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

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ISSN: 2056-9890

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

aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, bApplied Chemistry Research Centre, PCSIR Laboratories Complex, Lahore 54600, Pakistan, and cChemistry Department, Government College University, Lahore, Pakistan
*Correspondence e-mail: tanveerhusari@yahoo.com

(Received 23 June 2008; accepted 27 June 2008; online 5 July 2008)

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[Akhtar, T., Hameed, S., Lu, X., Yasin, K. A. & &Khan, M. H. (2006). Anal. Sci. X-ray Struct. Anal. Online, 22, x307-308.], 2007[Akhtar, T., Hameed, S., Al-Masoudi, N. A. & Khan, K. M. (2007). Heteroatom. Chem. 18, 316-322.], 2008[Akhtar, T., Hameed, S., Al-Masoudi, N. A., Loddo, R. & La Colla, P. (2008). Acta Pharm. 58, 135-149.]); Aoyama et al. (1984[Aoyama, Y., Yoshida, Y. & Sato, R. (1984). J. Biol. Chem. 259, 1661-1666.]); Al-Masoudi et al. (2006[Al-Masoudi, I. A., Al-Soud, Y. A., Al-Salihi, N. J. & Al-Masoudi, N. A. (2006). Chem. Heterocycl. Compd, 42, 1377-1403.]); Demirbas et al. (2002[Demirbas, N., Ugurluoglu, R. & Demirbas, A. (2002). Bioorg. Med. Chem. 10, 3717-3723.]); Lin et al. (2005[Lin, R., Connolly, P. J., Huang, S., Wetter, S. K., Lu, Y., Murray, W. V., Emanuel, S. L., Gruninger, R. H., Fuentes-Pesquera, A. R., Rugg, C. A., Middleton, S. A. & Jolliffe, L. K. (2005). J. Med. Chem. 48, 4208-4211.]); Torres et al. (2005[Torres, H. A., Hachem, R. Y., Chemaly, R. F., Kontoyiannis, D. P. & Raad, I. I. (2005). Lancet Infect. Dis. 5, 775-85.]); Witkowski et al. (1972[Witkowski, J. J., Robin, R. K., Sidwell, R. W. & Simon, L. N. (1972). J. Med. Chem. 15, 1150-1154.]).

[Scheme 1]

Experimental

Crystal data
  • C13H17N3O

  • Mr = 231.30

  • Orthorhombic, C c c 2

  • 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)

  • Rint = 0.066

Refinement
  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H22⋯O1i 0.94 (3) 1.84 (3) 2.775 (3) 170 (3)
Symmetry code: (i) [x, -y+1, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007[Bruker (2007). APEX2, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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.]) and PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON.

Supporting information


Comment top

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).

Related literature top

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

Experimental top

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 top

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.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 (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) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound showing the intramolecular hydrogen bond. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] 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.
4-n-Butyl-3-(3-methylphenyl)-1H-1,2,4-triazol-5(4H)-one top
Crystal data top
C13H17N3OF(000) = 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 = 3.0–22.2°
b = 18.139 (5) ŵ = 0.08 mm1
c = 8.145 (2) ÅT = 296 K
V = 2497.5 (11) Å3Orthorhombic, white
Z = 80.26 × 0.19 × 0.12 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer
1118 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.066
Graphite monochromatorθmax = 29.2°, θmin = 2.4°
Detector resolution: 7.40 pixels mm-1h = 2023
ϕ and ω scansk = 2324
8129 measured reflectionsl = 117
1791 independent 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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0435P)2]
where P = (Fo2 + 2Fc2)/3
1791 reflections(Δ/σ)max < 0.001
160 parametersΔρmax = 0.15 e Å3
1 restraintΔρmin = 0.25 e Å3
Crystal data top
C13H17N3OV = 2497.5 (11) Å3
Mr = 231.30Z = 8
Orthorhombic, Ccc2Mo Kα radiation
a = 16.905 (5) ŵ = 0.08 mm1
b = 18.139 (5) ÅT = 296 K
c = 8.145 (2) Å0.26 × 0.19 × 0.12 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer
1118 reflections with I > 2σ(I)
8129 measured reflectionsRint = 0.066
1791 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0461 restraint
wR(F2) = 0.106H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 0.15 e Å3
1791 reflectionsΔρmin = 0.25 e Å3
160 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
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)
H20.00900.23590.30720.054*
C30.0272 (2)0.13041 (15)0.2829 (4)0.0531 (9)
H30.01110.11000.35100.064*
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*
H13B0.24360.09510.01450.092*
H13C0.17820.03640.05430.092*
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) top
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, º) top
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—C30.6 (4)C6—C1—C7—N355.9 (4)
C7—C1—C2—C3177.3 (3)C2—C1—C7—N3122.1 (3)
C1—C2—C3—C40.5 (5)C6—C1—C7—N1125.7 (3)
C2—C3—C4—C51.7 (5)C2—C1—C7—N156.4 (4)
C3—C4—C5—C61.6 (5)N3—N2—C8—O1176.6 (3)
C3—C4—C5—C12178.8 (3)N3—N2—C8—N12.6 (3)
C4—C5—C6—C10.5 (4)C7—N1—C8—O1176.8 (3)
C12—C5—C6—C1179.9 (3)C9—N1—C8—O112.7 (5)
C2—C1—C6—C50.7 (4)C7—N1—C8—N22.5 (3)
C7—C1—C6—C5177.3 (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—C1080.5 (3)
C8—N1—C7—N31.6 (3)N1—C9—C10—C11178.9 (2)
C9—N1—C7—N3164.8 (3)C9—C10—C11—C13177.0 (2)
C8—N1—C7—C1179.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H22···O1i0.94 (3)1.84 (3)2.775 (3)170 (3)
Symmetry code: (i) x, y+1, z1/2.

Experimental details

Crystal data
Chemical formulaC13H17N3O
Mr231.30
Crystal system, space groupOrthorhombic, Ccc2
Temperature (K)296
a, b, c (Å)16.905 (5), 18.139 (5), 8.145 (2)
V3)2497.5 (11)
Z8
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.26 × 0.19 × 0.12
Data collection
DiffractometerBruker APEXII CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
8129, 1791, 1118
Rint0.066
(sin θ/λ)max1)0.685
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.106, 1.07
No. of reflections1791
No. of parameters160
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.15, 0.25

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003), WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H22···O1i0.94 (3)1.84 (3)2.775 (3)170 (3)
Symmetry code: (i) x, y+1, z1/2.
 

Acknowledgements

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

References

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