(2E)-3-(4-Fluoro­phen­yl)-1-[5-methyl-1-(4-methyl­phen­yl)-1H-1,2,3-triazol-4-yl]prop-2-en-1-one

Abdel-Wahab, B.F.; Mohamed, H.A.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536813008246

organic compounds

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ISSN: 2056-9890

Volume 69| Part 5| May 2013| Page o638

https://doi.org/10.1107/S1600536813008246

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(2E)-3-(4-Fluorophenyl)-1-[5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazol-4-yl]prop-2-en-1-one¹

Bakr F. Abdel-Wahab,^a Hanan A. Mohamed,^a Seik Weng Ng ^b,^c and Edward R. T. Tiekink ^b ^*

^aApplied Organic Chemistry Department, National Research Centre, Dokki, 12622 Giza, Egypt, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 25 March 2013; accepted 25 March 2013; online 5 April 2013)

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 molecules are connected by π–π interactions 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 interactions.

Related literature

For the biological activities of chalcone derivatives, see: Abdel-Wahab et al. (2012 ); Singh et al. (2012 ). For a related structure, see: Abdel-Wahab et al. (2013 ).

Experimental

Crystal data

C₁₉H₁₆FN₃O
M_r = 321.35
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.053
wR(F²) = 0.139
S = 1.03
3697 reflections
220 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.16 e Å⁻³

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) x+1, y, z; (ii) x, y, z+1.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536813008246/hb7061sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813008246/hb7061Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536813008246/hb7061Isup3.cml

checkCIF report

Comment top

Chalcone derivatives exhibit a range of biological activities (Abdel-Wahab et al., 2012; Singh et al., 2012) and in this connection, the title compound was synthesized and characterized crystallographically.

In (I), the p-tolyl ring attached to the triazole ring is inclined, forming a dihedral angle of 51.79 (11)°. By contrast, the chalcone residue is co-planar as seen in the values of the O1—C9—C10—N3 and C7—C8—C9—C10 torsion angles of -178.71 (19) and 178.42 (18)°, respectively. This co-planarity extends to include the terminal fluorobenzene ring [C6—C1—C7—C8 = 4.2 (3)°]. The conformation about the C7═C8 bond [1.328 (3) Å] is E, and the triazole-methyl and carbonyl-O1 substituents are syn. The conformation with respect to the triazole ring and chalcone residue resembles that found in a related compound (Abdel-Wahab et al., 2013).

In the crystal structure, centrosymmetrically related molecules are connected by π—π interactions between the triazole and p-tolyl rings [inter-centroid distance = 3.6599 (12) Å, angle of inclination = 2.30 (11)° for symmetry operation: 1 - x, 1 - y, 2 - z]. The dimeric aggregates are connected into a three-dimensional architecture by C—H···N and C—H···π interactions, Fig. 2 and Table 1.

Related literature top

For the biological activities of chalcone derivatives, see: Abdel-Wahab et al. (2012); Singh et al. (2012). For a related structure, see: Abdel-Wahab et al. (2013).

Experimental top

The title compound was prepared following the reported method (Abdel-Wahab et al., 2012). Colourless blocks were obtained from its DMF solution by slow evaporation at room temperature.

Structure description top

For the biological activities of chalcone derivatives, see: Abdel-Wahab et al. (2012); Singh et al. (2012). For a related structure, see: Abdel-Wahab et al. (2013).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); 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).

Figures top

	Fig. 1. The molecular structure of (I) showing displacement ellipsoids at the 35% probability level.
	Fig. 2. A view of the crystal packing in projection down the c axis. The C—H···N, C—H···π and π—π interactions are shown as blue, orange and purple dashed lines, respectively.

(2E)-3-(4-Fluorophenyl)-1-[5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazol-4-yl]prop-2-en-1-one top

Crystal data top

C₁₉H₁₆FN₃O	Z = 2
M_r = 321.35	F(000) = 336
Triclinic, P1	D_x = 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

Data collection top

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	R_int = 0.027
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 3.3°
ω scan	h = −8→6
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −12→14
T_min = 0.887, T_max = 1.000	l = −15→15
6854 measured reflections

Refinement top

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(F_o²) + (0.0416P)² + 0.2071P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
3697 reflections	Δρ_max = 0.18 e Å⁻³
220 parameters	Δρ_min = −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)

Crystal data top

C₁₉H₁₆FN₃O	γ = 91.634 (6)°
M_r = 321.35	V = 802.65 (11) Å³
Triclinic, P1	Z = 2
a = 6.2890 (5) Å	Mo Kα radiation
b = 10.8874 (8) Å	µ = 0.09 mm⁻¹
c = 11.9691 (9) Å	T = 295 K
α = 101.144 (7)°	0.35 × 0.35 × 0.35 mm
β = 92.634 (6)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3697 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2308 reflections with I > 2σ(I)
T_min = 0.887, T_max = 1.000	R_int = 0.027
6854 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.139	H-atom parameters constrained
S = 1.03	Δρ_max = 0.18 e Å⁻³
3697 reflections	Δρ_min = −0.16 e Å⁻³
220 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x+1, y, z; (ii) x, y, z+1.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₆FN₃O
M_r	321.35
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	6.2890 (5), 10.8874 (8), 11.9691 (9)
α, β, γ (°)	101.144 (7), 92.634 (6), 91.634 (6)
V (Å³)	802.65 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.35 × 0.35 × 0.35

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.887, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	6854, 3697, 2308
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.139, 1.03
No. of reflections	3697
No. of parameters	220
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.16

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

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) x+1, y, z; (ii) x, y, z+1.

Footnotes

¹Additional correspondence author, e-mail: bakrfatehy@yahoo.com.

Acknowledgements

We thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR–MOHE/SC/03).

References

Abdel-Wahab, B. F., Abdel-Latif, E., Mohamed, H. A. & Awad, G. E. A. (2012). Eur. J. Med. Chem. 52, 263–268. Web of Science CAS PubMed Google Scholar
Abdel-Wahab, B. F., Abdel-Latif, E., Ng, S. W. & Tiekink, E. R. T. (2013). Acta Cryst. E69, o639–o640. CSD CrossRef CAS IUCr Journals Google Scholar
Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England. Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Singh, P., Raj, R., Kumar, V., Mahajan, M. P., Bedi, P. M., Kaur, T. & Saxena, A. K. (2012). Eur. J. Med. Chem. 47, 594–600. Web of Science CrossRef CAS PubMed Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(2E)-3-(4-Fluoro­phen­yl)-1-[5-methyl-1-(4-methyl­phen­yl)-1H-1,2,3-triazol-4-yl]prop-2-en-1-one1

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

(2E)-3-(4-Fluorophenyl)-1-[5-methyl-1-(4-methylphenyl)-1H-1,2,3-triazol-4-yl]prop-2-en-1-one¹