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 rings is 22.90 (4)°. In the crystal, C-H⋯F and O-H⋯N hydrogen bonds link the mol-ecules into chains along [010].

Related literature

For related compounds containing a 2-(1H-1,2,4-triazol-1-yl)-1-phenyl­ethanol fragment, see: Bu et al. (2000 ▶). For related structures, see: Tao et al. (2007 ▶); Liu et al. (2011 ▶); Yu et al. (2011 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C10H9F2N3O

M = 225.20

Monoclinic,

a = 14.261 (3) Å

b = 5.6150 (11) Å

c = 25.823 (5) Å

β = 94.84 (3)°

V = 2060.4 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.12 mm−1

T = 293 K

0.30 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.964, T max = 0.988

1969 measured reflections

1886 independent reflections

1059 reflections with I > 2σ(I)

R int = 0.035

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.143

S = 1.01

1886 reflections

148 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.15 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812001110/zq2149sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812001110/zq2149Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812001110/zq2149Isup3.cml

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

C10H9F2N3O	F(000) = 928
Mr = 225.20	Dx = 1.452 Mg m−3
Monoclinic, C2/c	Melting point: 395 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 14.261 (3) Å	Cell parameters from 25 reflections
b = 5.6150 (11) Å	θ = 9–13°
c = 25.823 (5) Å	µ = 0.12 mm−1
β = 94.84 (3)°	T = 293 K
V = 2060.4 (7) Å3	Prism, colourless
Z = 8	0.30 × 0.10 × 0.10 mm

Enraf–Nonius CAD-4 diffractometer	1059 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.035
graphite	θmax = 25.4°, θmin = 1.6°
ω/2θ scans	h = 0→17
Absorption correction: ψ scan (North et al., 1968)	k = 0→6
Tmin = 0.964, Tmax = 0.988	l = −31→30
1969 measured reflections	3 standard reflections every 200 reflections
1886 independent reflections	intensity decay: 1%

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.070P)2] where P = (Fo2 + 2Fc2)/3
1886 reflections	(Δ/σ)max < 0.001
148 parameters	Δρmax = 0.17 e Å−3
3 restraints	Δρmin = −0.14 e Å−3

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.

	x	y	z	Uiso*/Ueq
O	0.06636 (12)	0.1378 (4)	0.69742 (7)	0.0730 (6)
H0A	0.080 (2)	0.037 (5)	0.7204 (11)	0.088*
N1	0.25384 (13)	0.1969 (4)	0.66832 (7)	0.0604 (6)
F1	−0.20749 (13)	−0.0256 (4)	0.49804 (8)	0.1263 (8)
C1	−0.05951 (18)	0.1696 (6)	0.60844 (11)	0.0895 (10)
H1A	−0.0572	0.2907	0.6331	0.107*
F2	0.07930 (15)	−0.3219 (4)	0.57292 (8)	0.1337 (9)
N2	0.30591 (16)	0.0018 (5)	0.68043 (10)	0.0848 (8)
C2	−0.13473 (19)	0.1639 (7)	0.57217 (12)	0.0971 (11)
H2B	−0.1831	0.2752	0.5718	0.117*
N3	0.36133 (15)	0.3146 (5)	0.72719 (8)	0.0787 (7)
C3	−0.1347 (2)	−0.0224 (7)	0.53496 (12)	0.0873 (10)
C4	−0.0688 (2)	−0.1827 (6)	0.53470 (12)	0.1006 (11)
H4A	−0.0714	−0.3041	0.5101	0.121*
C5	0.0087 (2)	−0.1631 (5)	0.57445 (11)	0.0821 (9)
C6	0.01250 (17)	0.0092 (5)	0.61091 (9)	0.0617 (7)
C7	0.09468 (17)	0.0301 (5)	0.65216 (9)	0.0604 (7)
H7A	0.1195	−0.1292	0.6607	0.072*
C8	0.17176 (16)	0.1809 (5)	0.63143 (9)	0.0686 (7)
H8A	0.1898	0.1118	0.5993	0.082*
H8B	0.1477	0.3397	0.6238	0.082*
C9	0.36890 (19)	0.0821 (6)	0.71531 (12)	0.0851 (9)
H9A	0.4161	−0.0143	0.7311	0.102*
C10	0.2871 (2)	0.3760 (5)	0.69662 (11)	0.0760 (8)
H10A	0.2613	0.5282	0.6952	0.091*

	U11	U22	U33	U12	U13	U23
O	0.0753 (11)	0.0893 (15)	0.0522 (10)	0.0145 (11)	−0.0081 (8)	0.0017 (10)
N1	0.0569 (11)	0.0675 (13)	0.0548 (12)	0.0103 (11)	−0.0083 (9)	−0.0079 (11)
F1	0.1093 (14)	0.1456 (18)	0.1112 (15)	−0.0102 (13)	−0.0652 (12)	0.0063 (13)
C1	0.0722 (17)	0.121 (3)	0.0707 (18)	0.0322 (19)	−0.0212 (14)	−0.0251 (19)
F2	0.1684 (18)	0.0919 (14)	0.1278 (16)	0.0621 (14)	−0.0645 (14)	−0.0378 (12)
N2	0.0710 (14)	0.0808 (16)	0.0969 (18)	0.0165 (13)	−0.0257 (13)	−0.0199 (14)
C2	0.0697 (17)	0.141 (3)	0.0767 (19)	0.039 (2)	−0.0157 (15)	−0.005 (2)
N3	0.0761 (15)	0.095 (2)	0.0616 (13)	−0.0125 (14)	−0.0126 (11)	−0.0080 (13)
C3	0.0747 (19)	0.104 (2)	0.078 (2)	−0.0099 (19)	−0.0289 (16)	0.0163 (19)
C4	0.127 (3)	0.073 (2)	0.091 (2)	−0.002 (2)	−0.051 (2)	−0.0071 (18)
C5	0.101 (2)	0.0584 (17)	0.0804 (19)	0.0165 (17)	−0.0334 (16)	−0.0083 (15)
C6	0.0612 (14)	0.0680 (16)	0.0533 (14)	0.0083 (14)	−0.0098 (11)	0.0007 (13)
C7	0.0643 (14)	0.0636 (16)	0.0506 (13)	0.0115 (12)	−0.0114 (11)	−0.0024 (12)
C8	0.0683 (15)	0.0824 (18)	0.0519 (13)	0.0105 (14)	−0.0147 (11)	0.0038 (14)
C9	0.0644 (17)	0.102 (3)	0.084 (2)	0.0084 (17)	−0.0214 (15)	−0.0041 (19)
C10	0.0809 (18)	0.0693 (18)	0.0763 (19)	−0.0009 (15)	−0.0025 (15)	−0.0094 (16)

O—C7	1.405 (3)	N3—C10	1.312 (3)
O—H0A	0.83 (3)	N3—C9	1.347 (4)
N1—C10	1.308 (3)	C3—C4	1.302 (4)
N1—N2	1.345 (3)	C4—C5	1.448 (3)
N1—C8	1.448 (3)	C4—H4A	0.9300
F1—C3	1.349 (3)	C5—C6	1.348 (3)
C1—C6	1.363 (3)	C6—C7	1.520 (3)
C1—C2	1.364 (3)	C7—C8	1.520 (4)
C1—H1A	0.9300	C7—H7A	0.9800
F2—C5	1.348 (3)	C8—H8A	0.9700
N2—C9	1.298 (3)	C8—H8B	0.9700
C2—C3	1.420 (4)	C9—H9A	0.9300
C2—H2B	0.9300	C10—H10A	0.9300
C7—O—H0A	104 (2)	C5—C6—C1	117.1 (2)
C10—N1—N2	109.2 (2)	C5—C6—C7	121.9 (2)
C10—N1—C8	130.5 (2)	C1—C6—C7	121.0 (2)
N2—N1—C8	120.1 (2)	O—C7—C8	108.7 (2)
C6—C1—C2	124.2 (3)	O—C7—C6	110.93 (19)
C6—C1—H1A	117.9	C8—C7—C6	109.5 (2)
C2—C1—H1A	117.9	O—C7—H7A	109.2
C9—N2—N1	102.4 (2)	C8—C7—H7A	109.2
C1—C2—C3	115.9 (3)	C6—C7—H7A	109.2
C1—C2—H2B	122.0	N1—C8—C7	111.78 (19)
C3—C2—H2B	122.0	N1—C8—H8A	109.3
C10—N3—C9	101.2 (2)	C7—C8—H8A	109.3
C4—C3—F1	120.0 (3)	N1—C8—H8B	109.3
C4—C3—C2	123.6 (3)	C7—C8—H8B	109.3
F1—C3—C2	116.4 (3)	H8A—C8—H8B	107.9
C3—C4—C5	116.9 (3)	N2—C9—N3	115.5 (3)
C3—C4—H4A	121.6	N2—C9—H9A	122.2
C5—C4—H4A	121.6	N3—C9—H9A	122.2
F2—C5—C6	120.6 (2)	N1—C10—N3	111.7 (3)
F2—C5—C4	117.2 (2)	N1—C10—H10A	124.1
C6—C5—C4	122.2 (3)	N3—C10—H10A	124.1
C10—N1—N2—C9	−1.0 (3)	C2—C1—C6—C7	179.1 (3)
C8—N1—N2—C9	−177.4 (2)	C5—C6—C7—O	−152.5 (3)
C6—C1—C2—C3	−0.7 (5)	C1—C6—C7—O	29.4 (4)
C1—C2—C3—C4	0.9 (5)	C5—C6—C7—C8	87.5 (3)
C1—C2—C3—F1	−178.2 (3)	C1—C6—C7—C8	−90.6 (3)
F1—C3—C4—C5	177.9 (3)	C10—N1—C8—C7	−108.9 (3)
C2—C3—C4—C5	−1.1 (5)	N2—N1—C8—C7	66.5 (3)
C3—C4—C5—F2	−177.0 (3)	O—C7—C8—N1	61.5 (3)
C3—C4—C5—C6	1.3 (5)	C6—C7—C8—N1	−177.2 (2)
F2—C5—C6—C1	177.0 (3)	N1—N2—C9—N3	0.5 (4)
C4—C5—C6—C1	−1.2 (5)	C10—N3—C9—N2	0.2 (4)
F2—C5—C6—C7	−1.1 (4)	N2—N1—C10—N3	1.3 (3)
C4—C5—C6—C7	−179.3 (3)	C8—N1—C10—N3	177.1 (2)
C2—C1—C6—C5	0.9 (5)	C9—N3—C10—N1	−0.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O—H0A···N3i	0.83 (3)	1.98 (3)	2.794 (3)	169 (3)
C8—H8B···F2ii	0.97	2.46	3.388 (4)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O—H0A⋯N3i	0.83 (3)	1.98 (3)	2.794 (3)	169 (3)
C8—H8B⋯F2ii	0.97	2.46	3.388 (4)	159

Symmetry codes: (i) ; (ii) .