1,2 Bis[5 oxo 3 (n prop­yl) 4,5 di­hydro 3H 1,2,4 triazol 4 yl]ethane dihydrate

organic papers

Acta Cryst.(2005). E61, o2699–o2700 doi:10.1107/S1600536805022853 O¨ zdemiret al. _C

12H20N6O22H2O

o2699

Structure Reports Online

ISSN 1600-5368

1,2-Bis[5-oxo-3-(

n

-propyl)-4,5-dihydro-3

H

-1,2,4-triazol-4-yl]ethane dihydrate

Gonca O¨ zdemir,a_{* S¸amil Is¸ık,}a

Kemal Sancak,bSelami S¸as¸mazb and Nazmi Turan Okumus¸og˘luc

a_{Department of Physics, Ondokuz Mayıs}

University, TR-55139 Samsun, Turkey,

b_{Department of Chemistry, Rize Arts and}

Sciences Faculty, Karadeniz Teknik University, Rize, Turkey, andc_{Department of Physics,}

Rize Arts and Sciences Faculty, Karadeniz Teknik University, Rize, Turkey

Correspondence e-mail: gozdemir@omu.edu.tr

Key indicators

Single-crystal X-ray study

T= 296 K

Mean(C–C) = 0.002 A˚

Rfactor = 0.046

wRfactor = 0.119

Data-to-parameter ratio = 12.7

For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

#2005 International Union of Crystallography Printed in Great Britain – all rights reserved

The molecule of the title compound, C12H20N6O22H2O, contains two planar triazole rings. The molecule has crystal-lographic twofold rotation symmetry. The crystal structure is stabilized by intermolecular hydrogen bonds, which form a three-dimensional network.

Comment

Triazole ring systems are planar and partially aromatic. Several articles have been devoted to the syntheses and pharmacological investigations of triazole compounds (Lønning et al., 1998). Apart from its extensive chemical significance, the 1,2,4-triazole nucleus is also found to be associated with diverse medicinal properties, such as analgesic, anti-asthmatic, diuretic and antifungal activities (Mohamedet al., 1993). 1,2,4-Triazole rings interact strongly with heme iron, and aromatic substituents on the triazoles are very effective for interacting with the active site of aromatase (Chenet al., 1997).

The title compound, (I), is shown in Fig. 1. The molecule has twofold rotation symmetry. Selected bond lengths and angles are listed in Table 1. In the crystal structure, there are inter-molecular N—H O, O—H O and O—H N hydrogen bonds (Table 2). The structures of the closely related compounds 4,40_{-butane-1,4-diylbis[3-ethyl-1H}

-1,2,4-triazole-5(4H)-one] and 4-hydroxy-3-n-propyl-1H -1,2,4-triazole-5(4H)-one were recently reported (Ocak I´skeleliet al., 2005).

Experimental

1,2-Bis[(3-n-propyl)-4,5-dihydro-1H-1,2,4-triazole-5-one-4-yl]ethane dihydrate (4.04 g, 0.02 mol) was treated with a solution of 1,3-diaminopropane (0.83 ml, 0.74 g, 0.01 mol) in water (50 ml), and the mixture was refluxed for 6 h. After cooling, the precipitate that formed was recrystallized from ethanol to give (I) (yield 44%, m.p.

462 K). IR: 3520–3440 (OH), 3240 (NH), 1690 (C O), 1393 (C N) cm1_; 1_{H NMR:}

11.35 [s, 2H(2NH)], 3.60 [t, 6H(3CH2)], 2.40 [t,

4H(2CH2)], 2.10 [s, 2H(H2O)], 1.35 [q, 4H(2CH2)], 0.85 [t,

6H(2CH3)]. Crystal data

C12H20N6O22H2O Mr= 316.37

Monoclinic,C2=c

˚

Dx= 1.317 Mg m

3

MoKradiation Cell parameters from 1008

Data collection

Stoe IPDS-II diffractometer

!scans

Absorption correction: integration (X-RED; Stoe & Cie, 2002)

Tmin= 0.954,Tmax= 0.985

5349 measured reflections 1887 independent reflections

1470 reflections withI> 2(I)

Rint= 0.031

max= 27.9 h=17!17

k=11!11

l=15!20

Refinement

Refinement onF2 R[F2> 2(F2)] = 0.046

wR(F2_{) = 0.120} S= 1.04 1887 reflections 149 parameters

All H-atom parameters refined

w= 1/[2_(F

o2) + (0.0836P)2]

whereP= (Fo2+ 2Fc2)/3

(/)max< 0.001 max= 0.40 e A˚

3

min=0.38 e A˚ 3

Extinction correction:SHELXL97

Extinction coefficient: 0.047 (4)

Table 1

Selected geometric parameters (A˚ ,_).

N1—C3 1.3725 (15)

N1—C1 1.3838 (15)

N2—C3 1.2966 (15)

N2—N3 1.3810 (14)

O1—C1 1.2261 (16)

N3—C1 1.3410 (17)

C2—C2i

1.515 (3)

N1—C2—C2i 112.85 (9)

Symmetry code: (i)xþ1;y;zþ3 2.

Table 2

Hydrogen-bond geometry (A˚ ,_).

D—H A D—H H A D A D—H A

N3—H3 O2 0.86 (2) 1.90 (2) 2.7576 (16) 177 (2) O2—H11B O1ii

0.85 (2) 1.91 (3) 2.7457 (16) 165 (2) O2—H11A N2iii

0.85 (3) 2.03 (3) 2.8815 (16) 178 (2)

Symmetry codes: (ii)xþ3 2;yþ

1 2;zþ

3

2; (iii)xþ1;yþ1;zþ1.

All H atoms were refined isotropically [C—H = 0.935 (17)– 1.03 (2) A˚ ].

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement:

X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS86(Sheldrick, 1985); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics:ORTEP-3 for Windows(Farrugia, 1997); software used to prepare material for publication:WinGX(Farrugia, 1999).

The authors thanks to the Faculty of Arts and Sciences, Ondokuz Mayis University, Turkey, for the use of the diffractometer.

References

Chen, S., Kao, Y. C. & Laughton, C. A. (1997).J. Steroid Biochem.61, 107–115. Farrugia, L. J. (1997).J. Appl. Cryst.30, 565.

Farrugia, L. J. (1999).J. Appl. Cryst.32, 837–838.

Ocak I´skeleli, N., Is¸ık, S¸., Sancak, K., S¸as¸maz, S., U¨ nver, Y. & Er, M. (2005).

Acta Cryst.C61, o363–o365. Figure 2

A packing diagram of (I), viewed along thebaxis. Hydrogen bonds are

shown by dashed lines. Figure 1

An ORTEP-3 (Farrugia, 1997) view of (I), with the atom-numbering scheme and 50% probability displacement ellipsoids for non-H atoms

[symmetry code: (i) 1x,y,3

2z]. The dashed line represents the N—

supporting information

sup-1 Acta Cryst. (2005). E61, o2699–o2700

supporting information

Acta Cryst. (2005). E61, o2699–o2700 [https://doi.org/10.1107/S1600536805022853]

1,2-Bis[5-oxo-3-(

n

-propyl)-4,5-dihydro-3

H

-1,2,4-triazol-4-yl]ethane dihydrate

Gonca

Ö

zdemir,

Ş

amil I

şı

k, Kemal Sancak, Selami

Ş

a

ş

maz and Nazmi Turan Okumu

ş

o

ğ

lu

1,2-Bis[5-oxo-3-(n-propyl)-4,5-dihydro-3H-1,2,4-triazol-4-yl]ethane dihydrate

Crystal data

C12H20N6O2·2H2O

Mr = 316.37

Monoclinic, C2/c

Hall symbol: -C 2yc

a = 13.0125 (12) Å

b = 8.5957 (6) Å

c = 15.4586 (12) Å

β = 112.655 (6)°

V = 1595.7 (2) Å3

Z = 4

F(000) = 680

Dx = 1.317 Mg m−3

Mo Kα radiation, λ = 0.71073 Å Cell parameters from 1008 reflections

θ = 2.9–27.9°

µ = 0.10 mm−1

T = 296 K Prism., colourless 0.50 × 0.43 × 0.23 mm

Data collection

Stoe IPDS-II diffractometer

Radiation source: fine-focus sealed tube Graphite monochromator

Detector resolution: 6.67 pixels mm-1

ω scans

Absorption correction: integration (X-RED; Stoe & Cie, 2002)

Tmin = 0.954, Tmax = 0.985

5349 measured reflections 1887 independent reflections 1470 reflections with I > 2σ(I)

Rint = 0.031

θmax = 27.9°, θmin = 2.9°

h = −17→17

k = −11→11

l = −15→20

Refinement

Refinement on F2

Least-squares matrix: full

R[F2 _{> 2σ(F}2_{)] = 0.046}

wR(F2_{) = 0.120}

S = 1.04 1887 reflections 149 parameters 0 restraints

Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map

Hydrogen site location: inferred from neighbouring sites

All H-atom parameters refined

w = 1/[σ2_(F

o2) + (0.0836P)2]

where P = (Fo2 + 2Fc2)/3

(Δ/σ)max < 0.001

Δρmax = 0.40 e Å−3

Δρmin = −0.38 e Å−3

Extinction correction: SHELXL97, Fc*_{=kFc[1+0.001xFc}2_λ3_/sin(2θ)]-1/4

Special details

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 F}2_,

conventional R-factors R are based on F, with F set to zero for negative F2_{. The threshold expression of F}2 _{> σ(F}2_{) 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₎

x y z Uiso*/Ueq

O2 0.62269 (11) 0.58035 (14) 0.61339 (9) 0.0732 (4) H11B 0.685 (2) 0.602 (3) 0.6574 (17) 0.089 (7)* H11A 0.5987 (19) 0.639 (3) 0.5655 (18) 0.085 (7)* H5B 0.2389 (15) 0.150 (2) 0.4424 (12) 0.057 (4)* H4A 0.3798 (15) −0.118 (2) 0.5171 (12) 0.061 (4)* H6A 0.2071 (18) −0.168 (3) 0.3682 (15) 0.087 (6)* H4B 0.3053 (14) −0.0388 (18) 0.5647 (12) 0.055 (4)* H5A 0.3151 (13) 0.0643 (18) 0.3929 (12) 0.056 (4)* H3 0.5753 (15) 0.373 (2) 0.6185 (13) 0.064 (5)* H6C 0.127 (2) −0.023 (3) 0.3209 (17) 0.087 (6)* H6B 0.1297 (17) −0.078 (2) 0.4187 (15) 0.077 (6)* H2A 0.5177 (13) −0.173 (2) 0.6817 (11) 0.051 (4)* H2B 0.6148 (14) −0.0892 (18) 0.7614 (11) 0.050 (4)* N1 0.52137 (8) 0.05384 (11) 0.66480 (7) 0.0390 (3) N2 0.45661 (9) 0.22537 (12) 0.55118 (7) 0.0427 (3) O1 0.67508 (9) 0.19240 (13) 0.76639 (7) 0.0601 (3) C3 0.44051 (9) 0.08846 (13) 0.57887 (8) 0.0367 (3) N3 0.55125 (9) 0.28091 (13) 0.62215 (8) 0.0459 (3) C5 0.27057 (10) 0.04572 (15) 0.43204 (9) 0.0436 (3) C1 0.59295 (10) 0.17967 (13) 0.69317 (9) 0.0427 (3) C4 0.34740 (10) −0.01814 (14) 0.52595 (9) 0.0426 (3) C2 0.53546 (12) −0.08619 (14) 0.72097 (9) 0.0468 (3) C6 0.17556 (14) −0.0646 (2) 0.38122 (13) 0.0622 (4)

Atomic displacement parameters (Å2₎

U11 _U22 _U33 _U12 _U13 _U23

supporting information

sup-3 Acta Cryst. (2005). E61, o2699–o2700

C2 0.0590 (8) 0.0328 (5) 0.0398 (6) 0.0081 (5) 0.0093 (6) 0.0002 (5) C6 0.0537 (8) 0.0618 (9) 0.0552 (9) −0.0151 (7) 0.0036 (7) −0.0075 (7)

Geometric parameters (Å, º)

O2—H11B 0.85 (2) C5—C6 1.5154 (19) O2—H11A 0.85 (3) C5—H5B 1.023 (18) N1—C3 1.3725 (15) C5—H5A 0.998 (18) N1—C1 1.3838 (15) C4—H4A 0.989 (18) N1—C2 1.4539 (15) C4—H4B 0.970 (18) N2—C3 1.2966 (15) C2—C2i _{1.515 (3)}

N2—N3 1.3810 (14) C2—H2A 0.935 (17) O1—C1 1.2261 (16) C2—H2B 0.980 (17) C3—C4 1.4877 (16) C6—H6A 1.03 (2) N3—C1 1.3410 (17) C6—H6C 0.97 (2) N3—H3 0.86 (2) C6—H6B 0.98 (2) C5—C4 1.5133 (18)

H11B—O2—H11A 119 (2) N3—C1—N1 103.72 (10) C3—N1—C1 107.98 (10) C3—C4—C5 113.65 (10) C3—N1—C2 129.12 (10) C3—C4—H4A 108.1 (10) C1—N1—C2 122.90 (10) C5—C4—H4A 110.0 (10) C3—N2—N3 105.05 (10) C3—C4—H4B 107.9 (10) N2—C3—N1 110.80 (10) C5—C4—H4B 109.7 (10) N2—C3—C4 125.34 (10) H4A—C4—H4B 107.4 (14) N1—C3—C4 123.85 (10) N1—C2—C2i _{112.85 (9)}

C1—N3—N2 112.45 (10) N1—C2—H2A 109.4 (10) C1—N3—H3 127.4 (12) C2i_{—C2—H2A 109.2 (10)}

N2—N3—H3 120.1 (12) N1—C2—H2B 105.2 (9) C4—C5—C6 112.08 (12) C2i_{—C2—H2B 110.8 (9)}

C4—C5—H5B 108.9 (10) H2A—C2—H2B 109.2 (14) C6—C5—H5B 109.3 (10) C5—C6—H6A 109.5 (13) C4—C5—H5A 108.4 (9) C5—C6—H6C 111.4 (14) C6—C5—H5A 109.5 (9) H6A—C6—H6C 107.0 (18) H5B—C5—H5A 108.5 (13) C5—C6—H6B 109.0 (12) O1—C1—N3 129.18 (12) H6A—C6—H6B 113.1 (18) O1—C1—N1 127.10 (12) H6C—C6—H6B 106.9 (19)

N2—N3—C1—O1 −179.72 (13) C3—N1—C2—C2i _{−83.05 (17)}

N2—N3—C1—N1 0.57 (14) C1—N1—C2—C2i _{96.72 (17)}

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A

N3—H3···O2 0.86 (2) 1.90 (2) 2.7576 (16) 176.9 (18) O2—H11B···O1ii _{0.85 (2) 1.91 (3) 2.7457 (16) 165 (2)}

O2—H11A···N2iii _{0.85 (3) 2.03 (3) 2.8815 (16) 178 (2)}