6-(4-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 at dihedral angles of 5.32 (4) and 9.41 (4)°, respectively with respect to trimethoxy-phenyl and pyridine rings. Intra-molecular C-H⋯N, C-H⋯O and C-H⋯S hydrogen bonds result in the formation of a nearly planar six-membered ring, which is oriented at a dihedral angle of 3.07 (5)° with respect to the central heterocylic ring system, and non-planar six- and five-membered rings having twist and envelope conformations, respectively. In the crystal structure, inter-molecular C-H⋯N and C-H⋯O hydrogen bonds link the mol-ecules. There is a C-H⋯π contact between the pyridine ring and a methyl group and a π-π contact between the central heterocylic ring system and the trimethoxy-phenyl ring [centroid-centroid distance = 3.758 (1) Å].

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

Triclinic,

a = 7.7051 (15) Å

b = 8.6684 (17) Å

c = 13.851 (3) Å

α = 105.00 (3)°

β = 104.18 (3)°

γ = 96.58 (3)°

V = 850.6 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.22 mm−1

T = 113 (2) K

0.22 × 0.20 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.953, T max = 0.974

4917 measured reflections

2970 independent reflections

2467 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.100

S = 1.09

2970 reflections

238 parameters

H-atom parameters constrained

Δρmax = 0.33 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/S1600536808023544/hk2505sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023544/hk2505Isup2.hkl

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

C17H15N5O3S	Z = 2
Mr = 369.40	F000 = 384
Triclinic, P1	Dx = 1.442 Mg m−3
Hall symbol: -P 1	Melting point: 447 K
a = 7.7051 (15) Å	Mo Kα radiation λ = 0.71073 Å
b = 8.6684 (17) Å	Cell parameters from 2198 reflections
c = 13.851 (3) Å	θ = 2.5–27.5º
α = 105.00 (3)º	µ = 0.22 mm−1
β = 104.18 (3)º	T = 113 (2) K
γ = 96.58 (3)º	Prism, colorless
V = 850.6 (4) Å3	0.22 × 0.20 × 0.12 mm

Rigaku Saturn CCD area-detector diffractometer	2970 independent reflections
Radiation source: rotating anode	2467 reflections with I > 2σ(I)
Monochromator: confocal	Rint = 0.021
T = 113(2) K	θmax = 25.0º
ω scans	θmin = 1.6º
Absorption correction: multi-scan(CrystalClear; Rigaku/MSC, 2005)	h = −9→8
Tmin = 0.953, Tmax = 0.974	k = −5→10
4917 measured reflections	l = −16→16

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)] = 0.033	H-atom parameters constrained
wR(F2) = 0.100	w = 1/[σ2(Fo2) + (0.0666P)2] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.001
2970 reflections	Δρmax = 0.33 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	0.12462 (5)	1.42520 (5)	0.15970 (3)	0.01718 (15)
O1	0.42347 (15)	0.65186 (14)	−0.05689 (9)	0.0207 (3)
O2	0.38351 (15)	0.55944 (14)	−0.26365 (10)	0.0221 (3)
O3	0.22791 (16)	0.72787 (15)	−0.38536 (9)	0.0237 (3)
N1	0.06954 (17)	1.22162 (16)	−0.13378 (11)	0.0173 (3)
N2	0.04356 (18)	1.35552 (17)	−0.06135 (11)	0.0174 (3)
N3	0.16107 (16)	1.18786 (16)	0.01937 (10)	0.0137 (3)
N4	0.22454 (17)	1.14340 (16)	0.10761 (11)	0.0153 (3)
N5	0.3721 (2)	1.2020 (2)	0.49150 (12)	0.0271 (4)
C1	0.2006 (2)	0.9733 (2)	−0.13125 (13)	0.0154 (4)
C2	0.2800 (2)	0.8834 (2)	−0.06844 (13)	0.0153 (4)
H2	0.2920	0.9157	0.0027	0.018*
C3	0.3410 (2)	0.7454 (2)	−0.11299 (13)	0.0159 (4)
C4	0.3211 (2)	0.6951 (2)	−0.21931 (14)	0.0172 (4)
C5	0.2417 (2)	0.7869 (2)	−0.28176 (13)	0.0183 (4)
C6	0.1823 (2)	0.9264 (2)	−0.23794 (13)	0.0176 (4)
H6	0.1308	0.9879	−0.2793	0.021*
C7	0.4203 (2)	0.6867 (2)	0.04955 (13)	0.0197 (4)
H7A	0.4866	0.7948	0.0879	0.030*
H7B	0.4757	0.6100	0.0798	0.030*
H7C	0.2963	0.6786	0.0522	0.030*
C8	0.2630 (3)	0.4101 (2)	−0.27988 (15)	0.0273 (4)
H8A	0.2430	0.4057	−0.2148	0.041*
H8B	0.3168	0.3198	−0.3067	0.041*
H8C	0.1488	0.4049	−0.3290	0.041*
C9	0.1605 (3)	0.8243 (2)	−0.45012 (15)	0.0285 (4)
H9A	0.0370	0.8318	−0.4506	0.043*
H9B	0.1644	0.7747	−0.5199	0.043*
H9C	0.2347	0.9313	−0.4235	0.043*
C10	0.1416 (2)	1.1222 (2)	−0.08494 (13)	0.0145 (3)
C11	0.1006 (2)	1.33163 (19)	0.03000 (13)	0.0151 (4)
C12	0.2130 (2)	1.2572 (2)	0.18640 (13)	0.0156 (4)
C13	0.2677 (2)	1.2409 (2)	0.29190 (13)	0.0163 (4)
C14	0.2786 (2)	1.3663 (2)	0.37991 (14)	0.0225 (4)
H14	0.2510	1.4657	0.3738	0.027*
C15	0.3307 (2)	1.3421 (2)	0.47678 (15)	0.0265 (4)
H15	0.3376	1.4276	0.5351	0.032*
C16	0.3604 (2)	1.0826 (2)	0.40556 (14)	0.0242 (4)
H16	0.3891	0.9846	0.4138	0.029*
C17	0.3089 (2)	1.0943 (2)	0.30574 (14)	0.0212 (4)
H17	0.3017	1.0063	0.2488	0.025*

	U11	U22	U33	U12	U13	U23
S1	0.0206 (2)	0.0148 (2)	0.0170 (2)	0.00664 (17)	0.00523 (17)	0.00510 (18)
O1	0.0273 (6)	0.0190 (7)	0.0201 (7)	0.0131 (5)	0.0084 (5)	0.0081 (5)
O2	0.0265 (6)	0.0152 (6)	0.0284 (7)	0.0078 (5)	0.0154 (5)	0.0040 (6)
O3	0.0328 (7)	0.0239 (7)	0.0151 (6)	0.0079 (5)	0.0091 (5)	0.0039 (6)
N1	0.0198 (7)	0.0153 (7)	0.0182 (8)	0.0056 (6)	0.0056 (6)	0.0064 (6)
N2	0.0213 (7)	0.0153 (7)	0.0172 (8)	0.0069 (6)	0.0057 (6)	0.0057 (6)
N3	0.0149 (7)	0.0117 (7)	0.0155 (7)	0.0040 (5)	0.0037 (5)	0.0055 (6)
N4	0.0161 (7)	0.0168 (7)	0.0148 (7)	0.0047 (6)	0.0039 (5)	0.0077 (6)
N5	0.0300 (8)	0.0316 (9)	0.0211 (9)	0.0062 (7)	0.0071 (7)	0.0105 (8)
C1	0.0126 (8)	0.0155 (9)	0.0177 (9)	0.0019 (6)	0.0043 (6)	0.0048 (7)
C2	0.0151 (8)	0.0146 (8)	0.0161 (9)	0.0027 (6)	0.0048 (6)	0.0039 (7)
C3	0.0127 (8)	0.0150 (9)	0.0206 (9)	0.0033 (6)	0.0045 (6)	0.0064 (7)
C4	0.0164 (8)	0.0128 (8)	0.0229 (9)	0.0025 (7)	0.0089 (7)	0.0030 (7)
C5	0.0169 (8)	0.0203 (9)	0.0169 (9)	0.0006 (7)	0.0061 (7)	0.0040 (8)
C6	0.0164 (8)	0.0181 (9)	0.0193 (9)	0.0048 (7)	0.0041 (7)	0.0074 (8)
C7	0.0232 (9)	0.0184 (9)	0.0204 (9)	0.0080 (7)	0.0050 (7)	0.0097 (8)
C8	0.0395 (11)	0.0180 (9)	0.0270 (10)	0.0051 (8)	0.0160 (8)	0.0050 (8)
C9	0.0341 (10)	0.0347 (11)	0.0181 (10)	0.0075 (9)	0.0088 (8)	0.0088 (9)
C10	0.0130 (7)	0.0151 (8)	0.0150 (8)	0.0003 (6)	0.0034 (6)	0.0052 (7)
C11	0.0131 (8)	0.0122 (8)	0.0212 (9)	0.0042 (6)	0.0059 (7)	0.0055 (7)
C12	0.0127 (8)	0.0147 (8)	0.0197 (9)	0.0027 (6)	0.0040 (6)	0.0057 (7)
C13	0.0124 (8)	0.0203 (9)	0.0166 (9)	0.0026 (7)	0.0036 (6)	0.0069 (7)
C14	0.0272 (9)	0.0187 (9)	0.0218 (10)	0.0048 (8)	0.0083 (7)	0.0050 (8)
C15	0.0314 (10)	0.0268 (11)	0.0191 (10)	0.0016 (8)	0.0086 (8)	0.0035 (8)
C16	0.0273 (9)	0.0259 (10)	0.0227 (10)	0.0085 (8)	0.0070 (7)	0.0114 (8)
C17	0.0224 (9)	0.0214 (9)	0.0203 (9)	0.0076 (7)	0.0047 (7)	0.0070 (8)

S1—C11	1.7226 (18)	C3—C4	1.387 (2)
S1—C12	1.7615 (17)	C4—C5	1.402 (2)
O1—C3	1.3664 (19)	C5—C6	1.387 (2)
O1—C7	1.433 (2)	C6—H6	0.9300
O2—C4	1.376 (2)	C7—H7A	0.9600
O2—C8	1.435 (2)	C7—H7B	0.9600
O3—C5	1.366 (2)	C7—H7C	0.9600
O3—C9	1.426 (2)	C8—H8A	0.9600
N1—C10	1.317 (2)	C8—H8B	0.9600
N1—N2	1.394 (2)	C8—H8C	0.9600
N2—C11	1.312 (2)	C9—H9A	0.9600
N3—C11	1.365 (2)	C9—H9B	0.9600
N3—N4	1.3694 (18)	C9—H9C	0.9600
N3—C10	1.372 (2)	C12—C13	1.467 (2)
N4—C12	1.297 (2)	C13—C14	1.385 (2)
N5—C16	1.336 (2)	C13—C17	1.393 (2)
N5—C15	1.343 (2)	C14—C15	1.381 (2)
C1—C2	1.392 (2)	C14—H14	0.9300
C1—C6	1.394 (2)	C15—H15	0.9300
C1—C10	1.460 (2)	C16—C17	1.376 (2)
C2—C3	1.387 (2)	C16—H16	0.9300
C2—H2	0.9300	C17—H17	0.9300
C11—S1—C12	87.35 (8)	O2—C8—H8B	109.5
C3—O1—C7	116.86 (13)	H8A—C8—H8B	109.5
C4—O2—C8	113.05 (12)	O2—C8—H8C	109.5
C5—O3—C9	116.86 (14)	H8A—C8—H8C	109.5
C10—N1—N2	109.38 (13)	H8B—C8—H8C	109.5
C11—N2—N1	106.05 (13)	O3—C9—H9A	109.5
C11—N3—N4	117.95 (14)	O3—C9—H9B	109.5
C11—N3—C10	106.53 (13)	H9A—C9—H9B	109.5
N4—N3—C10	135.51 (13)	O3—C9—H9C	109.5
C12—N4—N3	107.80 (13)	H9A—C9—H9C	109.5
C16—N5—C15	116.09 (16)	H9B—C9—H9C	109.5
C2—C1—C6	120.81 (15)	N1—C10—N3	107.71 (14)
C2—C1—C10	120.03 (15)	N1—C10—C1	126.81 (15)
C6—C1—C10	119.11 (15)	N3—C10—C1	125.40 (14)
C3—C2—C1	119.36 (16)	N2—C11—N3	110.32 (15)
C3—C2—H2	120.3	N2—C11—S1	139.95 (13)
C1—C2—H2	120.3	N3—C11—S1	109.73 (12)
O1—C3—C2	123.22 (15)	N4—C12—C13	120.08 (15)
O1—C3—C4	116.10 (14)	N4—C12—S1	117.15 (12)
C2—C3—C4	120.68 (15)	C13—C12—S1	122.75 (13)
O2—C4—C3	120.89 (15)	C14—C13—C17	117.81 (16)
O2—C4—C5	119.60 (15)	C14—C13—C12	122.40 (16)
C3—C4—C5	119.48 (15)	C17—C13—C12	119.78 (16)
O3—C5—C6	124.38 (15)	C15—C14—C13	119.24 (17)
O3—C5—C4	115.23 (15)	C15—C14—H14	120.4
C6—C5—C4	120.39 (15)	C13—C14—H14	120.4
C5—C6—C1	119.26 (15)	N5—C15—C14	123.67 (18)
C5—C6—H6	120.4	N5—C15—H15	118.2
C1—C6—H6	120.4	C14—C15—H15	118.2
O1—C7—H7A	109.5	N5—C16—C17	124.66 (17)
O1—C7—H7B	109.5	N5—C16—H16	117.7
H7A—C7—H7B	109.5	C17—C16—H16	117.7
O1—C7—H7C	109.5	C16—C17—C13	118.51 (18)
H7A—C7—H7C	109.5	C16—C17—H17	120.7
H7B—C7—H7C	109.5	C13—C17—H17	120.7
O2—C8—H8A	109.5
C10—N1—N2—C11	−0.40 (17)	N4—N3—C10—C1	−3.7 (3)
C11—N3—N4—C12	−0.60 (19)	C2—C1—C10—N1	177.96 (15)
C10—N3—N4—C12	178.75 (15)	C6—C1—C10—N1	0.3 (2)
C6—C1—C2—C3	−0.1 (2)	C2—C1—C10—N3	1.7 (2)
C10—C1—C2—C3	−177.80 (14)	C6—C1—C10—N3	−176.04 (13)
C7—O1—C3—C2	9.6 (2)	N1—N2—C11—N3	−0.34 (17)
C7—O1—C3—C4	−170.70 (13)	N1—N2—C11—S1	179.14 (15)
C1—C2—C3—O1	178.75 (13)	N4—N3—C11—N2	−179.55 (12)
C1—C2—C3—C4	−1.0 (2)	C10—N3—C11—N2	0.92 (17)
C8—O2—C4—C3	79.22 (19)	N4—N3—C11—S1	0.80 (17)
C8—O2—C4—C5	−102.87 (18)	C10—N3—C11—S1	−178.73 (9)
O1—C3—C4—O2	−0.6 (2)	C12—S1—C11—N2	179.97 (19)
C2—C3—C4—O2	179.15 (14)	C12—S1—C11—N3	−0.55 (11)
O1—C3—C4—C5	−178.51 (14)	N3—N4—C12—C13	178.53 (13)
C2—C3—C4—C5	1.2 (2)	N3—N4—C12—S1	0.12 (16)
C9—O3—C5—C6	5.0 (2)	C11—S1—C12—N4	0.26 (13)
C9—O3—C5—C4	−175.42 (14)	C11—S1—C12—C13	−178.10 (13)
O2—C4—C5—O3	2.1 (2)	N4—C12—C13—C14	172.23 (15)
C3—C4—C5—O3	180.00 (13)	S1—C12—C13—C14	−9.5 (2)
O2—C4—C5—C6	−178.33 (14)	N4—C12—C13—C17	−8.5 (2)
C3—C4—C5—C6	−0.4 (2)	S1—C12—C13—C17	169.79 (12)
O3—C5—C6—C1	178.88 (14)	C17—C13—C14—C15	0.6 (2)
C4—C5—C6—C1	−0.7 (2)	C12—C13—C14—C15	179.86 (14)
C2—C1—C6—C5	1.0 (2)	C16—N5—C15—C14	0.0 (3)
C10—C1—C6—C5	178.66 (14)	C13—C14—C15—N5	−0.1 (3)
N2—N1—C10—N3	0.96 (17)	C15—N5—C16—C17	−0.4 (3)
N2—N1—C10—C1	−175.87 (14)	N5—C16—C17—C13	0.8 (3)
C11—N3—C10—N1	−1.14 (17)	C14—C13—C17—C16	−0.9 (2)
N4—N3—C10—N1	179.45 (15)	C12—C13—C17—C16	179.80 (14)
C11—N3—C10—C1	175.75 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N4	0.93	2.32	3.016 (3)	131
C7—H7B···O1i	0.96	2.45	3.313 (3)	149
C8—H8A···O1	0.96	2.59	3.106 (3)	114
C8—H8A···N1ii	0.96	2.60	3.409 (3)	142
C14—H14···S1	0.93	2.80	3.185 (3)	106
C9—H9A···Cg3iii	0.96	3.07	3.974 (3)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯N4	0.93	2.32	3.016 (3)	131
C7—H7B⋯O1i	0.96	2.45	3.313 (3)	149
C8—H8A⋯O1	0.96	2.59	3.106 (3)	114
C8—H8A⋯N1ii	0.96	2.60	3.409 (3)	142
C14—H14⋯S1	0.93	2.80	3.185 (3)	106
C9—H9A⋯Cg3iii	0.96	3.07	3.974 (3)	157

Symmetry codes: (i) ; (ii) ; (iii) . Cg3 is the centroid of the N5/C13–C17 pyridine ring.