organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

3,3′-Di­methyl-4,4′-(hexane-1,6-di­yl)bis­­[1H-1,2,4-triazol-5(4H)-one]

aDepartment of Middle Education, Educational Faculty, Ondokuz Mayıs University, 55200 Atakum, Samsun, Turkey, bDepartment of Computer Education and Instructional Technology, Educational Faculty, Ondokuz Mayıs University, 55200 Atakum, Samsun, Turkey, cDepartment of Chemistry, Faculty of Arts and Sciences, Karadeniz Teknik University, 61080 Trabzon, Turkey, dDepartment of Physics, Hacettepe University, Beytepe 06800, Ankara, Turkey, and eAnadolu University, Faculty of Science, Department of Chemistry, 26470 Yenibaĝlar, Eskişehir, Turkey
*Correspondence e-mail: ucoruh@omu.edu.tr

(Received 7 September 2010; accepted 17 September 2010; online 25 September 2010)

The title compound, C12H20N6O2, has a centre of symmetry. The mol­ecule consists of two triazole rings joined by an aliphatic –(CH2)6– chain. The crystal structure is stabilized by inter­molecular N—H⋯O hydrogen bonds and by ππ stacking inter­actions between the triazole rings of inversion-related mol­ecules [centroid–centroid distance = 3.277 (8) Å].

Related literature

For background information including pharmacological studies, see: Chiu & Huskey (1998[Chiu, S.-H. L. & Huskey, S. E. W. (1998). Drug Metabol. Dispos. 26, 838-847.]); Clemons et al. (2004[Clemons, M., Colemon, R. E. & Verma, S. (2004). Cancer Treat. Rev. 30, 325-332.]); Dalloul & Boyle (2006[Dalloul, H. & Boyle, P. (2006). Turk. J. Chem. 30, 119-124.]); Eliott et al. (1986[Eliott, R., Sunley, R. L. & Griffin, D. A. (1986). UK Patent Appl. GB 2, 175.]); Griffin & Mannion (1986[Griffin, D. A. & Mannion, S. K. (1986). Eur. Patent Appl. EP 199, 474.]); Santen (2003[Santen, J. R. (2003). Steroids, 68, 559-567.]); Tanaka (1974[Tanaka, G. (1974). Japan Kokai, 973, 7495.]); Zamani et al. (2003[Zamani, K., Faghihi, K., Reza Sangi, M. & Zolgharnein, J. (2003). Turk. J. Chem. 27, 119-126.]). Related structures have been reported by Ustabaş et al. (2006[Ustabaş, R., Çoruh, U., Sancak, K., Düg~dü, E. & Vázquez-López, E. M. (2006). Acta Cryst. E62, o4265-o4267.], 2007[Ustabaş, R., Çoruh, U., Sancak, K. & Demirkan, E. (2007). Acta Cryst. E63, o3443.], 2009[Ustabaş, R., Ünver, Y., Suleymanoğlu, N., Çoruh, U. & Sancak, K. (2009). Acta Cryst. E65, o1006-o1007.]); Ünver et al. (2008[Ünver, Y., Düğdu, E., Sancak, K., Er, M. & Karaoğlu, Ş. A. (2008). Turk. J. Chem. 32, 441-455.], 2009[Ünver, Y., Düğdu, E., Sancak, K., Er, M. & Karaoğlu, Ş. A. (2009). Turk. J. Chem. 33, 135-147.]); Çoruh et al. (2003[Çoruh, U., Ustabaş, R., Sancak, K., Şaşmaz, S., Ağar, E. & Kim, Y. (2003). Acta Cryst. E59, o1277-o1279.]).

[Scheme 1]

Experimental

Crystal data
  • C12H20N6O2

  • Mr = 280.34

  • Triclinic, [P \overline 1]

  • 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[Bruker (2007). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.962, Tmax = 0.988

  • 6074 measured reflections

  • 1673 independent reflections

  • 1309 reflections with I > 2σ(I)

  • Rint = 0.033

Refinement
  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N3—H3⋯O1i 0.90 (2) 1.89 (2) 2.7707 (15) 167 (2)
Symmetry code: (i) -x+1, -y, -z+2.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information


Comment top

The 1,2,4-triazole compounds possess important pharmacological activities that include antifungal and antiviral properties. Examples of compounds bearing the 1,2,4-triazole group are fluconazole, the powerful azole antifungal agent as well as the potent antiviral N– nucleoside ribavirin (Ünver et al., 2008; Ünver et al., 2009). Furthermore, various 1,2,4-triazole derivatives have been reported as fungicidal (Zamani et al., 2003), insecticidal (Tanaka, 1974), antimicrobial (Griffin & Mannion, 1986), and some showed antitumor activity as well as having anticonvulsant (Dalloul & Boyle, 2006), antidepressant (Chiu & Huskey, 1998) and plant growth regulator anticoagulant activity (Eliott et al., 1986). It was reported that compounds having triazole moieties, such as Vorozole, Anastrozole and Letrozole appear to be very effective aromatase inhibitors and can be useful for preventing breast cancer (Santen, 2003; Clemons et al., 2004).

The molecular structure of the compound is shown in Fig.1. The molecule consists of two triazole rings, joined by an aliphatic —(CH2)6— chain connected to nitrogen atoms of the rings. The molecule has an inversion center in the middle of the chain, that connects the triazole rings. The length of the NC [N2C5= 1.3031 (17) Å] bond in the triazole ring is close to the those similar structures in the literature [1.296 (3)Å in C14H16N6O2S (Ustabaş et al., 2007); 1.288 (2)Å in C16H28N6O2 (Çoruh et al., 2003)]. The bond length of OC [O1C1= 1.2421 (16) Å] is in conformity with the values mentioned before[1.218 (3)Å in C16H20N6O2S (Ustabaş et al., 2006); 1.220 (2)Å in C24H20N4O2S (Ustabaş et al., 2009)]. The triazole ring is very close to planarity, with a maximum deviation from the least-squares plane of -0.014 (13)Å for atom C1.

In the crystal structure of the compound, there is a strong intermolecular N3—H3···O1 hydrogen-bonding interaction (Table 1). The compound also exhibits π-π stacking interactions between triazole rings (Cg1···Cg1= 3.277 (8) Å; symmetry code: –X, 2-Y, –Z).

Related literature top

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 top

The synthesis of 4,4'-(hexane-1,6-diyl)bis (5-ethyl-2H-1,2,4-triazol-3(4H)-one) to a solution of ethyl 2 (1-ethoxyethylidene)hydrazinecarboxylate (0.02 mol) in 50 ml water hexane-1,6-diamine (0.01 mol) was added. Having refluxed this mixture for 4 h the precipitate formed was filtered off. The solid product was washed with water and crystallized from ethanol/water (1/3)(yield 73.25%) to afford the desired compound.

Refinement top

All H atoms were located in a difference synthesis and refined [N—H = 0.902 (19) Å; ethylene C—H = 0.945 (18) Å-1.017 (18) Å; and methylene C—H= 0.952 Å-1.00 (2) Å].

Computing details top

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

Figures top
[Figure 1] Fig. 1. An ellipsoid plot of the title compound, with the atom numbering scheme. Atoms with primed labels are related via an inversion center (1-x, 1-y, 1-z). Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A packing diagram, viewed along b.
3,3'-Dimethyl-4,4'-(hexane-1,6-diyl)bis[1H-1,2,4-triazol- 5(4H)-one] top
Crystal data top
C12H20N6O2Z = 1
Mr = 280.34F(000) = 150
Triclinic, P1Dx = 1.377 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.3641 (2) ÅCell parameters from 1309 reflections
b = 7.3034 (2) Åθ = 2.8–28.3°
c = 7.7774 (2) ŵ = 0.10 mm1
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
Data collection top
Bruker Kappa APEXII CCD area-detector
diffractometer
1673 independent reflections
Radiation source: fine-focus sealed tube1309 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
ϕ and ω scansθmax = 28.3°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
h = 88
Tmin = 0.962, Tmax = 0.988k = 99
6074 measured reflectionsl = 1010
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112All 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 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.28 e Å3
Crystal data top
C12H20N6O2γ = 94.707 (2)°
Mr = 280.34V = 338.05 (2) Å3
Triclinic, P1Z = 1
a = 6.3641 (2) ÅMo Kα radiation
b = 7.3034 (2) ŵ = 0.10 mm1
c = 7.7774 (2) ÅT = 101 K
α = 93.299 (2)°0.40 × 0.16 × 0.12 mm
β = 109.578 (2)°
Data collection top
Bruker Kappa APEXII CCD area-detector
diffractometer
1673 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
1309 reflections with I > 2σ(I)
Tmin = 0.962, Tmax = 0.988Rint = 0.033
6074 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.112All H-atom parameters refined
S = 1.03Δρmax = 0.32 e Å3
1673 reflectionsΔρmin = 0.28 e Å3
131 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.49741 (15)0.02539 (13)0.76514 (13)0.0199 (3)
N10.84928 (18)0.18555 (15)0.81036 (15)0.0159 (3)
N20.98018 (18)0.22436 (15)1.11442 (15)0.0183 (3)
N30.76344 (18)0.13460 (15)1.04956 (15)0.0173 (3)
C10.6815 (2)0.10507 (17)0.86549 (18)0.0162 (3)
C20.8354 (2)0.1878 (2)0.61861 (18)0.0189 (3)
C30.7642 (2)0.36813 (19)0.54057 (19)0.0202 (3)
C40.5280 (2)0.40487 (19)0.53108 (19)0.0193 (3)
C51.0248 (2)0.25341 (17)0.96590 (18)0.0166 (3)
C61.2408 (2)0.3456 (2)0.9639 (2)0.0207 (3)
H210.981 (3)0.163 (2)0.609 (2)0.019 (4)*
H611.220 (3)0.461 (3)0.914 (2)0.030 (4)*
H320.772 (3)0.361 (2)0.415 (2)0.025 (4)*
H410.512 (3)0.397 (2)0.655 (2)0.018 (4)*
H310.876 (3)0.476 (2)0.614 (2)0.028 (4)*
H420.414 (3)0.309 (2)0.446 (2)0.022 (4)*
H220.732 (3)0.087 (2)0.551 (2)0.025 (4)*
H30.696 (3)0.089 (2)1.125 (3)0.036 (5)*
H621.310 (3)0.273 (3)0.887 (3)0.035 (5)*
H631.348 (3)0.368 (3)1.093 (3)0.041 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0140 (5)0.0240 (5)0.0184 (5)0.0042 (4)0.0030 (4)0.0004 (4)
N10.0126 (6)0.0162 (6)0.0181 (6)0.0005 (4)0.0043 (5)0.0024 (4)
N20.0123 (6)0.0186 (6)0.0213 (6)0.0005 (4)0.0028 (5)0.0012 (4)
N30.0127 (6)0.0192 (6)0.0183 (6)0.0006 (4)0.0035 (5)0.0026 (4)
C10.0134 (6)0.0150 (6)0.0197 (7)0.0028 (5)0.0047 (5)0.0025 (5)
C20.0156 (7)0.0230 (7)0.0169 (7)0.0009 (6)0.0049 (5)0.0001 (5)
C30.0163 (7)0.0237 (7)0.0202 (7)0.0017 (6)0.0065 (6)0.0039 (6)
C40.0160 (7)0.0213 (7)0.0184 (7)0.0029 (5)0.0039 (6)0.0035 (5)
C50.0130 (6)0.0153 (6)0.0198 (7)0.0033 (5)0.0028 (5)0.0018 (5)
C60.0131 (7)0.0208 (7)0.0261 (8)0.0005 (5)0.0045 (6)0.0021 (6)
Geometric parameters (Å, º) top
O1—C11.2421 (16)C3—C41.5271 (19)
N1—C51.3751 (17)C3—H320.991 (16)
N1—C11.3794 (16)C3—H311.017 (18)
N1—C21.4653 (16)C4—C4i1.528 (3)
N2—C51.3031 (17)C4—H411.007 (15)
N2—N31.3907 (15)C4—H421.000 (17)
N3—C11.3467 (18)C5—C61.4856 (19)
N3—H30.902 (19)C6—H610.952 (18)
C2—C31.521 (2)C6—H621.006 (18)
C2—H210.985 (15)C6—H631.00 (2)
C2—H220.945 (18)
C5—N1—C1107.39 (11)C2—C3—H31110.3 (10)
C5—N1—C2128.60 (11)C4—C3—H31109.3 (9)
C1—N1—C2123.98 (11)H32—C3—H31107.2 (13)
C5—N2—N3103.79 (11)C3—C4—C4i112.27 (14)
C1—N3—N2112.63 (11)C3—C4—H41110.2 (9)
C1—N3—H3124.9 (12)C4i—C4—H41108.2 (8)
N2—N3—H3122.0 (12)C3—C4—H42110.5 (9)
O1—C1—N3128.98 (12)C4i—C4—H42109.0 (9)
O1—C1—N1126.86 (12)H41—C4—H42106.5 (13)
N3—C1—N1104.16 (11)N2—C5—N1111.99 (11)
N1—C2—C3112.31 (11)N2—C5—C6124.26 (13)
N1—C2—H21108.9 (9)N1—C5—C6123.74 (12)
C3—C2—H21111.3 (9)C5—C6—H61110.6 (10)
N1—C2—H22107.6 (10)C5—C6—H62113.5 (10)
C3—C2—H22110.7 (10)H61—C6—H62105.9 (14)
H21—C2—H22105.8 (13)C5—C6—H63108.9 (11)
C2—C3—C4114.14 (11)H61—C6—H63108.3 (15)
C2—C3—H32106.5 (9)H62—C6—H63109.6 (14)
C4—C3—H32109.1 (9)
C5—N2—N3—C11.87 (14)N1—C2—C3—C464.04 (15)
N2—N3—C1—O1178.11 (12)C2—C3—C4—C4i174.64 (14)
N2—N3—C1—N12.33 (14)N3—N2—C5—N10.58 (14)
C5—N1—C1—O1178.57 (12)N3—N2—C5—C6179.47 (12)
C2—N1—C1—O10.5 (2)C1—N1—C5—N20.81 (15)
C5—N1—C1—N31.86 (13)C2—N1—C5—N2178.77 (12)
C2—N1—C1—N3179.93 (11)C1—N1—C5—C6178.09 (12)
C5—N1—C2—C384.62 (16)C2—N1—C5—C60.1 (2)
C1—N1—C2—C397.73 (14)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O1ii0.90 (2)1.89 (2)2.7707 (15)167 (2)
Symmetry code: (ii) x+1, y, z+2.

Experimental details

Crystal data
Chemical formulaC12H20N6O2
Mr280.34
Crystal system, space groupTriclinic, P1
Temperature (K)101
a, b, c (Å)6.3641 (2), 7.3034 (2), 7.7774 (2)
α, β, γ (°)93.299 (2), 109.578 (2), 94.707 (2)
V3)338.05 (2)
Z1
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.40 × 0.16 × 0.12
Data collection
DiffractometerBruker Kappa APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2007)
Tmin, Tmax0.962, 0.988
No. of measured, independent and
observed [I > 2σ(I)] reflections
6074, 1673, 1309
Rint0.033
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.112, 1.03
No. of reflections1673
No. of parameters131
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.32, 0.28

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O1i0.90 (2)1.89 (2)2.7707 (15)167 (2)
Symmetry code: (i) x+1, y, z+2.
 

References

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First citationUstabaş, R., Çoruh, U., Sancak, K. & Demirkan, E. (2007). Acta Cryst. E63, o3443.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationUstabaş, R., Çoruh, U., Sancak, K., Düg~dü, E. & Vázquez-López, E. M. (2006). Acta Cryst. E62, o4265–o4267.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationUstabaş, R., Ünver, Y., Suleymanoğlu, N., Çoruh, U. & Sancak, K. (2009). Acta Cryst. E65, o1006–o1007.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationZamani, K., Faghihi, K., Reza Sangi, M. & Zolgharnein, J. (2003). Turk. J. Chem. 27, 119–126.  CAS Google Scholar

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