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Acta Crystallogr Sect E Struct Rep Online. 2008 July 1; 64(Pt 7): o1254.
Published online 2008 June 13. doi:  10.1107/S1600536808017303
PMCID: PMC2961775

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

Abstract

In the title compound, C10H11N3O, the planar five- and six-membered rings are nearly parallel to each other, making a dihedral angle of 2.52 (5)°. Weak inter­molecular C—H(...)O hydrogen bonds link the mol­ecules into centrosymmetric dimers and strong inter­molecular O—H(...)N hydrogen bonds link the dimers into infinite chains along the b axis.

Related literature

For general backgroud, see: Holla et al. (1996 [triangle]); Sengupta et al. (1978 [triangle]); Paulvannan et al. (2001 [triangle]); Sui et al. (1998 [triangle]); Bodey (1992 [triangle]). For related literature, see: Peeters et al. (1979a [triangle],b [triangle]); Caira et al. (2004 [triangle]); Freer et al. (1986 [triangle]); Peeters et al. (1996 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1254-scheme1.jpg

Experimental

Crystal data

  • C10H11N3O
  • M r = 189.22
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1254-efi1.jpg
  • a = 11.5356 (2) Å
  • b = 10.1173 (2) Å
  • c = 8.7127 (2) Å
  • β = 108.581 (1)°
  • V = 963.85 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 294 (2) K
  • 0.55 × 0.25 × 0.10 mm

Data collection

  • Bruker–Nonius KappaCCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2007 [triangle]) T min = 0.972, T max = 0.989
  • 13352 measured reflections
  • 2208 independent reflections
  • 1647 reflections with I > 2σ(I)
  • R int = 0.040

Refinement

  • R[F 2 > 2σ(F 2)] = 0.042
  • wR(F 2) = 0.115
  • S = 1.03
  • 2208 reflections
  • 171 parameters
  • All H-atom parameters refined
  • Δρmax = 0.16 e Å−3
  • Δρmin = −0.21 e Å−3

Data collection: COLLECT (Hooft, 1998 [triangle]); cell refinement: DENZO (Otwinowski & Minor, 1997 [triangle]) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXL97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808017303/fl2201sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017303/fl2201Isup2.hkl

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

Acknowledgments

The authors acknowledge Zonguldak Karaelmas University Research Fund for support.

supplementary crystallographic information

Comment

Azole derivatives continue to occupy an important place among systemic antifungal drugs. 1,2,4-triazoles are biologically interesting and their chemistry is receiving considerable attention due to their antihypertensive, antifungal and antibacterial properties (Holla et al., 1996; Sengupta et al., 1978; Paulvannan et al., 2001; Sui et al., 1998). The azole antifungals possessing an imidazole or triazole ring (such as miconazole, ketoconazole, fluconazole, econazole and itraconazole) inhibit the synthesis of sterols in fungi by inhibiting cytochrome P-450-dependent 14α-lanosterol demethylase (P-45014DM) and prevent cytochrome P-450 activity (Bodey, 1992). The crystal structures of miconazole (Peeters et al., 1997a), ketoconazole (Peeters et al., 1979b), fluconazole (Caira et al., 2004), econazole (Freer et al., 1986) and itraconazole (Peeters et al., 1996) have already been reported. This paper describes the crystal structure of a 1,2,4-triazole derivative, (I).

In (I) the bond lengths and angles are generally within normal ranges (Fig. 1). The 1,2,4-triazole and benzene rings, A (N1—N3/C1/C2) and B (C5—C10), are planar and nearly parallel to each other with a dihedral angle of A/B = 2.52 (5)°. Atoms C3 and C4 are 0.040 (1) Å and -0.046 (1) Å away from the ring planes of A and B, respectively indicating that they are coplanar with the adjacent rings. The N1—C3—C4 [111.53 (10)°] and C3—C4—C5 [109.94 (10)°] bond angles are a little different from each other, while O—C4—C3 [109.53 (11)°] and O—C4—C5 [110.01 (10)°] bond angles are nearly equal. In ring A, the equivalent N1—N2—C1 [102.24 (12)°] and C1—N3—C2 [102.29 (13)°] bond angles are narrowed and approximately equal to one another, while the N3—C2—N1 [111.04 (15)°] and N3—C1—N2 [115.33 (15)°] bond angles are quite different and larger than normal, probably due to the strong intermolecular O—H···N hydrogen bonds (Table 1).

In the crystal packing weak intermolecular C—H···O hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers and strong intermolecular O—H···N hydrogen bonds (Table 1) link the dimers along the b axis (Fig. 2).

Experimental

For the preparation of the title compound, a mixture of 1-phenyl-2-(1H-1,2,4 -triazol-1-yl)ethanone (800 mg, 4.27 mmol) and sodiumborohydride (324 mg, 8.54 mmol) in ethanol (13 ml) was refluxed for 5 h. After evaporation of solvent, the mixture was neutralized with dilute HCl and then refluxed for 30 min. After the mixture was cooled, the solution was alkalinized with NaOH and the precipitate was collected and crystallized from benzene to obtain colorless crystals (yield; 577 mg, 71%).

Refinement

H atoms were located in difference syntheses and refined isotropically [O—H = 0.88 (2) Å, Uiso(H) = 0.096 (7) Å2 and C—H = 0.959 (16)–1.012 (17) Å, Uiso(H) = 0.034 (3)–0.081 (6) Å2].

Figures

Fig. 1.
The molecular structure of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
A packing diagram of (I). Hydrogen bonds are shown as dashed lines.

Crystal data

C10H11N3OF000 = 400
Mr = 189.22Dx = 1.304 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 12727 reflections
a = 11.5356 (2) Åθ = 2.9–27.5º
b = 10.1173 (2) ŵ = 0.09 mm1
c = 8.7127 (2) ÅT = 294 (2) K
β = 108.581 (1)ºBlock, colorless
V = 963.85 (3) Å30.55 × 0.25 × 0.10 mm
Z = 4

Data collection

Bruker–Nonius Roper CCD camera on κ-goniostat diffractometer2208 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode1647 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.040
Detector resolution: 9.091 pixels mm-1θmax = 27.5º
T = 120(2) Kθmin = 3.2º
[var phi] and ω scansh = −14→14
Absorption correction: multi-scan(SADABS; Sheldrick, 2007)k = −13→12
Tmin = 0.972, Tmax = 0.989l = −11→10
13352 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042All H-atom parameters refined
wR(F2) = 0.115  w = 1/[σ2(Fo2) + (0.0583P)2 + 0.1287P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
2208 reflectionsΔρmax = 0.16 e Å3
171 parametersΔρmin = −0.21 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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
O0.87872 (10)0.13609 (12)0.06628 (11)0.0588 (3)
H0.813 (2)0.182 (2)0.013 (3)0.096 (7)*
N10.72669 (9)0.10513 (11)0.27992 (13)0.0434 (3)
N20.68815 (10)0.20410 (13)0.35760 (14)0.0521 (3)
N30.52850 (11)0.11273 (16)0.16751 (19)0.0727 (4)
C10.56896 (13)0.20320 (19)0.2849 (2)0.0630 (4)
H10.5169 (17)0.2639 (19)0.316 (2)0.081 (6)*
C20.63083 (13)0.05341 (18)0.1683 (2)0.0596 (4)
H20.6363 (16)−0.0179 (19)0.098 (2)0.074 (5)*
C30.85650 (11)0.07494 (15)0.32125 (17)0.0445 (3)
H310.8629 (14)−0.0199 (17)0.288 (2)0.063 (5)*
H320.8938 (14)0.0825 (15)0.439 (2)0.059 (4)*
C40.91941 (11)0.16584 (13)0.23363 (14)0.0376 (3)
H40.8978 (11)0.2558 (13)0.2499 (15)0.034 (3)*
C51.05661 (10)0.14872 (12)0.30176 (14)0.0354 (3)
C61.12425 (12)0.22987 (15)0.42648 (16)0.0480 (3)
H61.0823 (15)0.2996 (17)0.467 (2)0.070 (5)*
C71.24947 (13)0.21333 (16)0.49370 (19)0.0572 (4)
H71.2961 (16)0.2732 (19)0.584 (2)0.079 (5)*
C81.30805 (13)0.11523 (17)0.4370 (2)0.0566 (4)
H81.3973 (17)0.1018 (18)0.484 (2)0.078 (5)*
C91.24185 (13)0.03446 (15)0.31286 (19)0.0529 (4)
H91.2826 (15)−0.0328 (17)0.269 (2)0.065 (5)*
C101.11643 (12)0.05072 (13)0.24487 (16)0.0426 (3)
H101.0711 (14)−0.0032 (15)0.1553 (19)0.055 (4)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O0.0489 (6)0.0914 (8)0.0316 (5)0.0183 (6)0.0065 (4)0.0033 (5)
N10.0314 (5)0.0530 (6)0.0427 (6)−0.0020 (4)0.0077 (5)0.0030 (5)
N20.0371 (6)0.0646 (8)0.0512 (7)−0.0016 (5)0.0095 (5)−0.0048 (6)
N30.0349 (6)0.0949 (11)0.0780 (10)−0.0047 (7)0.0036 (6)−0.0166 (8)
C10.0365 (7)0.0801 (11)0.0692 (10)0.0026 (7)0.0124 (7)−0.0067 (9)
C20.0399 (8)0.0711 (10)0.0607 (9)−0.0100 (7)0.0061 (7)−0.0121 (8)
C30.0321 (6)0.0542 (8)0.0438 (7)0.0021 (5)0.0075 (5)0.0098 (6)
C40.0363 (6)0.0399 (7)0.0345 (6)0.0042 (5)0.0084 (5)0.0021 (5)
C50.0347 (6)0.0380 (6)0.0345 (6)−0.0004 (5)0.0122 (5)0.0041 (5)
C60.0440 (7)0.0515 (8)0.0465 (7)−0.0005 (6)0.0116 (6)−0.0084 (6)
C70.0441 (8)0.0671 (10)0.0537 (8)−0.0100 (7)0.0060 (6)−0.0084 (8)
C80.0337 (7)0.0728 (10)0.0603 (9)0.0009 (7)0.0106 (6)0.0085 (8)
C90.0456 (8)0.0579 (9)0.0585 (8)0.0132 (7)0.0212 (7)0.0042 (7)
C100.0425 (7)0.0424 (7)0.0417 (7)0.0038 (6)0.0117 (6)0.0006 (6)

Geometric parameters (Å, °)

O—C41.4144 (15)C4—H40.966 (13)
O—H0.88 (2)C5—C41.5128 (16)
N1—N21.3602 (16)C5—C61.3869 (18)
N1—C21.3257 (18)C5—C101.3866 (18)
N1—C31.4565 (16)C6—C71.385 (2)
N2—C11.3178 (18)C6—H60.982 (18)
N3—C21.322 (2)C7—H71.01 (2)
C1—N31.341 (2)C8—C71.378 (2)
C1—H10.96 (2)C8—C91.376 (2)
C2—H20.961 (19)C8—H80.989 (19)
C3—H311.012 (17)C9—H90.974 (18)
C3—H320.977 (17)C10—C91.3875 (19)
C4—C31.5194 (18)C10—H100.959 (16)
C4—O—H112.0 (14)C3—C4—H4108.0 (7)
C2—N1—N2109.10 (12)C5—C4—C3109.94 (10)
C2—N1—C3130.55 (13)C5—C4—H4109.7 (7)
N2—N1—C3120.31 (11)C6—C5—C4119.78 (11)
C1—N2—N1102.24 (12)C10—C5—C4121.28 (11)
C2—N3—C1102.29 (13)C10—C5—C6118.92 (12)
N2—C1—N3115.33 (15)C5—C6—H6119.2 (10)
N2—C1—H1120.7 (11)C7—C6—C5120.68 (13)
N3—C1—H1123.9 (11)C7—C6—H6120.1 (10)
N1—C2—H2123.7 (11)C6—C7—H7119.0 (10)
N3—C2—N1111.04 (15)C8—C7—C6120.00 (14)
N3—C2—H2125.2 (11)C8—C7—H7121.0 (10)
N1—C3—C4111.53 (10)C7—C8—H8120.9 (11)
N1—C3—H31107.0 (9)C9—C8—C7119.79 (13)
N1—C3—H32108.5 (9)C9—C8—H8119.3 (11)
C4—C3—H31109.9 (9)C8—C9—C10120.47 (14)
C4—C3—H32110.9 (9)C8—C9—H9120.6 (9)
H31—C3—H32109.0 (13)C10—C9—H9118.9 (9)
O—C4—C3109.53 (11)C5—C10—C9120.14 (13)
O—C4—C5110.01 (10)C5—C10—H10119.5 (9)
O—C4—H4109.6 (7)C9—C10—H10120.3 (9)
C2—N1—N2—C10.35 (16)C6—C5—C4—C3−92.44 (14)
C3—N1—N2—C1178.19 (12)C10—C5—C4—O−34.88 (15)
N2—N1—C2—N3−0.37 (19)C10—C5—C4—C385.83 (14)
C3—N1—C2—N3−177.91 (14)C4—C5—C6—C7178.13 (12)
C2—N1—C3—C494.22 (18)C10—C5—C6—C7−0.2 (2)
N2—N1—C3—C4−83.09 (15)C6—C5—C10—C90.30 (19)
N1—N2—C1—N3−0.24 (19)C4—C5—C10—C9−177.99 (12)
C1—N3—C2—N10.2 (2)C5—C6—C7—C8−0.2 (2)
N2—C1—N3—C20.0 (2)C9—C8—C7—C60.4 (2)
O—C4—C3—N1−69.27 (14)C7—C8—C9—C10−0.3 (2)
C5—C4—C3—N1169.73 (11)C5—C10—C9—C8−0.1 (2)
C6—C5—C4—O146.85 (12)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O—H···N2i0.88 (2)2.00 (2)2.8645 (17)166 (2)
C10—H10···Oii0.959 (16)2.566 (16)3.3198 (17)135.6 (13)

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+2, −y, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FL2201).

References

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