6-(3-Pyrid-yl)-3-(3,4,5-trimethoxy-phen-yl)-1,2,4-triazolo[3,4-b][1,3,4]thia-diazole.

In the mol-ecule of the title compound, C(17)H(15)N(5)O(3)S, the planar central heterocylic ring system is oriented with respect to the benzene and pyridine rings at dihedral angles of 6.61 (3) and 19.22 (3)°, respectively. An intra-molecular C-H⋯N hydrogen bond results in the formation of a six-membered ring, adopting a flattened boat conformation. In the crystal structure, inter-molecular C-H⋯N hydrogen bonds link the mol-ecules.

Related literature

For general background, see: Karabasanagouda et al. (2007 ▶); Mathew et al. (2007 ▶). For ring conformation puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C17H15N5O3S

M = 369.40

Monoclinic,

a = 7.4682 (15) Å

b = 14.128 (3) Å

c = 15.550 (3) Å

β = 90.46 (3)°

V = 1640.6 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 113 (2) K

0.20 × 0.06 × 0.04 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.956, T max = 0.991

18716 measured reflections

3620 independent reflections

3121 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.108

S = 1.17

3620 reflections

238 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.41 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2005 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808019855/hk2481sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019855/hk2481Isup2.hkl

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

C17H15N5O3S	F000 = 768
Mr = 369.40	Dx = 1.496 Mg m−3
Monoclinic, P21/c	Melting point: 448K K
Hall symbol: -P 2ybc	Mo Kα radiation λ = 0.71073 Å
a = 7.4682 (15) Å	Cell parameters from 4807 reflections
b = 14.128 (3) Å	θ = 1.9–27.1º
c = 15.550 (3) Å	µ = 0.23 mm−1
β = 90.46 (3)º	T = 113 (2) K
V = 1640.6 (6) Å3	Prism, colourless
Z = 4	0.20 × 0.06 × 0.04 mm

Rigaku Saturn CCD area-detector diffractometer	3620 independent reflections
Radiation source: rotating anode	3121 reflections with I > 2σ(I)
Monochromator: confocal	Rint = 0.034
Detector resolution: 7.31 pixels mm-1	θmax = 27.2º
T = 113(2) K	θmin = 2.0º
φ and ω scans	h = −9→9
Absorption correction: multi-scan(CrystalClear; Rigaku/MSC, 2005)	k = −18→18
Tmin = 0.956, Tmax = 0.991	l = −19→19
18716 measured reflections

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)] = 0.032	H-atom parameters constrained
wR(F2) = 0.108	w = 1/[σ2(Fo2) + (0.0643P)2 + 0.1727P] where P = (Fo2 + 2Fc2)/3
S = 1.17	(Δ/σ)max = 0.001
3620 reflections	Δρmax = 0.48 e Å−3
238 parameters	Δρmin = −0.41 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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 > 2sigma(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
S1	0.47268 (5)	0.30203 (2)	0.32685 (2)	0.01906 (12)
O1	0.09766 (15)	0.49470 (8)	0.82026 (7)	0.0250 (3)
O2	−0.02336 (14)	0.65367 (8)	0.74798 (7)	0.0239 (3)
O3	0.02728 (14)	0.69219 (7)	0.58349 (7)	0.0236 (3)
N1	0.46168 (17)	0.25227 (9)	0.50417 (8)	0.0228 (3)
N2	0.39750 (17)	0.30533 (9)	0.57349 (8)	0.0217 (3)
N3	0.36415 (15)	0.39115 (8)	0.45790 (8)	0.0167 (3)
N4	0.32966 (15)	0.45519 (8)	0.39312 (7)	0.0167 (3)
N5	0.32739 (18)	0.61126 (9)	0.16139 (9)	0.0242 (3)
C1	0.24914 (18)	0.45989 (10)	0.59768 (9)	0.0178 (3)
C2	0.18824 (19)	0.54403 (10)	0.56074 (9)	0.0183 (3)
H2	0.2085	0.5569	0.5017	0.022*
C3	0.09733 (18)	0.60873 (10)	0.61183 (9)	0.0184 (3)
C4	0.07026 (18)	0.59006 (10)	0.69890 (9)	0.0186 (3)
C5	0.13206 (18)	0.50562 (11)	0.73504 (9)	0.0192 (3)
C6	0.22174 (18)	0.43975 (10)	0.68450 (9)	0.0189 (3)
H6	0.2636	0.3820	0.7087	0.023*
C7	0.1537 (2)	0.40859 (12)	0.85975 (10)	0.0285 (4)
H7A	0.0953	0.3551	0.8309	0.043*
H7B	0.1206	0.4092	0.9206	0.043*
H7C	0.2839	0.4023	0.8549	0.043*
C8	0.0881 (2)	0.72143 (13)	0.78883 (11)	0.0321 (4)
H8A	0.1680	0.6895	0.8298	0.048*
H8B	0.0139	0.7674	0.8194	0.048*
H8C	0.1596	0.7543	0.7455	0.048*
C9	0.0629 (2)	0.71792 (11)	0.49656 (10)	0.0240 (3)
H9A	0.1922	0.7258	0.4890	0.036*
H9B	0.0019	0.7776	0.4830	0.036*
H9C	0.0190	0.6681	0.4580	0.036*
C10	0.33868 (18)	0.38808 (10)	0.54526 (9)	0.0176 (3)
C11	0.43862 (19)	0.30623 (10)	0.43654 (10)	0.0183 (3)
C12	0.38009 (18)	0.41649 (10)	0.32131 (9)	0.0166 (3)
C13	0.36482 (18)	0.46502 (10)	0.23842 (9)	0.0171 (3)
C14	0.37053 (19)	0.41517 (10)	0.16155 (9)	0.0207 (3)
H14	0.3865	0.3485	0.1614	0.025*
C15	0.3526 (2)	0.46451 (11)	0.08527 (10)	0.0237 (3)
H15	0.3555	0.4322	0.0317	0.028*
C16	0.3304 (2)	0.56120 (11)	0.08802 (10)	0.0234 (3)
H16	0.3166	0.5943	0.0352	0.028*
C17	0.34453 (19)	0.56304 (10)	0.23455 (10)	0.0207 (3)
H17	0.3428	0.5973	0.2871	0.025*

	U11	U22	U33	U12	U13	U23
S1	0.0235 (2)	0.01467 (19)	0.0190 (2)	0.00266 (13)	0.00292 (15)	−0.00077 (12)
O1	0.0308 (6)	0.0273 (6)	0.0169 (5)	0.0015 (5)	0.0062 (4)	0.0028 (4)
O2	0.0222 (5)	0.0234 (6)	0.0262 (6)	0.0008 (4)	0.0076 (4)	−0.0053 (4)
O3	0.0308 (6)	0.0189 (5)	0.0211 (6)	0.0049 (4)	0.0035 (5)	0.0012 (4)
N1	0.0290 (7)	0.0187 (6)	0.0208 (7)	0.0034 (5)	0.0040 (5)	0.0011 (5)
N2	0.0263 (7)	0.0186 (6)	0.0202 (7)	0.0021 (5)	0.0023 (5)	0.0004 (5)
N3	0.0183 (6)	0.0140 (6)	0.0176 (6)	0.0004 (5)	0.0011 (5)	0.0001 (4)
N4	0.0173 (6)	0.0154 (6)	0.0172 (6)	−0.0005 (4)	−0.0001 (5)	0.0022 (4)
N5	0.0308 (7)	0.0171 (6)	0.0248 (7)	0.0010 (5)	0.0001 (6)	0.0014 (5)
C1	0.0158 (6)	0.0181 (7)	0.0194 (7)	−0.0026 (5)	0.0001 (6)	−0.0021 (5)
C2	0.0194 (7)	0.0192 (7)	0.0162 (7)	−0.0024 (5)	0.0011 (5)	−0.0001 (5)
C3	0.0167 (7)	0.0165 (7)	0.0218 (7)	−0.0020 (5)	−0.0009 (6)	−0.0013 (5)
C4	0.0161 (6)	0.0196 (7)	0.0202 (7)	−0.0029 (5)	0.0042 (6)	−0.0042 (6)
C5	0.0180 (7)	0.0230 (7)	0.0167 (7)	−0.0054 (6)	0.0021 (6)	−0.0008 (6)
C6	0.0176 (7)	0.0187 (7)	0.0206 (7)	−0.0019 (6)	−0.0003 (6)	−0.0001 (5)
C7	0.0331 (9)	0.0328 (9)	0.0195 (8)	0.0028 (7)	0.0024 (7)	0.0065 (7)
C8	0.0359 (9)	0.0312 (9)	0.0293 (9)	0.0037 (7)	−0.0016 (7)	−0.0147 (7)
C9	0.0274 (8)	0.0205 (7)	0.0240 (8)	0.0011 (6)	0.0009 (6)	0.0031 (6)
C10	0.0180 (7)	0.0184 (7)	0.0163 (7)	−0.0036 (5)	0.0005 (5)	0.0005 (5)
C11	0.0187 (7)	0.0148 (7)	0.0214 (7)	0.0004 (5)	0.0022 (6)	−0.0008 (5)
C12	0.0162 (6)	0.0135 (6)	0.0200 (7)	−0.0012 (5)	0.0007 (5)	−0.0013 (5)
C13	0.0150 (6)	0.0171 (7)	0.0192 (7)	−0.0009 (5)	0.0022 (5)	0.0003 (5)
C14	0.0238 (7)	0.0159 (7)	0.0225 (7)	−0.0009 (6)	0.0032 (6)	−0.0014 (5)
C15	0.0269 (8)	0.0243 (8)	0.0199 (7)	−0.0032 (6)	0.0035 (6)	−0.0020 (6)
C16	0.0249 (7)	0.0254 (8)	0.0200 (7)	−0.0010 (6)	0.0000 (6)	0.0048 (6)
C17	0.0247 (7)	0.0169 (7)	0.0205 (7)	0.0009 (6)	−0.0004 (6)	−0.0023 (5)

S1—C11	1.7275 (15)	C3—C4	1.396 (2)
S1—C12	1.7606 (14)	C4—C5	1.396 (2)
O1—C5	1.3607 (17)	C5—C6	1.393 (2)
O1—C7	1.4242 (19)	C6—H6	0.9500
O2—C4	1.3739 (17)	C7—H7A	0.9800
O2—C8	1.416 (2)	C7—H7B	0.9800
O3—C3	1.3616 (17)	C7—H7C	0.9800
O3—C9	1.4269 (18)	C8—H8A	0.9800
N1—C11	1.3092 (19)	C8—H8B	0.9800
N1—N2	1.4007 (17)	C8—H8C	0.9800
N2—C10	1.3225 (19)	C9—H9A	0.9800
N3—C11	1.3645 (18)	C9—H9B	0.9800
N3—C10	1.3739 (18)	C9—H9C	0.9800
N3—N4	1.3767 (16)	C12—C13	1.4637 (19)
N4—C12	1.3016 (18)	C13—C14	1.388 (2)
N5—C17	1.331 (2)	C13—C17	1.394 (2)
N5—C16	1.343 (2)	C14—C15	1.381 (2)
C1—C2	1.395 (2)	C14—H14	0.9500
C1—C6	1.396 (2)	C15—C16	1.377 (2)
C1—C10	1.466 (2)	C15—H15	0.9500
C2—C3	1.392 (2)	C16—H16	0.9500
C2—H2	0.9500	C17—H17	0.9500
C11—S1—C12	87.47 (7)	O2—C8—H8B	109.5
C5—O1—C7	117.36 (12)	H8A—C8—H8B	109.5
C4—O2—C8	113.05 (11)	O2—C8—H8C	109.5
C3—O3—C9	116.95 (11)	H8A—C8—H8C	109.5
C11—N1—N2	105.24 (12)	H8B—C8—H8C	109.5
C10—N2—N1	109.42 (12)	O3—C9—H9A	109.5
C11—N3—C10	105.84 (12)	O3—C9—H9B	109.5
C11—N3—N4	118.28 (12)	H9A—C9—H9B	109.5
C10—N3—N4	135.86 (12)	O3—C9—H9C	109.5
C12—N4—N3	107.34 (11)	H9A—C9—H9C	109.5
C17—N5—C16	117.03 (13)	H9B—C9—H9C	109.5
C2—C1—C6	121.46 (13)	N2—C10—N3	107.93 (12)
C2—C1—C10	120.62 (13)	N2—C10—C1	125.37 (13)
C6—C1—C10	117.88 (13)	N3—C10—C1	126.53 (13)
C3—C2—C1	118.93 (13)	N1—C11—N3	111.57 (13)
C3—C2—H2	120.5	N1—C11—S1	138.90 (12)
C1—C2—H2	120.5	N3—C11—S1	109.52 (10)
O3—C3—C2	124.89 (13)	N4—C12—C13	122.53 (13)
O3—C3—C4	114.79 (13)	N4—C12—S1	117.39 (11)
C2—C3—C4	120.32 (13)	C13—C12—S1	120.07 (10)
O2—C4—C5	120.23 (13)	C14—C13—C17	118.08 (14)
O2—C4—C3	119.58 (13)	C14—C13—C12	121.19 (13)
C5—C4—C3	120.15 (13)	C17—C13—C12	120.72 (13)
O1—C5—C6	124.69 (14)	C15—C14—C13	118.68 (14)
O1—C5—C4	115.13 (12)	C15—C14—H14	120.7
C6—C5—C4	120.18 (13)	C13—C14—H14	120.7
C5—C6—C1	118.96 (14)	C16—C15—C14	119.00 (14)
C5—C6—H6	120.5	C16—C15—H15	120.5
C1—C6—H6	120.5	C14—C15—H15	120.5
O1—C7—H7A	109.5	N5—C16—C15	123.50 (14)
O1—C7—H7B	109.5	N5—C16—H16	118.3
H7A—C7—H7B	109.5	C15—C16—H16	118.3
O1—C7—H7C	109.5	N5—C17—C13	123.69 (14)
H7A—C7—H7C	109.5	N5—C17—H17	118.2
H7B—C7—H7C	109.5	C13—C17—H17	118.2
O2—C8—H8A	109.5
C11—N1—N2—C10	0.12 (16)	N4—N3—C10—C1	3.5 (2)
C11—N3—N4—C12	0.04 (16)	C2—C1—C10—N2	−178.36 (14)
C10—N3—N4—C12	−178.10 (15)	C6—C1—C10—N2	−0.5 (2)
C6—C1—C2—C3	−0.4 (2)	C2—C1—C10—N3	−3.7 (2)
C10—C1—C2—C3	177.37 (13)	C6—C1—C10—N3	174.15 (13)
C9—O3—C3—C2	−5.2 (2)	N2—N1—C11—N3	0.27 (16)
C9—O3—C3—C4	175.44 (12)	N2—N1—C11—S1	−179.02 (14)
C1—C2—C3—O3	−178.33 (13)	C10—N3—C11—N1	−0.54 (16)
C1—C2—C3—C4	1.0 (2)	N4—N3—C11—N1	−179.19 (12)
C8—O2—C4—C5	90.63 (17)	C10—N3—C11—S1	178.96 (9)
C8—O2—C4—C3	−91.79 (17)	N4—N3—C11—S1	0.31 (15)
O3—C3—C4—O2	0.86 (19)	C12—S1—C11—N1	178.89 (18)
C2—C3—C4—O2	−178.51 (13)	C12—S1—C11—N3	−0.40 (10)
O3—C3—C4—C5	178.45 (13)	N3—N4—C12—C13	−179.41 (12)
C2—C3—C4—C5	−0.9 (2)	N3—N4—C12—S1	−0.38 (14)
C7—O1—C5—C6	−1.6 (2)	C11—S1—C12—N4	0.48 (11)
C7—O1—C5—C4	178.36 (13)	C11—S1—C12—C13	179.54 (12)
O2—C4—C5—O1	−2.16 (19)	N4—C12—C13—C14	−161.57 (13)
C3—C4—C5—O1	−179.73 (12)	S1—C12—C13—C14	19.42 (18)
O2—C4—C5—C6	177.85 (13)	N4—C12—C13—C17	18.6 (2)
C3—C4—C5—C6	0.3 (2)	S1—C12—C13—C17	−160.41 (11)
O1—C5—C6—C1	−179.70 (13)	C17—C13—C14—C15	−1.2 (2)
C4—C5—C6—C1	0.3 (2)	C12—C13—C14—C15	178.97 (13)
C2—C1—C6—C5	−0.2 (2)	C13—C14—C15—C16	0.3 (2)
C10—C1—C6—C5	−178.05 (13)	C17—N5—C16—C15	−0.9 (2)
N1—N2—C10—N3	−0.46 (16)	C14—C15—C16—N5	0.9 (2)
N1—N2—C10—C1	175.04 (13)	C16—N5—C17—C13	−0.1 (2)
C11—N3—C10—N2	0.60 (15)	C14—C13—C17—N5	1.1 (2)
N4—N3—C10—N2	178.89 (14)	C12—C13—C17—N5	−179.02 (13)
C11—N3—C10—C1	−174.83 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N4	0.95	2.40	3.0869 (19)	129
C9—H9A···N1i	0.98	2.60	3.576 (2)	171
C8—H8C···N5ii	0.98	2.63	3.573 (2)	161
C14—H14···N2iii	0.95	2.57	3.410 (2)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯N4	0.95	2.40	3.0869 (19)	129
C9—H9A⋯N1i	0.98	2.60	3.576 (2)	171
C8—H8C⋯N5ii	0.98	2.63	3.573 (2)	161
C14—H14⋯N2iii	0.95	2.57	3.410 (2)	148

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