1-(2,4-Difluoro-phen-yl)-2-(1H-1,2,4-triazol-1-yl)ethanol.

In the title compound, C(10)H(9)F(2)N(3)O, the dihedral angle between the mean planes of the triazole and benzene rings is 20.6 (2)°. In the crystal, mol-ecules 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 inter-actions 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 = 225.20

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 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

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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812020661/su2423sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812020661/su2423Isup3.cml

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

C10H9F2N3O	F(000) = 464
Mr = 225.20	Dx = 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

Nonius KappaCCD area-detector diffractometer	1344 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.081
Graphite monochromator	θmax = 28.7°, θmin = 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 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(Fo2) + (0.0491P)2 + 0.3301P] where P = (Fo2 + 2Fc2)/3
1536 reflections	(Δ/σ)max < 0.001
146 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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···F2iv	0.93	2.48	3.270 (4)	142

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⋯F2iv	0.93	2.48	3.270 (4)	142

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .