1-[5-Methyl-1-(4-methyl­phen­yl)-1H-1,2,3-triazol-4-yl]ethanone

El-Hiti, G.A.; Abdel-Wahab, B.F.; Alotaibi, M.H.; Hegazy, A.S.; Kariuki, B.M.

doi:10.1107/S2414314617017825

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 12| December 2017| x171782

https://doi.org/10.1107/S2414314617017825

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1-[5-Methyl-1-(4-methylphenyl)-1H-1,2,3-triazol-4-yl]ethanone

Gamal A. El-Hiti,^a ^* Bakr F. Abdel-Wahab,^b,^c Mohammad Hayal Alotaibi,^d Amany S. Hegazy ^e and Benson M. Kariuki ^e ‡

^aCornea Research Chair, Department of Optometry, College of Applied Medical Sciences, King Saud University, PO Box 10219, Riyadh 11433, Saudi Arabia, ^bDepartment of Chemistry, College of Science and Humanities, Shaqra University, Duwadimi, Saudi Arabia, ^cApplied Organic Chemistry Department, National Research Centre, Dokki, Giza, Egypt, ^dNational Center for Petrochemicals Technology, King Abdulaziz City for Science and Technology, PO Box 6086, Riyadh 11442, Saudi Arabia, and ^eSchool of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, UK
^*Correspondence e-mail: gelhiti@ksu.edu.sa

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 30 November 2017; accepted 13 December 2017; online 15 December 2017)

In the title compound, C₁₂H₁₃N₃O, the p-tolyl ring is twisted away from the mean plane (r.m.s. deviation = 0.044 Å) of the rest of the molecule by 50.84 (6)°. In the crystal, molecules are linked by C—H⋯π interactions, forming zigzag chains propagating in the b-axis direction.

Keywords: crystal structure; triazole; C—H⋯π interactions.

CCDC reference: 1810966

Structure description

1,2,3-Triazole derivatives can be synthesized using a variety of simple and efficient procedures. The most common one involves cycloaddition of azides and alkynes in the presence of a catalyst (Rostovtsev et al., 2002 ; Himo et al., 2005 ; Boren et al., 2008 ; Quan et al., 2014 ; Banday & Hruby, 2014 ; Kolarovič et al., 2011 ; Shao et al., 2011 ; Liu & Reiser, 2011 ). A number of heterocycles containing the 1,2,3-triazole moiety show various medicinal applications (Bock et al., 2006 , 2007 ; Agalave et al., 2011 ).

The molecule of the title compound, illustrated in Fig. 1, is not planar as the p-toly ring (C2–C7) is twisted by 50.84 (6)° away from the mean plane of the rest of the molecule (O1/N1—N3/C8—C12; r.m.s. deviation = 0.044 Å).

Figure 1
A view of the molecular structure of the title molecule, with the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

In the crystal, zigzag chains, propagating along the b-axis direction (Fig. 2), are formed via molecules being linked by C—H⋯π interaction (Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1C⋯Cgⁱ	0.96	2.82	3.729 (3)	159
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 2
A view along the a axis of the crystal packing of the title compound. The C—H⋯π interactions are represented by dashed lines [see Table 1

; only H atom H1C (grey ball) has been included].

Synthesis and crystallization

The title compound was synthesized from the reaction of 1-azido-4-methylbenzene (10 mmol, 1.33 g) and pentane-2,4-dione (10 mmol, 1.00 g) in anhydrous ethanol (10 mL) in the presence of anhydrous potassium carbonate (15 mmol, 2.07 g). The reaction was heated under reflux for 2 h. The solid obtained on cooling was filtered, washed with ethanol and recrystallized from dimethylformamide solution, to give colourless block-like crystals of the title compound (m.p. 378–380 K; cf. data reported by Pokhodylo et al., 2009 ).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₂H₁₃N₃O
M_r	215.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	5.7747 (4), 6.5171 (5), 30.234 (2)
β (°)	95.342 (7)
V (Å³)	1132.88 (14)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.08
Crystal size (mm)	0.28 × 0.20 × 0.11

Data collection
Diffractometer	Agilent SuperNova Dual Source diffractometer with an Atlas detector
Absorption correction	Gaussian (CrysAlis PRO; Agilent, 2014 )
T_min, T_max	0.978, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	6757, 2745, 1930
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.698

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.152, 1.07
No. of reflections	2745
No. of parameters	149
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.16
Computer programs: CrysAlis PRO (Agilent, 2014), SHELXS2013 (Sheldrick, 2008 ), WinGX (Farrugia, 2012 ), Mercury (Macrae et al., 2008 ), SHELXL2013 (Sheldrick, 2015 ), PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1810966

Crystal structure: contains datablocks I, Global. DOI: https://doi.org/10.1107/S2414314617017825/su5411sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617017825/su5411Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617017825/su5411Isup3.cml

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: WinGX (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2015), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

1-[5-Methyl-1-(4-methylphenyl)-1H-1,2,3-triazol-4-yl]ethanone top

Crystal data top

C₁₂H₁₃N₃O	F(000) = 456
M_r = 215.25	D_x = 1.262 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.7747 (4) Å	Cell parameters from 2318 reflections
b = 6.5171 (5) Å	θ = 4.2–28.9°
c = 30.234 (2) Å	µ = 0.08 mm⁻¹
β = 95.342 (7)°	T = 296 K
V = 1132.88 (14) Å³	Block, colourless
Z = 4	0.28 × 0.20 × 0.11 mm

Data collection top

Agilent SuperNova Dual Source diffractometer with an Atlas detector	1930 reflections with I > 2σ(I)
ω scans	R_int = 0.027
Absorption correction: gaussian (CrysAlis PRO; Agilent, 2014)	θ_max = 29.8°, θ_min = 3.4°
T_min = 0.978, T_max = 0.989	h = −8→7
6757 measured reflections	k = −7→8
2745 independent reflections	l = −39→31

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)] = 0.060	H-atom parameters constrained
wR(F²) = 0.152	w = 1/[σ²(F_o²) + (0.0534P)² + 0.4633P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
2745 reflections	Δρ_max = 0.22 e Å⁻³
149 parameters	Δρ_min = −0.16 e Å⁻³
0 restraints	Extinction correction: SHELXL2013 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.009 (2)

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
C1	0.8118 (4)	0.7032 (4)	0.27023 (8)	0.0618 (6)
H1A	0.8921	0.6129	0.2517	0.093*
H1B	0.9230	0.7810	0.2889	0.093*
H1C	0.7147	0.7950	0.2519	0.093*
C2	0.6633 (3)	0.5785 (3)	0.29871 (6)	0.0451 (5)
C3	0.7163 (3)	0.3765 (3)	0.30953 (7)	0.0489 (5)
H3	0.8467	0.3163	0.2991	0.059*
C4	0.5796 (3)	0.2620 (3)	0.33559 (6)	0.0446 (5)
H4	0.6178	0.1265	0.3426	0.054*
C5	0.3860 (3)	0.3514 (3)	0.35103 (6)	0.0397 (4)
C6	0.3286 (3)	0.5524 (3)	0.34067 (6)	0.0457 (5)
H6	0.1977	0.6121	0.3510	0.055*
C7	0.4684 (4)	0.6643 (3)	0.31467 (7)	0.0476 (5)
H7	0.4303	0.8000	0.3078	0.057*
C8	0.1361 (3)	0.2725 (3)	0.41319 (6)	0.0447 (5)
C9	0.1918 (5)	0.4577 (4)	0.44114 (8)	0.0720 (7)
H9A	0.3572	0.4774	0.4448	0.108*
H9B	0.1350	0.4389	0.4697	0.108*
H9C	0.1190	0.5759	0.4269	0.108*
C10	−0.0073 (3)	0.1067 (3)	0.41849 (6)	0.0451 (5)
C11	−0.1760 (4)	0.0730 (4)	0.45140 (7)	0.0567 (6)
C12	−0.3247 (4)	−0.1147 (4)	0.44668 (9)	0.0703 (7)
H12A	−0.4442	−0.1063	0.4667	0.105*
H12B	−0.2306	−0.2339	0.4537	0.105*
H12C	−0.3948	−0.1246	0.4167	0.105*
N1	0.2356 (3)	0.2300 (2)	0.37565 (5)	0.0408 (4)
N2	0.1592 (3)	0.0449 (2)	0.35832 (5)	0.0474 (4)
N3	0.0134 (3)	−0.0285 (2)	0.38449 (6)	0.0487 (4)
O1	−0.1958 (4)	0.1974 (3)	0.48064 (7)	0.0915 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0540 (12)	0.0736 (15)	0.0592 (14)	−0.0061 (12)	0.0137 (10)	0.0128 (11)
C2	0.0411 (10)	0.0536 (12)	0.0409 (10)	−0.0041 (9)	0.0049 (8)	−0.0008 (8)
C3	0.0393 (10)	0.0578 (12)	0.0505 (11)	0.0045 (9)	0.0100 (8)	−0.0026 (9)
C4	0.0420 (10)	0.0432 (10)	0.0488 (11)	0.0058 (9)	0.0050 (8)	0.0009 (8)
C5	0.0412 (10)	0.0405 (10)	0.0380 (9)	0.0003 (8)	0.0075 (7)	−0.0028 (7)
C6	0.0463 (11)	0.0408 (10)	0.0517 (11)	0.0044 (9)	0.0138 (9)	−0.0041 (8)
C7	0.0534 (11)	0.0392 (10)	0.0513 (11)	−0.0008 (9)	0.0103 (9)	0.0008 (8)
C8	0.0521 (11)	0.0433 (10)	0.0399 (10)	0.0026 (9)	0.0109 (8)	−0.0037 (8)
C9	0.102 (2)	0.0596 (14)	0.0586 (14)	−0.0184 (14)	0.0299 (13)	−0.0191 (11)
C10	0.0484 (11)	0.0439 (10)	0.0440 (10)	0.0030 (9)	0.0096 (8)	0.0001 (8)
C11	0.0587 (13)	0.0601 (13)	0.0535 (12)	0.0004 (11)	0.0180 (10)	0.0019 (10)
C12	0.0670 (15)	0.0763 (16)	0.0711 (15)	−0.0135 (13)	0.0260 (12)	0.0055 (13)
N1	0.0463 (9)	0.0358 (8)	0.0415 (8)	0.0012 (7)	0.0101 (7)	−0.0028 (6)
N2	0.0530 (10)	0.0393 (9)	0.0518 (10)	−0.0018 (8)	0.0153 (8)	−0.0075 (7)
N3	0.0535 (10)	0.0429 (9)	0.0517 (10)	−0.0016 (8)	0.0144 (8)	−0.0032 (7)
O1	0.1084 (15)	0.0912 (13)	0.0840 (13)	−0.0220 (12)	0.0574 (11)	−0.0271 (11)

Geometric parameters (Å, º) top

C1—C2	1.508 (3)	C8—N1	1.348 (2)
C1—H1A	0.9600	C8—C10	1.380 (3)
C1—H1B	0.9600	C8—C9	1.491 (3)
C1—H1C	0.9600	C9—H9A	0.9600
C2—C7	1.383 (3)	C9—H9B	0.9600
C2—C3	1.384 (3)	C9—H9C	0.9600
C3—C4	1.384 (3)	C10—N3	1.368 (2)
C3—H3	0.9300	C10—C11	1.472 (3)
C4—C5	1.380 (3)	C11—O1	1.212 (3)
C4—H4	0.9300	C11—C12	1.494 (3)
C5—C6	1.380 (3)	C12—H12A	0.9600
C5—N1	1.434 (2)	C12—H12B	0.9600
C6—C7	1.385 (3)	C12—H12C	0.9600
C6—H6	0.9300	N1—N2	1.372 (2)
C7—H7	0.9300	N2—N3	1.299 (2)

C2—C1—H1A	109.5	N1—C8—C9	123.86 (19)
C2—C1—H1B	109.5	C10—C8—C9	131.93 (18)
H1A—C1—H1B	109.5	C8—C9—H9A	109.5
C2—C1—H1C	109.5	C8—C9—H9B	109.5
H1A—C1—H1C	109.5	H9A—C9—H9B	109.5
H1B—C1—H1C	109.5	C8—C9—H9C	109.5
C7—C2—C3	118.11 (18)	H9A—C9—H9C	109.5
C7—C2—C1	120.38 (19)	H9B—C9—H9C	109.5
C3—C2—C1	121.51 (19)	N3—C10—C8	108.77 (16)
C2—C3—C4	121.47 (18)	N3—C10—C11	121.45 (18)
C2—C3—H3	119.3	C8—C10—C11	129.58 (18)
C4—C3—H3	119.3	O1—C11—C10	120.4 (2)
C5—C4—C3	119.20 (18)	O1—C11—C12	121.7 (2)
C5—C4—H4	120.4	C10—C11—C12	117.9 (2)
C3—C4—H4	120.4	C11—C12—H12A	109.5
C4—C5—C6	120.60 (18)	C11—C12—H12B	109.5
C4—C5—N1	119.44 (16)	H12A—C12—H12B	109.5
C6—C5—N1	119.84 (16)	C11—C12—H12C	109.5
C5—C6—C7	119.21 (18)	H12A—C12—H12C	109.5
C5—C6—H6	120.4	H12B—C12—H12C	109.5
C7—C6—H6	120.4	C8—N1—N2	110.80 (15)
C2—C7—C6	121.42 (18)	C8—N1—C5	130.56 (16)
C2—C7—H7	119.3	N2—N1—C5	118.44 (14)
C6—C7—H7	119.3	N3—N2—N1	107.14 (14)
N1—C8—C10	104.15 (16)	N2—N3—C10	109.14 (16)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1C···Cgⁱ	0.96	2.82	3.729 (3)	159

Symmetry code: (i) −x+1, y+1/2, −z+1/2.

Footnotes

‡Additional correspondence author, e-mail: kariukib@cardiff.ac.uk

Funding information

This project was supported by King Saud University, Deanship of Scientific Research, Research Chairs.

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