1,4-Bis(5-methyl-1H-1,2,4-triazol-3-yl)benzene tetra-hydrate.

In the title compound, C(12)H(12)N(6)·4H(2)O, the two triazole rings adopt a cis configuration with a crystallographic twofold axis passing through the central benzene group. The benzene and triazole rings are almost coplanar with a dihedral angle of 5.5 (1)°. In the crystal, water mol-ecules are joined together by OW-H⋯OW hydrogen bonds to form a one-dimensional zigzag chain. These water chains are further connected to the organic mol-ecule, forming a three-dimensional network by inter-molecular OW-H⋯N and N-H⋯OW hydrogen bonds. Moreover, π-π stacking inter-actions between triazole rings [centroid-centroid distances = 3.667 (1)-3.731 (1) Å] are observed. One of the water mol-ecules shows one of the H atoms to be disordered over two positions.

Related literature

For applications of 1,2,4-triazole and its derivatives in coordination chemistry, see: Zhang et al. (2005 ▶); Ouellette et al. (2006 ▶); Zhu et al. (2009 ▶). For the structures of ruthenium complexes with pyridine-2-yl-1,2,4-triazole-based ligands, see: Passaniti et al. (2002 ▶). For the previous synthesis of the title compound, see: Bahçeci et al. (2005 ▶).

Experimental

Crystal data

C12H12N6·4H2O

M = 312.34

Monoclinic,

a = 12.7343 (19) Å

b = 13.937 (2) Å

c = 9.0648 (14) Å

β = 100.893 (3)°

V = 1579.8 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.35 × 0.28 × 0.08 mm

Data collection

Bruker APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.966, T max = 0.992

4670 measured reflections

1542 independent reflections

1286 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.148

S = 1.04

1542 reflections

102 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.25 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/S1600536811015133/im2280sup1.cif

Supplementary material file. DOI: 10.1107/S1600536811015133/im2280Isup2.cdx

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811015133/im2280Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536811015133/im2280Isup4.cml

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

C12H12N6·4H2O	Z = 4
Mr = 312.34	F(000) = 664
Monoclinic, C2/c	Dx = 1.313 Mg m−3
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 12.7343 (19) Å	µ = 0.10 mm−1
b = 13.937 (2) Å	T = 293 K
c = 9.0648 (14) Å	Plate, yellow
β = 100.893 (3)°	0.35 × 0.28 × 0.08 mm
V = 1579.8 (4) Å3

Bruker APEX CCD diffractometer	1542 independent reflections
Radiation source: fine-focus sealed tube	1286 reflections with I > 2σ(I)
graphite	Rint = 0.021
ω scans	θmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
Tmin = 0.966, Tmax = 0.992	k = −15→17
4670 measured reflections	l = −11→11

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0816P)2 + 0.7602P] where P = (Fo2 + 2Fc2)/3
1542 reflections	(Δ/σ)max < 0.001
102 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.25 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. One hydrogen atom from O2W is disordered over two positions in a 0.52 (3):0.48 (3) ratio, which is freely refined with command 'PART'.

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.66106 (13)	0.34969 (11)	−0.19565 (17)	0.0531 (5)
H1D	0.6874	0.3847	−0.2578	0.064*
N2	0.62354 (14)	0.38395 (11)	−0.07499 (17)	0.0522 (5)
N3	0.60877 (12)	0.22386 (10)	−0.09140 (16)	0.0454 (4)
C1	0.68428 (18)	0.19667 (15)	−0.3248 (2)	0.0590 (6)
H1A	0.7292	0.1449	−0.2805	0.088*
H1B	0.7230	0.2361	−0.3830	0.088*
H1C	0.6218	0.1711	−0.3887	0.088*
C2	0.65166 (14)	0.25529 (13)	−0.20444 (18)	0.0448 (4)
C3	0.59264 (14)	0.30486 (12)	−0.01538 (19)	0.0425 (4)
C4	0.54472 (14)	0.30544 (12)	0.12072 (19)	0.0421 (4)
C5	0.52248 (17)	0.22014 (13)	0.1863 (2)	0.0510 (5)
H5A	0.5379	0.1622	0.1443	0.061*
C6	0.52170 (16)	0.39108 (13)	0.1860 (2)	0.0510 (5)
H6A	0.5358	0.4491	0.1429	0.061*
O1W	0.73472 (14)	0.45314 (11)	−0.41166 (19)	0.0757 (5)
H1WA	0.6969	0.4969	−0.4609	0.091*
H1WB	0.8001	0.4691	−0.4017	0.091*
O2W	0.44076 (12)	−0.02791 (9)	0.10493 (16)	0.0602 (4)
H2WA	0.4240	−0.0868	0.0928	0.072*
H2WB	0.4790	−0.0006	0.0500	0.072*	0.52 (3)
H2WC	0.4784	−0.0277	0.1930	0.072*	0.48 (3)

	U11	U22	U33	U12	U13	U23
N1	0.0657 (11)	0.0516 (10)	0.0484 (8)	−0.0032 (8)	0.0274 (8)	0.0074 (7)
N2	0.0662 (11)	0.0437 (9)	0.0523 (9)	−0.0025 (7)	0.0257 (8)	0.0035 (7)
N3	0.0540 (9)	0.0428 (8)	0.0425 (8)	−0.0035 (7)	0.0166 (7)	−0.0015 (6)
C1	0.0649 (13)	0.0672 (13)	0.0495 (10)	−0.0045 (10)	0.0232 (9)	−0.0060 (9)
C2	0.0467 (10)	0.0488 (10)	0.0401 (9)	−0.0022 (8)	0.0115 (7)	0.0016 (7)
C3	0.0452 (10)	0.0437 (9)	0.0397 (9)	−0.0003 (7)	0.0108 (7)	0.0012 (7)
C4	0.0448 (10)	0.0431 (10)	0.0396 (9)	−0.0001 (7)	0.0109 (7)	0.0010 (7)
C5	0.0774 (14)	0.0368 (9)	0.0429 (9)	0.0004 (9)	0.0218 (9)	−0.0027 (7)
C6	0.0603 (12)	0.0380 (10)	0.0604 (11)	−0.0004 (8)	0.0260 (9)	0.0049 (8)
O1W	0.0804 (11)	0.0679 (10)	0.0871 (11)	0.0058 (8)	0.0373 (9)	0.0277 (8)
O2W	0.0809 (11)	0.0447 (7)	0.0611 (9)	−0.0064 (7)	0.0289 (8)	−0.0014 (6)

N1—C2	1.322 (3)	C4—C5	1.382 (2)
N1—N2	1.360 (2)	C4—C6	1.388 (2)
N1—H1D	0.8600	C5—C5i	1.383 (4)
N2—C3	1.320 (2)	C5—H5A	0.9300
N3—C2	1.324 (2)	C6—C6i	1.376 (4)
N3—C3	1.358 (2)	C6—H6A	0.9300
C1—C2	1.484 (3)	O1W—H1WA	0.8500
C1—H1A	0.9600	O1W—H1WB	0.8500
C1—H1B	0.9600	O2W—H2WA	0.8500
C1—H1C	0.9600	O2W—H2WB	0.8501
C3—C4	1.476 (2)	O2W—H2WC	0.8499
C2—N1—N2	110.87 (14)	N2—C3—C4	122.67 (15)
C2—N1—H1D	124.6	N3—C3—C4	123.69 (15)
N2—N1—H1D	124.6	C5—C4—C6	118.63 (17)
C3—N2—N1	102.31 (15)	C5—C4—C3	120.35 (15)
C2—N3—C3	104.00 (15)	C6—C4—C3	121.01 (15)
C2—C1—H1A	109.5	C4—C5—C5i	120.67 (10)
C2—C1—H1B	109.5	C4—C5—H5A	119.7
H1A—C1—H1B	109.5	C5i—C5—H5A	119.7
C2—C1—H1C	109.5	C6i—C6—C4	120.69 (10)
H1A—C1—H1C	109.5	C6i—C6—H6A	119.7
H1B—C1—H1C	109.5	C4—C6—H6A	119.7
N1—C2—N3	109.18 (15)	H1WA—O1W—H1WB	108.3
N1—C2—C1	123.88 (16)	H2WA—O2W—H2WB	121.0
N3—C2—C1	126.93 (17)	H2WA—O2W—H2WC	102.0
N2—C3—N3	113.64 (16)	H2WB—O2W—H2WC	105.4

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1D···O1W	0.86	1.88	2.736 (2)	173.
O1W—H1WA···N2ii	0.85	2.08	2.926 (2)	172.
O1W—H1WB···O2Wiii	0.85	1.96	2.801 (2)	170.
O2W—H2WA···N3iv	0.85	1.95	2.800 (2)	173.
O2W—H2WB···O2Wiv	0.85	1.93	2.754 (3)	164.
O2W—H2WC···O2Wi	0.85	1.92	2.774 (3)	178.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1D⋯O1W	0.86	1.88	2.736 (2)	173
O1W—H1WA⋯N2i	0.85	2.08	2.926 (2)	172
O1W—H1WB⋯O2Wii	0.85	1.96	2.801 (2)	170
O2W—H2WA⋯N3iii	0.85	1.95	2.800 (2)	173
O2W—H2WB⋯O2Wiii	0.85	1.93	2.754 (3)	164
O2W—H2WC⋯O2Wiv	0.85	1.92	2.774 (3)	178

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