Ethyl 5-[6-(furan-2-yl)-1,2,4-triazolo[3,4-b][1,3,4]thia-diazol-3-yl]-2,6-di-methylnicotinate.

In the title compound, C(17)H(15)N(5)O(3)S, the plane of the triazolo-thia-diazole system forms dihedral angles of 15.68 and 4.46° with the planes of the pyridine and furan rings, respectively. In the mol-ecule, there is an intra-molecular C-H⋯N inter-action. The crystal structure also contains other inter-molecular inter-actions, such as C-H⋯O hydrogen bonds, π-π stacking (centroid-centroid distances = 3.746 and 3.444 Å), non-bonded S⋯N [3.026 (2) Å] and C-H⋯π inter-actions.

Related literature

For related literature, see: Borbulevych et al. (1998 ▶); Bruno et al. (2003 ▶); Collin et al. (2003 ▶); Cooper & Steele (1990 ▶); Dinçer et al. (2005 ▶); Golgolab et al. (1973 ▶); Holla et al. (1994 ▶, 1998 ▶, 2002 ▶); Lu et al. (2007 ▶); Shen et al. (2006 ▶); Tsukuda et al. (1998 ▶); Wagner et al. (2005 ▶); Witkoaski et al. (1972 ▶); Zhang & Wen (1998 ▶); Özbey et al. (2000 ▶).

Experimental

Crystal data

C17H15N5O3S

M = 369.40

Triclinic,

a = 8.094 (4) Å

b = 10.535 (5) Å

c = 10.996 (5) Å

α = 66.699 (5)°

β = 73.683 (5)°

γ = 80.998 (5)°

V = 825.4 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 296 (2) K

0.30 × 0.30 × 0.25 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.935, T max = 0.946

4297 measured reflections

2860 independent reflections

2531 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.100

S = 1.06

2860 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 2000 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807061144/av3123sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807061144/av3123Isup2.hkl

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

C17H15N5O3S	Z = 2
Mr = 369.40	F000 = 384
Triclinic, P1	Dx = 1.486 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 8.094 (4) Å	Cell parameters from 2601 reflections
b = 10.535 (5) Å	θ = 2.4–27.3º
c = 10.996 (5) Å	µ = 0.23 mm−1
α = 66.699 (5)º	T = 296 (2) K
β = 73.683 (5)º	Block, brown
γ = 80.998 (5)º	0.30 × 0.30 × 0.25 mm
V = 825.4 (7) Å3

Bruker SMART CCD area-detector diffractometer	2860 independent reflections
Radiation source: fine-focus sealed tube	2531 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.017
T = 296(2) K	θmax = 25.0º
φ and ω scans	θmin = 2.4º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.935, Tmax = 0.946	k = −12→12
4297 measured reflections	l = −13→11

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.038	w = 1/[σ2(Fo2) + (0.0502P)2 + 0.2861P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.100	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.22 e Å−3
2860 reflections	Δρmin = −0.25 e Å−3
235 parameters	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.013 (3)
Secondary atom site location: difference Fourier map

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > 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
N1	0.82163 (19)	0.64436 (15)	−0.06646 (15)	0.0380 (4)
N2	0.6722 (2)	0.25738 (17)	−0.06479 (16)	0.0448 (4)
N3	0.5890 (2)	0.13509 (17)	−0.02295 (17)	0.0473 (4)
N4	0.54173 (18)	0.20294 (14)	0.15000 (14)	0.0320 (3)
N5	0.46583 (19)	0.19007 (14)	0.28238 (15)	0.0349 (3)
O1	0.19535 (18)	−0.07982 (13)	0.53282 (14)	0.0469 (3)
O2	0.7628 (2)	0.63716 (16)	0.33760 (15)	0.0646 (5)
O3	0.7023 (2)	0.41744 (14)	0.41061 (14)	0.0572 (4)
S1	0.37936 (6)	−0.01525 (5)	0.23778 (5)	0.04173 (16)
C1	0.8076 (2)	0.65217 (18)	0.05519 (19)	0.0361 (4)
C2	0.7476 (2)	0.54134 (18)	0.17662 (18)	0.0337 (4)
C3	0.6956 (2)	0.42634 (18)	0.16808 (18)	0.0342 (4)
H3	0.6540	0.3523	0.2477	0.041*
C4	0.7047 (2)	0.42024 (17)	0.04290 (18)	0.0322 (4)
C5	0.7739 (2)	0.53224 (18)	−0.07487 (18)	0.0340 (4)
C6	0.8008 (3)	0.5362 (2)	−0.21624 (19)	0.0442 (5)
H6A	0.8492	0.6220	−0.2808	0.066*
H6B	0.6922	0.5286	−0.2315	0.066*
H6C	0.8782	0.4604	−0.2274	0.066*
C7	0.8615 (3)	0.7848 (2)	0.0491 (2)	0.0515 (5)
H7A	0.8978	0.8454	−0.0444	0.077*
H7B	0.9552	0.7655	0.0925	0.077*
H7C	0.7660	0.8284	0.0955	0.077*
C8	0.7393 (2)	0.54110 (19)	0.31403 (19)	0.0385 (4)
C9	0.6430 (2)	0.29802 (18)	0.03893 (18)	0.0340 (4)
C10	0.5122 (2)	0.10682 (18)	0.10579 (19)	0.0366 (4)
C11	0.3772 (2)	0.07975 (17)	0.33896 (18)	0.0352 (4)
C12	0.2798 (2)	0.04004 (17)	0.47908 (18)	0.0363 (4)
C13	0.2505 (3)	0.0984 (2)	0.5722 (2)	0.0456 (5)
H13	0.2936	0.1803	0.5607	0.055*
C14	0.1413 (3)	0.0111 (2)	0.6913 (2)	0.0501 (5)
H14	0.0985	0.0245	0.7734	0.060*
C15	0.1114 (3)	−0.0941 (2)	0.6634 (2)	0.0492 (5)
H15	0.0428	−0.1670	0.7245	0.059*
C16	0.7021 (3)	0.3943 (2)	0.5502 (2)	0.0541 (5)
H16A	0.6072	0.3378	0.6130	0.065*
H16B	0.6864	0.4822	0.5622	0.065*
C17	0.8677 (3)	0.3237 (2)	0.5807 (2)	0.0533 (5)
H17A	0.8826	0.2366	0.5692	0.080*
H17B	0.8664	0.3083	0.6730	0.080*
H17C	0.9611	0.3807	0.5195	0.080*

	U11	U22	U33	U12	U13	U23
N1	0.0420 (9)	0.0342 (8)	0.0382 (9)	−0.0062 (6)	−0.0090 (7)	−0.0126 (7)
N2	0.0553 (10)	0.0447 (9)	0.0382 (9)	−0.0173 (7)	−0.0012 (7)	−0.0207 (7)
N3	0.0605 (11)	0.0479 (9)	0.0407 (9)	−0.0211 (8)	−0.0009 (8)	−0.0249 (8)
N4	0.0370 (8)	0.0317 (7)	0.0311 (8)	−0.0054 (6)	−0.0067 (6)	−0.0152 (6)
N5	0.0403 (8)	0.0340 (8)	0.0323 (8)	−0.0061 (6)	−0.0056 (6)	−0.0148 (6)
O1	0.0598 (9)	0.0393 (7)	0.0412 (7)	−0.0186 (6)	−0.0027 (6)	−0.0150 (6)
O2	0.1001 (13)	0.0548 (9)	0.0505 (9)	−0.0282 (9)	−0.0098 (8)	−0.0283 (8)
O3	0.0959 (12)	0.0451 (8)	0.0385 (8)	−0.0120 (8)	−0.0231 (8)	−0.0158 (6)
S1	0.0537 (3)	0.0365 (3)	0.0392 (3)	−0.0147 (2)	−0.0047 (2)	−0.0183 (2)
C1	0.0346 (9)	0.0340 (9)	0.0425 (10)	−0.0045 (7)	−0.0107 (8)	−0.0151 (8)
C2	0.0320 (9)	0.0357 (9)	0.0372 (10)	−0.0038 (7)	−0.0091 (7)	−0.0164 (8)
C3	0.0358 (9)	0.0333 (9)	0.0348 (9)	−0.0067 (7)	−0.0067 (7)	−0.0135 (7)
C4	0.0326 (9)	0.0321 (9)	0.0350 (9)	−0.0032 (7)	−0.0079 (7)	−0.0151 (7)
C5	0.0324 (9)	0.0349 (9)	0.0356 (9)	−0.0013 (7)	−0.0076 (7)	−0.0147 (8)
C6	0.0554 (12)	0.0417 (10)	0.0341 (10)	−0.0073 (9)	−0.0054 (9)	−0.0144 (8)
C7	0.0695 (14)	0.0388 (11)	0.0503 (12)	−0.0178 (10)	−0.0155 (10)	−0.0146 (9)
C8	0.0373 (10)	0.0418 (10)	0.0422 (10)	−0.0069 (8)	−0.0076 (8)	−0.0214 (9)
C9	0.0373 (9)	0.0348 (9)	0.0322 (9)	−0.0064 (7)	−0.0063 (7)	−0.0145 (8)
C10	0.0438 (10)	0.0349 (9)	0.0382 (10)	−0.0068 (8)	−0.0093 (8)	−0.0196 (8)
C11	0.0395 (9)	0.0318 (9)	0.0371 (10)	−0.0041 (7)	−0.0093 (8)	−0.0151 (8)
C12	0.0402 (10)	0.0311 (9)	0.0382 (10)	−0.0058 (7)	−0.0082 (8)	−0.0129 (8)
C13	0.0534 (12)	0.0414 (11)	0.0457 (11)	−0.0087 (9)	−0.0059 (9)	−0.0218 (9)
C14	0.0568 (13)	0.0534 (12)	0.0380 (11)	−0.0045 (10)	−0.0011 (9)	−0.0211 (9)
C15	0.0525 (12)	0.0483 (11)	0.0378 (11)	−0.0122 (9)	−0.0014 (9)	−0.0095 (9)
C16	0.0740 (15)	0.0556 (13)	0.0356 (11)	−0.0058 (11)	−0.0124 (10)	−0.0195 (10)
C17	0.0652 (14)	0.0550 (12)	0.0472 (12)	−0.0138 (10)	−0.0126 (10)	−0.0236 (10)

N1—C5	1.343 (2)	C4—C5	1.405 (2)
N1—C1	1.345 (2)	C4—C9	1.472 (2)
N2—C9	1.320 (2)	C5—C6	1.493 (3)
N2—N3	1.398 (2)	C6—H6A	0.9600
N3—C10	1.307 (2)	C6—H6B	0.9600
N4—C10	1.360 (2)	C6—H6C	0.9600
N4—N5	1.372 (2)	C7—H7A	0.9600
N4—C9	1.376 (2)	C7—H7B	0.9600
N5—C11	1.300 (2)	C7—H7C	0.9600
O1—C15	1.364 (2)	C11—C12	1.443 (3)
O1—C12	1.365 (2)	C12—C13	1.342 (3)
O2—C8	1.193 (2)	C13—C14	1.411 (3)
O3—C8	1.328 (2)	C13—H13	0.9300
O3—C16	1.455 (2)	C14—C15	1.332 (3)
S1—C10	1.7308 (19)	C14—H14	0.9300
S1—C11	1.7618 (18)	C15—H15	0.9300
C1—C2	1.401 (3)	C16—C17	1.485 (3)
C1—C7	1.499 (3)	C16—H16A	0.9700
C2—C3	1.388 (2)	C16—H16B	0.9700
C2—C8	1.492 (3)	C17—H17A	0.9600
C3—C4	1.384 (3)	C17—H17B	0.9600
C3—H3	0.9300	C17—H17C	0.9600
C5—N1—C1	121.07 (15)	O2—C8—O3	122.87 (18)
C9—N2—N3	109.45 (15)	O2—C8—C2	125.99 (18)
C10—N3—N2	105.44 (14)	O3—C8—C2	111.14 (15)
C10—N4—N5	118.56 (14)	N2—C9—N4	107.67 (15)
C10—N4—C9	106.04 (15)	N2—C9—C4	128.65 (16)
N5—N4—C9	135.33 (14)	N4—C9—C4	123.68 (15)
C11—N5—N4	107.20 (14)	N3—C10—N4	111.39 (16)
C15—O1—C12	105.97 (15)	N3—C10—S1	139.04 (14)
C8—O3—C16	118.99 (15)	N4—C10—S1	109.55 (13)
C10—S1—C11	87.13 (9)	N5—C11—C12	120.11 (16)
N1—C1—C2	120.65 (16)	N5—C11—S1	117.56 (14)
N1—C1—C7	115.27 (16)	C12—C11—S1	122.33 (13)
C2—C1—C7	124.07 (17)	C13—C12—O1	110.19 (17)
C3—C2—C1	118.28 (17)	C13—C12—C11	133.14 (17)
C3—C2—C8	118.83 (16)	O1—C12—C11	116.66 (15)
C1—C2—C8	122.88 (16)	C12—C13—C14	106.50 (18)
C4—C3—C2	121.00 (16)	C12—C13—H13	126.7
C4—C3—H3	119.5	C14—C13—H13	126.7
C2—C3—H3	119.5	C15—C14—C13	106.87 (18)
C3—C4—C5	117.68 (16)	C15—C14—H14	126.6
C3—C4—C9	119.08 (16)	C13—C14—H14	126.6
C5—C4—C9	123.23 (16)	C14—C15—O1	110.47 (17)
N1—C5—C4	121.21 (16)	C14—C15—H15	124.8
N1—C5—C6	115.29 (16)	O1—C15—H15	124.8
C4—C5—C6	123.50 (16)	O3—C16—C17	109.93 (18)
C5—C6—H6A	109.5	O3—C16—H16A	109.7
C5—C6—H6B	109.5	C17—C16—H16A	109.7
H6A—C6—H6B	109.5	O3—C16—H16B	109.7
C5—C6—H6C	109.5	C17—C16—H16B	109.7
H6A—C6—H6C	109.5	H16A—C16—H16B	108.2
H6B—C6—H6C	109.5	C16—C17—H17A	109.5
C1—C7—H7A	109.5	C16—C17—H17B	109.5
C1—C7—H7B	109.5	H17A—C17—H17B	109.5
H7A—C7—H7B	109.5	C16—C17—H17C	109.5
C1—C7—H7C	109.5	H17A—C17—H17C	109.5
H7A—C7—H7C	109.5	H17B—C17—H17C	109.5
H7B—C7—H7C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N5	0.93	2.31	2.982 (3)	128
C13—H13···O2i	0.93	2.51	3.285 (3)	141
C17—H17A···O1ii	0.96	2.56	3.424 (3)	149

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the furan ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯N5	0.93	2.31	2.982 (3)	128
C13—H13⋯O2i	0.93	2.51	3.285 (3)	141
C17—H17A⋯O1ii	0.96	2.56	3.424 (3)	149
C17—H17A⋯Cgiii	0.96	3.29	4.008 (3)	134

Symmetry codes: (i) ; (ii) ; (iii) .