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

Yan, C.-Y.; Wang, G.-Z.; Zhou, C.-H.

doi:10.1107/S1600536809029821

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o2054

doi:10.1107/S1600536809029821

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

Cong-Yan Yan,^a Guang-Zhou Wang ^a and Cheng-He Zhou ^a ^*

^aLaboratory of Bioorganic & Medicinal Chemistry, School of Chemistry and Chemical Engineering, Southwest University, Chongqing, 400715, People's Republic of China
^*Correspondence e-mail: zhouch@swu.edu.cn

(Received 23 July 2009; accepted 27 July 2009; online 31 July 2009)

In the title molecule, C₁₇H₁₁F₂N₃O, the triazole ring makes dihedral angles of 83.00 (5) and 16.63 (5)°, respectively, with the phenyl and benzene rings. Weak intermolecular C—H⋯F and C—H⋯N interactions 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_r = 311.29
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.040
wR(F²) = 0.101
S = 1.02
2681 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.11 e Å⁻³
Δρ_min = −0.19 e Å⁻³

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) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

Chalcones, considered as the precursors of flavonoids and isoflavonoids, are abundant in edible plants. Chalcones exhibit a variety of beneficial pharmacological activities such as antitumor, antibacterial, antifungal, antiinflammatory, antimalarial, antivirus and so on (Reichwald et al., 2008). In view of the therapeutic potentials of chalcones, we synthesized the title compound (I). Herewith we report its crystal structure.

In (I) (Fig. 1), the triazole ring makes the dihedral angles of 83.00 (5)° and 16.63 (5)°, respectively, with the phenyl and benzene rings. Weak intermolecular C—H···F and C—H···N interactions (Table 1) contribute to the crystal packing stability.

Related literature top

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

Experimental top

Compound (I) was synthesized according to the procedure of Wang et al. (2009). A crystal of (I) suitable for X-ray analysis was grown from a mixture solution of ethyl acetate and petroleum ether by slow evaporation at room temperature.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT-Plus (Bruker, 1997); data reduction: SAINT-Plus (Bruker, 1997); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

(Z)-1-(2,4-Difluorophenyl)-3-phenyl-2-(1H-1,2,4-triazol- 1-yl)prop-2-en-1-one top

Crystal data top

C₁₇H₁₁F₂N₃O	F(000) = 640
M_r = 311.29	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0432P)² + 0.2887P] where P = (F_o² + 2F_c²)/3
2681 reflections	(Δ/σ)_max < 0.001
208 parameters	Δρ_max = 0.11 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₇H₁₁F₂N₃O	V = 1446.4 (3) Å³
M_r = 311.29	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.7595 (16) Å	µ = 0.11 mm⁻¹
b = 7.580 (1) Å	T = 296 K
c = 17.068 (2) Å	0.25 × 0.21 × 0.14 mm
β = 108.067 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2681 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	1940 reflections with I > 2σ(I)
T_min = 0.973, T_max = 0.985	R_int = 0.029
10616 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 1.02	Δρ_max = 0.11 e Å⁻³
2681 reflections	Δρ_min = −0.19 e Å⁻³
208 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) −x+3/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₁F₂N₃O
M_r	311.29
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	11.7595 (16), 7.580 (1), 17.068 (2)
β (°)	108.067 (2)
V (Å³)	1446.4 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.25 × 0.21 × 0.14

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1997)
T_min, T_max	0.973, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	10616, 2681, 1940
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.101, 1.02
No. of reflections	2681
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.11, −0.19

Computer programs: SMART (Bruker, 1997), SAINT-Plus (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···N3ⁱ	0.93	2.68	3.540 (2)	153.6
C17—H17···F1ⁱⁱ	0.93	2.62	3.280 (2)	128.4

Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) −x+3/2, y+1/2, −z+1/2.

Acknowledgements

We thank the Southwest University (grant Nos. SWUB2006018 & XSGX0602) and Natural Science Foundation of Chongqing (grant No. 2007BB5369) for financial support.

References

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