4-Amino-3-(p-tolyl-oxymeth-yl)-1H-1,2,4-triazole-5(4H)-thione.

In the title triazole compound, C(10)H(12)N(4)OS, the triazole ring is essentially planar [maximum deviation = 0.009 (1) Å] and forms a dihedral angle of 5.78 (4)° with the benzene ring. In the crystal structure, mol-ecules are linked into dimers by centrosymmetric N-H⋯S inter-actions. These dimers are linked into two-mol-ecule-wide tapes by N-H⋯N and S⋯S [3.2634 (3) Å] inter-actions. In addition, they are further inter-connected by weak N-H⋯S inter-actions into sheets parallel to the ab plane. The crystal structure is further stabilized by weak inter-molecular C-H⋯π inter-actions.

Related literature

For general background and applications of triazole derivatives, see: Amir et al. (2008 ▶); Kuş et al. (2008 ▶); Krzysztof et al. (2008 ▶); Padmavathi et al. (2008 ▶). For the preparation, see: Conti (1964 ▶). For related structures, see: Fun et al. (2008 ▶, 2009 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C10H12N4OS

M = 236.30

Triclinic,

a = 5.9977 (1) Å

b = 6.4002 (1) Å

c = 15.5506 (2) Å

α = 89.352 (1)°

β = 83.157 (1)°

γ = 65.562 (1)°

V = 539.11 (1) Å3

Z = 2

Mo Kα radiation

μ = 0.28 mm−1

T = 100 K

0.47 × 0.30 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.878, T max = 0.975

19910 measured reflections

4712 independent reflections

4228 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.095

S = 1.05

4712 reflections

193 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.59 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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/S1600536809027664/tk2497sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027664/tk2497Isup2.hkl

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

C10H12N4OS	Z = 2
Mr = 236.30	F(000) = 248
Triclinic, P1	Dx = 1.456 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.9977 (1) Å	Cell parameters from 9925 reflections
b = 6.4002 (1) Å	θ = 2.6–35.2°
c = 15.5506 (2) Å	µ = 0.28 mm−1
α = 89.352 (1)°	T = 100 K
β = 83.157 (1)°	Plate, colourless
γ = 65.562 (1)°	0.47 × 0.30 × 0.09 mm
V = 539.11 (1) Å3

Bruker SMART APEXII CCD area-detector diffractometer	4712 independent reflections
Radiation source: fine-focus sealed tube	4228 reflections with I > 2σ(I)
graphite	Rint = 0.022
φ and ω scans	θmax = 35.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→9
Tmin = 0.878, Tmax = 0.975	k = −10→10
19910 measured reflections	l = −25→24

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0648P)2 + 0.0513P] where P = (Fo2 + 2Fc2)/3
4712 reflections	(Δ/σ)max = 0.001
193 parameters	Δρmax = 0.59 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

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

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.

	x	y	z	Uiso*/Ueq
S1	0.84328 (3)	0.26155 (3)	0.040453 (11)	0.01525 (6)
O1	0.06661 (10)	1.12912 (9)	0.24927 (4)	0.01568 (10)
N1	0.49686 (12)	0.89098 (11)	0.14036 (4)	0.01591 (11)
N2	0.69184 (11)	0.71323 (11)	0.09371 (4)	0.01581 (11)
H1N2	0.820 (2)	0.732 (2)	0.0596 (9)	0.024 (3)*
N3	0.43624 (11)	0.57330 (10)	0.13942 (4)	0.01199 (10)
N4	0.30133 (12)	0.43979 (11)	0.15295 (4)	0.01506 (11)
H1N4	0.405 (2)	0.293 (3)	0.1674 (9)	0.023 (3)*
H2N4	0.258 (3)	0.419 (3)	0.1018 (10)	0.035 (4)*
C1	0.66067 (12)	0.51754 (12)	0.09031 (4)	0.01305 (11)
C2	0.34451 (12)	0.79838 (12)	0.16710 (4)	0.01274 (11)
C3	0.09665 (12)	0.91116 (11)	0.21854 (5)	0.01325 (11)
H3A	−0.034 (2)	0.927 (2)	0.1804 (8)	0.018 (3)*
H3B	0.086 (2)	0.808 (2)	0.2649 (8)	0.016 (3)*
C4	−0.16049 (12)	1.26194 (12)	0.29390 (4)	0.01307 (12)
C5	−0.34570 (13)	1.18698 (13)	0.31707 (5)	0.01573 (12)
H5A	−0.333 (2)	1.039 (2)	0.2991 (9)	0.026 (3)*
C6	−0.56524 (13)	1.33505 (13)	0.36639 (5)	0.01718 (13)
H6A	−0.682 (3)	1.275 (2)	0.3802 (9)	0.027 (3)*
C7	−0.60421 (13)	1.55609 (12)	0.39238 (5)	0.01587 (13)
C8	−0.41667 (15)	1.62850 (13)	0.36627 (5)	0.01808 (13)
H8A	−0.443 (3)	1.785 (3)	0.3837 (9)	0.028 (3)*
C9	−0.19792 (14)	1.48515 (12)	0.31738 (5)	0.01693 (13)
H9A	−0.070 (3)	1.533 (3)	0.2975 (10)	0.031 (4)*
C10	−0.83720 (14)	1.71372 (15)	0.44753 (5)	0.02093 (15)
H10A	−0.902 (3)	1.871 (3)	0.4283 (11)	0.042 (4)*
H10B	−0.971 (3)	1.672 (3)	0.4484 (11)	0.046 (4)*
H10C	−0.807 (3)	1.720 (3)	0.5070 (12)	0.049 (5)*

	U11	U22	U33	U12	U13	U23
S1	0.01469 (9)	0.01076 (8)	0.01619 (9)	−0.00247 (6)	0.00295 (6)	−0.00124 (6)
O1	0.0137 (2)	0.0113 (2)	0.0208 (2)	−0.00540 (17)	0.00364 (18)	−0.00495 (18)
N1	0.0146 (2)	0.0125 (2)	0.0193 (3)	−0.0056 (2)	0.0033 (2)	−0.0034 (2)
N2	0.0138 (2)	0.0134 (2)	0.0194 (3)	−0.0062 (2)	0.0036 (2)	−0.0032 (2)
N3	0.0118 (2)	0.0090 (2)	0.0141 (2)	−0.00392 (18)	0.00088 (18)	−0.00093 (18)
N4	0.0165 (3)	0.0110 (2)	0.0186 (3)	−0.0073 (2)	0.0007 (2)	0.0000 (2)
C1	0.0118 (2)	0.0120 (3)	0.0136 (3)	−0.0037 (2)	0.0004 (2)	−0.0002 (2)
C2	0.0130 (2)	0.0099 (2)	0.0139 (3)	−0.0038 (2)	0.0002 (2)	−0.0013 (2)
C3	0.0126 (3)	0.0095 (2)	0.0156 (3)	−0.0035 (2)	0.0018 (2)	−0.0025 (2)
C4	0.0125 (3)	0.0106 (3)	0.0143 (3)	−0.0035 (2)	0.0008 (2)	−0.0015 (2)
C5	0.0140 (3)	0.0128 (3)	0.0195 (3)	−0.0055 (2)	0.0011 (2)	−0.0024 (2)
C6	0.0134 (3)	0.0163 (3)	0.0199 (3)	−0.0051 (2)	0.0015 (2)	−0.0026 (2)
C7	0.0141 (3)	0.0143 (3)	0.0147 (3)	−0.0017 (2)	−0.0003 (2)	−0.0011 (2)
C8	0.0192 (3)	0.0113 (3)	0.0204 (3)	−0.0041 (2)	0.0018 (2)	−0.0028 (2)
C9	0.0179 (3)	0.0117 (3)	0.0201 (3)	−0.0064 (2)	0.0028 (2)	−0.0026 (2)
C10	0.0164 (3)	0.0199 (3)	0.0193 (3)	−0.0011 (3)	0.0014 (2)	−0.0041 (3)

S1—C1	1.6812 (7)	C4—C5	1.3913 (10)
O1—C4	1.3746 (8)	C4—C9	1.3970 (10)
O1—C3	1.4119 (9)	C5—C6	1.4012 (10)
N1—C2	1.3080 (9)	C5—H5A	0.962 (14)
N1—N2	1.3798 (9)	C6—C7	1.3915 (10)
N2—C1	1.3432 (9)	C6—H6A	0.930 (14)
N2—H1N2	0.932 (13)	C7—C8	1.4011 (11)
N3—C2	1.3657 (9)	C7—C10	1.5078 (10)
N3—C1	1.3734 (9)	C8—C9	1.3868 (10)
N3—N4	1.3988 (8)	C8—H8A	0.984 (14)
N4—H1N4	0.928 (14)	C9—H9A	0.959 (14)
N4—H2N4	0.894 (15)	C10—H10A	0.975 (17)
C2—C3	1.4875 (9)	C10—H10B	0.944 (17)
C3—H3A	1.011 (12)	C10—H10C	0.968 (18)
C3—H3B	0.986 (12)
C4—O1—C3	115.53 (5)	O1—C4—C9	115.49 (6)
C2—N1—N2	103.33 (6)	C5—C4—C9	119.96 (6)
C1—N2—N1	113.75 (6)	C4—C5—C6	119.23 (7)
C1—N2—H1N2	121.9 (9)	C4—C5—H5A	122.9 (8)
N1—N2—H1N2	123.5 (9)	C6—C5—H5A	117.8 (8)
C2—N3—C1	108.49 (6)	C7—C6—C5	121.82 (7)
C2—N3—N4	122.95 (6)	C7—C6—H6A	122.7 (9)
C1—N3—N4	128.18 (6)	C5—C6—H6A	115.4 (9)
N3—N4—H1N4	109.3 (8)	C6—C7—C8	117.60 (7)
N3—N4—H2N4	107.2 (10)	C6—C7—C10	122.01 (7)
H1N4—N4—H2N4	104.5 (13)	C8—C7—C10	120.39 (7)
N2—C1—N3	102.99 (6)	C9—C8—C7	121.62 (7)
N2—C1—S1	130.61 (6)	C9—C8—H8A	120.1 (8)
N3—C1—S1	126.40 (5)	C7—C8—H8A	118.3 (8)
N1—C2—N3	111.41 (6)	C8—C9—C4	119.73 (7)
N1—C2—C3	127.78 (6)	C8—C9—H9A	122.7 (9)
N3—C2—C3	120.78 (6)	C4—C9—H9A	117.5 (9)
O1—C3—C2	108.32 (6)	C7—C10—H10A	112.9 (10)
O1—C3—H3A	110.4 (7)	C7—C10—H10B	114.7 (11)
C2—C3—H3A	109.3 (7)	H10A—C10—H10B	104.2 (14)
O1—C3—H3B	113.9 (7)	C7—C10—H10C	110.4 (11)
C2—C3—H3B	107.8 (7)	H10A—C10—H10C	107.1 (14)
H3A—C3—H3B	107.0 (10)	H10B—C10—H10C	107.1 (15)
O1—C4—C5	124.54 (6)
C2—N1—N2—C1	0.94 (8)	N1—C2—C3—O1	−11.09 (10)
N1—N2—C1—N3	−1.56 (8)	N3—C2—C3—O1	171.04 (6)
N1—N2—C1—S1	178.86 (6)	C3—O1—C4—C5	6.66 (10)
C2—N3—C1—N2	1.55 (8)	C3—O1—C4—C9	−174.38 (6)
N4—N3—C1—N2	174.57 (7)	O1—C4—C5—C6	176.82 (7)
C2—N3—C1—S1	−178.85 (5)	C9—C4—C5—C6	−2.10 (11)
N4—N3—C1—S1	−5.83 (11)	C4—C5—C6—C7	0.49 (12)
N2—N1—C2—N3	0.13 (8)	C5—C6—C7—C8	1.01 (11)
N2—N1—C2—C3	−177.90 (7)	C5—C6—C7—C10	−178.28 (7)
C1—N3—C2—N1	−1.10 (8)	C6—C7—C8—C9	−0.94 (12)
N4—N3—C2—N1	−174.56 (6)	C10—C7—C8—C9	178.36 (7)
C1—N3—C2—C3	177.09 (6)	C7—C8—C9—C4	−0.64 (12)
N4—N3—C2—C3	3.62 (10)	O1—C4—C9—C8	−176.84 (7)
C4—O1—C3—C2	176.18 (6)	C5—C4—C9—C8	2.18 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···S1i	0.930 (13)	2.412 (13)	3.3364 (7)	172.5 (11)
N4—H1N4···N1ii	0.930 (17)	2.428 (17)	3.2100 (9)	141.6 (12)
N4—H2N4···S1iii	0.894 (15)	2.937 (16)	3.5456 (7)	126.8 (12)
C10—H10C···Cg2iv	0.968 (18)	2.697 (19)	3.6250 (9)	160.8 (14)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯S1i	0.930 (13)	2.412 (13)	3.3364 (7)	172.5 (11)
N4—H1N4⋯N1ii	0.930 (17)	2.428 (17)	3.2100 (9)	141.6 (12)
N4—H2N4⋯S1iii	0.894 (15)	2.937 (16)	3.5456 (7)	126.8 (12)
C10—H10C⋯Cg2iv	0.968 (18)	2.697 (19)	3.6250 (9)	160.8 (14)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg2 is the centroid of the C4–C9 ring.