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Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): o1978.
Published online 2010 July 10. doi:  10.1107/S160053681002653X
PMCID: PMC3007452

1-(4-Meth­oxy­phen­yl)-2-(1H-1,2,4-triazol-1-yl)ethanone

Abstract

In the title compound, C11H11N3O2, the dihedral angle between the central ethanone fragment and the 4-meth­oxy­phenyl group is 2.9 (2)°, while that between the ethanone fragment and the triazole ring is 83.4 (2)°. The dihedral angle between the planes of the triazole and benzene rings is 81.7 (1)°. The 4-meth­oxy­phenyl group is cis with respect to the ethanone fragment O atom across the exocyclic C—C bond. In the crystal, mol­ecules are linked by C—H(...)N inter­actions into C(9) chains along [001].

Related literature

For the biological activity of fungal infections, see: Wingard & Leather (2004 [triangle]); Lamb et al. (1999 [triangle]). For the synthesis, see: Emami et al. (2008 [triangle]); Upadhayaya et al. (2009 [triangle]); Schiaffella et al. (2005 [triangle]); Dawood et al. (2006 [triangle]). For hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1978-scheme1.jpg

Experimental

Crystal data

  • C11H11N3O2
  • M r = 217.23
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1978-efi1.jpg
  • a = 23.409 (3) Å
  • b = 4.8347 (7) Å
  • c = 20.607 (2) Å
  • β = 116.275 (8)°
  • V = 2091.2 (5) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 173 K
  • 0.29 × 0.25 × 0.21 mm

Data collection

  • Stoe IPDS II two-circle diffractometer
  • 4675 measured reflections
  • 1944 independent reflections
  • 1260 reflections with I > 2σ(I)
  • R int = 0.053

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.101
  • S = 0.89
  • 1944 reflections
  • 147 parameters
  • H-atom parameters constrained
  • Δρmax = 0.16 e Å−3
  • Δρmin = −0.16 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 [triangle]); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: XP (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681002653X/fl2306sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681002653X/fl2306Isup2.hkl

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

Acknowledgments

We thank the Spanish Research Council (CSIC) for providing us with a free-of-charge license for the CSD system. MP-F thanks the Universidad de Antofagasta for PhD fellowships.

supplementary crystallographic information

Comment

Fungal infections caused by pathogenic species, often characterized by high mortality rates, has been increasing over the past two decades. In the treatment of fungal infections the number of efficacious antifungal drugs is limited (Wingard & Leather, 2004). Many of the currently available drugs are toxic, produce recurrence because they are fungistatic and not fungicides or lead to the development of resistance due in part to the prolonged periods of administration of the available antifungal drugs (Lamb et al., 1999). In order to seek new antifungal agents we are preparing a series of substituted triazoles, fluconazole analogues (Emami et al., 2008).

In this article we report the synthesis and crystal structure of the titl compound, (I). In (I), Fig. 1, the dihedral angle between the central OCC ethanone fragment and the o-methoxyphenyl group is 2.9 (2)°, while that with group triazole is 83.4 (2)°. The dihedral angle between the plane of triazole and benzene ring is 81.7 (1)°. The o-methoxyphenyl group is cis with respect to the ethanone fragment O atom across the C11—C1 bond. In the crystal molecules are linked by C—H···N interactions into chains with graph-set notation C(9) along [001] (Bernstein et al., 1995), Table 1, Fig. 2.

Experimental

Compound (II), was synthesized as described by Upadhayaya, et al., (2009). Compound (I) was synthesized from (II) as described by Schiaffella et al., (2005) and Dawood et al., (2006) as shown in scheme 1. Recrystallization of (I) from methanol/chloroform (9/1) at room temperature afforded colourless crystals suitable for X-ray diffraction analysis.

Refinement

All H atoms could be located by difference Fourier synthesis but were ultimately placed in calculated positions using a riding model with C—H(aromatic) = 0.95 Å, CH(methylene) = 0.99 Å and CH(methyl) = 0.98 Å with fixed individual displacement parameters [Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(Cmethyl)].

Figures

Fig. 1.
Perspective view of (I) with the atom numbering; displacement ellipsoids are at the 50% probability level (arbitrary spheres for the H atoms).
Fig. 2.
Packing diagram for (I) showing the formation of a C(9) chain along [001]. Hydrogen bond shown as dashed lines.
Fig. 3.
The formation of the title compound.

Crystal data

C11H11N3O2F(000) = 912
Mr = 217.23Dx = 1.380 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3087 reflections
a = 23.409 (3) Åθ = 3.6–25.9°
b = 4.8347 (7) ŵ = 0.10 mm1
c = 20.607 (2) ÅT = 173 K
β = 116.275 (8)°Block, colourless
V = 2091.2 (5) Å30.29 × 0.25 × 0.21 mm
Z = 8

Data collection

Stoe IPDS II two-circle diffractometer1260 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.053
graphiteθmax = 25.6°, θmin = 3.5°
ω scansh = −27→28
4675 measured reflectionsk = −5→5
1944 independent reflectionsl = −24→24

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.101w = 1/[σ2(Fo2) + (0.0547P)2] where P = (Fo2 + 2Fc2)/3
S = 0.89(Δ/σ)max < 0.001
1944 reflectionsΔρmax = 0.16 e Å3
147 parametersΔρmin = −0.16 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0060 (8)

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
O10.34820 (7)0.4726 (3)0.43819 (7)0.0493 (4)
C10.37507 (9)0.6336 (4)0.41489 (9)0.0347 (4)
C20.42565 (9)0.8304 (4)0.46522 (9)0.0358 (4)
H2A0.46510.80430.45950.043*
H2B0.41101.02300.45120.043*
N10.43985 (8)0.7900 (3)0.54036 (8)0.0355 (4)
N20.47973 (9)0.5846 (4)0.57991 (8)0.0521 (5)
C30.47828 (12)0.6132 (5)0.64287 (10)0.0512 (6)
H30.50220.49710.68300.061*
N40.44080 (9)0.8176 (4)0.64643 (8)0.0486 (5)
C50.41747 (10)0.9240 (4)0.58069 (10)0.0428 (5)
H50.38871.07530.56440.051*
C110.36082 (8)0.6444 (4)0.33756 (9)0.0307 (4)
C120.31663 (9)0.4624 (4)0.28896 (9)0.0344 (4)
H120.29540.33540.30600.041*
C130.30274 (9)0.4612 (4)0.21646 (9)0.0353 (4)
H130.27240.33510.18410.042*
C140.33387 (9)0.6477 (4)0.19143 (8)0.0335 (4)
C150.37810 (9)0.8315 (4)0.23879 (9)0.0366 (4)
H150.39930.95810.22150.044*
C160.39130 (9)0.8305 (4)0.31086 (9)0.0354 (4)
H160.42150.95770.34300.042*
O170.32364 (7)0.6657 (3)0.12113 (6)0.0433 (4)
C170.28122 (11)0.4693 (5)0.07117 (10)0.0513 (6)
H17A0.29510.28170.08930.077*
H17B0.28150.49180.02400.077*
H17C0.23800.49980.06590.077*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0624 (10)0.0507 (9)0.0465 (8)−0.0140 (8)0.0348 (7)−0.0002 (6)
C10.0380 (10)0.0301 (9)0.0422 (9)0.0052 (9)0.0235 (8)0.0035 (8)
C20.0422 (11)0.0346 (10)0.0345 (9)0.0008 (9)0.0205 (8)0.0003 (7)
N10.0396 (9)0.0362 (9)0.0349 (7)0.0056 (7)0.0202 (7)0.0004 (6)
N20.0676 (13)0.0570 (11)0.0409 (8)0.0258 (10)0.0325 (9)0.0113 (8)
C30.0627 (14)0.0583 (13)0.0397 (10)0.0182 (12)0.0290 (10)0.0059 (10)
N40.0523 (11)0.0584 (11)0.0425 (9)0.0069 (9)0.0278 (8)−0.0072 (8)
C50.0439 (12)0.0443 (12)0.0424 (10)0.0044 (10)0.0210 (9)−0.0097 (9)
C110.0313 (10)0.0272 (9)0.0374 (8)0.0038 (8)0.0187 (8)0.0020 (7)
C120.0342 (10)0.0297 (9)0.0434 (9)−0.0003 (8)0.0209 (8)0.0033 (8)
C130.0334 (10)0.0331 (10)0.0385 (9)−0.0021 (8)0.0151 (8)−0.0028 (7)
C140.0352 (10)0.0330 (10)0.0343 (9)0.0061 (8)0.0172 (8)0.0030 (7)
C150.0419 (11)0.0330 (10)0.0390 (9)−0.0042 (9)0.0214 (8)0.0035 (7)
C160.0380 (11)0.0308 (10)0.0391 (9)−0.0040 (8)0.0187 (8)−0.0010 (7)
O170.0515 (9)0.0453 (8)0.0334 (6)−0.0071 (7)0.0192 (6)−0.0014 (6)
C170.0568 (14)0.0580 (13)0.0361 (9)−0.0122 (11)0.0178 (10)−0.0087 (9)

Geometric parameters (Å, °)

O1—C11.225 (2)C11—C161.403 (2)
C1—C111.477 (2)C12—C131.381 (2)
C1—C21.515 (3)C12—H120.9500
C2—N11.446 (2)C13—C141.394 (2)
C2—H2A0.9900C13—H130.9500
C2—H2B0.9900C14—O171.3624 (19)
N1—C51.330 (2)C14—C151.386 (3)
N1—N21.360 (2)C15—C161.377 (2)
N2—C31.320 (2)C15—H150.9500
C3—N41.345 (3)C16—H160.9500
C3—H30.9500O17—C171.429 (2)
N4—C51.320 (2)C17—H17A0.9800
C5—H50.9500C17—H17B0.9800
C11—C121.389 (3)C17—H17C0.9800
O1—C1—C11122.36 (18)C13—C12—C11121.74 (16)
O1—C1—C2120.80 (15)C13—C12—H12119.1
C11—C1—C2116.83 (14)C11—C12—H12119.1
N1—C2—C1112.82 (14)C12—C13—C14119.11 (17)
N1—C2—H2A109.0C12—C13—H13120.4
C1—C2—H2A109.0C14—C13—H13120.4
N1—C2—H2B109.0O17—C14—C15115.64 (15)
C1—C2—H2B109.0O17—C14—C13124.08 (17)
H2A—C2—H2B107.8C15—C14—C13120.28 (15)
C5—N1—N2109.70 (14)C16—C15—C14119.90 (16)
C5—N1—C2129.47 (17)C16—C15—H15120.0
N2—N1—C2120.79 (14)C14—C15—H15120.0
C3—N2—N1101.70 (15)C15—C16—C11121.00 (18)
N2—C3—N4115.60 (18)C15—C16—H16119.5
N2—C3—H3122.2C11—C16—H16119.5
N4—C3—H3122.2C14—O17—C17117.55 (14)
C5—N4—C3102.33 (15)O17—C17—H17A109.5
N4—C5—N1110.67 (18)O17—C17—H17B109.5
N4—C5—H5124.7H17A—C17—H17B109.5
N1—C5—H5124.7O17—C17—H17C109.5
C12—C11—C16117.97 (15)H17A—C17—H17C109.5
C12—C11—C1119.73 (15)H17B—C17—H17C109.5
C16—C11—C1122.29 (17)
O1—C1—C2—N13.8 (2)C2—C1—C11—C16−1.2 (3)
C11—C1—C2—N1−175.44 (15)C16—C11—C12—C130.2 (3)
C1—C2—N1—C5−96.6 (2)C1—C11—C12—C13−178.68 (17)
C1—C2—N1—N280.8 (2)C11—C12—C13—C140.0 (3)
C5—N1—N2—C3−0.3 (2)C12—C13—C14—O17−179.61 (17)
C2—N1—N2—C3−178.21 (18)C12—C13—C14—C150.0 (3)
N1—N2—C3—N40.3 (3)O17—C14—C15—C16179.50 (17)
N2—C3—N4—C5−0.2 (3)C13—C14—C15—C16−0.1 (3)
C3—N4—C5—N10.0 (2)C14—C15—C16—C110.3 (3)
N2—N1—C5—N40.1 (2)C12—C11—C16—C15−0.4 (3)
C2—N1—C5—N4177.86 (19)C1—C11—C16—C15178.51 (17)
O1—C1—C11—C12−1.6 (3)C15—C14—O17—C17176.40 (18)
C2—C1—C11—C12177.64 (16)C13—C14—O17—C17−4.0 (3)
O1—C1—C11—C16179.50 (18)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C15—H15···N4i0.952.423.336 (3)162

Symmetry codes: (i) x, −y+2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FL2306).

References

  • Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl.34, 1555–1573.
  • Dawood, K. M., Abdel-Gawad, H., Rageb, E. A., Ellitheyc, M. & Mohamed, H. A. (2006). Bioorg. Med. Chem.14, 3672–3680. [PubMed]
  • Emami, S., Foroumadi, A., Falahati, M., Lotfali, E. S., Rajabalian, S., Ebrahimi, S. A., Farahyarc, S. & Shafieeb, A. (2008). Bioorg. Med. Chem. Lett. 18, 141–146. [PubMed]
  • Lamb, D., Kelly, D. & Kelly, S. (1999). Drug Resit. Updat.2, 390–402. [PubMed]
  • Schiaffella, F., Macchiarulo, A., Milanese, L., Vecchiarelli, A. & Fringuelli, R. (2005). J. Med. Chem.48 7658–7666. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Stoe & Cie (2001). X-AREA Stoe & Cie, Darmstadt, Germany.
  • Upadhayaya, R. S., Kulkarni, G. M., Vasireddy, N. R., Vandavasi, J. K., Dixit, S. S., Sharma, V. & Chattopadhyaya, J. (2009). Bioorg. Med. Chem.17, 4681–4692 [PubMed]
  • Wingard, J. R. & Leather, H. (2004). Biol. Blood Marrow Transplant.10, 73–90. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography