Bis(5-phenyl-1H-1,2,4-triazol-3-yl) disulfide dihydrate.

A crystallographic twofold axis passing through the centre of the disulfide linkage in the title compound, C(16)H(12)N(6)S(2)·2H(2)O, results in one-half of the mol-ecule and one uncoordinated water mol-ecule described in the asymmetric unit. In the mol-ecule, the mean planes of the benzene and triazole rings are close to being coplanar and are separated by a dihedral angle of 2.08 (15)°. The triazole rings are twisted by a dihedral angle of 37.67 (6)° from the disulfide linkage. The crystal packing is stabilized by inter-molecular N-H⋯O and O-H⋯N hydrogen bonds with the water mol-ecules, forming a three-dimensional supra-molecular network.

Related literature

For applications of 1,2,4-triazole and its derivatives in coordination chemistry, see: Zhang et al. (2005 ▶); Ouellette et al. (2007 ▶); Zhu et al. (2009 ▶). For the related structure of a 1,2,4-triazole-based disulfide compound, see: Jiang et al. (2007 ▶). For the previous synthesis of the title compound, see: El-Wareth & Sarhan (2000 ▶).

Experimental

Crystal data

C16H12N6S2·2H2O

M = 388.47

Monoclinic,

a = 12.3911 (13) Å

b = 14.7125 (16) Å

c = 10.2966 (11) Å

β = 104.125 (2)°

V = 1820.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.32 mm−1

T = 293 K

0.40 × 0.20 × 0.18 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.884, T max = 0.945

7210 measured reflections

1953 independent reflections

1679 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.120

S = 1.06

1953 reflections

118 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811014607/jj2087sup1.cif

Supplementary material file. DOI: 10.1107/S1600536811014607/jj2087Isup2.cdx

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811014607/jj2087Isup3.hkl

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

C16H12N6S2·2H2O	F(000) = 808
Mr = 388.47	Dx = 1.417 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3134 reflections
a = 12.3911 (13) Å	θ = 2.7–26.4°
b = 14.7125 (16) Å	µ = 0.32 mm−1
c = 10.2966 (11) Å	T = 293 K
β = 104.125 (2)°	Polyhedron, yellow
V = 1820.4 (3) Å3	0.40 × 0.20 × 0.18 mm
Z = 4

Bruker SMART APEX CCD diffractometer	1953 independent reflections
Radiation source: fine-focus sealed tube	1679 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω scans	θmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
Tmin = 0.884, Tmax = 0.945	k = −18→18
7210 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0691P)2 + 0.5857P] where P = (Fo2 + 2Fc2)/3
1953 reflections	(Δ/σ)max < 0.001
118 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.18 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	0.43278 (4)	0.48004 (3)	0.16853 (5)	0.0605 (2)
N1	0.26234 (13)	0.68205 (9)	0.22572 (14)	0.0535 (4)
H1B	0.2373	0.7366	0.2112	0.064*
N2	0.33478 (13)	0.64316 (9)	0.16425 (15)	0.0554 (4)
N3	0.28640 (12)	0.54543 (9)	0.30878 (14)	0.0501 (3)
C1	0.13764 (18)	0.58140 (14)	0.4862 (2)	0.0673 (5)
H1A	0.1698	0.5240	0.4897	0.081*
C2	0.0682 (2)	0.60203 (17)	0.5693 (2)	0.0792 (6)
H2A	0.0543	0.5586	0.6288	0.095*
C3	0.01979 (18)	0.68669 (16)	0.5640 (2)	0.0729 (6)
H3A	−0.0284	0.6999	0.6180	0.087*
C4	0.0428 (2)	0.75119 (16)	0.4792 (2)	0.0723 (6)
H4A	0.0115	0.8088	0.4773	0.087*
C5	0.11194 (17)	0.73153 (13)	0.3963 (2)	0.0615 (5)
H5A	0.1270	0.7759	0.3388	0.074*
C6	0.15919 (13)	0.64584 (11)	0.39834 (16)	0.0478 (4)
C7	0.23446 (14)	0.62407 (11)	0.31284 (16)	0.0461 (4)
C8	0.34687 (14)	0.56106 (11)	0.21779 (17)	0.0503 (4)
O1	0.27936 (14)	0.35247 (9)	0.37303 (13)	0.0762 (5)
H1D	0.3018	0.3501	0.4572	0.091*
H1C	0.2833	0.4118	0.3533	0.091*

	U11	U22	U33	U12	U13	U23
S1	0.0728 (4)	0.0462 (3)	0.0721 (3)	−0.00574 (19)	0.0364 (3)	−0.01332 (19)
N1	0.0701 (9)	0.0405 (7)	0.0563 (8)	0.0046 (6)	0.0276 (7)	0.0048 (6)
N2	0.0731 (9)	0.0448 (8)	0.0561 (8)	−0.0012 (7)	0.0305 (7)	0.0014 (6)
N3	0.0584 (8)	0.0412 (7)	0.0564 (8)	−0.0014 (6)	0.0248 (6)	0.0027 (6)
C1	0.0780 (13)	0.0589 (11)	0.0745 (12)	0.0101 (9)	0.0371 (10)	0.0135 (9)
C2	0.0917 (16)	0.0835 (15)	0.0757 (14)	0.0031 (12)	0.0463 (12)	0.0154 (11)
C3	0.0697 (13)	0.0864 (15)	0.0716 (13)	0.0043 (11)	0.0347 (10)	−0.0062 (11)
C4	0.0757 (13)	0.0681 (13)	0.0813 (14)	0.0161 (10)	0.0347 (11)	−0.0006 (10)
C5	0.0693 (12)	0.0539 (10)	0.0671 (11)	0.0098 (9)	0.0278 (9)	0.0082 (8)
C6	0.0478 (8)	0.0494 (9)	0.0477 (8)	−0.0011 (7)	0.0142 (7)	0.0003 (7)
C7	0.0517 (9)	0.0405 (8)	0.0476 (8)	−0.0031 (6)	0.0150 (7)	0.0014 (6)
C8	0.0596 (10)	0.0420 (8)	0.0543 (9)	−0.0052 (7)	0.0233 (7)	−0.0033 (7)
O1	0.1323 (14)	0.0421 (7)	0.0576 (8)	−0.0052 (7)	0.0300 (8)	−0.0033 (5)

S1—C8	1.7536 (17)	C2—C3	1.378 (3)
S1—S1i	2.0556 (11)	C2—H2A	0.9300
N1—C7	1.343 (2)	C3—C4	1.366 (3)
N1—N2	1.346 (2)	C3—H3A	0.9300
N1—H1B	0.8600	C4—C5	1.380 (3)
N2—C8	1.321 (2)	C4—H4A	0.9300
N3—C7	1.330 (2)	C5—C6	1.388 (2)
N3—C8	1.355 (2)	C5—H5A	0.9300
C1—C6	1.381 (2)	C6—C7	1.466 (2)
C1—C2	1.386 (3)	O1—H1D	0.8434
C1—H1A	0.9300	O1—H1C	0.9007
C8—S1—S1i	101.08 (6)	C3—C4—H4A	119.7
C7—N1—N2	110.73 (14)	C5—C4—H4A	119.7
C7—N1—H1B	124.6	C4—C5—C6	120.28 (19)
N2—N1—H1B	124.6	C4—C5—H5A	119.9
C8—N2—N1	102.31 (13)	C6—C5—H5A	119.9
C7—N3—C8	103.16 (14)	C1—C6—C5	119.04 (17)
C6—C1—C2	120.15 (19)	C1—C6—C7	119.78 (16)
C6—C1—H1A	119.9	C5—C6—C7	121.14 (16)
C2—C1—H1A	119.9	N3—C7—N1	109.05 (14)
C3—C2—C1	120.2 (2)	N3—C7—C6	126.37 (15)
C3—C2—H2A	119.9	N1—C7—C6	124.58 (15)
C1—C2—H2A	119.9	N2—C8—N3	114.73 (15)
C4—C3—C2	119.78 (19)	N2—C8—S1	121.06 (13)
C4—C3—H3A	120.1	N3—C8—S1	124.19 (13)
C2—C3—H3A	120.1	H1D—O1—H1C	104.4
C3—C4—C5	120.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1C···N3	0.90	2.02	2.9210 (19)	178.
N1—H1B···O1ii	0.86	1.90	2.7077 (19)	156.
O1—H1D···N2iii	0.84	2.07	2.909 (2)	171.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1C⋯N3	0.90	2.02	2.9210 (19)	178
N1—H1B⋯O1i	0.86	1.90	2.7077 (19)	156
O1—H1D⋯N2ii	0.84	2.07	2.909 (2)	171

Symmetry codes: (i) ; (ii) .