Crystal structure of 4-{[(1H-1,2,4-triazol-1-yl)meth-yl]sulfan-yl}phenol.

In the title compound, C9H9N3OS, the plane of the benzene ring forms a dihedral angle of 33.40 (5)° with that of the triazole group. In the crystal, mol-ecules are linked by O-H⋯N hydrogen bonds involving the phenol -OH group and one of the unsubstituted N atoms of the triazole ring, resulting in chains along [010]. These chains are further extended into a layer parallel to (001) by weak C-H⋯N hydrogen-bond inter-actions. Aromatic π-π stacking [centroid-centroid separation = 3.556 (1) Å] between the triazole rings links the layers into a three-dimensional network.

Related literature

For the biological activity of related compounds, see: Sidwell et al. (1972 ▶); Khan et al. (2010 ▶); Xu et al. (2011 ▶); Jubie et al. (2011 ▶); Patel et al. (2013 ▶); Salgın-Gökşen et al. (2007 ▶); Lin et al. (2005 ▶); Coucouvanis (2007 ▶).

Experimental

Crystal data

C9H9N3OS

M = 207.25

Monoclinic,

a = 5.3975 (10) Å

b = 10.0099 (19) Å

c = 18.311 (3) Å

β = 91.010 (3)°

V = 989.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.30 mm−1

T = 296 K

0.28 × 0.22 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.922, T max = 0.943

4977 measured reflections

1755 independent reflections

1453 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.077

S = 1.05

1755 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2003 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2001 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814019965/ds2243sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814019965/ds2243Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814019965/ds2243Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814019965/ds2243fig1.tif

The mol­ecular structure of the title compound with the atom numbering scheme. The displacement ellipsoids are drawn at the 40% probability level.

Click here for additional data file.

. DOI: 10.1107/S1600536814019965/ds2243fig2.tif

A view of the hydrogen bonded polymeric layer. The hydrogen bonds are shown as dashed lines.

CCDC reference: 1022888

Additional supporting information: crystallographic information; 3D view; checkCIF report

C9H9N3OS	F(000) = 432
Mr = 207.25	Dx = 1.392 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1691 reflections
a = 5.3975 (10) Å	θ = 2.3–23.8°
b = 10.0099 (19) Å	µ = 0.30 mm−1
c = 18.311 (3) Å	T = 296 K
β = 91.010 (3)°	Strip, colorless
V = 989.2 (3) Å3	0.28 × 0.22 × 0.20 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	1755 independent reflections
Radiation source: fine-focus sealed tube	1453 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
phi and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −6→6
Tmin = 0.922, Tmax = 0.943	k = −11→11
4977 measured reflections	l = −18→21

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) = 0.077	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0294P)2 + 0.2664P] where P = (Fo2 + 2Fc2)/3
1755 reflections	(Δ/σ)max < 0.001
128 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

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	0.66005 (10)	0.44273 (5)	0.08502 (3)	0.05715 (18)
O1	1.2294 (3)	0.31388 (12)	0.35509 (7)	0.0530 (4)
H1	1.3233	0.3747	0.3671	0.080*
N1	0.8498 (2)	0.20284 (13)	0.04543 (7)	0.0369 (3)
N2	0.6462 (2)	0.12317 (15)	0.04545 (8)	0.0450 (4)
N3	0.9755 (3)	0.01570 (15)	0.09366 (8)	0.0475 (4)
C1	0.7326 (3)	0.01291 (19)	0.07461 (9)	0.0461 (4)
H1A	0.6339	−0.0620	0.0817	0.055*
C2	1.0418 (3)	0.13729 (18)	0.07465 (9)	0.0440 (4)
H2	1.2004	0.1724	0.0808	0.053*
C3	0.8344 (3)	0.34022 (18)	0.02238 (10)	0.0483 (5)
H3A	0.7561	0.3442	−0.0257	0.058*
H3B	1.0006	0.3762	0.0185	0.058*
C4	0.8297 (3)	0.40921 (17)	0.16692 (9)	0.0436 (4)
C5	0.7646 (3)	0.30194 (19)	0.21040 (10)	0.0487 (5)
H5	0.6281	0.2499	0.1974	0.058*
C6	0.9001 (4)	0.27158 (18)	0.27266 (10)	0.0487 (5)
H6	0.8549	0.1990	0.3012	0.058*
C7	1.1036 (3)	0.34846 (16)	0.29307 (9)	0.0403 (4)
C8	1.1682 (3)	0.45690 (18)	0.25025 (10)	0.0458 (4)
H8	1.3035	0.5096	0.2636	0.055*
C9	1.0315 (4)	0.48657 (18)	0.18780 (10)	0.0477 (5)
H9	1.0757	0.5595	0.1594	0.057*

	U11	U22	U33	U12	U13	U23
S1	0.0629 (3)	0.0550 (3)	0.0531 (3)	0.0208 (2)	−0.0116 (2)	−0.0047 (2)
O1	0.0666 (9)	0.0444 (7)	0.0476 (7)	−0.0068 (6)	−0.0120 (6)	0.0013 (6)
N1	0.0317 (7)	0.0419 (8)	0.0370 (8)	−0.0003 (6)	−0.0013 (6)	−0.0019 (6)
N2	0.0338 (8)	0.0530 (9)	0.0481 (9)	−0.0058 (7)	−0.0062 (6)	−0.0003 (7)
N3	0.0478 (9)	0.0500 (9)	0.0443 (9)	0.0054 (7)	−0.0067 (7)	0.0001 (7)
C1	0.0470 (11)	0.0484 (11)	0.0427 (10)	−0.0062 (8)	−0.0011 (8)	0.0010 (8)
C2	0.0309 (9)	0.0542 (12)	0.0466 (10)	0.0011 (8)	−0.0041 (7)	−0.0057 (9)
C3	0.0553 (11)	0.0473 (11)	0.0424 (10)	0.0003 (9)	−0.0001 (8)	0.0043 (8)
C4	0.0471 (10)	0.0402 (10)	0.0434 (10)	0.0082 (8)	−0.0015 (8)	−0.0072 (8)
C5	0.0476 (10)	0.0489 (11)	0.0496 (11)	−0.0088 (8)	−0.0010 (8)	−0.0080 (9)
C6	0.0609 (12)	0.0402 (10)	0.0449 (10)	−0.0115 (9)	0.0023 (9)	0.0005 (8)
C7	0.0473 (10)	0.0369 (9)	0.0366 (9)	0.0017 (8)	0.0012 (7)	−0.0057 (7)
C8	0.0463 (10)	0.0414 (10)	0.0495 (11)	−0.0077 (8)	−0.0002 (8)	−0.0027 (8)
C9	0.0583 (11)	0.0376 (10)	0.0473 (11)	−0.0001 (8)	0.0044 (9)	0.0021 (8)

S1—C4	1.7753 (18)	C3—H3A	0.9700
S1—C3	1.8146 (18)	C3—H3B	0.9700
O1—C7	1.358 (2)	C4—C9	1.385 (3)
O1—H1	0.8200	C4—C5	1.386 (3)
N1—C2	1.331 (2)	C5—C6	1.378 (3)
N1—N2	1.3578 (18)	C5—H5	0.9300
N1—C3	1.440 (2)	C6—C7	1.387 (2)
N2—C1	1.308 (2)	C6—H6	0.9300
N3—C2	1.317 (2)	C7—C8	1.387 (2)
N3—C1	1.351 (2)	C8—C9	1.382 (2)
C1—H1A	0.9300	C8—H8	0.9300
C2—H2	0.9300	C9—H9	0.9300
C4—S1—C3	99.29 (8)	C9—C4—C5	118.74 (17)
C7—O1—H1	109.5	C9—C4—S1	121.27 (14)
C2—N1—N2	109.56 (14)	C5—C4—S1	119.97 (14)
C2—N1—C3	128.98 (15)	C6—C5—C4	120.68 (17)
N2—N1—C3	121.22 (14)	C6—C5—H5	119.7
C1—N2—N1	102.31 (13)	C4—C5—H5	119.7
C2—N3—C1	102.59 (15)	C5—C6—C7	120.46 (17)
N2—C1—N3	115.15 (16)	C5—C6—H6	119.8
N2—C1—H1A	122.4	C7—C6—H6	119.8
N3—C1—H1A	122.4	O1—C7—C6	117.77 (15)
N3—C2—N1	110.40 (15)	O1—C7—C8	123.04 (15)
N3—C2—H2	124.8	C6—C7—C8	119.19 (16)
N1—C2—H2	124.8	C9—C8—C7	120.00 (17)
N1—C3—S1	112.49 (12)	C9—C8—H8	120.0
N1—C3—H3A	109.1	C7—C8—H8	120.0
S1—C3—H3A	109.1	C8—C9—C4	120.93 (17)
N1—C3—H3B	109.1	C8—C9—H9	119.5
S1—C3—H3B	109.1	C4—C9—H9	119.5
H3A—C3—H3B	107.8
C2—N1—N2—C1	−0.58 (18)	C3—S1—C4—C5	−88.92 (16)
C3—N1—N2—C1	−175.34 (14)	C9—C4—C5—C6	−0.9 (3)
N1—N2—C1—N3	0.3 (2)	S1—C4—C5—C6	177.54 (14)
C2—N3—C1—N2	0.1 (2)	C4—C5—C6—C7	0.3 (3)
C1—N3—C2—N1	−0.45 (19)	C5—C6—C7—O1	179.81 (16)
N2—N1—C2—N3	0.68 (19)	C5—C6—C7—C8	0.4 (3)
C3—N1—C2—N3	174.91 (15)	O1—C7—C8—C9	−179.87 (16)
C2—N1—C3—S1	−105.58 (18)	C6—C7—C8—C9	−0.5 (3)
N2—N1—C3—S1	68.07 (18)	C7—C8—C9—C4	−0.1 (3)
C4—S1—C3—N1	55.54 (14)	C5—C4—C9—C8	0.8 (3)
C3—S1—C4—C9	89.51 (16)	S1—C4—C9—C8	−177.62 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N3i	0.82	1.91	2.7290 (19)	173
C2—H2···N2ii	0.93	2.55	3.318 (2)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N3i	0.82	1.91	2.7290 (19)	173
C2—H2⋯N2ii	0.93	2.55	3.318 (2)	140

Symmetry codes: (i) ; (ii) .