(2E)-3-(4-Fluoro-phen-yl)-1-[5-methyl-1-(4-methyl-phen-yl)-1H-1,2,3-triazol-4-yl]prop-2-en-1-one.

With respect to the triazole ring in the title compound, C19H16FN3O, the p-tolyl ring is inclined [dihedral angle = 51.79 (11)°], whereas the chalcone residue is almost coplanar [O-C-C-N and C-C-C-C torsion angles = -178.71 (19) and 178.42 (18)°, respectively]. The conformation about the C=C bond [1.328 (3) Å] is E, and the triazole methyl group and the carbonyl O atom are syn. In the crystal, centrosymmetrically related mol-ecules are connected by π-π inter-actions between the triazole and p-tolyl rings [centroid-centroid distance = 3.6599 (12) Å] and these are linked into a three-dimensional architecture by C-H⋯N and C-H⋯π inter-actions.

Related literature

For the biological activities of chalcone derivatives, see: Abdel-Wahab et al. (2012 ▶); n class="Gene">Singh et al. (2012 ▶). For a related structure, see: Abdel-Wahab et al. (2013 ▶).

Experimental

Crystal data

C19H16FN3O

M = 321.35

Triclinic,

a = 6.2890 (5) Å

b = 10.8874 (8) Å

c = 11.9691 (9) Å

α = 101.144 (7)°

β = 92.634 (6)°

γ = 91.634 (6)°

V = 802.65 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.35 × 0.35 × 0.35 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.887, T max = 1.000

6854 measured reflections

3697 independent reflections

2308 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.139

S = 1.03

3697 reflections

220 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.16 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813008246/hb7061sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813008246/hb7061Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813008246/hb7061Isup3.cml

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

C19H16FN3O	Z = 2
Mr = 321.35	F(000) = 336
Triclinic, P1	Dx = 1.330 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.2890 (5) Å	Cell parameters from 1657 reflections
b = 10.8874 (8) Å	θ = 3.2–27.5°
c = 11.9691 (9) Å	µ = 0.09 mm−1
α = 101.144 (7)°	T = 295 K
β = 92.634 (6)°	Block, colourless
γ = 91.634 (6)°	0.35 × 0.35 × 0.35 mm
V = 802.65 (11) Å3

Agilent SuperNova Dual diffractometer with an Atlas detector	3697 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2308 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.027
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 3.3°
ω scan	h = −8→6
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −12→14
Tmin = 0.887, Tmax = 1.000	l = −15→15
6854 measured reflections

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)] = 0.053	H-atom parameters constrained
wR(F2) = 0.139	w = 1/[σ2(Fo2) + (0.0416P)2 + 0.2071P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
3697 reflections	Δρmax = 0.18 e Å−3
220 parameters	Δρmin = −0.16 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: 0.015 (2)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
F1	−0.0563 (2)	0.53130 (13)	1.39178 (11)	0.0761 (4)
N1	0.6205 (2)	0.22322 (14)	0.56828 (13)	0.0432 (4)
N2	0.4313 (3)	0.27912 (17)	0.59390 (14)	0.0540 (5)
N3	0.4258 (3)	0.30257 (16)	0.70426 (14)	0.0520 (4)
O1	0.8127 (3)	0.23574 (16)	0.91088 (12)	0.0704 (5)
C1	0.3444 (3)	0.37835 (17)	1.14542 (15)	0.0457 (5)
C2	0.4017 (3)	0.38896 (19)	1.26083 (16)	0.0498 (5)
H2	0.5333	0.3613	1.2821	0.060*
C3	0.2675 (4)	0.43951 (19)	1.34448 (16)	0.0529 (5)
H3	0.3067	0.4456	1.4213	0.064*
C4	0.0766 (4)	0.48017 (19)	1.31138 (17)	0.0515 (5)
C5	0.0113 (4)	0.4712 (2)	1.19918 (17)	0.0558 (6)
H5	−0.1206	0.4995	1.1793	0.067*
C6	0.1452 (3)	0.4193 (2)	1.11674 (17)	0.0533 (5)
H6	0.1018	0.4114	1.0403	0.064*
C7	0.4949 (3)	0.32849 (18)	1.06035 (17)	0.0501 (5)
H7	0.6196	0.2985	1.0881	0.060*
C8	0.4757 (4)	0.32071 (19)	0.94822 (16)	0.0521 (5)
H8	0.3522	0.3474	0.9161	0.063*
C9	0.6455 (3)	0.27077 (18)	0.87383 (16)	0.0483 (5)
C10	0.6071 (3)	0.26277 (17)	0.75028 (16)	0.0429 (5)
C11	0.7336 (3)	0.21146 (17)	0.66377 (15)	0.0415 (4)
C12	0.9405 (3)	0.1506 (2)	0.66496 (19)	0.0604 (6)
H12A	0.9507	0.0908	0.5952	0.091*
H12B	0.9511	0.1085	0.7284	0.091*
H12C	1.0540	0.2128	0.6721	0.091*
C13	0.6637 (3)	0.17915 (17)	0.45098 (16)	0.0441 (5)
C14	0.8548 (3)	0.21016 (19)	0.40945 (17)	0.0512 (5)
H14	0.9561	0.2620	0.4565	0.061*
C15	0.8934 (4)	0.1630 (2)	0.29706 (18)	0.0574 (6)
H15	1.0225	0.1835	0.2690	0.069*
C16	0.7455 (4)	0.08618 (19)	0.22491 (17)	0.0562 (6)
C17	0.5531 (4)	0.0601 (2)	0.26836 (18)	0.0601 (6)
H17	0.4492	0.0111	0.2207	0.072*
C18	0.5117 (4)	0.10497 (19)	0.38069 (17)	0.0543 (5)
H18	0.3822	0.0853	0.4087	0.065*
C19	0.7960 (5)	0.0318 (2)	0.10330 (19)	0.0821 (8)
H19A	0.6658	0.0068	0.0585	0.123*
H19B	0.8820	−0.0399	0.1022	0.123*
H19C	0.8722	0.0938	0.0720	0.123*

	U11	U22	U33	U12	U13	U23
F1	0.0828 (10)	0.0924 (10)	0.0550 (8)	0.0284 (8)	0.0226 (7)	0.0114 (7)
N1	0.0393 (9)	0.0511 (9)	0.0388 (9)	0.0029 (7)	0.0042 (7)	0.0068 (7)
N2	0.0441 (10)	0.0750 (12)	0.0431 (9)	0.0127 (9)	0.0055 (8)	0.0093 (9)
N3	0.0472 (10)	0.0665 (11)	0.0428 (9)	0.0104 (8)	0.0077 (8)	0.0095 (8)
O1	0.0638 (11)	0.1007 (13)	0.0487 (9)	0.0244 (9)	0.0017 (8)	0.0170 (9)
C1	0.0545 (13)	0.0444 (11)	0.0382 (10)	0.0018 (9)	0.0039 (9)	0.0078 (9)
C2	0.0528 (13)	0.0565 (12)	0.0416 (11)	0.0052 (10)	−0.0002 (9)	0.0138 (9)
C3	0.0643 (15)	0.0604 (13)	0.0334 (10)	0.0001 (11)	0.0014 (10)	0.0080 (9)
C4	0.0610 (14)	0.0514 (12)	0.0432 (11)	0.0070 (10)	0.0123 (10)	0.0085 (9)
C5	0.0539 (14)	0.0654 (14)	0.0494 (12)	0.0118 (11)	0.0015 (10)	0.0135 (11)
C6	0.0592 (14)	0.0644 (13)	0.0356 (10)	0.0053 (11)	−0.0031 (10)	0.0090 (10)
C7	0.0556 (13)	0.0509 (11)	0.0444 (11)	0.0054 (10)	0.0038 (10)	0.0098 (9)
C8	0.0594 (14)	0.0567 (12)	0.0412 (11)	0.0093 (10)	0.0060 (10)	0.0099 (9)
C9	0.0554 (14)	0.0474 (11)	0.0418 (11)	0.0031 (10)	0.0043 (10)	0.0076 (9)
C10	0.0426 (11)	0.0441 (10)	0.0415 (10)	−0.0001 (8)	0.0038 (9)	0.0074 (9)
C11	0.0404 (11)	0.0436 (10)	0.0410 (10)	−0.0005 (8)	0.0018 (9)	0.0101 (8)
C12	0.0488 (13)	0.0772 (15)	0.0562 (13)	0.0137 (11)	0.0039 (10)	0.0139 (12)
C13	0.0495 (12)	0.0443 (10)	0.0382 (10)	0.0024 (9)	0.0065 (9)	0.0065 (8)
C14	0.0504 (13)	0.0537 (12)	0.0479 (11)	−0.0015 (10)	0.0074 (10)	0.0053 (10)
C15	0.0613 (15)	0.0612 (13)	0.0529 (13)	0.0061 (11)	0.0198 (11)	0.0145 (11)
C16	0.0801 (17)	0.0473 (12)	0.0438 (11)	0.0160 (11)	0.0120 (11)	0.0112 (10)
C17	0.0747 (17)	0.0545 (13)	0.0479 (12)	−0.0054 (11)	−0.0024 (11)	0.0042 (10)
C18	0.0556 (14)	0.0586 (13)	0.0475 (12)	−0.0072 (10)	0.0049 (10)	0.0085 (10)
C19	0.122 (2)	0.0779 (17)	0.0474 (13)	0.0249 (16)	0.0189 (15)	0.0076 (12)

F1—C4	1.352 (2)	C8—H8	0.9300
N1—C11	1.348 (2)	C9—C10	1.473 (3)
N1—N2	1.372 (2)	C10—C11	1.376 (2)
N1—C13	1.434 (2)	C11—C12	1.478 (3)
N2—N3	1.298 (2)	C12—H12A	0.9600
N3—C10	1.362 (3)	C12—H12B	0.9600
O1—C9	1.222 (2)	C12—H12C	0.9600
C1—C6	1.392 (3)	C13—C18	1.376 (3)
C1—C2	1.393 (3)	C13—C14	1.380 (3)
C1—C7	1.460 (3)	C14—C15	1.379 (3)
C2—C3	1.381 (3)	C14—H14	0.9300
C2—H2	0.9300	C15—C16	1.384 (3)
C3—C4	1.360 (3)	C15—H15	0.9300
C3—H3	0.9300	C16—C17	1.382 (3)
C4—C5	1.370 (3)	C16—C19	1.513 (3)
C5—C6	1.374 (3)	C17—C18	1.378 (3)
C5—H5	0.9300	C17—H17	0.9300
C6—H6	0.9300	C18—H18	0.9300
C7—C8	1.328 (3)	C19—H19A	0.9600
C7—H7	0.9300	C19—H19B	0.9600
C8—C9	1.471 (3)	C19—H19C	0.9600
C11—N1—N2	111.07 (15)	C11—C10—C9	128.12 (19)
C11—N1—C13	129.77 (16)	N1—C11—C10	103.79 (17)
N2—N1—C13	118.99 (15)	N1—C11—C12	124.33 (17)
N3—N2—N1	106.75 (15)	C10—C11—C12	131.83 (18)
N2—N3—C10	109.28 (15)	C11—C12—H12A	109.5
C6—C1—C2	117.65 (18)	C11—C12—H12B	109.5
C6—C1—C7	122.83 (18)	H12A—C12—H12B	109.5
C2—C1—C7	119.50 (19)	C11—C12—H12C	109.5
C3—C2—C1	121.6 (2)	H12A—C12—H12C	109.5
C3—C2—H2	119.2	H12B—C12—H12C	109.5
C1—C2—H2	119.2	C18—C13—C14	120.54 (18)
C4—C3—C2	118.14 (19)	C18—C13—N1	118.91 (17)
C4—C3—H3	120.9	C14—C13—N1	120.55 (18)
C2—C3—H3	120.9	C15—C14—C13	118.9 (2)
F1—C4—C3	119.19 (19)	C15—C14—H14	120.5
F1—C4—C5	118.0 (2)	C13—C14—H14	120.5
C3—C4—C5	122.79 (19)	C14—C15—C16	121.8 (2)
C4—C5—C6	118.5 (2)	C14—C15—H15	119.1
C4—C5—H5	120.7	C16—C15—H15	119.1
C6—C5—H5	120.7	C17—C16—C15	117.70 (19)
C5—C6—C1	121.32 (19)	C17—C16—C19	121.7 (2)
C5—C6—H6	119.3	C15—C16—C19	120.6 (2)
C1—C6—H6	119.3	C18—C17—C16	121.5 (2)
C8—C7—C1	128.0 (2)	C18—C17—H17	119.2
C8—C7—H7	116.0	C16—C17—H17	119.2
C1—C7—H7	116.0	C13—C18—C17	119.4 (2)
C7—C8—C9	121.4 (2)	C13—C18—H18	120.3
C7—C8—H8	119.3	C17—C18—H18	120.3
C9—C8—H8	119.3	C16—C19—H19A	109.5
O1—C9—C8	122.50 (19)	C16—C19—H19B	109.5
O1—C9—C10	120.09 (18)	H19A—C19—H19B	109.5
C8—C9—C10	117.41 (19)	C16—C19—H19C	109.5
N3—C10—C11	109.11 (17)	H19A—C19—H19C	109.5
N3—C10—C9	122.71 (17)	H19B—C19—H19C	109.5
C11—N1—N2—N3	0.2 (2)	C8—C9—C10—C11	−174.80 (18)
C13—N1—N2—N3	175.93 (15)	N2—N1—C11—C10	−0.2 (2)
N1—N2—N3—C10	−0.1 (2)	C13—N1—C11—C10	−175.33 (17)
C6—C1—C2—C3	−0.7 (3)	N2—N1—C11—C12	177.50 (18)
C7—C1—C2—C3	177.77 (18)	C13—N1—C11—C12	2.3 (3)
C1—C2—C3—C4	−0.5 (3)	N3—C10—C11—N1	0.1 (2)
C2—C3—C4—F1	−179.26 (18)	C9—C10—C11—N1	177.11 (18)
C2—C3—C4—C5	1.1 (3)	N3—C10—C11—C12	−177.3 (2)
F1—C4—C5—C6	−179.99 (18)	C9—C10—C11—C12	−0.3 (3)
C3—C4—C5—C6	−0.3 (3)	C11—N1—C13—C18	125.1 (2)
C4—C5—C6—C1	−1.0 (3)	N2—N1—C13—C18	−49.8 (2)
C2—C1—C6—C5	1.5 (3)	C11—N1—C13—C14	−54.7 (3)
C7—C1—C6—C5	−176.93 (19)	N2—N1—C13—C14	130.5 (2)
C6—C1—C7—C8	4.2 (3)	C18—C13—C14—C15	−1.6 (3)
C2—C1—C7—C8	−174.2 (2)	N1—C13—C14—C15	178.08 (18)
C1—C7—C8—C9	178.30 (18)	C13—C14—C15—C16	0.3 (3)
C7—C8—C9—O1	−1.0 (3)	C14—C15—C16—C17	1.6 (3)
C7—C8—C9—C10	178.42 (18)	C14—C15—C16—C19	−177.6 (2)
N2—N3—C10—C11	0.0 (2)	C15—C16—C17—C18	−2.3 (3)
N2—N3—C10—C9	−177.20 (17)	C19—C16—C17—C18	176.8 (2)
O1—C9—C10—N3	−178.71 (19)	C14—C13—C18—C17	0.9 (3)
C8—C9—C10—N3	1.9 (3)	N1—C13—C18—C17	−178.76 (18)
O1—C9—C10—C11	4.6 (3)	C16—C17—C18—C13	1.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12C···N3i	0.96	2.49	3.399 (3)	158
C2—H2···Cg1ii	0.93	2.91	3.650 (2)	138

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C13–C18 benzene

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12C⋯N3i	0.96	2.49	3.399 (3)	158
C2—H2⋯Cg1ii	0.93	2.91	3.650 (2)	138

Symmetry codes: (i) ; (ii) .