3-(1-Benzofuran-2-yl)-1H-1,2,4-triazole-5(4H)-thione monohydrate.

In the title hydrate, C(10)H(7)N(3)OS·H(2)O, the essentially planar benzofuran [maximum deviation = 0.006 (1) Å] and 4,5-dihydro-1H-1,2,4-triazole [maximum deviation = 0.007 (1) Å] rings form a dihedral angle of 11.67 (6)°. In the crystal, O-H⋯N, O-H⋯S, N-H⋯O and N-H⋯S hydrogen bonds link the mol-ecules into sheets lying parallel to the bc plane. Aromatic π-π stacking inter-actions [centroid-centroid distances = 3.5078 (8)-3.6113 (8) Å] are also observed.

Related literature

For background to 1,2,4-triazoles, see: Shujuan et al. (2004 ▶); Clemons et al. (2004 ▶); Johnston (2002 ▶); Wei et al. (2007 ▶). For related structures, see: Jing et al. (2012 ▶); Fun et al. (2011 ▶); Abdel-Aziz et al. (2011 ▶). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C10H7N3OS·H2O

M = 235.26

Monoclinic,

a = 7.1446 (1) Å

b = 8.8075 (1) Å

c = 17.3274 (2) Å

β = 111.942 (1)°

V = 1011.36 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 100 K

0.39 × 0.20 × 0.15 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.891, T max = 0.955

19917 measured reflections

4162 independent reflections

3347 reflections with > I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.108

S = 1.07

4162 reflections

153 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.61 e Å−3

Δρmin = −0.31 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 datablock(s) global, I. DOI: 10.1107/S1600536812025305/hb6837sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812025305/hb6837Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812025305/hb6837Isup3.cml

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

C10H7N3OS·H2O	F(000) = 488
Mr = 235.26	Dx = 1.545 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6273 reflections
a = 7.1446 (1) Å	θ = 2.5–33.4°
b = 8.8075 (1) Å	µ = 0.31 mm−1
c = 17.3274 (2) Å	T = 100 K
β = 111.942 (1)°	Block, yellow
V = 1011.36 (2) Å3	0.39 × 0.20 × 0.15 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	4162 independent reflections
Radiation source: fine-focus sealed tube	3347 reflections with > I > 2σ(I)
Graphite monochromator	Rint = 0.039
φ and ω scans	θmax = 34.2°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
Tmin = 0.891, Tmax = 0.955	k = −13→13
19917 measured reflections	l = −26→27

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0491P)2 + 0.4347P] where P = (Fo2 + 2Fc2)/3
4162 reflections	(Δ/σ)max = 0.001
153 parameters	Δρmax = 0.61 e Å−3
0 restraints	Δρmin = −0.31 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	1.16013 (5)	−0.27662 (3)	0.789110 (18)	0.01410 (8)
O1	0.76589 (13)	0.12211 (10)	0.53014 (5)	0.01383 (17)
N1	1.01801 (16)	−0.33637 (12)	0.62307 (6)	0.01333 (19)
N2	0.91410 (16)	−0.27263 (11)	0.54676 (6)	0.01371 (19)
N3	0.95013 (15)	−0.11026 (11)	0.64872 (6)	0.01228 (18)
C1	1.04179 (18)	−0.24126 (13)	0.68643 (7)	0.0121 (2)
C2	0.87285 (17)	−0.13492 (13)	0.56444 (7)	0.0120 (2)
C3	0.76153 (17)	−0.02501 (13)	0.50237 (7)	0.0122 (2)
C4	0.65217 (18)	−0.03918 (13)	0.41967 (7)	0.0139 (2)
H4A	0.6284	−0.1277	0.3882	0.017*
C5	0.58061 (17)	0.11092 (14)	0.39077 (7)	0.0134 (2)
C6	0.46309 (19)	0.17499 (15)	0.31360 (8)	0.0169 (2)
H6A	0.4126	0.1157	0.2658	0.020*
C7	0.42492 (19)	0.32943 (16)	0.31110 (8)	0.0185 (2)
H7A	0.3474	0.3741	0.2606	0.022*
C8	0.5000 (2)	0.42034 (15)	0.38265 (9)	0.0193 (2)
H8A	0.4710	0.5236	0.3784	0.023*
C9	0.6168 (2)	0.35953 (14)	0.45977 (8)	0.0175 (2)
H9A	0.6675	0.4189	0.5075	0.021*
C10	0.65281 (18)	0.20498 (13)	0.46092 (7)	0.0128 (2)
O1W	0.12342 (14)	0.13102 (10)	0.11923 (6)	0.01697 (18)
H1OW	0.0827	0.1677	0.0673	0.025*
H2OW	0.0538	0.1810	0.1383	0.025*
H1N1	1.062 (3)	−0.433 (2)	0.6261 (12)	0.032 (5)*
H1N3	0.933 (3)	−0.032 (2)	0.6736 (11)	0.016 (4)*

	U11	U22	U33	U12	U13	U23
S1	0.01807 (14)	0.01305 (13)	0.00963 (13)	0.00052 (9)	0.00341 (10)	0.00123 (9)
O1	0.0168 (4)	0.0119 (4)	0.0113 (4)	0.0021 (3)	0.0035 (3)	−0.0001 (3)
N1	0.0172 (5)	0.0122 (4)	0.0099 (4)	0.0022 (3)	0.0043 (3)	0.0014 (3)
N2	0.0167 (5)	0.0130 (4)	0.0103 (4)	0.0017 (3)	0.0038 (3)	0.0009 (3)
N3	0.0158 (4)	0.0110 (4)	0.0098 (4)	0.0021 (3)	0.0044 (3)	0.0005 (3)
C1	0.0137 (5)	0.0112 (4)	0.0118 (5)	0.0005 (4)	0.0051 (4)	0.0013 (4)
C2	0.0132 (5)	0.0126 (5)	0.0100 (5)	0.0005 (4)	0.0040 (4)	0.0004 (4)
C3	0.0130 (5)	0.0121 (5)	0.0108 (5)	0.0008 (4)	0.0036 (4)	0.0007 (4)
C4	0.0152 (5)	0.0132 (5)	0.0115 (5)	0.0006 (4)	0.0027 (4)	−0.0001 (4)
C5	0.0123 (5)	0.0159 (5)	0.0113 (5)	0.0007 (4)	0.0038 (4)	0.0024 (4)
C6	0.0156 (5)	0.0214 (6)	0.0120 (5)	0.0006 (4)	0.0030 (4)	0.0029 (4)
C7	0.0153 (5)	0.0224 (6)	0.0168 (6)	0.0041 (4)	0.0049 (4)	0.0085 (5)
C8	0.0187 (5)	0.0166 (5)	0.0236 (6)	0.0048 (4)	0.0090 (5)	0.0061 (5)
C9	0.0200 (6)	0.0147 (5)	0.0182 (6)	0.0029 (4)	0.0077 (4)	0.0010 (4)
C10	0.0134 (5)	0.0135 (5)	0.0108 (5)	0.0018 (4)	0.0037 (4)	0.0026 (4)
O1W	0.0225 (4)	0.0144 (4)	0.0136 (4)	0.0006 (3)	0.0064 (3)	0.0009 (3)

S1—C1	1.6892 (12)	C4—H4A	0.9300
O1—C10	1.3784 (14)	C5—C10	1.4003 (17)
O1—C3	1.3785 (14)	C5—C6	1.4045 (17)
N1—C1	1.3403 (16)	C6—C7	1.3848 (19)
N1—N2	1.3715 (14)	C6—H6A	0.9300
N1—H1N1	0.90 (2)	C7—C8	1.403 (2)
N2—C2	1.3112 (15)	C7—H7A	0.9300
N3—C1	1.3664 (15)	C8—C9	1.3914 (18)
N3—C2	1.3718 (15)	C8—H8A	0.9300
N3—H1N3	0.844 (18)	C9—C10	1.3840 (17)
C2—C3	1.4448 (16)	C9—H9A	0.9300
C3—C4	1.3575 (16)	O1W—H1OW	0.8961
C4—C5	1.4382 (16)	O1W—H2OW	0.8208
C10—O1—C3	105.34 (9)	C10—C5—C6	118.94 (11)
C1—N1—N2	113.03 (10)	C10—C5—C4	105.90 (10)
C1—N1—H1N1	127.4 (13)	C6—C5—C4	135.16 (12)
N2—N1—H1N1	119.6 (13)	C7—C6—C5	117.72 (12)
C2—N2—N1	103.96 (10)	C7—C6—H6A	121.1
C1—N3—C2	107.80 (10)	C5—C6—H6A	121.1
C1—N3—H1N3	125.3 (12)	C6—C7—C8	121.81 (12)
C2—N3—H1N3	126.5 (12)	C6—C7—H7A	119.1
N1—C1—N3	104.16 (10)	C8—C7—H7A	119.1
N1—C1—S1	127.44 (9)	C9—C8—C7	121.54 (12)
N3—C1—S1	128.40 (9)	C9—C8—H8A	119.2
N2—C2—N3	111.04 (10)	C7—C8—H8A	119.2
N2—C2—C3	123.72 (11)	C10—C9—C8	115.71 (12)
N3—C2—C3	125.24 (10)	C10—C9—H9A	122.1
C4—C3—O1	112.58 (10)	C8—C9—H9A	122.1
C4—C3—C2	131.59 (11)	O1—C10—C9	125.35 (11)
O1—C3—C2	115.82 (10)	O1—C10—C5	110.37 (10)
C3—C4—C5	105.81 (10)	C9—C10—C5	124.28 (11)
C3—C4—H4A	127.1	H1OW—O1W—H2OW	101.1
C5—C4—H4A	127.1
C1—N1—N2—C2	−0.29 (14)	C2—C3—C4—C5	−178.79 (12)
N2—N1—C1—N3	−0.49 (13)	C3—C4—C5—C10	−0.85 (13)
N2—N1—C1—S1	179.94 (9)	C3—C4—C5—C6	179.54 (14)
C2—N3—C1—N1	1.06 (13)	C10—C5—C6—C7	0.09 (18)
C2—N3—C1—S1	−179.38 (9)	C4—C5—C6—C7	179.66 (13)
N1—N2—C2—N3	0.98 (13)	C5—C6—C7—C8	0.00 (19)
N1—N2—C2—C3	−179.39 (11)	C6—C7—C8—C9	0.0 (2)
C1—N3—C2—N2	−1.34 (14)	C7—C8—C9—C10	−0.17 (19)
C1—N3—C2—C3	179.04 (11)	C3—O1—C10—C9	−179.75 (12)
C10—O1—C3—C4	0.01 (13)	C3—O1—C10—C5	−0.58 (13)
C10—O1—C3—C2	179.45 (10)	C8—C9—C10—O1	179.33 (11)
N2—C2—C3—C4	11.6 (2)	C8—C9—C10—C5	0.28 (19)
N3—C2—C3—C4	−168.79 (13)	C6—C5—C10—O1	−179.42 (10)
N2—C2—C3—O1	−167.68 (11)	C4—C5—C10—O1	0.90 (13)
N3—C2—C3—O1	11.90 (17)	C6—C5—C10—C9	−0.24 (19)
O1—C3—C4—C5	0.54 (14)	C4—C5—C10—C9	−179.92 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1OW···N2i	0.90	2.05	2.9135 (14)	160
O1W—H2OW···S1ii	0.82	2.46	3.2674 (11)	167
N1—H1N1···O1Wiii	0.90 (2)	1.81 (2)	2.7100 (14)	172.6 (19)
N3—H1N3···S1iv	0.846 (18)	2.498 (18)	3.3242 (10)	165.7 (16)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1OW⋯N2i	0.90	2.05	2.9135 (14)	160
O1W—H2OW⋯S1ii	0.82	2.46	3.2674 (11)	167
N1—H1N1⋯O1W iii	0.90 (2)	1.81 (2)	2.7100 (14)	172.6 (19)
N3—H1N3⋯S1iv	0.846 (18)	2.498 (18)	3.3242 (10)	165.7 (16)

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