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

The non-H atoms of the title compound, C(10)H(8)N(4)OS, lie approximately in a common plane (r.m.s. deviation = 0.058 Å). In the crystal, two mol-ecules are linked across a center of inversion by a pair of N-H⋯N hydrogen bonds, forming a a dimer.

Related literature

For the synthesis, see: Al-Salahi & Geffken (2011 ▶). For a related compound, see: Al-Salahi et al. (2011 ▶).

Experimental

Crystal data

C10H8N4OS

M = 232.26

Monoclinic,

a = 10.4150 (1) Å

b = 5.0631 (1) Å

c = 18.6564 (3) Å

β = 96.857 (1)°

V = 976.76 (3) Å3

Z = 4

Cu Kα radiation

μ = 2.81 mm−1

T = 294 K

0.35 × 0.15 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.439, T max = 0.766

15980 measured reflections

2052 independent reflections

1996 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.089

S = 1.05

2052 reflections

151 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); 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: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812021757/bt5914sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812021757/bt5914Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812021757/bt5914Isup3.cml

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

C10H8N4OS	F(000) = 480
Mr = 232.26	Dx = 1.579 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 10679 reflections
a = 10.4150 (1) Å	θ = 4.3–76.7°
b = 5.0631 (1) Å	µ = 2.81 mm−1
c = 18.6564 (3) Å	T = 294 K
β = 96.857 (1)°	Prism, colorless
V = 976.76 (3) Å3	0.35 × 0.15 × 0.10 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	2052 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	1996 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.033
Detector resolution: 10.4041 pixels mm-1	θmax = 76.9°, θmin = 4.3°
ω scan	h = −13→13
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −6→6
Tmin = 0.439, Tmax = 0.766	l = −23→23
15980 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)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.089	w = 1/[σ2(Fo2) + (0.0547P)2 + 0.2828P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
2052 reflections	Δρmax = 0.24 e Å−3
151 parameters	Δρmin = −0.21 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0089 (9)

	x	y	z	Uiso*/Ueq
S1	0.07695 (3)	0.09449 (7)	0.203762 (17)	0.03356 (15)
O1	0.19589 (12)	1.1102 (2)	−0.05498 (6)	0.0527 (3)
N1	0.25468 (10)	0.6522 (2)	0.12100 (5)	0.0284 (2)
N2	0.24857 (10)	0.4808 (2)	0.17833 (5)	0.0299 (2)
N3	0.07817 (11)	0.4211 (2)	0.09036 (6)	0.0327 (3)
N4	0.13609 (11)	0.7645 (3)	0.01027 (6)	0.0365 (3)
C1	0.34851 (12)	0.8433 (3)	0.11483 (6)	0.0282 (3)
C2	0.45835 (13)	0.8685 (3)	0.16496 (7)	0.0331 (3)
H2	0.4716	0.7559	0.2045	0.040*
C3	0.54687 (13)	1.0631 (3)	0.15483 (8)	0.0357 (3)
H3	0.6209	1.0803	0.1877	0.043*
C4	0.52720 (14)	1.2342 (3)	0.09627 (8)	0.0381 (3)
H4A	0.5867	1.3674	0.0908	0.046*
C5	0.41916 (13)	1.2058 (3)	0.04634 (7)	0.0365 (3)
H5	0.4066	1.3195	0.0070	0.044*
C6	0.32892 (12)	1.0088 (3)	0.05434 (7)	0.0311 (3)
C7	0.21660 (14)	0.9725 (3)	−0.00156 (7)	0.0359 (3)
C8	0.15228 (12)	0.6134 (3)	0.07104 (7)	0.0303 (3)
C9	0.14125 (12)	0.3490 (3)	0.15648 (7)	0.0291 (3)
C10	0.18994 (15)	0.0881 (3)	0.28453 (8)	0.0443 (4)
H10A	0.1713	−0.0598	0.3138	0.066*
H10B	0.1826	0.2487	0.3111	0.066*
H10C	0.2763	0.0721	0.2718	0.066*
H4	0.072 (2)	0.722 (4)	−0.0199 (11)	0.062 (6)*

	U11	U22	U33	U12	U13	U23
S1	0.0327 (2)	0.0351 (2)	0.0319 (2)	−0.00273 (12)	−0.00017 (14)	0.00156 (12)
O1	0.0552 (7)	0.0637 (8)	0.0356 (6)	−0.0047 (5)	−0.0093 (5)	0.0204 (5)
N1	0.0297 (5)	0.0316 (5)	0.0225 (5)	0.0011 (4)	−0.0028 (4)	0.0021 (4)
N2	0.0315 (5)	0.0323 (6)	0.0249 (5)	0.0010 (4)	−0.0010 (4)	0.0025 (4)
N3	0.0308 (5)	0.0381 (6)	0.0273 (5)	−0.0004 (4)	−0.0038 (4)	0.0003 (4)
N4	0.0364 (6)	0.0439 (7)	0.0263 (5)	−0.0022 (5)	−0.0087 (4)	0.0045 (5)
C1	0.0298 (6)	0.0300 (6)	0.0246 (6)	0.0029 (5)	0.0018 (5)	−0.0023 (5)
C2	0.0345 (6)	0.0356 (7)	0.0275 (6)	0.0012 (5)	−0.0031 (5)	0.0007 (5)
C3	0.0328 (6)	0.0399 (7)	0.0328 (7)	−0.0007 (5)	−0.0020 (5)	−0.0048 (5)
C4	0.0394 (7)	0.0364 (7)	0.0387 (7)	−0.0050 (6)	0.0051 (6)	−0.0020 (6)
C5	0.0428 (7)	0.0356 (7)	0.0312 (7)	0.0012 (6)	0.0049 (6)	0.0046 (5)
C6	0.0335 (6)	0.0335 (7)	0.0258 (6)	0.0039 (5)	0.0015 (5)	0.0000 (5)
C7	0.0385 (7)	0.0413 (7)	0.0269 (6)	0.0034 (6)	−0.0008 (5)	0.0035 (6)
C8	0.0310 (6)	0.0340 (7)	0.0245 (6)	0.0030 (5)	−0.0029 (5)	−0.0009 (5)
C9	0.0291 (6)	0.0314 (6)	0.0260 (6)	0.0027 (5)	0.0000 (5)	−0.0023 (5)
C10	0.0442 (8)	0.0510 (9)	0.0354 (7)	−0.0051 (6)	−0.0041 (6)	0.0098 (6)

S1—C9	1.7402 (14)	C1—C6	1.4008 (18)
S1—C10	1.7980 (15)	C2—C3	1.378 (2)
O1—C7	1.2145 (18)	C2—H2	0.9300
N1—C8	1.3443 (15)	C3—C4	1.390 (2)
N1—N2	1.3848 (15)	C3—H3	0.9300
N1—C1	1.3897 (17)	C4—C5	1.3800 (19)
N2—C9	1.3237 (17)	C4—H4A	0.9300
N3—C8	1.3192 (18)	C5—C6	1.391 (2)
N3—C9	1.3759 (16)	C5—H5	0.9300
N4—C8	1.3614 (17)	C6—C7	1.4828 (18)
N4—C7	1.3800 (19)	C10—H10A	0.9600
N4—H4	0.85 (2)	C10—H10B	0.9600
C1—C2	1.3942 (17)	C10—H10C	0.9600
C9—S1—C10	100.67 (7)	C4—C5—C6	120.60 (13)
C8—N1—N2	109.76 (10)	C4—C5—H5	119.7
C8—N1—C1	123.49 (11)	C6—C5—H5	119.7
N2—N1—C1	126.72 (10)	C5—C6—C1	118.70 (12)
C9—N2—N1	101.13 (10)	C5—C6—C7	120.00 (12)
C8—N3—C9	102.03 (11)	C1—C6—C7	121.28 (13)
C8—N4—C7	123.00 (11)	O1—C7—N4	121.17 (13)
C8—N4—H4	114.7 (15)	O1—C7—C6	123.63 (14)
C7—N4—H4	122.3 (15)	N4—C7—C6	115.18 (12)
N1—C1—C2	122.47 (12)	N3—C8—N1	111.11 (11)
N1—C1—C6	116.55 (11)	N3—C8—N4	128.60 (11)
C2—C1—C6	120.97 (12)	N1—C8—N4	120.29 (12)
C3—C2—C1	118.83 (13)	N2—C9—N3	115.95 (12)
C3—C2—H2	120.6	N2—C9—S1	125.39 (9)
C1—C2—H2	120.6	N3—C9—S1	118.65 (10)
C2—C3—C4	121.01 (13)	S1—C10—H10A	109.5
C2—C3—H3	119.5	S1—C10—H10B	109.5
C4—C3—H3	119.5	H10A—C10—H10B	109.5
C5—C4—C3	119.85 (13)	S1—C10—H10C	109.5
C5—C4—H4A	120.1	H10A—C10—H10C	109.5
C3—C4—H4A	120.1	H10B—C10—H10C	109.5
C8—N1—N2—C9	0.85 (13)	C5—C6—C7—O1	−1.4 (2)
C1—N1—N2—C9	179.10 (12)	C1—C6—C7—O1	−179.72 (14)
C8—N1—C1—C2	−175.64 (12)	C5—C6—C7—N4	177.42 (13)
N2—N1—C1—C2	6.33 (19)	C1—C6—C7—N4	−0.88 (19)
C8—N1—C1—C6	3.12 (18)	C9—N3—C8—N1	1.23 (14)
N2—N1—C1—C6	−174.91 (11)	C9—N3—C8—N4	−178.64 (14)
N1—C1—C2—C3	179.92 (12)	N2—N1—C8—N3	−1.39 (15)
C6—C1—C2—C3	1.2 (2)	C1—N1—C8—N3	−179.71 (11)
C1—C2—C3—C4	0.7 (2)	N2—N1—C8—N4	178.50 (11)
C2—C3—C4—C5	−1.6 (2)	C1—N1—C8—N4	0.17 (19)
C3—C4—C5—C6	0.6 (2)	C7—N4—C8—N3	175.64 (14)
C4—C5—C6—C1	1.3 (2)	C7—N4—C8—N1	−4.2 (2)
C4—C5—C6—C7	−177.05 (13)	N1—N2—C9—N3	−0.07 (14)
N1—C1—C6—C5	179.03 (12)	N1—N2—C9—S1	179.08 (9)
C2—C1—C6—C5	−2.2 (2)	C8—N3—C9—N2	−0.71 (15)
N1—C1—C6—C7	−2.66 (18)	C8—N3—C9—S1	−179.93 (9)
C2—C1—C6—C7	176.13 (12)	C10—S1—C9—N2	2.50 (13)
C8—N4—C7—O1	−176.73 (14)	C10—S1—C9—N3	−178.36 (11)
C8—N4—C7—C6	4.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···N3i	0.85 (2)	2.05 (2)	2.896 (2)	174 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯N3i	0.85 (2)	2.05 (2)	2.896 (2)	174 (2)

Symmetry code: (i) .