Ethyl 2-[1-(3-methyl­but­yl)-4-phenyl-1H-1,2,3-triazol-5-yl]-2-oxo­acetate

Ahmed, M.N.; Yasin, K.A.; Tahir, M.N.; Hafeez, M.; Aziz, S.

doi:10.1107/S1600536813030420

organic compounds

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ISSN: 2056-9890

Volume 69| Part 12| December 2013| Page o1768

doi:10.1107/S1600536813030420

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Ethyl 2-[1-(3-methylbutyl)-4-phenyl-1H-1,2,3-triazol-5-yl]-2-oxoacetate

Muhammad Naeem Ahmed,^a Khawaja Ansar Yasin,^a M. Nawaz Tahir,^b ^* Muhammad Hafeez ^a and Shahid Aziz ^a

^aDepartment of Chemistry, The University of Azad Jammu and Kashmir, Muzaffarabad 13100, Pakistan, and ^bUniversity of Sargodha, Department of Physics, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 17 October 2013; accepted 6 November 2013; online 13 November 2013)

In the title compound, C₁₇H₂₁N₃O₃, the non-planar (r.m.s. deviation = 0.212 Å) ethyl (oxo)acetate group is oriented towards the phenyl substituent. The triazole and benzene rings are twisted with respect to each other, making a dihedral angle of 41.69 (6)°. In the crystal, molecules are arranged into centrosymmetric R₂²(10) dimers via pairs of C—H⋯O interactions involving the ethyl (oxo)acetate groups. In addition, the triazole rings show π–π stacking interactions, with their centroids at a distance of 3.745 (2) Å.

CCDC reference: 970558

Related literature

For the biological activity of 1,4,5-trisubstituted 1,2,3-triazoles, see: Siddiqi & Ahsan (2010 ); Siddiqi et al. (2011 ). For the synthesis, see: Wang et al. (2013 ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₇H₂₁N₃O₃
M_r = 315.37
Triclinic, $[P \overline 1]$
a = 8.1710 (8) Å
b = 10.0684 (9) Å
c = 10.6066 (10) Å
α = 98.331 (3)°
β = 94.220 (3)°
γ = 95.367 (3)°
V = 856.23 (14) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.32 × 0.25 × 0.21 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.973, T_max = 0.982
11605 measured reflections
4189 independent reflections
3196 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.156
S = 1.06
4189 reflections
211 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11B⋯O2ⁱ	0.97	2.59	3.338 (2)	134
Symmetry code: (i) -x+3, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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 PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Supporting information

CCDC reference: 970558

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813030420/gk2593sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813030420/gk2593Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813030420/gk2593Isup3.cml

checkCIF report

Comment top

1,4,5-Trisubstituted 1,2,3-triazoles are important compounds due to their diverse biological activities including antibacterial, antifungal, antimalarial, antiviral, anticonvulsant, antidepressant and anticancer (Siddiqi & Ahsan, 2010; Siddiqi et al., 2011). Taking the biological activity of 1,2,3-triazole derivatives into account some novel 1, 2, 3-triazoles have been designed and synthesized. Here we report the crystal structure of title compound (Fig. 1).

The benzene ring A (C1–C6) and the triazol ring B (C7/C8/N1/N2/N3) are planar with r. m. s. deviations of 0.0062 Å and 0.0066 Å, respectively. The dihedral angle between A/B is 41.69 (6)°. The intermolecular C—H···O hydrogen bond (Table 1, Fig. 2) generates centrosymmetric R₂²(10) motif (Bernstein et al., 1995) and molecules form dimers. There is also π–π interaction between the triazole rings with their centroids at a distance of 3.745 (2) Å [Cg—Cgⁱ: i = 2 - x, 1 - y, -z, where Cg is the centroid of triazol ring].

Related literature top

For related studies, see: Siddiqi & Ahsan (2010); Siddiqi et al. (2011). For the synthesis, see: Wang et al. (2013). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

To a suspension of 1-azido-3-methylbutane (0.068 g, 0.6 mmol) and 1-copper(I)phenylethyne (0.082 g, 0.5 mmol) in chlorobenzene (1 ml) was added ethyl chloro(oxo)acetate (0.068 g, 0.5 mmol). The resultant mixture was stirred at room temperature for 4 h and then passed through a column [silica gel, 10% EtOAc in petroleum ether (333–363 K)] to give the title compound as a white solid (yield 89%, m.p. 340–342 K).Crystals suitable for crystallographic study were grown by slow evaporation of an ethanol solution at room temperature (Wang et al., 2013).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Molecular structure of the title compound. The displacement ellipsoids are drawn at the 50% probability level. H-atoms are shown by small circles of arbitrary radii.
	Fig. 2. The dimers formed via C-H···O inteactions (PLATON: Spek, 2009).

Ethyl 2-[1-(3-methylbutyl)-4-phenyl-1H-1,2,3-triazol-5-yl]-2-oxoacetate top

Crystal data top

C₁₇H₂₁N₃O₃	Z = 2
M_r = 315.37	F(000) = 336
Triclinic, P1	D_x = 1.223 Mg m⁻³
a = 8.1710 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.0684 (9) Å	Cell parameters from 3196 reflections
c = 10.6066 (10) Å	θ = 2.0–28.4°
α = 98.331 (3)°	µ = 0.09 mm⁻¹
β = 94.220 (3)°	T = 296 K
γ = 95.367 (3)°	Block, colorless
V = 856.23 (14) Å³	0.32 × 0.25 × 0.21 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	4189 independent reflections
Radiation source: fine-focus sealed tube	3196 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
Detector resolution: 7.50 pixels mm^-1	θ_max = 28.4°, θ_min = 2.0°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −13→13
T_min = 0.973, T_max = 0.982	l = −8→14
11605 measured reflections

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.156	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0847P)² + 0.1314P] where P = (F_o² + 2F_c²)/3
4189 reflections	(Δ/σ)_max < 0.001
211 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₇H₂₁N₃O₃	γ = 95.367 (3)°
M_r = 315.37	V = 856.23 (14) Å³
Triclinic, P1	Z = 2
a = 8.1710 (8) Å	Mo Kα radiation
b = 10.0684 (9) Å	µ = 0.09 mm⁻¹
c = 10.6066 (10) Å	T = 296 K
α = 98.331 (3)°	0.32 × 0.25 × 0.21 mm
β = 94.220 (3)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	4189 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3196 reflections with I > 2σ(I)
T_min = 0.973, T_max = 0.982	R_int = 0.021
11605 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.156	H-atom parameters constrained
S = 1.06	Δρ_max = 0.23 e Å⁻³
4189 reflections	Δρ_min = −0.18 e Å⁻³
211 parameters

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.

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
O1	1.02397 (18)	0.67468 (12)	0.33208 (13)	0.0700 (4)
O2	1.21537 (16)	0.52473 (15)	0.48236 (11)	0.0699 (4)
O3	1.28070 (12)	0.43994 (10)	0.28644 (10)	0.0466 (3)
N1	0.82997 (15)	0.30393 (13)	0.04196 (12)	0.0477 (3)
N2	0.78007 (16)	0.41791 (14)	0.01373 (12)	0.0510 (3)
N3	0.84537 (14)	0.51779 (12)	0.10506 (11)	0.0423 (3)
C1	0.99415 (18)	0.22438 (14)	0.34572 (14)	0.0440 (3)
H1	0.9492	0.2933	0.3956	0.053*
C2	1.0607 (2)	0.12404 (16)	0.40227 (16)	0.0533 (4)
H2	1.0625	0.1265	0.4904	0.064*
C3	1.1249 (2)	0.01966 (16)	0.32834 (17)	0.0554 (4)
H3	1.1698	−0.0476	0.3669	0.067*
C4	1.1224 (2)	0.01532 (15)	0.19828 (16)	0.0513 (4)
H4	1.1642	−0.0556	0.1488	0.062*
C5	1.05780 (18)	0.11619 (14)	0.14049 (14)	0.0436 (3)
H5	1.0568	0.1130	0.0524	0.052*
C6	0.99416 (16)	0.22261 (12)	0.21412 (13)	0.0363 (3)
C7	0.92856 (16)	0.33138 (13)	0.15338 (12)	0.0366 (3)
C8	0.94279 (16)	0.46949 (13)	0.19486 (12)	0.0371 (3)
C9	1.04460 (18)	0.55757 (14)	0.29903 (14)	0.0434 (3)
C10	1.18948 (18)	0.50382 (15)	0.36822 (14)	0.0450 (3)
C11	1.4239 (2)	0.3868 (2)	0.34301 (17)	0.0611 (4)
H11A	1.3911	0.3339	0.4082	0.073*
H11B	1.5047	0.4605	0.3827	0.073*
C12	1.4958 (2)	0.3015 (2)	0.2411 (2)	0.0755 (6)
H12A	1.4173	0.2259	0.2058	0.113*
H12B	1.5939	0.2696	0.2760	0.113*
H12C	1.5230	0.3534	0.1750	0.113*
C13	0.7973 (2)	0.65445 (16)	0.10329 (16)	0.0499 (4)
H13A	0.7548	0.6630	0.0174	0.060*
H13B	0.8935	0.7198	0.1274	0.060*
C14	0.6661 (2)	0.68401 (19)	0.19540 (19)	0.0588 (4)
H14A	0.6940	0.6483	0.2735	0.071*
H14B	0.5608	0.6375	0.1573	0.071*
C15	0.6481 (2)	0.8346 (2)	0.22911 (18)	0.0639 (5)
H15	0.7564	0.8809	0.2636	0.077*
C16	0.5290 (4)	0.8555 (3)	0.3333 (3)	0.1128 (11)
H16A	0.5197	0.9501	0.3558	0.169*
H16B	0.5701	0.8201	0.4074	0.169*
H16C	0.4224	0.8093	0.3020	0.169*
C17	0.5911 (3)	0.8960 (2)	0.1140 (2)	0.0793 (6)
H17A	0.4850	0.8518	0.0786	0.119*
H17B	0.6691	0.8847	0.0509	0.119*
H17C	0.5829	0.9904	0.1394	0.119*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0919 (9)	0.0403 (6)	0.0726 (8)	0.0232 (6)	−0.0114 (7)	−0.0099 (5)
O2	0.0643 (7)	0.0953 (10)	0.0446 (6)	0.0281 (7)	−0.0090 (5)	−0.0131 (6)
O3	0.0415 (5)	0.0511 (6)	0.0460 (5)	0.0120 (4)	−0.0003 (4)	0.0009 (4)
N1	0.0489 (7)	0.0491 (7)	0.0431 (7)	0.0109 (5)	−0.0040 (5)	0.0006 (5)
N2	0.0509 (7)	0.0575 (8)	0.0442 (7)	0.0152 (6)	−0.0049 (5)	0.0045 (6)
N3	0.0432 (6)	0.0440 (6)	0.0428 (6)	0.0167 (5)	0.0026 (5)	0.0095 (5)
C1	0.0544 (8)	0.0363 (7)	0.0429 (7)	0.0117 (6)	0.0101 (6)	0.0037 (5)
C2	0.0700 (10)	0.0466 (8)	0.0471 (8)	0.0130 (7)	0.0080 (7)	0.0136 (6)
C3	0.0622 (9)	0.0414 (8)	0.0678 (10)	0.0170 (7)	0.0071 (8)	0.0173 (7)
C4	0.0579 (9)	0.0342 (7)	0.0631 (10)	0.0159 (6)	0.0125 (7)	0.0010 (6)
C5	0.0511 (8)	0.0343 (7)	0.0439 (7)	0.0078 (6)	0.0074 (6)	−0.0027 (5)
C6	0.0379 (6)	0.0292 (6)	0.0412 (7)	0.0068 (5)	0.0043 (5)	0.0004 (5)
C7	0.0368 (6)	0.0365 (6)	0.0363 (6)	0.0101 (5)	0.0038 (5)	0.0005 (5)
C8	0.0380 (6)	0.0366 (7)	0.0383 (6)	0.0128 (5)	0.0035 (5)	0.0053 (5)
C9	0.0485 (7)	0.0357 (7)	0.0451 (7)	0.0111 (6)	0.0019 (6)	0.0003 (5)
C10	0.0434 (7)	0.0426 (7)	0.0450 (8)	0.0072 (6)	−0.0027 (6)	−0.0046 (6)
C11	0.0444 (8)	0.0788 (12)	0.0589 (10)	0.0218 (8)	−0.0053 (7)	0.0015 (8)
C12	0.0546 (10)	0.0810 (13)	0.0877 (14)	0.0252 (9)	0.0058 (10)	−0.0090 (11)
C13	0.0537 (8)	0.0490 (8)	0.0548 (9)	0.0249 (7)	0.0094 (7)	0.0193 (7)
C14	0.0534 (9)	0.0615 (10)	0.0717 (11)	0.0276 (8)	0.0182 (8)	0.0240 (8)
C15	0.0625 (10)	0.0658 (11)	0.0666 (11)	0.0318 (9)	0.0047 (8)	0.0055 (8)
C16	0.137 (2)	0.129 (2)	0.0923 (18)	0.086 (2)	0.0459 (17)	0.0216 (16)
C17	0.0965 (15)	0.0644 (12)	0.0859 (14)	0.0416 (11)	0.0122 (12)	0.0181 (10)

Geometric parameters (Å, º) top

O1—C9	1.2115 (17)	C9—C10	1.530 (2)
O2—C10	1.1978 (19)	C11—C12	1.473 (2)
O3—C10	1.3209 (17)	C11—H11A	0.9700
O3—C11	1.4565 (18)	C11—H11B	0.9700
N1—N2	1.3199 (18)	C12—H12A	0.9600
N1—C7	1.3585 (18)	C12—H12B	0.9600
N2—N3	1.3325 (18)	C12—H12C	0.9600
N3—C8	1.3684 (17)	C13—C14	1.524 (2)
N3—C13	1.4680 (18)	C13—H13A	0.9700
C1—C2	1.381 (2)	C13—H13B	0.9700
C1—C6	1.3934 (19)	C14—C15	1.530 (2)
C1—H1	0.9300	C14—H14A	0.9700
C2—C3	1.385 (2)	C14—H14B	0.9700
C2—H2	0.9300	C15—C17	1.509 (3)
C3—C4	1.373 (2)	C15—C16	1.530 (3)
C3—H3	0.9300	C15—H15	0.9800
C4—C5	1.385 (2)	C16—H16A	0.9600
C4—H4	0.9300	C16—H16B	0.9600
C5—C6	1.3964 (17)	C16—H16C	0.9600
C5—H5	0.9300	C17—H17A	0.9600
C6—C7	1.4714 (17)	C17—H17B	0.9600
C7—C8	1.3877 (18)	C17—H17C	0.9600
C8—C9	1.464 (2)

C10—O3—C11	115.68 (12)	O3—C11—H11B	110.0
N2—N1—C7	108.62 (12)	C12—C11—H11B	110.0
N1—N2—N3	108.25 (11)	H11A—C11—H11B	108.4
N2—N3—C8	110.66 (11)	C11—C12—H12A	109.5
N2—N3—C13	119.48 (12)	C11—C12—H12B	109.5
C8—N3—C13	129.67 (13)	H12A—C12—H12B	109.5
C2—C1—C6	120.11 (13)	C11—C12—H12C	109.5
C2—C1—H1	119.9	H12A—C12—H12C	109.5
C6—C1—H1	119.9	H12B—C12—H12C	109.5
C1—C2—C3	120.28 (15)	N3—C13—C14	110.78 (13)
C1—C2—H2	119.9	N3—C13—H13A	109.5
C3—C2—H2	119.9	C14—C13—H13A	109.5
C4—C3—C2	120.11 (14)	N3—C13—H13B	109.5
C4—C3—H3	119.9	C14—C13—H13B	109.5
C2—C3—H3	119.9	H13A—C13—H13B	108.1
C3—C4—C5	120.21 (13)	C13—C14—C15	113.33 (15)
C3—C4—H4	119.9	C13—C14—H14A	108.9
C5—C4—H4	119.9	C15—C14—H14A	108.9
C4—C5—C6	120.22 (14)	C13—C14—H14B	108.9
C4—C5—H5	119.9	C15—C14—H14B	108.9
C6—C5—H5	119.9	H14A—C14—H14B	107.7
C1—C6—C5	119.05 (12)	C17—C15—C14	112.37 (17)
C1—C6—C7	120.60 (11)	C17—C15—C16	110.58 (17)
C5—C6—C7	120.36 (12)	C14—C15—C16	109.5 (2)
N1—C7—C8	108.50 (11)	C17—C15—H15	108.1
N1—C7—C6	121.22 (12)	C14—C15—H15	108.1
C8—C7—C6	130.19 (12)	C16—C15—H15	108.1
N3—C8—C7	103.94 (12)	C15—C16—H16A	109.5
N3—C8—C9	122.89 (12)	C15—C16—H16B	109.5
C7—C8—C9	132.91 (12)	H16A—C16—H16B	109.5
O1—C9—C8	123.30 (13)	C15—C16—H16C	109.5
O1—C9—C10	116.91 (13)	H16A—C16—H16C	109.5
C8—C9—C10	119.75 (12)	H16B—C16—H16C	109.5
O2—C10—O3	126.60 (14)	C15—C17—H17A	109.5
O2—C10—C9	121.89 (14)	C15—C17—H17B	109.5
O3—C10—C9	111.44 (12)	H17A—C17—H17B	109.5
O3—C11—C12	108.46 (14)	C15—C17—H17C	109.5
O3—C11—H11A	110.0	H17A—C17—H17C	109.5
C12—C11—H11A	110.0	H17B—C17—H17C	109.5

C7—N1—N2—N3	0.13 (16)	N1—C7—C8—N3	1.65 (15)
N1—N2—N3—C8	0.96 (16)	C6—C7—C8—N3	−174.92 (13)
N1—N2—N3—C13	−174.42 (12)	N1—C7—C8—C9	−172.46 (15)
C6—C1—C2—C3	−1.3 (2)	C6—C7—C8—C9	11.0 (2)
C1—C2—C3—C4	−0.1 (3)	N3—C8—C9—O1	17.4 (2)
C2—C3—C4—C5	0.9 (3)	C7—C8—C9—O1	−169.39 (16)
C3—C4—C5—C6	−0.3 (2)	N3—C8—C9—C10	−160.12 (13)
C2—C1—C6—C5	1.9 (2)	C7—C8—C9—C10	13.1 (2)
C2—C1—C6—C7	−177.97 (14)	C11—O3—C10—O2	2.0 (2)
C4—C5—C6—C1	−1.1 (2)	C11—O3—C10—C9	178.99 (14)
C4—C5—C6—C7	178.75 (13)	O1—C9—C10—O2	46.5 (2)
N2—N1—C7—C8	−1.15 (16)	C8—C9—C10—O2	−135.78 (17)
N2—N1—C7—C6	175.78 (12)	O1—C9—C10—O3	−130.63 (16)
C1—C6—C7—N1	−136.58 (14)	C8—C9—C10—O3	47.07 (19)
C5—C6—C7—N1	43.59 (19)	C10—O3—C11—C12	171.29 (15)
C1—C6—C7—C8	39.6 (2)	N2—N3—C13—C14	99.01 (17)
C5—C6—C7—C8	−140.22 (15)	C8—N3—C13—C14	−75.4 (2)
N2—N3—C8—C7	−1.60 (15)	N3—C13—C14—C15	162.54 (15)
C13—N3—C8—C7	173.17 (13)	C13—C14—C15—C17	63.3 (2)
N2—N3—C8—C9	173.26 (13)	C13—C14—C15—C16	−173.43 (19)
C13—N3—C8—C9	−12.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···O2ⁱ	0.97	2.59	3.338 (2)	134

Symmetry code: (i) −x+3, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···O2ⁱ	0.97	2.59	3.338 (2)	134

Symmetry code: (i) −x+3, −y+1, −z+1.

Acknowledgements

MNA is very thankful to the Higher Education Commission, Pakistan, for financial support.

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