2-(6-Phenyl-7H-1,2,4-triazolo[3,4-b][1,3,4]thia-diazin-3-yl)-1,3-benzothia-zole.

In the title compound, C(17)H(11)N(5)S(2), the dihedral angles formed between the triazole ring and the benzene ring and the 1,3-benzothia-zole ring system are 8.67 (8) and 13.90 (9)°, respectively. The conformation of the triazolo-thia-diazin-3-yl fused ring system is a twisted half-chair. Overall, the mol-ecule adopts a flattened shape. Supra-molecular helical chains along the a axis sustained by C-H⋯N inter-actions are found in the crystal structure. These are linked via C-H⋯π contacts as well as π-π [centroid-centroid distance = 3.5911 (12) Å] inter-actions between the triazole and thia-zole rings.

Related literature

For background to the synthesis and biological activity of benzothia­zoles and [1,2,4]triazolo[3,4-b][1,3,4]thia­diazines, see: Abdel-Aziz et al. (2007 ▶, 2010 ▶); Dawood et al. (2005 ▶).

Experimental

Crystal data

C17H11N5S2

M = 349.43

Orthorhombic,

a = 12.1437 (3) Å

b = 21.2950 (5) Å

c = 5.7946 (1) Å

V = 1498.48 (6) Å3

Z = 4

Cu Kα radiation

μ = 3.29 mm−1

T = 100 K

0.25 × 0.25 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.715, T max = 1.000

5754 measured reflections

2902 independent reflections

2751 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.083

S = 1.06

2902 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.30 e Å−3

Absolute structure: Flack (1983 ▶), 1150 Friedel pairs

Flack parameter: −0.006 (16)

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811036452/hg5092sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036452/hg5092Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811036452/hg5092Isup3.cml

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

C17H11N5S2	F(000) = 720
Mr = 349.43	Dx = 1.549 Mg m−3
Orthorhombic, P21212	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: P 2 2ab	Cell parameters from 3513 reflections
a = 12.1437 (3) Å	θ = 3.6–74.3°
b = 21.2950 (5) Å	µ = 3.29 mm−1
c = 5.7946 (1) Å	T = 100 K
V = 1498.48 (6) Å3	Plate, light-brown
Z = 4	0.25 × 0.25 × 0.05 mm

Agilent SuperNova Dual diffractometer with Atlas detector	2902 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2751 reflections with I > 2σ(I)
mirror	Rint = 0.029
Detector resolution: 10.4041 pixels mm-1	θmax = 74.5°, θmin = 4.2°
ω scan	h = −15→13
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −13→26
Tmin = 0.715, Tmax = 1.000	l = −6→6
5754 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) = 0.083	w = 1/[σ2(Fo2) + (0.0507P)2 + 0.021P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
2902 reflections	Δρmax = 0.21 e Å−3
217 parameters	Δρmin = −0.30 e Å−3
0 restraints	Absolute structure: Flack (1983), 1150 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.006 (16)

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
S1	0.41692 (4)	0.42415 (2)	0.72377 (10)	0.01863 (14)
S2	0.51497 (4)	0.25815 (2)	1.48903 (10)	0.01803 (13)
N1	0.21298 (15)	0.38633 (8)	0.7555 (3)	0.0165 (4)
N2	0.24914 (15)	0.31575 (9)	1.1796 (3)	0.0170 (4)
N3	0.30068 (16)	0.28150 (8)	1.3539 (3)	0.0177 (4)
N4	0.42913 (15)	0.32303 (8)	1.1339 (3)	0.0142 (4)
N5	0.52940 (15)	0.34569 (8)	1.0531 (3)	0.0155 (4)
C1	0.32276 (18)	0.45294 (9)	0.5251 (4)	0.0173 (4)
C2	0.34046 (19)	0.49351 (11)	0.3396 (4)	0.0214 (5)
H2	0.4105	0.5121	0.3138	0.026*
C3	0.25298 (18)	0.50565 (10)	0.1955 (4)	0.0204 (5)
H3	0.2635	0.5325	0.0664	0.024*
C4	0.14936 (18)	0.47958 (9)	0.2342 (4)	0.0202 (5)
H4	0.0908	0.4887	0.1309	0.024*
C5	0.13077 (18)	0.44076 (10)	0.4203 (4)	0.0191 (5)
H5	0.0597	0.4237	0.4478	0.023*
C6	0.21838 (18)	0.42704 (9)	0.5676 (4)	0.0149 (4)
C7	0.30956 (18)	0.38046 (9)	0.8490 (4)	0.0139 (4)
C8	0.32714 (17)	0.34057 (9)	1.0515 (4)	0.0149 (4)
C9	0.40792 (19)	0.28660 (9)	1.3227 (4)	0.0153 (4)
C10	0.61131 (16)	0.25386 (9)	1.2505 (4)	0.0175 (4)
H10A	0.6859	0.2451	1.3118	0.021*
H10B	0.5904	0.2184	1.1489	0.021*
C11	0.61482 (18)	0.31330 (9)	1.1098 (4)	0.0143 (4)
C12	0.72157 (16)	0.33574 (8)	1.0201 (4)	0.0140 (4)
C13	0.72667 (19)	0.36733 (9)	0.8082 (4)	0.0171 (4)
H13	0.6617	0.3728	0.7193	0.021*
C14	0.82592 (18)	0.39051 (9)	0.7279 (4)	0.0180 (4)
H14	0.8288	0.4122	0.5846	0.022*
C15	0.92123 (19)	0.38220 (10)	0.8562 (4)	0.0186 (4)
H15	0.9891	0.3985	0.8010	0.022*
C16	0.91816 (19)	0.35013 (10)	1.0651 (4)	0.0184 (4)
H16	0.9838	0.3443	1.1518	0.022*
C17	0.81865 (18)	0.32671 (9)	1.1466 (4)	0.0159 (4)
H17	0.8164	0.3045	1.2886	0.019*

	U11	U22	U33	U12	U13	U23
S1	0.0133 (2)	0.0176 (2)	0.0250 (3)	−0.00121 (19)	−0.0008 (2)	0.0079 (2)
S2	0.0186 (3)	0.0185 (3)	0.0170 (3)	0.00037 (19)	−0.0012 (2)	0.00396 (19)
N1	0.0172 (9)	0.0139 (8)	0.0184 (9)	−0.0010 (7)	−0.0006 (8)	0.0007 (8)
N2	0.0168 (9)	0.0155 (8)	0.0186 (9)	−0.0002 (7)	0.0009 (8)	0.0010 (7)
N3	0.0185 (9)	0.0171 (9)	0.0175 (10)	−0.0008 (7)	0.0015 (7)	0.0035 (7)
N4	0.0129 (9)	0.0131 (8)	0.0167 (9)	−0.0003 (7)	−0.0003 (7)	0.0014 (7)
N5	0.0134 (9)	0.0136 (8)	0.0195 (10)	−0.0017 (7)	0.0019 (7)	0.0015 (7)
C1	0.0158 (10)	0.0138 (9)	0.0224 (11)	0.0024 (8)	0.0009 (9)	0.0014 (9)
C2	0.0168 (11)	0.0181 (10)	0.0295 (13)	−0.0004 (9)	0.0018 (10)	0.0066 (9)
C3	0.0231 (12)	0.0158 (10)	0.0223 (11)	0.0039 (9)	0.0017 (10)	0.0065 (9)
C4	0.0201 (11)	0.0195 (10)	0.0211 (12)	0.0042 (8)	−0.0038 (10)	0.0012 (9)
C5	0.0139 (11)	0.0198 (10)	0.0237 (12)	0.0009 (8)	−0.0021 (9)	0.0014 (9)
C6	0.0173 (11)	0.0118 (8)	0.0157 (10)	0.0011 (8)	0.0013 (8)	−0.0008 (8)
C7	0.0137 (9)	0.0105 (9)	0.0175 (11)	−0.0002 (8)	0.0008 (8)	−0.0011 (8)
C8	0.0127 (10)	0.0138 (9)	0.0183 (11)	0.0017 (8)	−0.0010 (8)	−0.0012 (8)
C9	0.0176 (10)	0.0121 (9)	0.0161 (10)	0.0003 (8)	0.0001 (8)	0.0004 (7)
C10	0.0139 (9)	0.0134 (9)	0.0252 (11)	0.0001 (8)	−0.0016 (9)	0.0024 (9)
C11	0.0145 (10)	0.0122 (9)	0.0161 (10)	−0.0022 (8)	−0.0012 (8)	−0.0024 (8)
C12	0.0143 (10)	0.0093 (8)	0.0184 (10)	−0.0001 (7)	−0.0001 (8)	−0.0015 (8)
C13	0.0199 (11)	0.0124 (9)	0.0191 (11)	−0.0002 (8)	−0.0015 (9)	0.0005 (8)
C14	0.0218 (11)	0.0159 (9)	0.0161 (11)	0.0000 (8)	0.0033 (9)	0.0007 (9)
C15	0.0160 (10)	0.0180 (10)	0.0219 (11)	−0.0031 (9)	0.0039 (9)	−0.0027 (9)
C16	0.0161 (10)	0.0169 (9)	0.0221 (12)	0.0003 (8)	−0.0015 (9)	−0.0010 (8)
C17	0.0175 (11)	0.0123 (9)	0.0177 (11)	0.0013 (8)	−0.0017 (9)	−0.0002 (8)

S1—C1	1.734 (2)	C4—H4	0.9500
S1—C7	1.758 (2)	C5—C6	1.395 (3)
S2—C9	1.728 (2)	C5—H5	0.9500
S2—C10	1.813 (2)	C7—C8	1.464 (3)
N1—C7	1.298 (3)	C10—C11	1.507 (3)
N1—C6	1.393 (3)	C10—H10A	0.9900
N2—C8	1.314 (3)	C10—H10B	0.9900
N2—N3	1.394 (3)	C11—C12	1.476 (3)
N3—C9	1.319 (3)	C12—C13	1.402 (3)
N4—C9	1.366 (3)	C12—C17	1.401 (3)
N4—C8	1.379 (3)	C13—C14	1.383 (3)
N4—N5	1.391 (2)	C13—H13	0.9500
N5—C11	1.288 (3)	C14—C15	1.387 (3)
C1—C2	1.396 (3)	C14—H14	0.9500
C1—C6	1.404 (3)	C15—C16	1.391 (3)
C2—C3	1.376 (3)	C15—H15	0.9500
C2—H2	0.9500	C16—C17	1.390 (3)
C3—C4	1.394 (3)	C16—H16	0.9500
C3—H3	0.9500	C17—H17	0.9500
C4—C5	1.377 (3)
C1—S1—C7	88.40 (10)	N4—C8—C7	124.43 (19)
C9—S2—C10	94.47 (10)	N3—C9—N4	110.04 (19)
C7—N1—C6	110.09 (18)	N3—C9—S2	129.60 (17)
C8—N2—N3	107.21 (18)	N4—C9—S2	120.26 (17)
C9—N3—N2	107.51 (17)	C11—C10—S2	112.86 (14)
C9—N4—C8	105.17 (18)	C11—C10—H10A	109.0
C9—N4—N5	129.18 (19)	S2—C10—H10A	109.0
C8—N4—N5	125.17 (17)	C11—C10—H10B	109.0
C11—N5—N4	115.69 (17)	S2—C10—H10B	109.0
C2—C1—C6	121.1 (2)	H10A—C10—H10B	107.8
C2—C1—S1	128.93 (17)	N5—C11—C12	116.37 (18)
C6—C1—S1	109.87 (16)	N5—C11—C10	124.40 (19)
C3—C2—C1	117.7 (2)	C12—C11—C10	119.17 (18)
C3—C2—H2	121.1	C13—C12—C17	119.1 (2)
C1—C2—H2	121.1	C13—C12—C11	120.2 (2)
C2—C3—C4	121.6 (2)	C17—C12—C11	120.7 (2)
C2—C3—H3	119.2	C14—C13—C12	120.3 (2)
C4—C3—H3	119.2	C14—C13—H13	119.8
C5—C4—C3	120.9 (2)	C12—C13—H13	119.8
C5—C4—H4	119.6	C13—C14—C15	120.1 (2)
C3—C4—H4	119.6	C13—C14—H14	120.0
C4—C5—C6	118.7 (2)	C15—C14—H14	120.0
C4—C5—H5	120.7	C14—C15—C16	120.5 (2)
C6—C5—H5	120.7	C14—C15—H15	119.8
C5—C6—N1	124.9 (2)	C16—C15—H15	119.8
C5—C6—C1	119.93 (19)	C17—C16—C15	119.7 (2)
N1—C6—C1	115.08 (19)	C17—C16—H16	120.2
N1—C7—C8	121.47 (19)	C15—C16—H16	120.2
N1—C7—S1	116.54 (16)	C16—C17—C12	120.3 (2)
C8—C7—S1	121.97 (16)	C16—C17—H17	119.8
N2—C8—N4	110.06 (18)	C12—C17—H17	119.8
N2—C8—C7	125.50 (19)
C8—N2—N3—C9	−0.5 (2)	S1—C7—C8—N2	166.92 (17)
C9—N4—N5—C11	25.6 (3)	N1—C7—C8—N4	167.6 (2)
C8—N4—N5—C11	−163.6 (2)	S1—C7—C8—N4	−13.8 (3)
C7—S1—C1—C2	−177.9 (2)	N2—N3—C9—N4	0.0 (2)
C7—S1—C1—C6	−0.48 (16)	N2—N3—C9—S2	176.46 (16)
C6—C1—C2—C3	−2.0 (3)	C8—N4—C9—N3	0.5 (2)
S1—C1—C2—C3	175.07 (18)	N5—N4—C9—N3	172.72 (19)
C1—C2—C3—C4	1.2 (4)	C8—N4—C9—S2	−176.35 (15)
C2—C3—C4—C5	0.4 (4)	N5—N4—C9—S2	−4.1 (3)
C3—C4—C5—C6	−1.2 (3)	C10—S2—C9—N3	153.5 (2)
C4—C5—C6—N1	−176.8 (2)	C10—S2—C9—N4	−30.35 (18)
C4—C5—C6—C1	0.3 (3)	C9—S2—C10—C11	48.76 (17)
C7—N1—C6—C5	176.0 (2)	N4—N5—C11—C12	178.39 (18)
C7—N1—C6—C1	−1.3 (3)	N4—N5—C11—C10	1.0 (3)
C2—C1—C6—C5	1.3 (3)	S2—C10—C11—N5	−41.2 (3)
S1—C1—C6—C5	−176.30 (16)	S2—C10—C11—C12	141.45 (17)
C2—C1—C6—N1	178.7 (2)	N5—C11—C12—C13	−30.4 (3)
S1—C1—C6—N1	1.1 (2)	C10—C11—C12—C13	147.11 (19)
C6—N1—C7—C8	179.56 (17)	N5—C11—C12—C17	148.6 (2)
C6—N1—C7—S1	0.9 (2)	C10—C11—C12—C17	−33.9 (3)
C1—S1—C7—N1	−0.26 (18)	C17—C12—C13—C14	−1.5 (3)
C1—S1—C7—C8	−178.90 (18)	C11—C12—C13—C14	177.53 (19)
N3—N2—C8—N4	0.9 (2)	C12—C13—C14—C15	0.5 (3)
N3—N2—C8—C7	−179.81 (18)	C13—C14—C15—C16	0.6 (3)
C9—N4—C8—N2	−0.8 (2)	C14—C15—C16—C17	−0.5 (3)
N5—N4—C8—N2	−173.48 (19)	C15—C16—C17—C12	−0.5 (3)
C9—N4—C8—C7	179.81 (18)	C13—C12—C17—C16	1.5 (3)
N5—N4—C8—C7	7.2 (3)	C11—C12—C17—C16	−177.49 (19)
N1—C7—C8—N2	−11.7 (3)

Cg1 is the centroid of the C12–C17 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10a···N3i	0.99	2.45	3.333 (3)	148
C3—H3···Cg1ii	0.95	2.65	3.377 (2)	134

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C12–C17 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10a⋯N3i	0.99	2.45	3.333 (3)	148
C3—H3⋯Cg1ii	0.95	2.65	3.377 (2)	134

Symmetry codes: (i) ; (ii) .