2-Methyl-sulfanyl-1,2,4-triazolo[1,5-a]quinazoline-5(4H)-thione.

In the title compound, C10H8N4S2, comprising fused six-, six- and five-membered rings, the mol-ecule is close to being planar (r.m.s. deviation of the non-H atoms = 0.041 Å). The S-bound methyl group is folded away from the single N atom of the triazole ring and the NH group of the six-membered ring, allowing for the formation of centrosymmetric eight-membered {⋯HNCN}2 synthons in the crystal. The resulting inversion dimers are connected into supra-molecular stacks aligned along the b-axis direction by π-π inter-actions [centroid-centroid distances = 3.6531 (12) and 3.7182 (12) Å].

Related literature

For background to the biological activity of triazoloquinazolines, see: Pierce et al. (2004 ▶); Al-Salahi & Geffken (2010 ▶, 2011 ▶); Al-Salahi et al. (2011 ▶, 2013 ▶).

Experimental

Crystal data

C10H8N4S2

M = 248.32

Monoclinic,

a = 10.5414 (11) Å

b = 4.9335 (6) Å

c = 20.0943 (19) Å

β = 99.127 (10)°

V = 1031.79 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.49 mm−1

T = 295 K

0.30 × 0.15 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.864, T max = 1.000

5096 measured reflections

2389 independent reflections

1667 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.098

S = 0.93

2389 reflections

149 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); 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 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813004881/hb7045sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813004881/hb7045Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813004881/hb7045Isup3.cml

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

C10H8N4S2	F(000) = 512
Mr = 248.32	Dx = 1.599 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1314 reflections
a = 10.5414 (11) Å	θ = 3.1–27.5°
b = 4.9335 (6) Å	µ = 0.49 mm−1
c = 20.0943 (19) Å	T = 295 K
β = 99.127 (10)°	Prism, yellow
V = 1031.79 (19) Å3	0.30 × 0.15 × 0.05 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	2389 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1667 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.035
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 3.1°
ω scan	h = −13→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −5→6
Tmin = 0.864, Tmax = 1.000	l = −22→26
5096 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 0.93	w = 1/[σ2(Fo2) + (0.0452P)2] where P = (Fo2 + 2Fc2)/3
2389 reflections	(Δ/σ)max = 0.001
149 parameters	Δρmax = 0.28 e Å−3
1 restraint	Δρmin = −0.29 e Å−3

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	0.57415 (5)	0.09061 (12)	0.69579 (3)	0.03633 (18)
S2	0.69330 (6)	1.14441 (14)	0.43364 (3)	0.0455 (2)
N1	0.63890 (16)	0.7597 (4)	0.51388 (8)	0.0334 (4)
H1	0.5735 (15)	0.728 (5)	0.4828 (9)	0.052 (7)*
N2	0.75333 (14)	0.6491 (3)	0.61961 (8)	0.0288 (4)
N3	0.74549 (16)	0.4772 (3)	0.67308 (8)	0.0309 (4)
N4	0.57690 (15)	0.4139 (4)	0.58757 (8)	0.0325 (4)
C1	0.72154 (19)	0.9632 (4)	0.50311 (10)	0.0316 (5)
C2	0.83231 (19)	1.0021 (4)	0.55680 (10)	0.0306 (5)
C3	0.92564 (19)	1.1992 (5)	0.55164 (11)	0.0363 (5)
H3	0.9169	1.3102	0.5138	0.044*
C4	1.0296 (2)	1.2317 (5)	0.60125 (11)	0.0403 (6)
H4	1.0906	1.3640	0.5970	0.048*
C5	1.04387 (19)	1.0665 (5)	0.65804 (11)	0.0385 (5)
H5	1.1151	1.0883	0.6914	0.046*
C6	0.95443 (19)	0.8723 (4)	0.66552 (10)	0.0358 (5)
H6	0.9644	0.7626	0.7036	0.043*
C7	0.84829 (18)	0.8415 (4)	0.61517 (10)	0.0292 (5)
C8	0.65228 (18)	0.6076 (4)	0.57102 (9)	0.0294 (5)
C9	0.63785 (18)	0.3432 (4)	0.65066 (10)	0.0296 (5)
C10	0.6908 (2)	0.0885 (5)	0.77103 (11)	0.0474 (6)
H10A	0.6676	−0.0456	0.8016	0.071*
H10B	0.6935	0.2637	0.7920	0.071*
H10C	0.7738	0.0461	0.7599	0.071*

	U11	U22	U33	U12	U13	U23
S1	0.0370 (3)	0.0390 (4)	0.0320 (3)	−0.0018 (3)	0.0023 (2)	0.0034 (3)
S2	0.0496 (4)	0.0525 (4)	0.0330 (3)	−0.0007 (3)	0.0019 (3)	0.0110 (3)
N1	0.0337 (9)	0.0388 (11)	0.0247 (9)	−0.0014 (9)	−0.0046 (8)	0.0023 (8)
N2	0.0291 (8)	0.0321 (10)	0.0237 (8)	0.0019 (8)	−0.0006 (7)	0.0006 (8)
N3	0.0339 (9)	0.0321 (10)	0.0256 (9)	0.0011 (8)	0.0015 (7)	0.0028 (8)
N4	0.0328 (9)	0.0369 (11)	0.0266 (9)	0.0011 (9)	0.0007 (7)	0.0016 (8)
C1	0.0351 (11)	0.0320 (12)	0.0285 (11)	0.0054 (10)	0.0070 (9)	−0.0012 (9)
C2	0.0329 (10)	0.0314 (12)	0.0282 (11)	0.0062 (10)	0.0069 (9)	−0.0035 (9)
C3	0.0380 (11)	0.0367 (13)	0.0354 (12)	−0.0001 (11)	0.0091 (10)	−0.0006 (10)
C4	0.0366 (12)	0.0394 (14)	0.0457 (13)	−0.0061 (11)	0.0090 (10)	−0.0064 (12)
C5	0.0306 (11)	0.0436 (14)	0.0387 (12)	0.0001 (11)	−0.0024 (10)	−0.0089 (11)
C6	0.0363 (11)	0.0380 (13)	0.0313 (11)	0.0050 (10)	−0.0007 (9)	−0.0009 (10)
C7	0.0287 (10)	0.0304 (11)	0.0283 (11)	0.0020 (9)	0.0044 (8)	−0.0040 (9)
C8	0.0316 (10)	0.0316 (12)	0.0234 (10)	0.0038 (10)	−0.0007 (8)	−0.0027 (9)
C9	0.0310 (10)	0.0302 (12)	0.0270 (10)	0.0044 (10)	0.0029 (9)	−0.0020 (9)
C10	0.0511 (14)	0.0587 (17)	0.0299 (12)	−0.0044 (13)	−0.0007 (10)	0.0097 (12)

S1—C9	1.738 (2)	C2—C3	1.399 (3)
S1—C10	1.791 (2)	C2—C7	1.403 (3)
S2—C1	1.645 (2)	C3—C4	1.369 (3)
N1—C8	1.360 (2)	C3—H3	0.9300
N1—C1	1.369 (3)	C4—C5	1.391 (3)
N1—H1	0.868 (10)	C4—H4	0.9300
N2—C8	1.342 (2)	C5—C6	1.369 (3)
N2—N3	1.381 (2)	C5—H5	0.9300
N2—C7	1.392 (2)	C6—C7	1.393 (3)
N3—C9	1.329 (2)	C6—H6	0.9300
N4—C8	1.319 (3)	C10—H10A	0.9600
N4—C9	1.372 (2)	C10—H10B	0.9600
C1—C2	1.471 (3)	C10—H10C	0.9600
C9—S1—C10	100.05 (10)	C6—C5—C4	120.89 (19)
C8—N1—C1	123.68 (17)	C6—C5—H5	119.6
C8—N1—H1	118.3 (16)	C4—C5—H5	119.6
C1—N1—H1	118.0 (16)	C5—C6—C7	119.0 (2)
C8—N2—N3	109.51 (16)	C5—C6—H6	120.5
C8—N2—C7	123.58 (17)	C7—C6—H6	120.5
N3—N2—C7	126.91 (15)	C6—C7—N2	122.05 (19)
C9—N3—N2	101.24 (15)	C6—C7—C2	121.4 (2)
C8—N4—C9	101.80 (16)	N2—C7—C2	116.50 (17)
N1—C1—C2	115.51 (18)	N4—C8—N2	111.57 (18)
N1—C1—S2	119.93 (15)	N4—C8—N1	128.80 (17)
C2—C1—S2	124.56 (17)	N2—C8—N1	119.63 (19)
C3—C2—C7	117.51 (18)	N3—C9—N4	115.88 (18)
C3—C2—C1	121.46 (19)	N3—C9—S1	124.04 (15)
C7—C2—C1	121.0 (2)	N4—C9—S1	120.09 (15)
C4—C3—C2	121.2 (2)	S1—C10—H10A	109.5
C4—C3—H3	119.4	S1—C10—H10B	109.5
C2—C3—H3	119.4	H10A—C10—H10B	109.5
C3—C4—C5	119.9 (2)	S1—C10—H10C	109.5
C3—C4—H4	120.0	H10A—C10—H10C	109.5
C5—C4—H4	120.0	H10B—C10—H10C	109.5
C8—N2—N3—C9	0.5 (2)	C3—C2—C7—C6	−1.4 (3)
C7—N2—N3—C9	179.49 (18)	C1—C2—C7—C6	178.41 (19)
C8—N1—C1—C2	2.8 (3)	C3—C2—C7—N2	179.17 (17)
C8—N1—C1—S2	−177.27 (16)	C1—C2—C7—N2	−1.0 (3)
N1—C1—C2—C3	178.67 (19)	C9—N4—C8—N2	1.2 (2)
S2—C1—C2—C3	−1.3 (3)	C9—N4—C8—N1	−178.6 (2)
N1—C1—C2—C7	−1.2 (3)	N3—N2—C8—N4	−1.2 (2)
S2—C1—C2—C7	178.89 (16)	C7—N2—C8—N4	179.82 (17)
C7—C2—C3—C4	0.9 (3)	N3—N2—C8—N1	178.65 (17)
C1—C2—C3—C4	−178.9 (2)	C7—N2—C8—N1	−0.4 (3)
C2—C3—C4—C5	0.1 (3)	C1—N1—C8—N4	177.7 (2)
C3—C4—C5—C6	−0.6 (3)	C1—N1—C8—N2	−2.1 (3)
C4—C5—C6—C7	0.1 (3)	N2—N3—C9—N4	0.3 (2)
C5—C6—C7—N2	−179.68 (19)	N2—N3—C9—S1	179.79 (14)
C5—C6—C7—C2	1.0 (3)	C8—N4—C9—N3	−0.9 (2)
C8—N2—C7—C6	−177.57 (19)	C8—N4—C9—S1	179.53 (15)
N3—N2—C7—C6	3.6 (3)	C10—S1—C9—N3	0.4 (2)
C8—N2—C7—C2	1.8 (3)	C10—S1—C9—N4	179.93 (17)
N3—N2—C7—C2	−177.02 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N4i	0.87 (1)	2.07 (1)	2.931 (2)	171 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N4i	0.87 (1)	2.07 (1)	2.931 (2)	171 (2)

Symmetry code: (i) .