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

Kesternich, V.; Nelson-González, R.; Pérez-Fehrmann, M.; Cárdenas, A.; Brito, I.

doi:10.1107/S1600536812020661

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1727

doi:10.1107/S1600536812020661

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

Victor Kesternich,^a Ronald Nelson-González,^a Marcia Pérez-Fehrmann,^a Alejandro Cárdenas ^b and Iván Brito ^c ^*

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

Experimental

Crystal data

C₁₀H₉F₂N₃O
M_r = 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)
R_int = 0.081

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.149
S = 1.16
1536 reflections
146 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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⋯F2^iv	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 ); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ); data reduction: DENZO-SMN; 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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812020661/su2423sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812020661/su2423Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812020661/su2423Isup3.cml

checkCIF report

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].

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

	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.
	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

C₁₀H₉F₂N₃O	F(000) = 464
M_r = 225.20	D_x = 1.415 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
a = 5.3770 (11) Å	µ = 0.12 mm⁻¹
b = 12.598 (3) Å	T = 295 K
c = 15.601 (3) Å	Plate, colourless
V = 1056.8 (3) Å³	0.60 × 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 tube	R_int = 0.081
Graphite monochromator	θ_max = 28.7°, θ_min = 4.2°
ϕ and ω scans with κ offsets	h = 0→7
9658 measured reflections	k = 0→16
1536 independent reflections	l = 0→21

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.149	H-atom parameters constrained
S = 1.16	w = 1/[σ²(F_o²) + (0.0491P)² + 0.3301P] where P = (F_o² + 2F_c²)/3
1536 reflections	(Δ/σ)_max < 0.001
146 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₀H₉F₂N₃O	V = 1056.8 (3) Å³
M_r = 225.20	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.3770 (11) Å	µ = 0.12 mm⁻¹
b = 12.598 (3) Å	T = 295 K
c = 15.601 (3) Å	0.60 × 0.29 × 0.08 mm

Data collection top

Nonius KappaCCD area-detector diffractometer	1344 reflections with I > 2σ(I)
9658 measured reflections	R_int = 0.081
1536 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	0 restraints
wR(F²) = 0.149	H-atom parameters constrained
S = 1.16	Δρ_max = 0.16 e Å⁻³
1536 reflections	Δρ_min = −0.16 e Å⁻³
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

	x	y	z	U_iso*/U_eq
F1	1.0193 (5)	0.0759 (2)	0.69521 (16)	0.0959 (9)
F2	0.7227 (6)	0.42266 (16)	0.67885 (15)	0.1001 (12)
O1	0.5799 (5)	−0.0141 (2)	0.49259 (14)	0.0733 (9)
N1	0.5125 (5)	−0.1766 (2)	0.62303 (17)	0.0583 (8)
N2	0.7087 (6)	−0.2399 (2)	0.6393 (2)	0.0725 (10)
N3	0.3927 (6)	−0.3347 (3)	0.5866 (2)	0.0716 (11)
C1	0.6906 (6)	0.1114 (2)	0.60153 (17)	0.0491 (8)
C2	0.8583 (6)	0.1469 (3)	0.6608 (2)	0.0615 (10)
C3	0.8761 (8)	0.2503 (3)	0.6881 (2)	0.0707 (11)
C4	0.7107 (8)	0.3195 (3)	0.6541 (2)	0.0686 (13)
C5	0.5350 (8)	0.2905 (3)	0.5961 (2)	0.0703 (13)
C6	0.5262 (7)	0.1855 (3)	0.5700 (2)	0.0614 (10)
C7	0.6804 (6)	−0.0045 (2)	0.57500 (18)	0.0528 (9)
C8	0.5227 (7)	−0.0634 (3)	0.6398 (2)	0.0655 (11)
C9	0.3289 (7)	−0.2346 (3)	0.5921 (2)	0.0699 (11)
C10	0.6262 (8)	−0.3331 (3)	0.6162 (3)	0.0744 (14)
H1	0.66000	−0.05800	0.46520	0.1100*
H3	0.99530	0.27150	0.72770	0.0850*
H5	0.42310	0.34000	0.57450	0.0840*
H6	0.40680	0.16460	0.53030	0.0740*
H7	0.84910	−0.03400	0.57530	0.0630*
H8A	0.59030	−0.05180	0.69660	0.0790*
H8B	0.35530	−0.03490	0.63880	0.0790*
H9	0.17440	−0.20790	0.57620	0.0840*
H10	0.72300	−0.39410	0.62000	0.0900*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0860 (16)	0.0923 (16)	0.1095 (16)	0.0289 (14)	−0.0421 (15)	−0.0148 (14)
F2	0.157 (3)	0.0540 (11)	0.0894 (14)	−0.0013 (15)	0.0206 (18)	−0.0154 (10)
O1	0.0848 (18)	0.0700 (15)	0.0650 (12)	0.0173 (14)	−0.0112 (13)	−0.0159 (11)
N1	0.0499 (13)	0.0594 (14)	0.0656 (14)	0.0022 (13)	−0.0011 (13)	−0.0030 (12)
N2	0.0575 (17)	0.0571 (16)	0.103 (2)	0.0034 (13)	−0.0163 (18)	0.0053 (15)
N3	0.0719 (19)	0.0660 (18)	0.0770 (18)	−0.0127 (16)	0.0007 (16)	−0.0090 (14)
C1	0.0462 (15)	0.0494 (14)	0.0517 (13)	0.0050 (12)	0.0040 (12)	−0.0018 (12)
C2	0.0571 (18)	0.0657 (19)	0.0616 (17)	0.0112 (16)	−0.0070 (15)	−0.0052 (15)
C3	0.072 (2)	0.075 (2)	0.0650 (18)	−0.0056 (19)	−0.0057 (19)	−0.0142 (17)
C4	0.091 (3)	0.0569 (17)	0.0578 (16)	0.001 (2)	0.016 (2)	−0.0059 (14)
C5	0.085 (3)	0.0578 (18)	0.0682 (19)	0.0215 (19)	0.007 (2)	0.0092 (15)
C6	0.0638 (19)	0.0613 (17)	0.0590 (16)	0.0096 (17)	−0.0086 (16)	−0.0008 (14)
C7	0.0481 (15)	0.0521 (15)	0.0581 (15)	0.0081 (14)	−0.0015 (14)	−0.0054 (13)
C8	0.0637 (19)	0.0569 (17)	0.076 (2)	0.0040 (17)	0.0088 (18)	−0.0080 (15)
C9	0.0487 (17)	0.080 (2)	0.081 (2)	−0.0026 (18)	−0.0050 (17)	−0.0055 (19)
C10	0.070 (2)	0.0563 (19)	0.097 (3)	0.0018 (18)	−0.008 (2)	0.0063 (18)

Geometric parameters (Å, º) top

F1—C2	1.356 (4)	C2—C3	1.374 (5)
F2—C4	1.357 (4)	C3—C4	1.354 (6)
O1—C7	1.400 (4)	C4—C5	1.358 (5)
O1—H1	0.8200	C5—C6	1.385 (5)
N1—C8	1.451 (5)	C7—C8	1.514 (5)
N1—C9	1.320 (5)	C3—H3	0.9300
N1—N2	1.347 (4)	C5—H5	0.9300
N2—C10	1.306 (5)	C6—H6	0.9300
N3—C10	1.338 (5)	C7—H7	0.9800
N3—C9	1.310 (5)	C8—H8A	0.9700
C1—C2	1.367 (4)	C8—H8B	0.9700
C1—C7	1.519 (4)	C9—H9	0.9300
C1—C6	1.377 (5)	C10—H10	0.9300

C7—O1—H1	109.00	N1—C8—C7	112.5 (3)
N2—N1—C8	121.2 (3)	N1—C9—N3	111.2 (3)
C8—N1—C9	129.7 (3)	N2—C10—N3	115.3 (4)
N2—N1—C9	109.1 (3)	C2—C3—H3	122.00
N1—N2—C10	102.4 (3)	C4—C3—H3	122.00
C9—N3—C10	102.1 (3)	C4—C5—H5	121.00
C2—C1—C7	121.5 (3)	C6—C5—H5	121.00
C6—C1—C7	122.1 (3)	C1—C6—H6	119.00
C2—C1—C6	116.3 (3)	C5—C6—H6	119.00
F1—C2—C3	117.3 (3)	O1—C7—H7	109.00
C1—C2—C3	124.5 (3)	C1—C7—H7	109.00
F1—C2—C1	118.3 (3)	C8—C7—H7	109.00
C2—C3—C4	116.3 (3)	N1—C8—H8A	109.00
F2—C4—C3	118.3 (3)	N1—C8—H8B	109.00
C3—C4—C5	123.0 (4)	C7—C8—H8A	109.00
F2—C4—C5	118.7 (3)	C7—C8—H8B	109.00
C4—C5—C6	118.5 (4)	H8A—C8—H8B	108.00
C1—C6—C5	121.4 (3)	N1—C9—H9	124.00
O1—C7—C8	110.8 (3)	N3—C9—H9	124.00
C1—C7—C8	108.0 (2)	N2—C10—H10	122.00
O1—C7—C1	110.3 (2)	N3—C10—H10	122.00

C8—N1—N2—C10	179.9 (3)	C7—C1—C6—C5	178.8 (3)
C9—N1—N2—C10	0.1 (4)	C2—C1—C7—O1	−154.7 (3)
N2—N1—C8—C7	73.8 (4)	C2—C1—C7—C8	84.1 (4)
C9—N1—C8—C7	−106.5 (4)	C6—C1—C7—O1	27.9 (4)
N2—N1—C9—N3	−0.1 (4)	C6—C1—C7—C8	−93.3 (3)
C8—N1—C9—N3	−179.9 (3)	F1—C2—C3—C4	−178.8 (3)
N1—N2—C10—N3	−0.1 (5)	C1—C2—C3—C4	1.3 (5)
C10—N3—C9—N1	0.0 (4)	C2—C3—C4—F2	−179.6 (3)
C9—N3—C10—N2	0.1 (5)	C2—C3—C4—C5	0.0 (6)
C6—C1—C2—F1	178.3 (3)	F2—C4—C5—C6	179.0 (3)
C6—C1—C2—C3	−1.9 (5)	C3—C4—C5—C6	−0.6 (6)
C7—C1—C2—F1	0.7 (4)	C4—C5—C6—C1	0.0 (5)
C7—C1—C2—C3	−179.5 (3)	O1—C7—C8—N1	62.4 (3)
C2—C1—C6—C5	1.2 (5)	C1—C7—C8—N1	−176.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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···F2^iv	0.93	2.48	3.270 (4)	142

Symmetry codes: (i) x+1/2, −y−1/2, −z+1; (ii) −x+2, y+1/2, −z+3/2; (iii) x−1, y, z; (iv) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₀H₉F₂N₃O
M_r	225.20
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	295
a, b, c (Å)	5.3770 (11), 12.598 (3), 15.601 (3)
V (Å³)	1056.8 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.60 × 0.29 × 0.08

Data collection
Diffractometer	Nonius KappaCCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9658, 1536, 1344
R_int	0.081
(sin θ/λ)_max (Å⁻¹)	0.675

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.149, 1.16
No. of reflections	1536
No. of parameters	146
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	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···F2^iv	0.93	2.48	3.270 (4)	142

Symmetry codes: (i) x+1/2, −y−1/2, −z+1; (ii) −x+2, y+1/2, −z+3/2; (iii) x−1, y, z; (iv) x, y−1, 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

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