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

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ISSN: 2056-9890

1-(2,4-Di­fluoro­phen­yl)-2-(1H-1,2,4-triazol-1-yl)ethanol

aDepartamento de Química, Universidad Católica del Norte, Casilla 1280, Antofagasta, Chile, bDepartamento de Física, Facultad de Ciencias Básicas, Universidad de Antofagasta, Casilla 170, Antofagasta, Chile, and cDepartamento de Química, Facultad de Ciencias Básicas, Universidad de Antofagasta, Casilla 170, Antofagasta, Chile
*Correspondence e-mail: ivanbritob@yahoo.com

(Received 3 May 2012; accepted 7 May 2012; online 16 May 2012)

In the title compound, C10H9F2N3O, the dihedral angle between the mean planes of the triazole and benzene rings is 20.6 (2)°. In the crystal, mol­ecules are linked by strong O—H⋯ N hydrogen bonds into chains with graph-set notation C(9) along [100]. Weak C—H⋯N and C—H⋯F inter­actions are also observed.

Related literature

For phenacyl­azole derivatives, see: Emami et al. (2008[Emami, S., Foroumadi, A., Falahati, M., Lotfali, E., Rajabalian, S., Ebrahimi, S., Farahyar, S. & Shafie, A. (2008). Bioorg. Med. Chem. Lett. 18, 141-146.], 2009[Emami, S., Behdad, M., Foroumadi, A., Falahati, M., Lotfali, E. & Sharifynia, S. (2009). Chem. Biol. Drug Des. 73, 388-395.]). For their biological properties, see: Schiaffella et al. (2005[Schiaffella, F., Macchiarulo, M., Milanese, L., Vecchiarelli, A., Costantino, G., Pietrella, D. & Fringuelli, R. (2005). J. Med. Chem. 48, 7658-7666.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C10H9F2N3O

  • Mr = 225.20

  • Orthorhombic, P 21 21 21

  • a = 5.3770 (11) Å

  • b = 12.598 (3) Å

  • c = 15.601 (3) Å

  • V = 1056.8 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.12 mm−1

  • T = 295 K

  • 0.60 × 0.29 × 0.08 mm

Data collection
  • Nonius KappaCCD area-detector diffractometer

  • 9658 measured reflections

  • 1536 independent reflections

  • 1344 reflections with I > 2σ(I)

  • Rint = 0.081

Refinement
  • R[F2 > 2σ(F2)] = 0.063

  • wR(F2) = 0.149

  • S = 1.16

  • 1536 reflections

  • 146 parameters

  • H-atom parameters constrained

  • Δρmax = 0.16 e Å−3

  • Δρmin = −0.16 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯N3i 0.82 2.01 2.826 (4) 171
C3—H3⋯N2ii 0.93 2.62 3.500 (5) 158
C8—H8B⋯F1iii 0.97 2.45 3.340 (5) 153
C10—H10⋯F2iv 0.93 2.48 3.270 (4) 142
Symmetry codes: (i) [x+{\script{1\over 2}}, -y-{\script{1\over 2}}, -z+1]; (ii) [-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) x-1, y, z; (iv) x, y-1, z.

Data collection: COLLECT (Nonius, 2000[Nonius (2000). COLLECT BV, Delft, The Netherlands.]); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York; Academic Press.]); data reduction: DENZO-SMN; 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: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

Phenacyl azole derivatives (Emami et al., 2008; Emami et al., 2009) are very important due to their antifungal properties (Schiaffella et al., 2005). We report herein on the synthesis and crystal structure of the title compound, a member of this important family of compounds.

In the title molecule, Fig. 1, the dihedral angle between the mean planes of the triazole and benzene rings is 20.6 (2)°.

In the crystal, molecules are linked by strong O—H··· N hydrogen bonds (Fig. 2 and Table 1) into chains propagating along [100] which have a C(9) graph-set notation (Bernstein et al., 1995). There are also weak C-H···N and C-H···F interactions present (Table 1).

Related literature top

For phenacylazole derivatives, see: Emami et al. (2008, 2009). For their biological properties, see: Schiaffella et al. (2005). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

To a stirred solution of 1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone (6.00 g, 26.88 mmol) in methanol (50 ml), sodium borohydride (1.12 g, 29.57 mmol) dissolved in methanol (20 ml), was added drop wise. The reaction mixture was then stirred at room temperature for 30 min. After completion of the reaction, the solvent was removed under vacuum, and 25 ml of cold water was added. Extraction was performed with dichloromethane (3 × 40 ml), and the organic extracts were washed with water (3 × 30 ml). The organic phase was then dried over anhydrous sodium sulfate. After evaporation of the solvent under vacuum, the residue was purified by crystallization in ethanol to provide the title compound as colourless crystals [85% yield; M.p.: 391-393 K].

Refinement top

All of the H atoms could be located in difference Fourier maps. In the final cycles of refinement they were included in calculated positions and treated as riding atoms: O-H = 0.82 Å, C—H = 0.93 and 0.97 Å for CH and CH2 H atoms, respectively, with Uiso(H) = k × Ueq(O,C), where k = 1.5 for the OH H atom, and = 1.2 for other H atoms. In the final cycles of refinement, in the absence of significant anomalous scattering effects, 1126 Friedel pairs were merged and Δf " set to zero.

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of the title molecule, with the atom numbering. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A partial view along the c axis of the crystal packing of the title compound, showing the formation of the O—H··· N hydrogen bonded chain [dashed lines; see Table 1 for details; the H-atoms not involved in hydrogen-bonding have been omitted for clarity]
1-(2,4-Difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanol top
Crystal data top
C10H9F2N3OF(000) = 464
Mr = 225.20Dx = 1.415 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
a = 5.3770 (11) ŵ = 0.12 mm1
b = 12.598 (3) ÅT = 295 K
c = 15.601 (3) ÅPlate, colourless
V = 1056.8 (3) Å30.60 × 0.29 × 0.08 mm
Z = 4
Data collection top
Nonius KappaCCD area-detector
diffractometer
1344 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.081
Graphite monochromatorθmax = 28.7°, θmin = 4.2°
ϕ and ω scans with κ offsetsh = 07
9658 measured reflectionsk = 016
1536 independent reflectionsl = 021
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)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149H-atom parameters constrained
S = 1.16 w = 1/[σ2(Fo2) + (0.0491P)2 + 0.3301P]
where P = (Fo2 + 2Fc2)/3
1536 reflections(Δ/σ)max < 0.001
146 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.16 e Å3
Crystal data top
C10H9F2N3OV = 1056.8 (3) Å3
Mr = 225.20Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 5.3770 (11) ŵ = 0.12 mm1
b = 12.598 (3) ÅT = 295 K
c = 15.601 (3) Å0.60 × 0.29 × 0.08 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
1344 reflections with I > 2σ(I)
9658 measured reflectionsRint = 0.081
1536 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0630 restraints
wR(F2) = 0.149H-atom parameters constrained
S = 1.16Δρmax = 0.16 e Å3
1536 reflectionsΔρmin = 0.16 e Å3
146 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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 > 2σ(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
F11.0193 (5)0.0759 (2)0.69521 (16)0.0959 (9)
F20.7227 (6)0.42266 (16)0.67885 (15)0.1001 (12)
O10.5799 (5)0.0141 (2)0.49259 (14)0.0733 (9)
N10.5125 (5)0.1766 (2)0.62303 (17)0.0583 (8)
N20.7087 (6)0.2399 (2)0.6393 (2)0.0725 (10)
N30.3927 (6)0.3347 (3)0.5866 (2)0.0716 (11)
C10.6906 (6)0.1114 (2)0.60153 (17)0.0491 (8)
C20.8583 (6)0.1469 (3)0.6608 (2)0.0615 (10)
C30.8761 (8)0.2503 (3)0.6881 (2)0.0707 (11)
C40.7107 (8)0.3195 (3)0.6541 (2)0.0686 (13)
C50.5350 (8)0.2905 (3)0.5961 (2)0.0703 (13)
C60.5262 (7)0.1855 (3)0.5700 (2)0.0614 (10)
C70.6804 (6)0.0045 (2)0.57500 (18)0.0528 (9)
C80.5227 (7)0.0634 (3)0.6398 (2)0.0655 (11)
C90.3289 (7)0.2346 (3)0.5921 (2)0.0699 (11)
C100.6262 (8)0.3331 (3)0.6162 (3)0.0744 (14)
H10.660000.058000.465200.1100*
H30.995300.271500.727700.0850*
H50.423100.340000.574500.0840*
H60.406800.164600.530300.0740*
H70.849100.034000.575300.0630*
H8A0.590300.051800.696600.0790*
H8B0.355300.034900.638800.0790*
H90.174400.207900.576200.0840*
H100.723000.394100.620000.0900*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0860 (16)0.0923 (16)0.1095 (16)0.0289 (14)0.0421 (15)0.0148 (14)
F20.157 (3)0.0540 (11)0.0894 (14)0.0013 (15)0.0206 (18)0.0154 (10)
O10.0848 (18)0.0700 (15)0.0650 (12)0.0173 (14)0.0112 (13)0.0159 (11)
N10.0499 (13)0.0594 (14)0.0656 (14)0.0022 (13)0.0011 (13)0.0030 (12)
N20.0575 (17)0.0571 (16)0.103 (2)0.0034 (13)0.0163 (18)0.0053 (15)
N30.0719 (19)0.0660 (18)0.0770 (18)0.0127 (16)0.0007 (16)0.0090 (14)
C10.0462 (15)0.0494 (14)0.0517 (13)0.0050 (12)0.0040 (12)0.0018 (12)
C20.0571 (18)0.0657 (19)0.0616 (17)0.0112 (16)0.0070 (15)0.0052 (15)
C30.072 (2)0.075 (2)0.0650 (18)0.0056 (19)0.0057 (19)0.0142 (17)
C40.091 (3)0.0569 (17)0.0578 (16)0.001 (2)0.016 (2)0.0059 (14)
C50.085 (3)0.0578 (18)0.0682 (19)0.0215 (19)0.007 (2)0.0092 (15)
C60.0638 (19)0.0613 (17)0.0590 (16)0.0096 (17)0.0086 (16)0.0008 (14)
C70.0481 (15)0.0521 (15)0.0581 (15)0.0081 (14)0.0015 (14)0.0054 (13)
C80.0637 (19)0.0569 (17)0.076 (2)0.0040 (17)0.0088 (18)0.0080 (15)
C90.0487 (17)0.080 (2)0.081 (2)0.0026 (18)0.0050 (17)0.0055 (19)
C100.070 (2)0.0563 (19)0.097 (3)0.0018 (18)0.008 (2)0.0063 (18)
Geometric parameters (Å, º) top
F1—C21.356 (4)C2—C31.374 (5)
F2—C41.357 (4)C3—C41.354 (6)
O1—C71.400 (4)C4—C51.358 (5)
O1—H10.8200C5—C61.385 (5)
N1—C81.451 (5)C7—C81.514 (5)
N1—C91.320 (5)C3—H30.9300
N1—N21.347 (4)C5—H50.9300
N2—C101.306 (5)C6—H60.9300
N3—C101.338 (5)C7—H70.9800
N3—C91.310 (5)C8—H8A0.9700
C1—C21.367 (4)C8—H8B0.9700
C1—C71.519 (4)C9—H90.9300
C1—C61.377 (5)C10—H100.9300
C7—O1—H1109.00N1—C8—C7112.5 (3)
N2—N1—C8121.2 (3)N1—C9—N3111.2 (3)
C8—N1—C9129.7 (3)N2—C10—N3115.3 (4)
N2—N1—C9109.1 (3)C2—C3—H3122.00
N1—N2—C10102.4 (3)C4—C3—H3122.00
C9—N3—C10102.1 (3)C4—C5—H5121.00
C2—C1—C7121.5 (3)C6—C5—H5121.00
C6—C1—C7122.1 (3)C1—C6—H6119.00
C2—C1—C6116.3 (3)C5—C6—H6119.00
F1—C2—C3117.3 (3)O1—C7—H7109.00
C1—C2—C3124.5 (3)C1—C7—H7109.00
F1—C2—C1118.3 (3)C8—C7—H7109.00
C2—C3—C4116.3 (3)N1—C8—H8A109.00
F2—C4—C3118.3 (3)N1—C8—H8B109.00
C3—C4—C5123.0 (4)C7—C8—H8A109.00
F2—C4—C5118.7 (3)C7—C8—H8B109.00
C4—C5—C6118.5 (4)H8A—C8—H8B108.00
C1—C6—C5121.4 (3)N1—C9—H9124.00
O1—C7—C8110.8 (3)N3—C9—H9124.00
C1—C7—C8108.0 (2)N2—C10—H10122.00
O1—C7—C1110.3 (2)N3—C10—H10122.00
C8—N1—N2—C10179.9 (3)C7—C1—C6—C5178.8 (3)
C9—N1—N2—C100.1 (4)C2—C1—C7—O1154.7 (3)
N2—N1—C8—C773.8 (4)C2—C1—C7—C884.1 (4)
C9—N1—C8—C7106.5 (4)C6—C1—C7—O127.9 (4)
N2—N1—C9—N30.1 (4)C6—C1—C7—C893.3 (3)
C8—N1—C9—N3179.9 (3)F1—C2—C3—C4178.8 (3)
N1—N2—C10—N30.1 (5)C1—C2—C3—C41.3 (5)
C10—N3—C9—N10.0 (4)C2—C3—C4—F2179.6 (3)
C9—N3—C10—N20.1 (5)C2—C3—C4—C50.0 (6)
C6—C1—C2—F1178.3 (3)F2—C4—C5—C6179.0 (3)
C6—C1—C2—C31.9 (5)C3—C4—C5—C60.6 (6)
C7—C1—C2—F10.7 (4)C4—C5—C6—C10.0 (5)
C7—C1—C2—C3179.5 (3)O1—C7—C8—N162.4 (3)
C2—C1—C6—C51.2 (5)C1—C7—C8—N1176.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N3i0.822.012.826 (4)171
C3—H3···N2ii0.932.623.500 (5)158
C8—H8B···F1iii0.972.453.340 (5)153
C10—H10···F2iv0.932.483.270 (4)142
Symmetry codes: (i) x+1/2, y1/2, z+1; (ii) x+2, y+1/2, z+3/2; (iii) x1, y, z; (iv) x, y1, z.

Experimental details

Crystal data
Chemical formulaC10H9F2N3O
Mr225.20
Crystal system, space groupOrthorhombic, P212121
Temperature (K)295
a, b, c (Å)5.3770 (11), 12.598 (3), 15.601 (3)
V3)1056.8 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.12
Crystal size (mm)0.60 × 0.29 × 0.08
Data collection
DiffractometerNonius KappaCCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
9658, 1536, 1344
Rint0.081
(sin θ/λ)max1)0.675
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.063, 0.149, 1.16
No. of reflections1536
No. of parameters146
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.16, 0.16

Computer programs: COLLECT (Nonius, 2000), DENZO-SMN (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009), WinGX (Farrugia, 1999) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N3i0.822.012.826 (4)171
C3—H3···N2ii0.932.623.500 (5)158
C8—H8B···F1iii0.972.453.340 (5)153
C10—H10···F2iv0.932.483.270 (4)142
Symmetry codes: (i) x+1/2, y1/2, z+1; (ii) x+2, y+1/2, z+3/2; (iii) x1, y, z; (iv) x, y1, z.
 

Acknowledgements

We are grateful to the Consejo Superior de Investigaciones Científicas (CSIC) of Spain for the award of a licence for the use of the Cambridge Structural Database (CSD).

References

First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science Google Scholar
First citationDolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationEmami, S., Behdad, M., Foroumadi, A., Falahati, M., Lotfali, E. & Sharifynia, S. (2009). Chem. Biol. Drug Des. 73, 388–395.  Web of Science CrossRef PubMed CAS Google Scholar
First citationEmami, S., Foroumadi, A., Falahati, M., Lotfali, E., Rajabalian, S., Ebrahimi, S., Farahyar, S. & Shafie, A. (2008). Bioorg. Med. Chem. Lett. 18, 141–146.  Web of Science CrossRef PubMed CAS Google Scholar
First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
First citationNonius (2000). COLLECT BV, Delft, The Netherlands.  Google Scholar
First citationOtwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York; Academic Press.  Google Scholar
First citationSchiaffella, F., Macchiarulo, M., Milanese, L., Vecchiarelli, A., Costantino, G., Pietrella, D. & Fringuelli, R. (2005). J. Med. Chem. 48, 7658–7666.  Web of Science CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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