1-(4-Fluoro-phen-yl)-2-(1H-1,2,4-triazol-1-yl)ethanone hemihydrate.

In the title compound, C(10)H(8)FN(3)O·0.5H(2)O, the dihedral angle between the mean planes of the rings is 99.80 (4)°. The water mol-ecule lies on a twofold axis. Weak inter-molecular O-H⋯N and C-H⋯O hydrogen bonds link one water mol-ecule with four phenyl-ethanone mol-ecules, while inter-molecular C-H⋯O hydrogen bonds involving the ketone group link phenyl-ethanone mol-ecules into layers parallel to (100).

Related literature

For related compounds containing a 2-(1H-1,2,4-triazol-1-yl)-1-phenyl­ethanone fragment, see: Akira et al. (1985 ▶); Yoshimi et al. (2000 ▶); Yuan et al. (2007 ▶); Tao et al. (2007 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C10H8FN3O·0.5H2O

M = 214.2

Orthorhombic,

a = 24.419 (5) Å

b = 10.147 (2) Å

c = 8.2410 (16) Å

V = 2042.0 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.3 × 0.2 × 0.2 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.968, T max = 0.978

3626 measured reflections

1844 independent reflections

1087 reflections with I > 2σ(I)

R int = 0.057

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.160

S = 1.00

1844 reflections

145 parameters

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/S1600536811045429/zq2131sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811045429/zq2131Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811045429/zq2131Isup3.cml

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

C10H8FN3O·0.5H2O	Dx = 1.394 Mg m−3
Mr = 214.2	Melting point: 397 K
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 25 reflections
a = 24.419 (5) Å	θ = 9–13°
b = 10.147 (2) Å	µ = 0.11 mm−1
c = 8.2410 (16) Å	T = 293 K
V = 2042.0 (7) Å3	Prism, yellow
Z = 8	0.3 × 0.2 × 0.2 mm
F(000) = 888

Enraf–Nonius CAD-4 diffractometer	1087 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.057
graphite	θmax = 25.4°, θmin = 1.7°
ω/2θ scans	h = −29→29
Absorption correction: ψ scan (North et al., 1968)	k = −12→0
Tmin = 0.968, Tmax = 0.978	l = 0→9
3626 measured reflections	3 standard reflections every 200 reflections
1844 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)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.160	w = 1/[σ2(Fo2) + (0.084P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
1844 reflections	Δρmax = 0.17 e Å−3
145 parameters	Δρmin = −0.15 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.062 (7)

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	0.25394 (7)	0.00400 (18)	−0.0459 (2)	0.0749 (6)
F	0.50013 (8)	0.1731 (3)	−0.0667 (3)	0.1359 (10)
N1	0.10453 (9)	0.0848 (3)	0.1516 (3)	0.0769 (8)
C1	0.10833 (13)	0.1521 (3)	0.0121 (4)	0.0774 (9)
H1B	0.0787	0.1626	−0.0575	0.093*
N2	0.15669 (10)	0.2021 (3)	−0.0199 (3)	0.0722 (7)
C2	0.15429 (11)	0.0941 (3)	0.2103 (3)	0.0640 (7)
H2B	0.1658	0.0569	0.3076	0.077*
N3	0.18595 (8)	0.16374 (19)	0.1122 (2)	0.0546 (6)
C3	0.24381 (10)	0.1914 (2)	0.1215 (3)	0.0539 (7)
H3A	0.2558	0.1837	0.2333	0.065*
H3B	0.2504	0.2812	0.0864	0.065*
C4	0.27685 (10)	0.0978 (2)	0.0168 (3)	0.0492 (6)
C5	0.33581 (10)	0.1223 (2)	−0.0041 (3)	0.0496 (7)
C6	0.36302 (11)	0.2249 (3)	0.0712 (3)	0.0608 (7)
H6A	0.3436	0.2831	0.1367	0.073*
C7	0.41853 (13)	0.2421 (3)	0.0504 (4)	0.0759 (9)
H7A	0.4370	0.3103	0.1024	0.091*
C8	0.44541 (13)	0.1573 (4)	−0.0475 (4)	0.0867 (10)
C9	0.42071 (14)	0.0552 (3)	−0.1240 (4)	0.1019 (12)
H9A	0.4407	−0.0014	−0.1901	0.122*
C10	0.36552 (12)	0.0370 (3)	−0.1017 (3)	0.0778 (9)
H10A	0.3479	−0.0330	−0.1525	0.093*
OW	0.0000	−0.0387 (3)	0.2500	0.1023 (13)
HWA	0.0248 (15)	0.006 (4)	0.220 (5)	0.123*

	U11	U22	U33	U12	U13	U23
O	0.0593 (11)	0.0603 (11)	0.1051 (14)	−0.0056 (10)	−0.0064 (11)	−0.0288 (11)
F	0.0577 (12)	0.172 (2)	0.178 (2)	−0.0314 (14)	0.0201 (13)	−0.0477 (18)
N1	0.0560 (16)	0.0907 (18)	0.0842 (17)	0.0002 (13)	0.0055 (13)	−0.0031 (15)
C1	0.0541 (19)	0.099 (2)	0.079 (2)	0.0195 (17)	−0.0088 (15)	−0.0097 (19)
N2	0.0639 (16)	0.0880 (17)	0.0647 (15)	0.0182 (13)	−0.0064 (12)	0.0102 (12)
C2	0.0618 (18)	0.0686 (17)	0.0616 (16)	0.0001 (14)	0.0035 (14)	0.0044 (14)
N3	0.0553 (13)	0.0557 (12)	0.0528 (12)	0.0055 (10)	−0.0002 (10)	0.0006 (10)
C3	0.0585 (16)	0.0502 (13)	0.0530 (13)	−0.0014 (11)	0.0003 (12)	−0.0006 (12)
C4	0.0551 (15)	0.0431 (12)	0.0495 (14)	−0.0019 (11)	−0.0063 (11)	0.0005 (11)
C5	0.0520 (15)	0.0504 (14)	0.0465 (13)	−0.0037 (11)	−0.0024 (11)	0.0004 (11)
C6	0.0620 (17)	0.0580 (15)	0.0623 (15)	−0.0105 (13)	0.0025 (13)	−0.0093 (13)
C7	0.069 (2)	0.080 (2)	0.0786 (19)	−0.0229 (16)	0.0005 (16)	−0.0123 (16)
C8	0.057 (2)	0.107 (3)	0.096 (2)	−0.0199 (18)	0.0096 (17)	−0.015 (2)
C9	0.066 (2)	0.113 (3)	0.126 (3)	−0.0109 (19)	0.027 (2)	−0.053 (2)
C10	0.0627 (19)	0.082 (2)	0.088 (2)	−0.0122 (15)	0.0084 (16)	−0.0342 (17)
OW	0.071 (2)	0.085 (2)	0.150 (3)	0.000	0.034 (2)	0.000

O—C4	1.219 (3)	C4—C5	1.471 (3)
F—C8	1.355 (3)	C5—C6	1.382 (3)
N1—C2	1.311 (3)	C5—C10	1.387 (3)
N1—C1	1.341 (4)	C6—C7	1.377 (4)
C1—N2	1.312 (4)	C6—H6A	0.9300
C1—H1B	0.9300	C7—C8	1.350 (4)
N2—N3	1.359 (3)	C7—H7A	0.9300
C2—N3	1.323 (3)	C8—C9	1.354 (4)
C2—H2B	0.9300	C9—C10	1.372 (4)
N3—C3	1.443 (3)	C9—H9A	0.9300
C3—C4	1.516 (3)	C10—H10A	0.9300
C3—H3A	0.9700	OW—HWA	0.79 (4)
C3—H3B	0.9700
C2—N1—C1	102.4 (2)	C5—C4—C3	118.8 (2)
N2—C1—N1	115.6 (3)	C6—C5—C10	118.6 (2)
N2—C1—H1B	122.2	C6—C5—C4	123.1 (2)
N1—C1—H1B	122.2	C10—C5—C4	118.3 (2)
C1—N2—N3	101.6 (2)	C7—C6—C5	120.9 (3)
N1—C2—N3	110.8 (2)	C7—C6—H6A	119.6
N1—C2—H2B	124.6	C5—C6—H6A	119.6
N3—C2—H2B	124.6	C8—C7—C6	118.1 (3)
C2—N3—N2	109.6 (2)	C8—C7—H7A	120.9
C2—N3—C3	130.1 (2)	C6—C7—H7A	120.9
N2—N3—C3	120.1 (2)	C7—C8—C9	123.3 (3)
N3—C3—C4	111.66 (19)	C7—C8—F	118.3 (3)
N3—C3—H3A	109.3	C9—C8—F	118.4 (3)
C4—C3—H3A	109.3	C8—C9—C10	118.6 (3)
N3—C3—H3B	109.3	C8—C9—H9A	120.7
C4—C3—H3B	109.3	C10—C9—H9A	120.7
H3A—C3—H3B	107.9	C9—C10—C5	120.5 (3)
O—C4—C5	122.1 (2)	C9—C10—H10A	119.8
O—C4—C3	119.1 (2)	C5—C10—H10A	119.8
C2—N1—C1—N2	0.1 (3)	O—C4—C5—C10	1.6 (4)
N1—C1—N2—N3	−0.5 (3)	C3—C4—C5—C10	−179.2 (2)
C1—N1—C2—N3	0.4 (3)	C10—C5—C6—C7	−0.2 (4)
N1—C2—N3—N2	−0.8 (3)	C4—C5—C6—C7	178.6 (2)
N1—C2—N3—C3	−175.2 (2)	C5—C6—C7—C8	1.0 (4)
C1—N2—N3—C2	0.7 (3)	C6—C7—C8—C9	−1.1 (5)
C1—N2—N3—C3	175.8 (2)	C6—C7—C8—F	−179.2 (3)
C2—N3—C3—C4	97.0 (3)	C7—C8—C9—C10	0.3 (6)
N2—N3—C3—C4	−76.9 (3)	F—C8—C9—C10	178.5 (3)
N3—C3—C4—O	−8.4 (3)	C8—C9—C10—C5	0.5 (5)
N3—C3—C4—C5	172.43 (19)	C6—C5—C10—C9	−0.6 (4)
O—C4—C5—C6	−177.3 (2)	C4—C5—C10—C9	−179.5 (3)
C3—C4—C5—C6	1.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
OW—HWA···N1	0.80 (4)	2.18 (4)	2.957 (3)	166 (4)
C2—H2B···Oi	0.93	2.54	3.309 (3)	140.
C3—H3B···Oii	0.97	2.51	3.459 (3)	166.
C7—H7A···OWiii	0.93	2.49	3.407 (4)	169.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
OW—HWA⋯N1	0.80 (4)	2.18 (4)	2.957 (3)	166 (4)
C2—H2B⋯Oi	0.93	2.54	3.309 (3)	140
C3—H3B⋯Oii	0.97	2.51	3.459 (3)	166
C7—H7A⋯OWiii	0.93	2.49	3.407 (4)	169

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