1,2-Bis(1H-tetra-zol-5-yl)benzene dihydrate.

The asymmetric unit of the title compound, C(8)H(6)N(8)·2H(2)O, contains one half-mol-ecule, with the benzene ring on a centre of symmetry, and two uncoordinated water mol-ecules. The benzene ring is oriented at a dihedral angle of 34.43 (12)° with respect to the tetra-zole ring. Strong O-H⋯N hydrogen bonds link the water mol-ecules to the N atoms of the tetra-zole ring. In the crystal structure, strong inter-molecular O-H⋯O and O-H⋯N hydrogen bonds link the mol-ecules into a network. One of the water H atoms is disordered over two positions and was refined with occupancies of 0.50.

Related literature

For general background, see: Luo et al. (2006 ▶). For related structures, see: Guzei & Bikzhanova (2002 ▶); Pan et al. (2007 ▶).

Experimental

Crystal data

C8H6N8·2H2O

M = 286.27

Monoclinic,

a = 14.510 (3) Å

b = 12.427 (3) Å

c = 7.2576 (15) Å

β = 96.29 (3)°

V = 1300.7 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 294 K

0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.971, T max = 0.979

5963 measured reflections

1276 independent reflections

1041 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.098

S = 1.06

1276 reflections

101 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.15 e Å−3

Data collection: CrystalClear (Rigaku/MSC (2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809018224/hk2687sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018224/hk2687Isup2.hkl

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

C8H6N8·2H2O	F(000) = 600
Mr = 286.27	Dx = 1.462 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5656 reflections
a = 14.510 (3) Å	θ = 3.3–27.5°
b = 12.427 (3) Å	µ = 0.12 mm−1
c = 7.2576 (15) Å	T = 294 K
β = 96.29 (3)°	Prism, colorless
V = 1300.7 (5) Å3	0.20 × 0.20 × 0.20 mm
Z = 4

Rigaku SCXmini diffractometer	1276 independent reflections
Radiation source: fine-focus sealed tube	1041 reflections with I > 2σ(I)
graphite	Rint = 0.044
Detector resolution: 13.6612 pixels mm-1	θmax = 26.0°, θmin = 3.3°
ω scans	h = −17→17
Absorption correction: multi-scan (Blessing, 1995)	k = −15→15
Tmin = 0.971, Tmax = 0.979	l = −8→8
5963 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.098	w = 1/[σ2(Fo2) + (0.0394P)2 + 0.846P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
1276 reflections	Δρmax = 0.20 e Å−3
101 parameters	Δρmin = −0.15 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0220 (19)

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	Occ. (<1)
O1W	0.20523 (9)	−0.46870 (10)	0.4630 (2)	0.0479 (4)
H1WA	0.1982	−0.5343	0.4316	0.086 (9)*
H1WB	0.1528	−0.4390	0.4684	0.084 (9)*
O2W	0.52104 (9)	−0.10467 (11)	−0.0561 (2)	0.0467 (4)
H2WA	0.4931	−0.1528	−0.0003	0.076 (8)*
H2WB	0.5036	−0.0452	−0.0135	0.060 (15)*	0.50
H2WC	0.4968	−0.1163	−0.1663	0.078 (19)*	0.50
N1	0.40777 (10)	−0.24613 (11)	0.1426 (2)	0.0332 (4)
N2	0.33249 (10)	−0.18460 (11)	0.1621 (2)	0.0397 (4)
N3	0.27393 (10)	−0.23572 (12)	0.2522 (2)	0.0417 (4)
N4	0.31147 (10)	−0.33246 (12)	0.2923 (2)	0.0353 (4)
H4A	0.2797 (14)	−0.3834 (17)	0.350 (3)	0.053 (6)*
C1	0.45124 (10)	−0.43665 (12)	0.2407 (2)	0.0264 (4)
C2	0.40490 (11)	−0.53513 (12)	0.2324 (2)	0.0308 (4)
H2A	0.3404	−0.5358	0.2205	0.037*
C3	0.45222 (11)	−0.63163 (13)	0.2414 (2)	0.0327 (4)
H3A	0.4198	−0.6963	0.2360	0.039*
C4	0.39372 (11)	−0.33838 (12)	0.2258 (2)	0.0277 (4)

	U11	U22	U33	U12	U13	U23
O1W	0.0353 (8)	0.0370 (8)	0.0737 (10)	−0.0091 (6)	0.0168 (7)	−0.0132 (7)
O2W	0.0504 (9)	0.0396 (8)	0.0527 (9)	−0.0046 (6)	0.0166 (7)	0.0005 (7)
N1	0.0323 (8)	0.0253 (7)	0.0421 (9)	0.0035 (6)	0.0052 (6)	0.0021 (6)
N2	0.0379 (9)	0.0283 (8)	0.0528 (10)	0.0071 (6)	0.0040 (7)	0.0015 (7)
N3	0.0321 (9)	0.0304 (8)	0.0630 (11)	0.0082 (6)	0.0067 (8)	−0.0009 (7)
N4	0.0271 (8)	0.0262 (7)	0.0537 (10)	0.0020 (6)	0.0103 (7)	0.0017 (7)
C1	0.0265 (8)	0.0235 (8)	0.0298 (9)	0.0009 (6)	0.0059 (6)	0.0010 (7)
C2	0.0250 (9)	0.0280 (9)	0.0401 (10)	−0.0024 (6)	0.0065 (7)	−0.0014 (7)
C3	0.0357 (9)	0.0225 (8)	0.0408 (10)	−0.0050 (7)	0.0082 (8)	−0.0005 (7)
C4	0.0235 (8)	0.0255 (8)	0.0341 (9)	−0.0011 (6)	0.0026 (7)	−0.0017 (7)

O1W—H1WA	0.8500	C1—C2	1.394 (2)
O1W—H1WB	0.8501	C1—C1i	1.407 (3)
O2W—H2WA	0.8499	C1—C4	1.476 (2)
O2W—H2WB	0.8500	C2—C3	1.380 (2)
O2W—H2WC	0.8500	C2—H2A	0.9300
N1—N2	1.353 (2)	C3—C3i	1.378 (3)
N2—N3	1.294 (2)	C3—H3A	0.9300
N3—N4	1.339 (2)	C4—N1	1.322 (2)
N4—H4A	0.91 (2)	C4—N4	1.338 (2)
H1WA—O1W—H1WB	110.3	C2—C1—C4	117.17 (14)
H2WA—O2W—H2WB	105.2	C1i—C1—C4	124.17 (8)
H2WA—O2W—H2WC	99.2	C3—C2—C1	121.71 (15)
H2WB—O2W—H2WC	112.4	C3—C2—H2A	119.1
C4—N1—N2	105.99 (13)	C1—C2—H2A	119.1
N3—N2—N1	110.96 (14)	C3i—C3—C2	119.65 (9)
N2—N3—N4	106.06 (13)	C3i—C3—H3A	120.2
C4—N4—N3	109.19 (14)	C2—C3—H3A	120.2
C4—N4—H4A	130.1 (13)	N1—C4—N4	107.80 (14)
N3—N4—H4A	120.6 (13)	N1—C4—C1	129.54 (15)
C2—C1—C1i	118.65 (9)	N4—C4—C1	122.58 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O1W	0.91 (2)	1.78 (2)	2.682 (2)	171.9 (19)
O1W—H1WA···N2ii	0.85	2.02	2.8658 (19)	173
O1W—H1WB···O2Wiii	0.85	1.98	2.813 (2)	168
O2W—H2WA···N1	0.85	2.06	2.896 (2)	169
O2W—H2WB···O2Wiv	0.85	1.97	2.813 (3)	170
O2W—H2WC···O2Wv	0.85	2.01	2.814 (3)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯O1W	0.91 (2)	1.78 (2)	2.682 (2)	171.9 (19)
O1W—H1WA⋯N2i	0.85	2.02	2.8658 (19)	173
O1W—H1WB⋯O2Wii	0.85	1.98	2.813 (2)	168
O2W—H2WA⋯N1	0.85	2.06	2.896 (2)	169
O2W—H2WB⋯O2Wiii	0.85	1.97	2.813 (3)	170
O2W—H2WC⋯O2Wiv	0.85	2.01	2.814 (3)	158

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