3,3'-Dimethyl-4,4'-(hexane-1,6-di-yl)bis-[1H-1,2,4-triazol-5(4H)-one].

The title compound, C(12)H(20)N(6)O(2), has a centre of symmetry. The mol-ecule consists of two triazole rings joined by an aliphatic -(CH(2))(6)- chain. The crystal structure is stabilized by inter-molecular N-H⋯O hydrogen bonds and by π-π stacking inter-actions between the triazole rings of inversion-related mol-ecules [centroid-centroid distance = 3.277 (8) Å].

Related literature

For background information including pharmacological studies, see: Chiu & Huskey (1998 ▶); Clemons et al. (2004 ▶); Dalloul & Boyle (2006 ▶); Eliott et al. (1986 ▶); Griffin & Mannion (1986 ▶); Santen (2003 ▶); Tanaka (1974 ▶); Zamani et al. (2003 ▶). Related structures have been reported by Ustabaş et al. (2006 ▶, 2007 ▶, 2009 ▶); Ünver et al. (2008 ▶, 2009 ▶); Çoruh et al. (2003 ▶).

Experimental

Crystal data

C12H20N6O2

M = 280.34

Triclinic,

a = 6.3641 (2) Å

b = 7.3034 (2) Å

c = 7.7774 (2) Å

α = 93.299 (2)°

β = 109.578 (2)°

γ = 94.707 (2)°

V = 338.05 (2) Å3

Z = 1

Mo Kα radiation

μ = 0.10 mm−1

T = 101 K

0.40 × 0.16 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.962, T max = 0.988

6074 measured reflections

1673 independent reflections

1309 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.112

S = 1.03

1673 reflections

131 parameters

All H-atom parameters refined

Δρmax = 0.32 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810037311/pk2267sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810037311/pk2267Isup2.hkl

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

C12H20N6O2	Z = 1
Mr = 280.34	F(000) = 150
Triclinic, P1	Dx = 1.377 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.3641 (2) Å	Cell parameters from 1309 reflections
b = 7.3034 (2) Å	θ = 2.8–28.3°
c = 7.7774 (2) Å	µ = 0.10 mm−1
α = 93.299 (2)°	T = 101 K
β = 109.578 (2)°	Rod-shaped, colorless
γ = 94.707 (2)°	0.40 × 0.16 × 0.12 mm
V = 338.05 (2) Å3

Bruker Kappa APEXII CCD area-detector diffractometer	1673 independent reflections
Radiation source: fine-focus sealed tube	1309 reflections with I > 2σ(I)
graphite	Rint = 0.033
φ and ω scans	θmax = 28.3°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −8→8
Tmin = 0.962, Tmax = 0.988	k = −9→9
6074 measured reflections	l = −10→10

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	All H-atom parameters refined
S = 1.03	w = 1/[σ2(Fo2) + (0.062P)2 + 0.0594P] where P = (Fo2 + 2Fc2)/3
1673 reflections	(Δ/σ)max < 0.001
131 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.28 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
O1	0.49741 (15)	0.02539 (13)	0.76514 (13)	0.0199 (3)
N1	0.84928 (18)	0.18555 (15)	0.81036 (15)	0.0159 (3)
N2	0.98018 (18)	0.22436 (15)	1.11442 (15)	0.0183 (3)
N3	0.76344 (18)	0.13460 (15)	1.04956 (15)	0.0173 (3)
C1	0.6815 (2)	0.10507 (17)	0.86549 (18)	0.0162 (3)
C2	0.8354 (2)	0.1878 (2)	0.61861 (18)	0.0189 (3)
C3	0.7642 (2)	0.36813 (19)	0.54057 (19)	0.0202 (3)
C4	0.5280 (2)	0.40487 (19)	0.53108 (19)	0.0193 (3)
C5	1.0248 (2)	0.25341 (17)	0.96590 (18)	0.0166 (3)
C6	1.2408 (2)	0.3456 (2)	0.9639 (2)	0.0207 (3)
H21	0.981 (3)	0.163 (2)	0.609 (2)	0.019 (4)*
H61	1.220 (3)	0.461 (3)	0.914 (2)	0.030 (4)*
H32	0.772 (3)	0.361 (2)	0.415 (2)	0.025 (4)*
H41	0.512 (3)	0.397 (2)	0.655 (2)	0.018 (4)*
H31	0.876 (3)	0.476 (2)	0.614 (2)	0.028 (4)*
H42	0.414 (3)	0.309 (2)	0.446 (2)	0.022 (4)*
H22	0.732 (3)	0.087 (2)	0.551 (2)	0.025 (4)*
H3	0.696 (3)	0.089 (2)	1.125 (3)	0.036 (5)*
H62	1.310 (3)	0.273 (3)	0.887 (3)	0.035 (5)*
H63	1.348 (3)	0.368 (3)	1.093 (3)	0.041 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0140 (5)	0.0240 (5)	0.0184 (5)	−0.0042 (4)	0.0030 (4)	0.0004 (4)
N1	0.0126 (6)	0.0162 (6)	0.0181 (6)	0.0005 (4)	0.0043 (5)	0.0024 (4)
N2	0.0123 (6)	0.0186 (6)	0.0213 (6)	−0.0005 (4)	0.0028 (5)	0.0012 (4)
N3	0.0127 (6)	0.0192 (6)	0.0183 (6)	−0.0006 (4)	0.0035 (5)	0.0026 (4)
C1	0.0134 (6)	0.0150 (6)	0.0197 (7)	0.0028 (5)	0.0047 (5)	0.0025 (5)
C2	0.0156 (7)	0.0230 (7)	0.0169 (7)	−0.0009 (6)	0.0049 (5)	−0.0001 (5)
C3	0.0163 (7)	0.0237 (7)	0.0202 (7)	−0.0017 (6)	0.0065 (6)	0.0039 (6)
C4	0.0160 (7)	0.0213 (7)	0.0184 (7)	−0.0029 (5)	0.0039 (6)	0.0035 (5)
C5	0.0130 (6)	0.0153 (6)	0.0198 (7)	0.0033 (5)	0.0028 (5)	0.0018 (5)
C6	0.0131 (7)	0.0208 (7)	0.0261 (8)	−0.0005 (5)	0.0045 (6)	0.0021 (6)

O1—C1	1.2421 (16)	C3—C4	1.5271 (19)
N1—C5	1.3751 (17)	C3—H32	0.991 (16)
N1—C1	1.3794 (16)	C3—H31	1.017 (18)
N1—C2	1.4653 (16)	C4—C4i	1.528 (3)
N2—C5	1.3031 (17)	C4—H41	1.007 (15)
N2—N3	1.3907 (15)	C4—H42	1.000 (17)
N3—C1	1.3467 (18)	C5—C6	1.4856 (19)
N3—H3	0.902 (19)	C6—H61	0.952 (18)
C2—C3	1.521 (2)	C6—H62	1.006 (18)
C2—H21	0.985 (15)	C6—H63	1.00 (2)
C2—H22	0.945 (18)
C5—N1—C1	107.39 (11)	C2—C3—H31	110.3 (10)
C5—N1—C2	128.60 (11)	C4—C3—H31	109.3 (9)
C1—N1—C2	123.98 (11)	H32—C3—H31	107.2 (13)
C5—N2—N3	103.79 (11)	C3—C4—C4i	112.27 (14)
C1—N3—N2	112.63 (11)	C3—C4—H41	110.2 (9)
C1—N3—H3	124.9 (12)	C4i—C4—H41	108.2 (8)
N2—N3—H3	122.0 (12)	C3—C4—H42	110.5 (9)
O1—C1—N3	128.98 (12)	C4i—C4—H42	109.0 (9)
O1—C1—N1	126.86 (12)	H41—C4—H42	106.5 (13)
N3—C1—N1	104.16 (11)	N2—C5—N1	111.99 (11)
N1—C2—C3	112.31 (11)	N2—C5—C6	124.26 (13)
N1—C2—H21	108.9 (9)	N1—C5—C6	123.74 (12)
C3—C2—H21	111.3 (9)	C5—C6—H61	110.6 (10)
N1—C2—H22	107.6 (10)	C5—C6—H62	113.5 (10)
C3—C2—H22	110.7 (10)	H61—C6—H62	105.9 (14)
H21—C2—H22	105.8 (13)	C5—C6—H63	108.9 (11)
C2—C3—C4	114.14 (11)	H61—C6—H63	108.3 (15)
C2—C3—H32	106.5 (9)	H62—C6—H63	109.6 (14)
C4—C3—H32	109.1 (9)
C5—N2—N3—C1	1.87 (14)	N1—C2—C3—C4	−64.04 (15)
N2—N3—C1—O1	178.11 (12)	C2—C3—C4—C4i	174.64 (14)
N2—N3—C1—N1	−2.33 (14)	N3—N2—C5—N1	−0.58 (14)
C5—N1—C1—O1	−178.57 (12)	N3—N2—C5—C6	−179.47 (12)
C2—N1—C1—O1	−0.5 (2)	C1—N1—C5—N2	−0.81 (15)
C5—N1—C1—N3	1.86 (13)	C2—N1—C5—N2	−178.77 (12)
C2—N1—C1—N3	179.93 (11)	C1—N1—C5—C6	178.09 (12)
C5—N1—C2—C3	−84.62 (16)	C2—N1—C5—C6	0.1 (2)
C1—N1—C2—C3	97.73 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1ii	0.90 (2)	1.89 (2)	2.7707 (15)	167 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O1i	0.90 (2)	1.89 (2)	2.7707 (15)	167 (2)

Symmetry code: (i) .