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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1388.
Published online 2008 July 5. doi:  10.1107/S1600536808019661
PMCID: PMC2962021

4-n-Butyl-3-(3-methyl­phen­yl)-1H-1,2,4-triazol-5(4H)-one

Abstract

In the mol­ecule of the title compound, C13H17N3O, the two rings make a dihedral angle of 56.63 (13)°. Mol­ecules are linked by strong N—H(...)O inter­molecular hydrogen bonds into chains running along the c axis.

Related literature

For related literature, see: Akhtar et al. (2006 [triangle], 2007 [triangle], 2008 [triangle]); Aoyama et al. (1984 [triangle]); Al-Masoudi et al. (2006 [triangle]); Demirbas et al. (2002 [triangle]); Lin et al. (2005 [triangle]); Torres et al. (2005 [triangle]); Witkowski et al. (1972 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1388-scheme1.jpg

Experimental

Crystal data

  • C13H17N3O
  • M r = 231.30
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1388-efi1.jpg
  • a = 16.905 (5) Å
  • b = 18.139 (5) Å
  • c = 8.145 (2) Å
  • V = 2497.5 (11) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 296 (2) K
  • 0.26 × 0.19 × 0.12 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: none
  • 8129 measured reflections
  • 1791 independent reflections
  • 1118 reflections with I > 2σ(I)
  • R int = 0.066

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.106
  • S = 1.07
  • 1791 reflections
  • 160 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.15 e Å−3
  • Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]) and PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]) and PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808019661/bt2734sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019661/bt2734Isup2.hkl

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

Acknowledgments

The authors are grateful to the Higher Education Commission of Pakistan for a grant to purchase the diffractometer.

supplementary crystallographic information

Comment

1,2,4-Triazoles are known to possess a broad range of biological activities, finding applications as antifungal (Al-Masoudi et al., 2006; Torres et al., 2005), anticancer (Lin et al., 2005; Demirbas et al., 2002) and antiviral (Witkowski et al., 1972; Aoyama et al.,1984) activities. Besides, these derivatives have shown herbicidal, anticonvulsant and hypocholesteramic activities.

As part of our on going research on the synthesis of biologically active heterocyclic compounds (Akhtar et al., 2006, 2007, 2008), the title compound (I) was synthesized by cyclodehydration of 4-n-butyl-1-(3-methylbenzoyl) semicarbazide under basic conditions (Akhtar et al., 2006) to evaluate its biological activities.

The two rings enclose a dihedral angle of 56.63 (13)°. There is an intermolecular N—H···O=C hydrogen bond between the amino hydrogen and the carbonyl oxygen giving rise to a zigzag chain of molecules parallel to the c axis (Fig. 2).

Experimental

A solution of 4-n-butyl-1-(3-methylbenzoyl) semicarbazide (0.30 g) and aqueous sodium hydroxide (5%, 30 ml) was refluxed for a period of five hours till the complete consumption of semicarbazide. The reaction mixture was cooled to room temperature and neutralized with 6M HCl. The precipitated solid was filtered, washed with excess water, dried and recrystallized from aqueous ethanol to afford pure crystalline 4-n-butyl-5-(3-methyl phenyl)-2H-1,2,4-triazol-3(4H)-one.

Refinement

In the absence of anomalous scatterers Friedel pairs were merged. H atoms bonded were included in the refinements at geometrically idealized positions with aromatic and methyl C—H distances 0.95 and 0.96Å, respectively, and Uiso(H) values of 1.2Ueq of the atoms to which they were bonded. The methyl groups were allowed to rotate but not to tip. The H atom bonded to N was freely refined. The final difference map was free of any chemically significant features.

Figures

Fig. 1.
The asymmetric unit of the title compound showing the intramolecular hydrogen bond. Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
Perspective view of the three-dimensional crystal packing showing hydrogen-bonds and other intermolecular interactions (dashed lines). H atoms not involved in hydrogen bonding have been omitted for clarity.

Crystal data

C13H17N3OF000 = 992
Mr = 231.30Dx = 1.230 Mg m3
Orthorhombic, Ccc2Mo Kα radiation λ = 0.71073 Å
Hall symbol: C 2 -2cCell parameters from 1751 reflections
a = 16.905 (5) Åθ = 3.0–22.2º
b = 18.139 (5) ŵ = 0.08 mm1
c = 8.145 (2) ÅT = 296 (2) K
V = 2497.5 (11) Å3Orthorhombic, white
Z = 80.26 × 0.19 × 0.12 mm

Data collection

Bruker APEXII CCD area-detector diffractometer1791 independent reflections
Radiation source: fine-focus sealed tube1118 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.066
Detector resolution: 7.40 pixels mm-1θmax = 29.2º
T = 296(2) Kθmin = 2.4º
[var phi] and ω scansh = −20→23
Absorption correction: nonek = −23→24
8129 measured reflectionsl = −11→7

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.106  w = 1/[σ2(Fo2) + (0.0435P)2] where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
1791 reflectionsΔρmax = 0.15 e Å3
160 parametersΔρmin = −0.25 e Å3
1 restraintExtinction correction: none
Primary atom site location: structure-invariant direct methods

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 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)

xyzUiso*/Ueq
N10.09066 (14)0.37056 (10)0.2364 (3)0.0349 (5)
N20.08503 (15)0.41720 (12)−0.0051 (3)0.0407 (6)
N30.08408 (14)0.34149 (11)−0.0273 (3)0.0412 (6)
O10.09681 (11)0.49894 (11)0.2110 (2)0.0500 (6)
C10.08634 (17)0.23582 (14)0.1565 (3)0.0350 (6)
C20.02844 (17)0.20574 (14)0.2574 (4)0.0449 (8)
H2−0.00900.23590.30720.054*
C30.0272 (2)0.13041 (15)0.2829 (4)0.0531 (9)
H3−0.01110.11000.35100.064*
C40.08179 (19)0.08554 (16)0.2092 (4)0.0501 (8)
H40.07910.03490.22570.060*
C50.14059 (18)0.11403 (14)0.1111 (4)0.0423 (7)
C60.14204 (17)0.18975 (14)0.0851 (3)0.0389 (7)
H60.18110.20990.01850.047*
C70.08757 (16)0.31523 (14)0.1205 (3)0.0355 (6)
C80.09113 (17)0.43677 (14)0.1525 (3)0.0360 (6)
C90.11284 (18)0.36397 (14)0.4094 (3)0.0385 (7)
H9A0.09020.31920.45460.046*
H9B0.09160.40550.47010.046*
C100.20182 (18)0.36205 (16)0.4290 (4)0.0475 (7)
H10A0.22230.32020.36830.057*
H10B0.22390.40630.38030.057*
C110.22993 (18)0.35668 (17)0.6045 (4)0.0499 (8)
H11A0.20640.31370.65570.060*
H11B0.21250.39990.66460.060*
C120.2024 (2)0.06501 (17)0.0313 (5)0.0615 (10)
H13A0.22450.03250.11230.092*
H13B0.24360.0951−0.01450.092*
H13C0.17820.0364−0.05430.092*
H220.0837 (17)0.4487 (16)−0.097 (4)0.060 (10)*
C130.31893 (19)0.35095 (19)0.6144 (5)0.0622 (9)
H13D0.33660.30980.55000.093*
H13E0.33450.34400.72670.093*
H13F0.34230.39550.57300.093*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0461 (15)0.0309 (11)0.0277 (12)−0.0011 (10)−0.0020 (12)−0.0027 (9)
N20.0577 (17)0.0319 (12)0.0325 (14)−0.0033 (11)−0.0061 (12)0.0009 (10)
N30.0553 (15)0.0328 (12)0.0356 (14)−0.0028 (10)−0.0050 (12)−0.0019 (11)
O10.0770 (15)0.0307 (9)0.0422 (12)−0.0055 (11)−0.0009 (11)−0.0052 (9)
C10.0398 (16)0.0312 (13)0.0341 (15)−0.0004 (12)−0.0074 (13)−0.0035 (12)
C20.047 (2)0.0412 (15)0.0464 (18)−0.0008 (12)0.0070 (15)−0.0014 (14)
C30.056 (2)0.0449 (16)0.058 (2)−0.0091 (15)0.0099 (16)0.0072 (15)
C40.063 (2)0.0333 (14)0.054 (2)−0.0028 (14)−0.0098 (18)0.0041 (15)
C50.0478 (18)0.0347 (14)0.0444 (17)0.0043 (13)−0.0105 (16)−0.0025 (14)
C60.0432 (17)0.0385 (15)0.0350 (16)−0.0024 (12)−0.0011 (13)−0.0017 (13)
C70.0373 (16)0.0332 (13)0.0361 (16)−0.0021 (11)−0.0073 (14)−0.0013 (11)
C80.0434 (17)0.0343 (14)0.0303 (15)−0.0015 (12)−0.0013 (13)−0.0029 (12)
C90.0486 (19)0.0365 (14)0.0303 (15)−0.0052 (12)0.0002 (13)−0.0013 (12)
C100.052 (2)0.0548 (17)0.0358 (16)−0.0006 (14)−0.0003 (15)−0.0009 (13)
C110.057 (2)0.0537 (18)0.0393 (17)0.0043 (15)−0.0044 (16)0.0027 (14)
C120.068 (3)0.0503 (18)0.066 (2)0.0181 (17)−0.0004 (19)−0.0076 (17)
C130.059 (2)0.069 (2)0.059 (2)0.0085 (17)−0.012 (2)−0.0021 (18)

Geometric parameters (Å, °)

N1—C71.379 (3)C5—C121.518 (4)
N1—C81.382 (3)C6—H60.9300
N1—C91.463 (3)C9—C101.513 (4)
N2—C81.336 (4)C9—H9A0.9700
N2—N31.385 (3)C9—H9B0.9700
N2—H220.94 (3)C10—C111.509 (4)
N3—C71.296 (3)C10—H10A0.9700
O1—C81.228 (3)C10—H10B0.9700
C1—C61.387 (4)C11—C131.510 (4)
C1—C21.390 (4)C11—H11A0.9700
C1—C71.470 (4)C11—H11B0.9700
C2—C31.382 (3)C12—H13A0.9600
C2—H20.9300C12—H13B0.9600
C3—C41.369 (4)C12—H13C0.9600
C3—H30.9300C13—H13D0.9600
C4—C51.376 (4)C13—H13E0.9600
C4—H40.9300C13—H13F0.9600
C5—C61.390 (4)
C7—N1—C8107.1 (2)N1—C9—C10111.0 (2)
C7—N1—C9127.6 (2)N1—C9—H9A109.4
C8—N1—C9123.1 (2)C10—C9—H9A109.4
C8—N2—N3113.0 (2)N1—C9—H9B109.4
C8—N2—H22127.2 (19)C10—C9—H9B109.4
N3—N2—H22119.8 (19)H9A—C9—H9B108.0
C7—N3—N2104.0 (2)C11—C10—C9114.5 (3)
C6—C1—C2119.3 (2)C11—C10—H10A108.6
C6—C1—C7119.8 (3)C9—C10—H10A108.6
C2—C1—C7120.8 (3)C11—C10—H10B108.6
C3—C2—C1119.2 (3)C9—C10—H10B108.6
C3—C2—H2120.4H10A—C10—H10B107.6
C1—C2—H2120.4C10—C11—C13111.7 (3)
C4—C3—C2120.8 (3)C10—C11—H11A109.3
C4—C3—H3119.6C13—C11—H11A109.3
C2—C3—H3119.6C10—C11—H11B109.3
C3—C4—C5121.2 (3)C13—C11—H11B109.3
C3—C4—H4119.4H11A—C11—H11B108.0
C5—C4—H4119.4C5—C12—H13A109.5
C4—C5—C6118.2 (3)C5—C12—H13B109.5
C4—C5—C12121.7 (3)H13A—C12—H13B109.5
C6—C5—C12120.1 (3)C5—C12—H13C109.5
C5—C6—C1121.3 (3)H13A—C12—H13C109.5
C5—C6—H6119.3H13B—C12—H13C109.5
C1—C6—H6119.3C11—C13—H13D109.5
N3—C7—N1111.7 (2)C11—C13—H13E109.5
N3—C7—C1123.0 (2)H13D—C13—H13E109.5
N1—C7—C1125.2 (2)C11—C13—H13F109.5
O1—C8—N2128.5 (3)H13D—C13—H13F109.5
O1—C8—N1127.4 (2)H13E—C13—H13F109.5
N2—C8—N1104.1 (2)
C8—N2—N3—C71.7 (3)C9—N1—C7—C116.6 (4)
C6—C1—C2—C3−0.6 (4)C6—C1—C7—N355.9 (4)
C7—C1—C2—C3177.3 (3)C2—C1—C7—N3−122.1 (3)
C1—C2—C3—C4−0.5 (5)C6—C1—C7—N1−125.7 (3)
C2—C3—C4—C51.7 (5)C2—C1—C7—N156.4 (4)
C3—C4—C5—C6−1.6 (5)N3—N2—C8—O1176.6 (3)
C3—C4—C5—C12178.8 (3)N3—N2—C8—N1−2.6 (3)
C4—C5—C6—C10.5 (4)C7—N1—C8—O1−176.8 (3)
C12—C5—C6—C1−179.9 (3)C9—N1—C8—O1−12.7 (5)
C2—C1—C6—C50.7 (4)C7—N1—C8—N22.5 (3)
C7—C1—C6—C5−177.3 (3)C9—N1—C8—N2166.6 (3)
N2—N3—C7—N10.0 (3)C7—N1—C9—C1080.2 (3)
N2—N3—C7—C1178.7 (3)C8—N1—C9—C10−80.5 (3)
C8—N1—C7—N3−1.6 (3)N1—C9—C10—C11178.9 (2)
C9—N1—C7—N3−164.8 (3)C9—C10—C11—C13177.0 (2)
C8—N1—C7—C1179.8 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H22···O1i0.94 (3)1.84 (3)2.775 (3)170 (3)

Symmetry codes: (i) x, −y+1, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2734).

References

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