(Z)-1-(2,4-Difluoro-phen-yl)-3-phenyl-2-(1H-1,2,4-triazol-1-yl)prop-2-en-1-one.

In the title mol-ecule, C(17)H(11)F(2)N(3)O, the triazole ring makes dihedral angles of 83.00 (5) and 16.63 (5)°, respectively, with the phenyl and benzene rings. Weak inter-molecular C-H⋯F and C-H⋯N inter-actions contribute to the crystal packing.

Related literature

For details of the synthesis, see: Wang et al. (2009 ▶). For the pharmacological activity of chalcones, see: Reichwald et al. (2008 ▶).

Experimental

Crystal data

C17H11F2N3O

M = 311.29

Monoclinic,

a = 11.7595 (16) Å

b = 7.5800 (10) Å

c = 17.068 (2) Å

β = 108.067 (2)°

V = 1446.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.25 × 0.21 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.973, T max = 0.985

10616 measured reflections

2681 independent reflections

1940 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.101

S = 1.02

2681 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.11 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT-Plus (Bruker, 1997 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809029821/cv2596sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809029821/cv2596Isup2.hkl

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

C17H11F2N3O	F(000) = 640
Mr = 311.29	Dx = 1.429 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.7595 (16) Å	Cell parameters from 2124 reflections
b = 7.580 (1) Å	θ = 2.5–23.7°
c = 17.068 (2) Å	µ = 0.11 mm−1
β = 108.067 (2)°	T = 296 K
V = 1446.4 (3) Å3	Block, colourless
Z = 4	0.25 × 0.21 × 0.14 mm

Bruker SMART CCD area-detector diffractometer	2681 independent reflections
Radiation source: fine-focus sealed tube	1940 reflections with I > 2σ(I)
graphite	Rint = 0.029
φ and ω scans	θmax = 25.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −14→14
Tmin = 0.973, Tmax = 0.985	k = −9→9
10616 measured reflections	l = −20→20

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0432P)2 + 0.2887P] where P = (Fo2 + 2Fc2)/3
2681 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.11 e Å−3
0 restraints	Δρmin = −0.19 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
C1	0.37404 (14)	0.4189 (2)	0.17104 (10)	0.0410 (4)
C2	0.32338 (16)	0.3486 (2)	0.22725 (10)	0.0485 (5)
C3	0.20317 (17)	0.3192 (3)	0.20996 (12)	0.0563 (5)
H3	0.1718	0.2696	0.2486	0.068*
C4	0.13143 (16)	0.3665 (3)	0.13310 (13)	0.0540 (5)
C5	0.17475 (16)	0.4363 (3)	0.07450 (12)	0.0554 (5)
H5	0.1236	0.4666	0.0228	0.066*
C6	0.29653 (15)	0.4609 (2)	0.09396 (11)	0.0463 (4)
H6	0.3275	0.5068	0.0543	0.056*
C7	0.50387 (15)	0.4647 (2)	0.19524 (10)	0.0455 (4)
C8	0.57636 (13)	0.4110 (2)	0.14180 (9)	0.0380 (4)
C9	0.54142 (14)	0.2954 (2)	0.07984 (10)	0.0394 (4)
H9	0.4616	0.2613	0.0658	0.047*
C10	0.60984 (14)	0.2144 (2)	0.03078 (10)	0.0371 (4)
C11	0.54836 (15)	0.1629 (2)	−0.04971 (10)	0.0427 (4)
H11	0.4664	0.1823	−0.0707	0.051*
C12	0.60760 (17)	0.0835 (2)	−0.09852 (11)	0.0511 (5)
H12	0.5661	0.0534	−0.1527	0.061*
C13	0.72778 (18)	0.0488 (3)	−0.06717 (12)	0.0574 (5)
H13	0.7677	−0.0051	−0.1000	0.069*
C14	0.78932 (17)	0.0939 (3)	0.01321 (13)	0.0571 (5)
H14	0.8703	0.0677	0.0347	0.068*
C15	0.73151 (15)	0.1777 (2)	0.06192 (11)	0.0472 (4)
H15	0.7740	0.2096	0.1156	0.057*
C16	0.78369 (16)	0.4806 (3)	0.23361 (11)	0.0540 (5)
H16	0.7819	0.4182	0.2801	0.065*
C17	0.83462 (16)	0.6374 (3)	0.15148 (11)	0.0531 (5)
H17	0.8810	0.7101	0.1297	0.064*
F1	0.39533 (10)	0.30437 (19)	0.30320 (7)	0.0792 (4)
F2	0.01212 (10)	0.3410 (2)	0.11449 (8)	0.0874 (4)
N1	0.69278 (12)	0.48896 (18)	0.16383 (8)	0.0401 (3)
N2	0.72498 (12)	0.5930 (2)	0.10902 (9)	0.0479 (4)
N3	0.87605 (13)	0.5715 (2)	0.22846 (10)	0.0589 (4)
O1	0.55016 (12)	0.5454 (2)	0.25844 (8)	0.0737 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0413 (9)	0.0420 (10)	0.0427 (9)	0.0005 (7)	0.0173 (8)	−0.0015 (8)
C2	0.0525 (11)	0.0558 (11)	0.0415 (10)	0.0108 (9)	0.0209 (9)	0.0054 (9)
C3	0.0586 (12)	0.0590 (12)	0.0646 (13)	0.0022 (9)	0.0386 (10)	0.0056 (10)
C4	0.0387 (10)	0.0577 (12)	0.0700 (13)	−0.0016 (9)	0.0232 (9)	−0.0048 (10)
C5	0.0458 (11)	0.0632 (13)	0.0541 (11)	0.0015 (9)	0.0110 (9)	0.0039 (10)
C6	0.0463 (10)	0.0495 (11)	0.0461 (10)	−0.0032 (8)	0.0187 (8)	0.0062 (8)
C7	0.0456 (10)	0.0500 (11)	0.0404 (9)	−0.0005 (8)	0.0128 (8)	−0.0037 (8)
C8	0.0351 (9)	0.0424 (9)	0.0352 (9)	−0.0025 (7)	0.0092 (7)	0.0018 (8)
C9	0.0360 (9)	0.0425 (10)	0.0397 (9)	−0.0043 (7)	0.0119 (7)	0.0036 (8)
C10	0.0390 (9)	0.0339 (9)	0.0392 (9)	−0.0049 (7)	0.0133 (7)	0.0017 (7)
C11	0.0425 (9)	0.0406 (10)	0.0432 (9)	−0.0066 (8)	0.0107 (8)	−0.0015 (8)
C12	0.0644 (12)	0.0473 (11)	0.0429 (10)	−0.0099 (9)	0.0188 (9)	−0.0077 (8)
C13	0.0660 (14)	0.0501 (12)	0.0645 (13)	−0.0019 (9)	0.0324 (11)	−0.0123 (10)
C14	0.0443 (10)	0.0554 (12)	0.0722 (13)	0.0062 (9)	0.0192 (10)	−0.0041 (11)
C15	0.0454 (10)	0.0488 (11)	0.0443 (10)	−0.0006 (8)	0.0094 (8)	−0.0027 (8)
C16	0.0474 (11)	0.0662 (13)	0.0409 (10)	−0.0057 (9)	0.0030 (8)	−0.0005 (9)
C17	0.0427 (10)	0.0596 (12)	0.0579 (12)	−0.0127 (9)	0.0170 (9)	−0.0074 (10)
F1	0.0713 (8)	0.1213 (11)	0.0491 (7)	0.0211 (7)	0.0247 (6)	0.0255 (7)
F2	0.0441 (7)	0.1161 (11)	0.1074 (10)	−0.0115 (7)	0.0313 (7)	−0.0038 (9)
N1	0.0364 (8)	0.0457 (8)	0.0359 (7)	−0.0048 (6)	0.0079 (6)	−0.0025 (6)
N2	0.0423 (8)	0.0544 (9)	0.0476 (9)	−0.0067 (7)	0.0148 (7)	0.0024 (7)
N3	0.0430 (9)	0.0758 (12)	0.0519 (10)	−0.0112 (8)	0.0060 (7)	−0.0113 (9)
O1	0.0555 (9)	0.1069 (12)	0.0594 (9)	−0.0111 (8)	0.0190 (7)	−0.0381 (9)

C1—C2	1.384 (2)	C10—C15	1.391 (2)
C1—C6	1.385 (2)	C10—C11	1.395 (2)
C1—C7	1.494 (2)	C11—C12	1.379 (2)
C2—F1	1.3521 (19)	C11—H11	0.9300
C2—C3	1.370 (2)	C12—C13	1.373 (3)
C3—C4	1.369 (3)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.381 (3)
C4—F2	1.353 (2)	C13—H13	0.9300
C4—C5	1.362 (3)	C14—C15	1.381 (2)
C5—C6	1.379 (2)	C14—H14	0.9300
C5—H5	0.9300	C15—H15	0.9300
C6—H6	0.9300	C16—N3	1.312 (2)
C7—O1	1.212 (2)	C16—N1	1.332 (2)
C7—C8	1.485 (2)	C16—H16	0.9300
C8—C9	1.336 (2)	C17—N2	1.312 (2)
C8—N1	1.4302 (19)	C17—N3	1.348 (2)
C9—C10	1.464 (2)	C17—H17	0.9300
C9—H9	0.9300	N1—N2	1.3640 (19)
C2—C1—C6	116.68 (15)	C15—C10—C9	123.22 (15)
C2—C1—C7	121.38 (15)	C11—C10—C9	118.14 (14)
C6—C1—C7	121.63 (15)	C12—C11—C10	120.82 (16)
F1—C2—C3	117.62 (16)	C12—C11—H11	119.6
F1—C2—C1	118.97 (16)	C10—C11—H11	119.6
C3—C2—C1	123.41 (17)	C13—C12—C11	120.02 (17)
C4—C3—C2	116.88 (17)	C13—C12—H12	120.0
C4—C3—H3	121.6	C11—C12—H12	120.0
C2—C3—H3	121.6	C12—C13—C14	119.91 (17)
F2—C4—C5	118.67 (18)	C12—C13—H13	120.0
F2—C4—C3	118.26 (17)	C14—C13—H13	120.0
C5—C4—C3	123.06 (17)	C15—C14—C13	120.53 (17)
C4—C5—C6	118.19 (17)	C15—C14—H14	119.7
C4—C5—H5	120.9	C13—C14—H14	119.7
C6—C5—H5	120.9	C14—C15—C10	120.13 (16)
C5—C6—C1	121.76 (16)	C14—C15—H15	119.9
C5—C6—H6	119.1	C10—C15—H15	119.9
C1—C6—H6	119.1	N3—C16—N1	111.51 (17)
O1—C7—C8	119.98 (16)	N3—C16—H16	124.2
O1—C7—C1	120.11 (16)	N1—C16—H16	124.2
C8—C7—C1	119.91 (14)	N2—C17—N3	116.09 (17)
C9—C8—N1	120.88 (14)	N2—C17—H17	122.0
C9—C8—C7	124.84 (15)	N3—C17—H17	122.0
N1—C8—C7	114.23 (14)	C16—N1—N2	108.90 (14)
C8—C9—C10	129.73 (15)	C16—N1—C8	130.75 (15)
C8—C9—H9	115.1	N2—N1—C8	120.34 (12)
C10—C9—H9	115.1	C17—N2—N1	101.76 (14)
C15—C10—C11	118.54 (15)	C16—N3—C17	101.74 (15)
C6—C1—C2—F1	179.59 (16)	C7—C8—C9—C10	−170.57 (16)
C7—C1—C2—F1	−6.6 (3)	C8—C9—C10—C15	31.5 (3)
C6—C1—C2—C3	0.2 (3)	C8—C9—C10—C11	−152.16 (17)
C7—C1—C2—C3	173.98 (17)	C15—C10—C11—C12	−2.5 (2)
F1—C2—C3—C4	179.31 (17)	C9—C10—C11—C12	−179.05 (15)
C1—C2—C3—C4	−1.3 (3)	C10—C11—C12—C13	2.2 (3)
C2—C3—C4—F2	−179.28 (17)	C11—C12—C13—C14	−0.2 (3)
C2—C3—C4—C5	1.3 (3)	C12—C13—C14—C15	−1.5 (3)
F2—C4—C5—C6	−179.65 (17)	C13—C14—C15—C10	1.2 (3)
C3—C4—C5—C6	−0.3 (3)	C11—C10—C15—C14	0.8 (2)
C4—C5—C6—C1	−0.9 (3)	C9—C10—C15—C14	177.13 (16)
C2—C1—C6—C5	0.9 (3)	N3—C16—N1—N2	−0.9 (2)
C7—C1—C6—C5	−172.81 (17)	N3—C16—N1—C8	179.80 (16)
C2—C1—C7—O1	−46.0 (3)	C9—C8—N1—C16	−118.1 (2)
C6—C1—C7—O1	127.4 (2)	C7—C8—N1—C16	59.6 (2)
C2—C1—C7—C8	133.93 (18)	C9—C8—N1—N2	62.6 (2)
C6—C1—C7—C8	−52.6 (2)	C7—C8—N1—N2	−119.70 (16)
O1—C7—C8—C9	166.95 (18)	N3—C17—N2—N1	0.1 (2)
C1—C7—C8—C9	−13.0 (3)	C16—N1—N2—C17	0.46 (18)
O1—C7—C8—N1	−10.6 (2)	C8—N1—N2—C17	179.89 (15)
C1—C7—C8—N1	169.46 (14)	N1—C16—N3—C17	0.8 (2)
N1—C8—C9—C10	6.8 (3)	N2—C17—N3—C16	−0.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···N1	0.93	2.56	3.048 (2)	113
C12—H12···N3i	0.93	2.68	3.540 (2)	154
C17—H17···F1ii	0.93	2.62	3.280 (2)	128

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯N3i	0.93	2.68	3.540 (2)	154
C17—H17⋯F1ii	0.93	2.62	3.280 (2)	128

Symmetry codes: (i) ; (ii) .