2-({1-[2-(Methyl-sulfan-yl)phen-yl]-1H-tetra-zol-5-yl}sulfan-yl)acetic acid.

In the title compound, C10H10N4O2S2, the tetra-zole and benzene rings are almost normal to one another, with a dihedral angle between their planes of 84.33 (9)°. In the crystal, mol-ecules are linked via pairs of bifurcated O-H⋯(N,N) hydrogen bonds, forming inversion dimers with graph-set motif R 4 (4)(12). The dimers are linked by significant π-π inter-actions involving inversion-related tetra-zole rings and inversion-related benzene rings, with centroid-centroid distances of 3.7376 (14) and 3.8444 (15) Å, respectively.

Related literature

For details of the ZINC database, see: Irwin et al. (2012 ▶). For information on the biological properties of tetra­zoles, see: Kees et al. (1989 ▶); Nolte et al. (1998 ▶); Mafud & Nascimento (2013 ▶).

Experimental

Crystal data

C10H10N4O2S2

M = 282.34

Triclinic,

a = 7.1500 (3) Å

b = 8.3770 (3) Å

c = 11.0890 (5) Å

α = 74.7480 (14)°

β = 79.3090 (14)°

γ = 86.286 (3)°

V = 629.58 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.42 mm−1

T = 290 K

0.1 × 0.05 × 0.05 mm

Data collection

Bruker–Nonius KappaCCD diffractometer

Absorption correction: for a cylinder mounted on the ϕ axis (Dwiggins, 1975 ▶) T min = 0.861, T max = 0.862

15888 measured reflections

2335 independent reflections

1879 reflections with I > 2σ(I)

R int = 0.079

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.15

S = 1.04

2335 reflections

167 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.50 e Å−3

Δρmin = −0.30 e Å−3

Data collection: COLLECT (Nonius, 1999 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681300980X/su2571sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681300980X/su2571Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681300980X/su2571Isup3.cml

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

C10H10N4O2S2	Z = 2
Mr = 282.34	F(000) = 292
Triclinic, P1	none
Hall symbol: -P 1	Dx = 1.489 Mg m−3
a = 7.1500 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.3770 (3) Å	Cell parameters from 2086 reflections
c = 11.0890 (5) Å	θ = 10.4–19.8°
α = 74.7480 (14)°	µ = 0.42 mm−1
β = 79.3090 (14)°	T = 290 K
γ = 86.286 (3)°	Prism, yellow
V = 629.58 (4) Å3	0.1 × 0.05 × 0.05 mm

Bruker–Nonius KappaCCD diffractometer	2335 independent reflections
Radiation source: Fine-focus	1879 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.079
CCD scans	θmax = 25.7°, θmin = 3.8°
Absorption correction: for a cylinder mounted on the φ axis (Dwiggins, 1975)	h = −8→8
Tmin = 0.861, Tmax = 0.862	k = −10→10
15888 measured reflections	l = −13→13

Refinement on F2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.051	w = 1/[σ2(Fo2) + (0.0968P)2 + 0.1021P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.15	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.50 e Å−3
2335 reflections	Δρmin = −0.30 e Å−3
167 parameters

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 individuallno in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are onlno used when theno are defined bno crnostal snommetrno. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

	x	y	z	Uiso*/Ueq
S1	0.12427 (8)	0.32835 (9)	0.14822 (6)	0.0644 (3)
S2	0.31586 (12)	0.16473 (8)	0.46904 (6)	0.0744 (3)
O1	0.3263 (3)	0.0525 (3)	−0.07328 (19)	0.0753 (6)
H1	0.367 (6)	−0.039 (5)	−0.072 (4)	0.113*
O2	0.1581 (4)	−0.0338 (3)	0.1185 (2)	0.0973 (8)
N1	0.5089 (3)	0.2791 (3)	0.0763 (2)	0.0593 (5)
N2	0.6701 (3)	0.3173 (3)	0.1112 (2)	0.0621 (5)
N3	0.6313 (3)	0.3917 (3)	0.2004 (2)	0.0593 (5)
N4	0.4384 (2)	0.4047 (2)	0.22640 (17)	0.0490 (4)
C1	0.2079 (3)	0.0747 (3)	0.0282 (2)	0.0576 (6)
C2	0.1398 (3)	0.2518 (3)	0.0096 (2)	0.0546 (5)
H2A	0.0153	0.2615	−0.0148	0.066*
H2B	0.2261	0.3207	−0.0597	0.066*
C3	0.3657 (3)	0.3352 (3)	0.1496 (2)	0.0507 (5)
C4	0.3483 (3)	0.4803 (3)	0.3259 (2)	0.0497 (5)
C5	0.3341 (4)	0.6503 (3)	0.2979 (2)	0.0597 (6)
H5	0.3723	0.7138	0.2153	0.072*
C6	0.2621 (4)	0.7248 (4)	0.3944 (3)	0.0721 (7)
H6	0.2489	0.8394	0.3774	0.087*
C7	0.2099 (4)	0.6277 (4)	0.5165 (3)	0.0736 (8)
H7	0.1645	0.6782	0.5817	0.088*
C8	0.2235 (4)	0.4586 (4)	0.5438 (2)	0.0637 (6)
H8	0.1866	0.396	0.6267	0.076*
C9	0.2925 (3)	0.3800 (3)	0.4476 (2)	0.0539 (5)
C10	0.2427 (5)	0.0824 (4)	0.6350 (3)	0.0923 (10)
H10A	0.3274	0.1185	0.68	0.138*
H10B	0.2456	−0.0363	0.6544	0.138*
H10C	0.1156	0.1204	0.6604	0.138*

	U11	U22	U33	U12	U13	U23
S1	0.0435 (4)	0.0871 (5)	0.0716 (5)	−0.0001 (3)	−0.0027 (3)	−0.0413 (4)
S2	0.0991 (6)	0.0597 (4)	0.0580 (4)	−0.0016 (3)	−0.0056 (3)	−0.0094 (3)
O1	0.0897 (14)	0.0694 (12)	0.0682 (12)	0.0092 (10)	−0.0035 (10)	−0.0296 (10)
O2	0.1136 (18)	0.0716 (13)	0.0805 (14)	0.0116 (12)	0.0131 (12)	0.0020 (11)
N1	0.0483 (10)	0.0683 (12)	0.0648 (12)	−0.0004 (9)	0.0007 (8)	−0.0307 (10)
N2	0.0473 (10)	0.0726 (13)	0.0670 (13)	0.0032 (9)	−0.0015 (9)	−0.0260 (11)
N3	0.0434 (10)	0.0711 (13)	0.0628 (12)	0.0002 (8)	−0.0052 (8)	−0.0192 (10)
N4	0.0425 (9)	0.0543 (10)	0.0501 (10)	0.0014 (7)	−0.0045 (7)	−0.0163 (8)
C1	0.0544 (12)	0.0648 (14)	0.0558 (14)	−0.0015 (10)	−0.0109 (10)	−0.0186 (11)
C2	0.0496 (12)	0.0600 (13)	0.0571 (13)	−0.0012 (10)	−0.0111 (10)	−0.0188 (11)
C3	0.0475 (11)	0.0545 (12)	0.0522 (12)	0.0008 (9)	−0.0048 (9)	−0.0205 (10)
C4	0.0460 (11)	0.0569 (12)	0.0506 (12)	0.0024 (9)	−0.0103 (9)	−0.0206 (10)
C5	0.0611 (14)	0.0563 (14)	0.0640 (14)	0.0032 (10)	−0.0140 (11)	−0.0184 (11)
C6	0.0711 (16)	0.0646 (16)	0.094 (2)	0.0088 (12)	−0.0231 (14)	−0.0392 (15)
C7	0.0624 (15)	0.095 (2)	0.0812 (19)	0.0070 (14)	−0.0154 (13)	−0.0530 (17)
C8	0.0594 (14)	0.0837 (18)	0.0538 (13)	0.0016 (12)	−0.0090 (10)	−0.0289 (12)
C9	0.0481 (11)	0.0649 (14)	0.0514 (12)	0.0001 (10)	−0.0096 (9)	−0.0193 (10)
C10	0.096 (2)	0.093 (2)	0.0671 (18)	0.0006 (17)	−0.0007 (15)	0.0068 (16)

S1—C3	1.734 (2)	C2—H2B	0.97
S1—C2	1.798 (2)	C4—C5	1.376 (3)
S2—C9	1.757 (3)	C4—C9	1.391 (3)
S2—C10	1.778 (3)	C5—C6	1.381 (4)
O1—C1	1.324 (3)	C5—H5	0.93
O1—H1	0.80 (4)	C6—C7	1.380 (4)
O2—C1	1.177 (3)	C6—H6	0.93
N1—C3	1.327 (3)	C7—C8	1.369 (4)
N1—N2	1.364 (3)	C7—H7	0.93
N2—N3	1.282 (3)	C8—C9	1.395 (3)
N3—N4	1.359 (3)	C8—H8	0.93
N4—C3	1.341 (3)	C10—H10A	0.96
N4—C4	1.444 (3)	C10—H10B	0.96
C1—C2	1.504 (3)	C10—H10C	0.96
C2—H2A	0.97
C3—S1—C2	98.45 (10)	C9—C4—N4	118.91 (19)
C9—S2—C10	104.17 (14)	C4—C5—C6	118.8 (2)
C1—O1—H1	118 (3)	C4—C5—H5	120.6
C3—N1—N2	105.52 (19)	C6—C5—H5	120.6
N3—N2—N1	111.51 (18)	C7—C6—C5	119.3 (3)
N2—N3—N4	106.22 (18)	C7—C6—H6	120.3
C3—N4—N3	108.48 (17)	C5—C6—H6	120.3
C3—N4—C4	131.62 (18)	C8—C7—C6	121.6 (2)
N3—N4—C4	119.88 (18)	C8—C7—H7	119.2
O2—C1—O1	123.2 (2)	C6—C7—H7	119.2
O2—C1—C2	125.3 (2)	C7—C8—C9	120.2 (2)
O1—C1—C2	111.4 (2)	C7—C8—H8	119.9
C1—C2—S1	113.73 (17)	C9—C8—H8	119.9
C1—C2—H2A	108.8	C4—C9—C8	117.2 (2)
S1—C2—H2A	108.8	C4—C9—S2	117.76 (17)
C1—C2—H2B	108.8	C8—C9—S2	125.01 (19)
S1—C2—H2B	108.8	S2—C10—H10A	109.5
H2A—C2—H2B	107.7	S2—C10—H10B	109.5
N1—C3—N4	108.27 (19)	H10A—C10—H10B	109.5
N1—C3—S1	127.70 (17)	S2—C10—H10C	109.5
N4—C3—S1	124.01 (16)	H10A—C10—H10C	109.5
C5—C4—C9	122.8 (2)	H10B—C10—H10C	109.5
C5—C4—N4	118.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1i	0.81 (4)	2.15 (4)	2.952 (4)	176 (4)
O1—H1···N2i	0.81 (4)	2.51 (4)	3.232 (4)	149 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1i	0.81 (4)	2.15 (4)	2.952 (4)	176 (4)
O1—H1⋯N2i	0.81 (4)	2.51 (4)	3.232 (4)	149 (4)

Symmetry code: (i) .