


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810037311/pk2267sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536810037311/pk2267Isup2.hkl |
CCDC reference: 797806
Key indicators
- Single-crystal X-ray study
- T = 101 K
- Mean
(C-C) = 0.002 Å
- R factor = 0.041
- wR factor = 0.112
- Data-to-parameter ratio = 12.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 15
Alert level G PLAT153_ALERT_1_G The su's on the Cell Axes are Equal (x 100000) 20 Ang. PLAT154_ALERT_1_G The su's on the Cell Angles are Equal (x 10000) 200 Deg.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
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.
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].
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).
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 monochromator | 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 |
C12H20N6O2 | γ = 94.707 (2)° |
Mr = 280.34 | V = 338.05 (2) Å3 |
Triclinic, P1 | Z = 1 |
a = 6.3641 (2) Å | Mo Kα radiation |
b = 7.3034 (2) Å | µ = 0.10 mm−1 |
c = 7.7774 (2) Å | T = 101 K |
α = 93.299 (2)° | 0.40 × 0.16 × 0.12 mm |
β = 109.578 (2)° |
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 = 0.988 | Rint = 0.033 |
6074 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.112 | All H-atom parameters refined |
S = 1.03 | Δρmax = 0.32 e Å−3 |
1673 reflections | Δρmin = −0.28 e Å−3 |
131 parameters |
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) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
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) |
Symmetry code: (ii) −x+1, −y, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C12H20N6O2 |
Mr | 280.34 |
Crystal system, space group | Triclinic, 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) |
V (Å3) | 338.05 (2) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.40 × 0.16 × 0.12 |
Data collection | |
Diffractometer | Bruker Kappa APEXII CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2007) |
Tmin, Tmax | 0.962, 0.988 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6074, 1673, 1309 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.112, 1.03 |
No. of reflections | 1673 |
No. of parameters | 131 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 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).
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) −x+1, −y, −z+2. |
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 N═C [N2═C5= 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 O═C [O1═C1= 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).