Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The title compounds, C12H20N6O2, (I), and C5H9N3O2, (II), display the characteristic features of 1,2,4-triazole derivatives. Compound (I) lies about an inversion centre which is at the mid-point of the central C—C bond. Compound (II) also contains a planar 1,2,4-triazole ring but differs from (I) in that it has a hydr­oxy group attached to the ring. Mol­ecules of (I) are held together in the crystal structure by inter­molecular N—H...O contacts and by weak π–π stacking inter­actions between the 1,2,4-triazole moieties. Compound (II) contains inter­molecular O—H...O and N—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270105008449/gz1000sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270105008449/gz1000Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270105008449/gz1000IIsup3.hkl
Contains datablock II

CCDC references: 275523; 275524

Comment top

Recently, much attention has been focused on 1,2,4-triazole derivatives for their broad-spectrum fungicidal, insecticidal, herbicidal, anticonvulsant, antitumour and plant growth regulatory activity (Tsuda & Itoh, 2004; Chai et al., 2003; Er-Rahimini & Mornet, 1992; Nakib et al., 1994; Jenkins et al., 1989). Disubstituted 1,2,4-triazol derivatives have also been reported to show antituberculotic activities (Íkizler et al., 1998). In a previous work, we reported that some 1,2,4-triazol-5-one compounds have antimicrobial effect (Demirbaş et al., 2004). 3-Amino-1,2,4-triazole has been recognized as an inhibitor of chloroplast development, effecting both caretenoid and chlorophyll pigments (Wolf, 1960). The coordination chemistry of azoles acting as ligands for the production of organometallic compounds in the contex of modelling biological systems has gained much interest. In the 4-hydroxyazole tautomer (Íkizler & Sancak, 1992), the O atom of the hydroxy group adjacent to the donor N atom of the heterocyclic ring enables the formation of five-membered chelate ring with transition metal cations. Therefore, the formation of a chelate via an oxy/hydroxy tautomer is one of the major factors for the presence of intermolecular or intramolecular interactions (Kurtziel et al., 2003). Previously, spectroscopic and crystal structure data of some 1,2,4-triazoles have been reported (Çoruh et al., 2004; Zhu et al., 2000; Li et al., 2004). In this paper, we present the synthesis and molecular and crystal structure of 1,4-[di(3-ethyl-1,2,4-triazole-5-one-4-yl] butane, (I), and 3-n-propyl-4-hydroxy-1,2,4-triazole-5-one, (II).

Views of compounds (I) and (II), including the atom-numbering schemes, are shown in Figs. 1 and 2. Compound (I) consists of two 1,2,4-triazole rings, with ethyl groups connected to the 3-positions of the rings, carbonyl O atoms in the 5-positons of the rings and a butane group connecting the two rings at the 4-positions. Compound (II) consists of a 1,2,4-triazole ring with an n-propyl group connected to the 3-position of the ring, a carbonyl O atom on the 5-position of the ring and a hydroxy group on the 4-position of the ring.

In the crystal structure of (I), a strong intermolecular N1—H1···O1(x − 1/2, y, 1/2 − z) hydrogen-bonding interaction is formed. Also, (I) exhibits a weak ππ stacking interaction between the 1,2,4-triazole moieties, with a centroid–centroid distance of 3.917 (3) Å [Cg···Cg(1 − x, −y, −z)]. The crystal structure of (II) is formed by intermolecular hydrogen-bonding interactions of O1—H1···O1(−x, y, 3/2 − z) and N1—H2···O2(−x, 1 − y, 1 − z). These bonds are consistent with the previous report by Li et al. (2004).

Experimental top

For the synthesis of (I), ethylpropiyonatethoxycarbonylhydrazon (0.02 mol) was treated with a solution of 1,4-diaminobutane (0.01 mol) in water (50 ml), and the mixture was refluxed for 6 h. After cooling, the precipitate formed was recrystallized from ethanol–acetone (1:5) (yield 58%; m.p. 550–551 K). IR: 3155, 3053 (NH), 1675 (CO), 1563 (CN); 1H NMR: 1.63 (m, 2CH2), 1.85 (s, 2CH3), 2.54 (q, 2CH2), 3.70 (t, 2NCH2), 11.35 (s, 2NH). 13C NMR: 13.04 (2CH3), 18.67 (2CH2), 22.86 (2CH2), 38.98 (2NCH2), 149.51 (2 C3-triazol), 152.47 (2 C5-triazol). For the synthesis of (II), hydroxyamic acid n-propylethoxycarbonylhydrazid (0.01 mol) was dissolved in methanol (50 ml) and treated with 2 N NaOH (50 ml) with constant shaking·The mixture was refluxed for 2 h and cooled. After acidification with dilute HCl, the mixture was evaporated and the residue was dried. The solid residue was extracted with absolute ethanol. The extracts were collected and evaporated. Recrystallization of the crude product from acetone gave pure compound (II) (yield 72%; m.p. 406–407 K). IR 3310 (OH), 3150 (NH), 1735 (CO), 1652 (CN); 1H NMR: 0.85 (t, CH3), 1.56 (sext, CH2), 2.42 (t, CH2), 10.90 (s, OH); 11.35 (s, NH). 13C NMR: 13.35 (CH3), 18.71 (CH2), 25.98 (CH2), 145.65 (C3-triazol), 151.60 (C5-triazol).

Refinement top

H atoms were located geometrically and treated using a riding model, fixing the C—H distances to 0.97 (CH2 H atoms) and 0.96 Å (CH3 H atoms).

Computing details top

For both compounds, data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The molecule of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
[Figure 2] Fig. 2. The molecule of (II), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
(I) 1,4-Bis(3-ethyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-4-yl)butane top
Crystal data top
C12H20N6O2F(000) = 600
Mr = 280.34Dx = 1.327 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 8578 reflections
a = 8.326 (5) Åθ = 1.5–27.1°
b = 13.588 (5) ŵ = 0.10 mm1
c = 12.401 (5) ÅT = 293 K
V = 1403.0 (11) Å3Plate, colourless
Z = 40.80 × 0.54 × 0.22 mm
Data collection top
Stoe IPDS-II
diffractometer
1379 independent reflections
Radiation source: fine-focus sealed tube832 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.073
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 3.0°
ω scansh = 109
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 1616
Tmin = 0.951, Tmax = 0.992l = 1515
11694 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033H-atom parameters constrained
wR(F2) = 0.072 w = 1/[σ2(Fo2) + (0.0366P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.80(Δ/σ)max < 0.001
1379 reflectionsΔρmax = 0.16 e Å3
92 parametersΔρmin = 0.14 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0078 (9)
Crystal data top
C12H20N6O2V = 1403.0 (11) Å3
Mr = 280.34Z = 4
Orthorhombic, PbcaMo Kα radiation
a = 8.326 (5) ŵ = 0.10 mm1
b = 13.588 (5) ÅT = 293 K
c = 12.401 (5) Å0.80 × 0.54 × 0.22 mm
Data collection top
Stoe IPDS-II
diffractometer
1379 independent reflections
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
832 reflections with I > 2σ(I)
Tmin = 0.951, Tmax = 0.992Rint = 0.073
11694 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0330 restraints
wR(F2) = 0.072H-atom parameters constrained
S = 0.80Δρmax = 0.16 e Å3
1379 reflectionsΔρmin = 0.14 e Å3
92 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
C10.0259 (2)0.34133 (14)0.20400 (15)0.0610 (5)
H1A0.00710.32720.27650.091*
H1B0.07630.40480.20170.091*
H1C0.10060.29210.18020.091*
C20.1195 (2)0.34121 (15)0.13081 (13)0.0533 (5)
H2A0.17120.27740.13510.064*
H2B0.19550.39000.15660.064*
C30.08065 (17)0.36255 (11)0.01620 (12)0.0367 (4)
C50.11917 (16)0.39328 (12)0.15743 (12)0.0358 (4)
C60.36861 (16)0.39091 (12)0.04444 (12)0.0378 (4)
H6A0.40480.34470.01000.045*
H6B0.42470.37590.11100.045*
C70.41065 (16)0.49417 (12)0.00939 (13)0.0404 (4)
H7A0.37630.54030.06440.049*
H7B0.35340.50960.05660.049*
N10.03704 (13)0.38486 (10)0.13268 (10)0.0415 (3)
H10.11320.39090.17900.050*
N20.06240 (14)0.36536 (10)0.02443 (10)0.0423 (4)
N40.19611 (13)0.37842 (9)0.06105 (9)0.0337 (3)
O10.18120 (12)0.40998 (8)0.24644 (8)0.0507 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0802 (13)0.0610 (11)0.0418 (10)0.0018 (10)0.0164 (9)0.0049 (9)
C20.0521 (10)0.0675 (12)0.0401 (10)0.0019 (9)0.0005 (8)0.0108 (9)
C30.0341 (8)0.0391 (9)0.0370 (9)0.0029 (7)0.0022 (7)0.0001 (7)
C50.0309 (7)0.0416 (9)0.0349 (8)0.0013 (7)0.0017 (7)0.0051 (7)
C60.0276 (7)0.0474 (10)0.0383 (8)0.0011 (7)0.0030 (6)0.0049 (7)
C70.0303 (8)0.0454 (9)0.0455 (9)0.0004 (7)0.0024 (7)0.0054 (7)
N10.0302 (7)0.0611 (9)0.0332 (7)0.0020 (6)0.0038 (5)0.0012 (7)
N20.0343 (7)0.0527 (9)0.0399 (8)0.0049 (6)0.0027 (6)0.0032 (6)
N40.0266 (6)0.0419 (7)0.0326 (7)0.0031 (5)0.0013 (5)0.0021 (6)
O10.0397 (6)0.0802 (9)0.0322 (6)0.0013 (6)0.0050 (5)0.0006 (6)
Geometric parameters (Å, º) top
C1—C21.513 (2)C5—N41.3710 (19)
C1—H1A0.9600C6—N41.4608 (19)
C1—H1B0.9600C6—C71.510 (2)
C1—H1C0.9600C6—H6A0.9700
C2—C31.486 (2)C6—H6B0.9700
C2—H2A0.9700C7—C7i1.514 (3)
C2—H2B0.9700C7—H7A0.9700
C3—N21.2938 (19)C7—H7B0.9700
C3—N41.3742 (18)N1—N21.3846 (18)
C5—O11.2396 (18)N1—H10.8600
C5—N11.341 (2)
C2—C1—H1A109.5N4—C6—H6A109.2
C2—C1—H1B109.5C7—C6—H6A109.2
H1A—C1—H1B109.5N4—C6—H6B109.2
C2—C1—H1C109.5C7—C6—H6B109.2
H1A—C1—H1C109.5H6A—C6—H6B107.9
H1B—C1—H1C109.5C6—C7—C7i111.67 (16)
C3—C2—C1113.52 (14)C6—C7—H7A109.3
C3—C2—H2A108.9C7i—C7—H7A109.3
C1—C2—H2A108.9C6—C7—H7B109.3
C3—C2—H2B108.9C7i—C7—H7B109.3
C1—C2—H2B108.9H7A—C7—H7B107.9
H2A—C2—H2B107.7C5—N1—N2112.71 (12)
N2—C3—N4111.59 (13)C5—N1—H1123.6
N2—C3—C2125.36 (14)N2—N1—H1123.6
N4—C3—C2123.01 (13)C3—N2—N1104.05 (11)
O1—C5—N1128.56 (13)C5—N4—C3107.70 (12)
O1—C5—N4127.48 (13)C5—N4—C6124.42 (12)
N1—C5—N4103.95 (12)C3—N4—C6127.43 (12)
N4—C6—C7112.11 (13)
C1—C2—C3—N211.0 (2)N1—C5—N4—C30.39 (16)
C1—C2—C3—N4171.44 (15)O1—C5—N4—C67.3 (2)
N4—C6—C7—C7i179.05 (16)N1—C5—N4—C6173.08 (14)
O1—C5—N1—N2179.67 (16)N2—C3—N4—C50.62 (18)
N4—C5—N1—N20.06 (17)C2—C3—N4—C5178.47 (15)
N4—C3—N2—N10.55 (18)N2—C3—N4—C6173.03 (14)
C2—C3—N2—N1178.34 (15)C2—C3—N4—C69.1 (2)
C5—N1—N2—C30.30 (18)C7—C6—N4—C590.72 (17)
O1—C5—N4—C3180.00 (16)C7—C6—N4—C380.50 (19)
Symmetry code: (i) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1ii0.861.962.805 (2)166 (1)
Symmetry code: (ii) x1/2, y, z+1/2.
(II) 4-hydroxy-3-n-propyl-4,5-dihydro-1H-1,2,4-triazol-5-one top
Crystal data top
C5H9N3O2F(000) = 608
Mr = 143.15Dx = 1.383 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 5155 reflections
a = 27.010 (3) Åθ = 1.5–26.7°
b = 4.2067 (3) ŵ = 0.11 mm1
c = 12.1089 (14) ÅT = 293 K
β = 91.715 (9)°Prism, colourless
V = 1375.2 (2) Å30.50 × 0.35 × 0.22 mm
Z = 8
Data collection top
Stoe IPDS-II
diffractometer
1347 independent reflections
Radiation source: fine-focus sealed tube1207 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 1.5°
ω scansh = 3232
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 45
Tmin = 0.946, Tmax = 0.972l = 1414
5874 measured reflections
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)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H atoms treated by a mixture of independent and constrained refinement
S = 1.13 w = 1/[σ2(Fo2) + (0.0541P)2 + 0.2687P]
where P = (Fo2 + 2Fc2)/3
1347 reflections(Δ/σ)max < 0.001
95 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.24 e Å3
Crystal data top
C5H9N3O2V = 1375.2 (2) Å3
Mr = 143.15Z = 8
Monoclinic, C2/cMo Kα radiation
a = 27.010 (3) ŵ = 0.11 mm1
b = 4.2067 (3) ÅT = 293 K
c = 12.1089 (14) Å0.50 × 0.35 × 0.22 mm
β = 91.715 (9)°
Data collection top
Stoe IPDS-II
diffractometer
1347 independent reflections
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
1207 reflections with I > 2σ(I)
Tmin = 0.946, Tmax = 0.972Rint = 0.041
5874 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0350 restraints
wR(F2) = 0.098H atoms treated by a mixture of independent and constrained refinement
S = 1.13Δρmax = 0.16 e Å3
1347 reflectionsΔρmin = 0.24 e Å3
95 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
H10.0420 (6)0.043 (4)0.8054 (14)0.072 (5)*
C10.20467 (6)0.1342 (5)0.88243 (15)0.0754 (5)
H1A0.20070.19310.95880.113*
H1B0.21220.08840.87710.113*
H1C0.23120.25480.84870.113*
C20.15735 (5)0.2019 (4)0.82384 (12)0.0546 (4)
H2A0.13040.08720.86070.065*
H2B0.15000.42710.82960.065*
C30.11474 (4)0.1977 (3)0.64273 (9)0.0397 (3)
C40.15970 (4)0.1083 (3)0.70247 (11)0.0473 (3)
H4A0.16440.11980.69690.057*
H4B0.18820.20970.66700.057*
C50.03456 (4)0.2233 (3)0.60332 (9)0.0377 (3)
N10.06250 (4)0.4103 (3)0.53765 (8)0.0435 (3)
H20.05080.52500.48570.052*
N20.11232 (4)0.4000 (3)0.56215 (8)0.0452 (3)
N40.06835 (3)0.0842 (2)0.66942 (7)0.0372 (3)
O10.05747 (3)0.1542 (2)0.74336 (7)0.0431 (3)
O20.01132 (3)0.1830 (2)0.60593 (7)0.0449 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0611 (9)0.0942 (13)0.0723 (10)0.0027 (9)0.0246 (8)0.0037 (9)
C20.0507 (7)0.0631 (8)0.0505 (7)0.0017 (6)0.0097 (6)0.0012 (6)
C30.0385 (6)0.0427 (6)0.0376 (6)0.0024 (5)0.0018 (4)0.0043 (5)
C40.0382 (6)0.0519 (7)0.0516 (7)0.0012 (5)0.0005 (5)0.0004 (6)
C50.0409 (6)0.0414 (6)0.0306 (5)0.0024 (5)0.0010 (4)0.0036 (4)
N10.0431 (5)0.0516 (6)0.0360 (5)0.0055 (4)0.0046 (4)0.0061 (4)
N20.0421 (5)0.0525 (6)0.0410 (5)0.0071 (4)0.0006 (4)0.0015 (5)
N40.0386 (5)0.0381 (5)0.0348 (5)0.0009 (4)0.0010 (4)0.0014 (4)
O10.0475 (5)0.0385 (5)0.0429 (5)0.0023 (3)0.0054 (4)0.0054 (4)
O20.0389 (5)0.0564 (5)0.0394 (5)0.0040 (4)0.0033 (3)0.0040 (4)
Geometric parameters (Å, º) top
C1—C21.5073 (19)C4—H4A0.9700
C1—H1A0.9600C4—H4B0.9700
C1—H1B0.9600C5—O21.2502 (14)
C1—H1C0.9600C5—N11.3359 (15)
C2—C41.5210 (19)C5—N41.3637 (15)
C2—H2A0.9700N1—N21.3873 (14)
C2—H2B0.9700N1—H20.8600
C3—N21.2978 (16)N4—O11.3706 (12)
C3—N41.3702 (15)O1—H10.970 (19)
C3—C41.4806 (16)
C2—C1—H1A109.5C3—C4—H4A108.9
C2—C1—H1B109.5C2—C4—H4A108.9
H1A—C1—H1B109.5C3—C4—H4B108.9
C2—C1—H1C109.5C2—C4—H4B108.9
H1A—C1—H1C109.5H4A—C4—H4B107.7
H1B—C1—H1C109.5O2—C5—N1129.55 (11)
C1—C2—C4113.23 (13)O2—C5—N4127.39 (11)
C1—C2—H2A108.9N1—C5—N4103.06 (10)
C4—C2—H2A108.9C5—N1—N2112.86 (10)
C1—C2—H2B108.9C5—N1—H2123.6
C4—C2—H2B108.9N2—N1—H2123.6
H2A—C2—H2B107.7C3—N2—N1104.61 (9)
N2—C3—N4109.85 (10)C5—N4—C3109.59 (10)
N2—C3—C4126.46 (11)C5—N4—O1124.28 (9)
N4—C3—C4123.63 (11)C3—N4—O1125.85 (10)
C3—C4—C2113.28 (10)N4—O1—H1103.3 (11)
N2—C3—C4—C2115.71 (14)O2—C5—N4—C3178.17 (11)
N4—C3—C4—C261.24 (17)N1—C5—N4—C31.36 (12)
C1—C2—C4—C3175.46 (13)O2—C5—N4—O17.53 (18)
O2—C5—N1—N2177.87 (12)N1—C5—N4—O1172.94 (9)
N4—C5—N1—N21.65 (13)N2—C3—N4—C50.63 (14)
N4—C3—N2—N10.37 (13)C4—C3—N4—C5176.75 (10)
C4—C3—N2—N1177.67 (11)N2—C3—N4—O1173.55 (10)
C5—N1—N2—C31.32 (13)C4—C3—N4—O19.06 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.970 (19)1.640 (17)2.6000 (12)170.2 (15)
N1—H2···O2ii0.861.992.8292 (13)166
Symmetry codes: (i) x, y, z+3/2; (ii) x, y+1, z+1.

Experimental details

(I)(II)
Crystal data
Chemical formulaC12H20N6O2C5H9N3O2
Mr280.34143.15
Crystal system, space groupOrthorhombic, PbcaMonoclinic, C2/c
Temperature (K)293293
a, b, c (Å)8.326 (5), 13.588 (5), 12.401 (5)27.010 (3), 4.2067 (3), 12.1089 (14)
α, β, γ (°)90.000 (5), 90.000 (5), 90.000 (5)90, 91.715 (9), 90
V3)1403.0 (11)1375.2 (2)
Z48
Radiation typeMo KαMo Kα
µ (mm1)0.100.11
Crystal size (mm)0.80 × 0.54 × 0.220.50 × 0.35 × 0.22
Data collection
DiffractometerStoe IPDS-II
diffractometer
Stoe IPDS-II
diffractometer
Absorption correctionIntegration
(X-RED32; Stoe & Cie, 2002)
Integration
(X-RED32; Stoe & Cie, 2002)
Tmin, Tmax0.951, 0.9920.946, 0.972
No. of measured, independent and
observed [I > 2σ(I)] reflections
11694, 1379, 832 5874, 1347, 1207
Rint0.0730.041
(sin θ/λ)max1)0.6170.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.072, 0.80 0.035, 0.098, 1.13
No. of reflections13791347
No. of parameters9295
H-atom treatmentH-atom parameters constrainedH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.16, 0.140.16, 0.24

Computer programs: X-AREA (Stoe & Cie, 2002), X-AREA, X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) for (I) top
C3—N21.2938 (19)C5—N41.3710 (19)
C3—N41.3742 (18)C7—C7i1.514 (3)
C5—O11.2396 (18)N1—N21.3846 (18)
C5—N11.341 (2)
N4—C6—C7—C7i179.05 (16)
Symmetry code: (i) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1ii0.861.962.805 (2)166.11 (8)
Symmetry code: (ii) x1/2, y, z+1/2.
Selected bond lengths (Å) for (II) top
C3—N21.2978 (16)C5—N41.3637 (15)
C3—N41.3702 (15)N1—N21.3873 (14)
C5—O21.2502 (14)N4—O11.3706 (12)
C5—N11.3359 (15)
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.970 (19)1.640 (17)2.6000 (12)170.2 (15)
N1—H2···O2ii0.861.992.8292 (13)166
Symmetry codes: (i) x, y, z+3/2; (ii) x, y+1, z+1.
 

Subscribe to Acta Crystallographica Section C: Structural Chemistry

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds