(Z)-1-(2,4-Difluoro-phen-yl)-2-(1H-1,2,4-triazol-1-yl)ethanone oxime.

In the title compound, C(10)H(8)F(2)N(4)O, the dihedral angle between the rings is 65.4 (1)°. In the crystal, inter-molecular O-H⋯N and C-H⋯F hydrogen bonds link the mol-ecules in a stacked arrangement along the a and c axes, respectively.

Related literature

For applications of related compounds, see: Foroumadi et al. (2003 ▶); Mixich & Thiele (1979 ▶); Wolfgang et al. (1981 ▶). For a related structure, see: Tao et al. (2007 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C10H8F2N4O

M = 238.20

Monoclinic,

a = 8.6320 (17) Å

b = 12.433 (3) Å

c = 10.417 (2) Å

β = 104.85 (3)°

V = 1080.6 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 293 K

0.30 × 0.20 × 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

3127 measured reflections

1987 independent reflections

1217 reflections with I > 2σ(I)

R int = 0.042

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.171

S = 1.01

1987 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.53 e Å−3

Δρmin = −0.22 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/S1600536811050008/zq2136sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811050008/zq2136Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811050008/zq2136Isup3.cml

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

C10H8F2N4O	F(000) = 488
Mr = 238.20	Dx = 1.464 Mg m−3
Monoclinic, P21/n	Melting point: 400 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 8.6320 (17) Å	Cell parameters from 25 reflections
b = 12.433 (3) Å	θ = 9–13°
c = 10.417 (2) Å	µ = 0.12 mm−1
β = 104.85 (3)°	T = 293 K
V = 1080.6 (4) Å3	Black, white
Z = 4	0.30 × 0.20 × 0.10 mm

Enraf–Nonius CAD-4 diffractometer	1217 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.042
graphite	θmax = 25.4°, θmin = 2.6°
ω/2θ scans	h = 0→10
Absorption correction: ψ scan (North et al., 1968)	k = −5→14
Tmin = 0.964, Tmax = 0.988	l = −12→12
3127 measured reflections	3 standard reflections every 200 reflections
1987 independent reflections	intensity decay: 1%

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.060	H-atom parameters constrained
wR(F2) = 0.171	w = 1/[σ2(Fo2) + (0.090P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
1987 reflections	Δρmax = 0.53 e Å−3
154 parameters	Δρmin = −0.22 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.034 (5)

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
O1	−0.0689 (3)	0.1304 (2)	0.0266 (2)	0.0885 (7)
H1A	−0.1670	0.1325	0.0102	0.133*
F1	0.0628 (2)	0.39466 (19)	−0.12253 (18)	0.1082 (8)
N1	−0.0109 (3)	0.2303 (3)	0.0363 (2)	0.0787 (8)
C1	0.3526 (3)	0.3487 (3)	0.1896 (3)	0.0689 (8)
H1	0.3862	0.2944	0.2520	0.083*
N2	0.3725 (2)	0.13025 (17)	0.0097 (2)	0.0535 (6)
C2	0.4296 (4)	0.4452 (3)	0.2083 (3)	0.0880 (11)
H2	0.5142	0.4572	0.2826	0.106*
F2	0.4618 (4)	0.61943 (18)	0.1316 (3)	0.1508 (12)
N3	0.3361 (2)	0.1384 (2)	−0.1226 (2)	0.0654 (7)
C3	0.3801 (5)	0.5240 (3)	0.1156 (4)	0.0917 (10)
N4	0.6005 (2)	0.1436 (2)	−0.0387 (2)	0.0679 (7)
C4	0.2564 (4)	0.5106 (3)	0.0065 (3)	0.0944 (11)
H4	0.2229	0.5659	−0.0545	0.113*
C5	0.1822 (3)	0.4114 (3)	−0.0101 (3)	0.0707 (9)
C6	0.2250 (3)	0.3288 (2)	0.0798 (2)	0.0538 (7)
C7	0.1461 (3)	0.2225 (3)	0.0625 (2)	0.0619 (8)
C8	0.2467 (3)	0.1224 (2)	0.0803 (3)	0.0605 (8)
H8A	0.2951	0.1110	0.1741	0.073*
H8B	0.1789	0.0609	0.0471	0.073*
C9	0.4781 (3)	0.1454 (2)	−0.1470 (3)	0.0663 (8)
H9	0.4918	0.1511	−0.2324	0.080*
C10	0.5286 (3)	0.1362 (2)	0.0578 (3)	0.0597 (7)
H10	0.5810	0.1353	0.1477	0.072*

	U11	U22	U33	U12	U13	U23
O1	0.0712 (14)	0.0982 (19)	0.0951 (17)	0.0097 (14)	0.0198 (12)	−0.0037 (14)
F1	0.0744 (12)	0.160 (2)	0.0717 (12)	−0.0057 (12)	−0.0146 (10)	0.0297 (11)
N1	0.0610 (14)	0.115 (3)	0.0608 (15)	−0.0278 (15)	0.0177 (11)	−0.0027 (15)
C1	0.0595 (16)	0.078 (2)	0.0599 (16)	0.0107 (16)	−0.0024 (13)	−0.0075 (15)
N2	0.0337 (10)	0.0662 (15)	0.0611 (13)	−0.0045 (10)	0.0133 (9)	0.0006 (11)
C2	0.095 (2)	0.087 (3)	0.0639 (19)	0.012 (2)	−0.0120 (18)	−0.0177 (19)
F2	0.183 (3)	0.0744 (16)	0.161 (2)	−0.0211 (16)	−0.017 (2)	−0.0079 (15)
N3	0.0441 (11)	0.093 (2)	0.0577 (13)	−0.0116 (12)	0.0107 (10)	−0.0005 (12)
C3	0.106 (3)	0.067 (2)	0.091 (2)	0.002 (2)	0.004 (2)	−0.014 (2)
N4	0.0449 (12)	0.0795 (18)	0.0822 (16)	−0.0011 (11)	0.0216 (12)	−0.0008 (13)
C4	0.108 (3)	0.078 (3)	0.085 (2)	0.016 (2)	0.002 (2)	0.014 (2)
C5	0.0594 (16)	0.100 (3)	0.0456 (15)	0.0192 (18)	0.0007 (13)	0.0074 (16)
C6	0.0283 (11)	0.084 (2)	0.0503 (14)	0.0060 (12)	0.0120 (10)	−0.0023 (14)
C7	0.0463 (13)	0.096 (2)	0.0464 (14)	0.0039 (15)	0.0175 (11)	0.0027 (14)
C8	0.0363 (12)	0.080 (2)	0.0674 (17)	−0.0076 (13)	0.0175 (12)	0.0078 (15)
C9	0.0470 (14)	0.089 (2)	0.0659 (17)	−0.0109 (15)	0.0205 (13)	−0.0046 (16)
C10	0.0297 (11)	0.075 (2)	0.0724 (17)	0.0046 (12)	0.0091 (11)	0.0088 (14)

O1—N1	1.334 (3)	N3—C9	1.317 (3)
O1—H1A	0.8200	C3—C4	1.356 (5)
F1—C5	1.364 (3)	N4—C10	1.313 (3)
N1—C7	1.315 (3)	N4—C9	1.333 (3)
C1—C2	1.362 (4)	C4—C5	1.380 (5)
C1—C6	1.392 (3)	C4—H4	0.9300
C1—H1	0.9300	C5—C6	1.375 (4)
N2—C10	1.314 (3)	C6—C7	1.477 (4)
N2—N3	1.337 (3)	C7—C8	1.502 (4)
N2—C8	1.463 (3)	C8—H8A	0.9700
C2—C3	1.365 (5)	C8—H8B	0.9700
C2—H2	0.9300	C9—H9	0.9300
F2—C3	1.368 (4)	C10—H10	0.9300
N1—O1—H1A	109.5	F1—C5—C4	117.9 (3)
C7—N1—O1	107.1 (3)	C6—C5—C4	123.2 (3)
C2—C1—C6	121.9 (3)	C5—C6—C1	116.4 (3)
C2—C1—H1	119.0	C5—C6—C7	123.4 (2)
C6—C1—H1	119.0	C1—C6—C7	120.1 (3)
C10—N2—N3	109.6 (2)	N1—C7—C6	112.2 (3)
C10—N2—C8	129.3 (2)	N1—C7—C8	128.2 (3)
N3—N2—C8	120.97 (18)	C6—C7—C8	119.5 (2)
C1—C2—C3	118.6 (3)	N2—C8—C7	111.3 (2)
C1—C2—H2	120.7	N2—C8—H8A	109.4
C3—C2—H2	120.7	C7—C8—H8A	109.4
C9—N3—N2	102.7 (2)	N2—C8—H8B	109.4
C4—C3—C2	122.8 (4)	C7—C8—H8B	109.4
C4—C3—F2	118.6 (4)	H8A—C8—H8B	108.0
C2—C3—F2	118.6 (3)	N3—C9—N4	114.2 (2)
C10—N4—C9	102.8 (2)	N3—C9—H9	122.9
C3—C4—C5	117.1 (3)	N4—C9—H9	122.9
C3—C4—H4	121.5	N4—C10—N2	110.6 (2)
C5—C4—H4	121.5	N4—C10—H10	124.7
F1—C5—C6	118.8 (3)	N2—C10—H10	124.7
C6—C1—C2—C3	−0.5 (5)	O1—N1—C7—C6	−178.2 (2)
C10—N2—N3—C9	2.1 (3)	O1—N1—C7—C8	−0.5 (4)
C8—N2—N3—C9	179.0 (2)	C5—C6—C7—N1	−50.9 (3)
C1—C2—C3—C4	0.7 (6)	C1—C6—C7—N1	130.8 (3)
C1—C2—C3—F2	−177.3 (3)	C5—C6—C7—C8	131.1 (3)
C2—C3—C4—C5	−1.5 (6)	C1—C6—C7—C8	−47.1 (3)
F2—C3—C4—C5	176.6 (3)	C10—N2—C8—C7	112.4 (3)
C3—C4—C5—F1	−176.8 (3)	N3—N2—C8—C7	−63.8 (3)
C3—C4—C5—C6	2.0 (5)	N1—C7—C8—N2	135.8 (3)
F1—C5—C6—C1	177.1 (2)	C6—C7—C8—N2	−46.7 (3)
C4—C5—C6—C1	−1.7 (4)	N2—N3—C9—N4	−0.9 (3)
F1—C5—C6—C7	−1.2 (4)	C10—N4—C9—N3	−0.7 (4)
C4—C5—C6—C7	180.0 (3)	C9—N4—C10—N2	2.0 (3)
C2—C1—C6—C5	0.9 (4)	N3—N2—C10—N4	−2.7 (3)
C2—C1—C6—C7	179.3 (3)	C8—N2—C10—N4	−179.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N4i	0.82	1.94	2.764 (3)	176
C10—H10···F1ii	0.93	2.47	3.289 (4)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N4i	0.82	1.94	2.764 (3)	176
C10—H10⋯F1ii	0.93	2.47	3.289 (4)	148

Symmetry codes: (i) ; (ii) .