Ethyl 2-[1-(3-methyl-but-yl)-4-phenyl-1H-1,2,3-triazol-5-yl]-2-oxo-acetate.

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, mol-ecules are arranged into centrosymmetric R 2 (2)(10) dimers via pairs of C-H⋯O inter-actions involving the ethyl (oxo)acetate groups. In addition, the triazole rings show π-π stacking inter-actions, with their centroids at a distance of 3.745 (2) Å.

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 = 315.37

Triclinic,

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[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.156

S = 1.06

4189 reflections

211 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.18 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813030420/gk2593sup1.cif

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813030420/gk2593Isup3.cml

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

C17H21N3O3	Z = 2
Mr = 315.37	F(000) = 336
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0847P)2 + 0.1314P] where P = (Fo2 + 2Fc2)/3
4189 reflections	(Δ/σ)max < 0.001
211 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .