761 (14)	C4—H4A	0.9300
N3—C10	1.3375 (15)	C5—C6	1.3942 (18)
N3—H1N3	0.85 (2)	C5—H5A	0.9300
N4—C10	1.3695 (15)	C6—C7	1.4974 (17)
N4—C9	1.3780 (14)	C8—C9	1.4975 (16)
N4—N5	1.4028 (14)	C8—H8A	0.9700
N5—H1N5	0.84 (2)	C8—H8B	0.9700
N5—H2N5	0.880 (17)	C11—H11A	0.9600
C1—C2	1.3885 (19)	C11—H11B	0.9600
C1—C6	1.3938 (18)	C11—H11C	0.9600
C7—N1—C8	122.19 (10)	C4—C5—H5A	120.0
C7—N1—H1N1	119.9 (12)	C6—C5—H5A	120.0
C8—N1—H1N1	116.3 (12)	C1—C6—C5	119.31 (12)
C9—N2—N3	103.97 (9)	C1—C6—C7	117.83 (11)
C10—N3—N2	113.57 (10)	C5—C6—C7	122.85 (12)
C10—N3—H1N3	126.8 (14)	O1—C7—N1	122.72 (11)
N2—N3—H1N3	119.4 (14)	O1—C7—C6	121.40 (11)
C10—N4—C9	108.24 (10)	N1—C7—C6	115.87 (10)
C10—N4—N5	122.18 (10)	N1—C8—C9	110.91 (9)
C9—N4—N5	129.57 (10)	N1—C8—H8A	109.5
N4—N5—H1N5	106.3 (12)	C9—C8—H8A	109.5
N4—N5—H2N5	106.4 (11)	N1—C8—H8B	109.5
H1N5—N5—H2N5	110.9 (17)	C9—C8—H8B	109.5
C2—C1—C6	120.09 (13)	H8A—C8—H8B	108.0
C2—C1—H1A	120.0	N2—C9—N4	110.76 (10)
C6—C1—H1A	120.0	N2—C9—C8	124.43 (10)
C1—C2—C3	121.12 (14)	N4—C9—C8	124.61 (10)
C1—C2—H2A	119.4	N3—C10—N4	103.45 (10)
C3—C2—H2A	119.4	N3—C10—S1	129.53 (9)
C2—C3—C4	118.42 (13)	N4—C10—S1	126.98 (9)
C2—C3—C11	120.65 (15)	C3—C11—H11A	109.5
C4—C3—C11	120.93 (15)	C3—C11—H11B	109.5
C3—C4—C5	121.10 (13)	H11A—C11—H11B	109.5
C3—C4—H4A	119.4	C3—C11—H11C	109.5
C5—C4—H4A	119.4	H11A—C11—H11C	109.5
C4—C5—C6	119.90 (13)	H11B—C11—H11C	109.5
C9—N2—N3—C10	−0.49 (13)	C5—C6—C7—N1	25.57 (17)
C6—C1—C2—C3	0.5 (2)	C7—N1—C8—C9	−84.82 (13)
C1—C2—C3—C4	1.7 (2)	N3—N2—C9—N4	−0.06 (12)
C1—C2—C3—C11	−178.05 (14)	N3—N2—C9—C8	175.06 (10)
C2—C3—C4—C5	−2.4 (2)	C10—N4—C9—N2	0.57 (13)
C11—C3—C4—C5	177.38 (14)	N5—N4—C9—N2	−177.73 (11)
C3—C4—C5—C6	0.8 (2)	C10—N4—C9—C8	−174.55 (11)
C2—C1—C6—C5	−2.1 (2)	N5—N4—C9—C8	7.15 (19)
C2—C1—C6—C7	177.06 (12)	N1—C8—C9—N2	−82.22 (14)
C4—C5—C6—C1	1.5 (2)	N1—C8—C9—N4	92.24 (13)
C4—C5—C6—C7	−177.69 (12)	N2—N3—C10—N4	0.81 (13)
C8—N1—C7—O1	0.08 (18)	N2—N3—C10—S1	−177.08 (9)
C8—N1—C7—C6	178.70 (10)	C9—N4—C10—N3	−0.81 (12)
C1—C6—C7—O1	25.05 (17)	N5—N4—C10—N3	177.64 (10)
C5—C6—C7—O1	−155.80 (13)	C9—N4—C10—S1	177.16 (9)
C1—C6—C7—N1	−153.59 (12)	N5—N4—C10—S1	−4.39 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1i	0.841 (18)	2.187 (17)	2.9824 (14)	157.7 (17)
N3—H1N3···S1ii	0.851 (19)	2.524 (19)	3.2168 (11)	139.2 (15)
N3—H1N3···N5ii	0.851 (19)	2.276 (18)	2.9738 (15)	139.3 (16)
N5—H1N5···O1	0.843 (19)	2.169 (18)	2.9587 (15)	155.9 (16)
N5—H2N5···S1iii	0.880 (18)	2.666 (18)	3.5381 (12)	171.2 (14)
C8—H8A···S1iv	0.97	2.87	3.4456 (12)	119

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1i	0.841 (18)	2.187 (17)	2.9824 (14)	157.7 (17)
N3—H1N3⋯S1ii	0.851 (19)	2.524 (19)	3.2168 (11)	139.2 (15)
N3—H1N3⋯N5ii	0.851 (19)	2.276 (18)	2.9738 (15)	139.3 (16)
N5—H1N5⋯O1	0.843 (19)	2.169 (18)	2.9587 (15)	155.9 (16)
N5—H2N5⋯S1iii	0.880 (18)	2.666 (18)	3.5381 (12)	171.2 (14)
C8—H8A⋯S1iv	0.97	2.87	3.4456 (12)	119

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .