2-Methyl-sulfanyl-9H-1,3,4-thia-diazolo[2,3-b]quinazolin-9-one.

In the title compound, C(10)H(7)N(3)OS(2), the 16 non-H atoms are almost planar (r.m.s. deviation = 0.037 Å) and the S-bound methyl group is syn to the ketone O atom. In the crystal, centrosymmetrically related mol-ecules are connected by pairs of C-H⋯O inter-actions between the ketone O and methyl H atoms. The dimeric aggregates are connected into a linear supra-molecular chain along the b axis via π-π inter-actions occurring between the five-membered and benzene rings [centroid-centroid distance = 3.6123 (9) Å]. The chains assemble into layers in the bc plane via S⋯S inter-actions involving the endocyclic S atoms [S⋯S = 3.4607 (6) and 3.4792 (6) Å].

Related literature

For recent studies on the synthesis and biological properties of quinazoline-4(3H)-one derivatives, see: El-Azab & ElTahir (2012 ▶); El-Azab et al. (2011 ▶). For the synthesis and anti-microbial activity of the title compound, see: El-Azab (2007 ▶).

Experimental

Crystal data

C10H7N3OS2

M = 249.31

Monoclinic,

a = 11.8193 (4) Å

b = 4.9841 (2) Å

c = 17.4985 (6) Å

β = 91.453 (3)°

V = 1030.48 (6) Å3

Z = 4

Cu Kα radiation

μ = 4.53 mm−1

T = 100 K

0.30 × 0.10 × 0.03 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.344, T max = 0.876

3781 measured reflections

2110 independent reflections

1937 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.082

S = 1.09

2110 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.27 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: 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/S1600536812026189/hb6843sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812026189/hb6843Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812026189/hb6843Isup3.cml

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

C10H7N3OS2	F(000) = 512
Mr = 249.31	Dx = 1.607 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 2166 reflections
a = 11.8193 (4) Å	θ = 3.7–76.5°
b = 4.9841 (2) Å	µ = 4.53 mm−1
c = 17.4985 (6) Å	T = 100 K
β = 91.453 (3)°	Prism, colourless
V = 1030.48 (6) Å3	0.30 × 0.10 × 0.03 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	2110 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	1937 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.018
Detector resolution: 10.4041 pixels mm-1	θmax = 76.7°, θmin = 3.7°
ω scan	h = −12→14
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −5→6
Tmin = 0.344, Tmax = 0.876	l = −15→21
3781 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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0457P)2 + 0.3686P] where P = (Fo2 + 2Fc2)/3
2110 reflections	(Δ/σ)max = 0.001
145 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

	x	y	z	Uiso*/Ueq
S1	0.90968 (3)	0.75129 (8)	0.46619 (2)	0.01702 (12)
S2	0.76245 (3)	1.12015 (8)	0.55613 (2)	0.01660 (12)
N1	0.90012 (11)	0.3645 (3)	0.35873 (8)	0.0160 (3)
N2	0.72981 (11)	0.5607 (3)	0.40394 (7)	0.0145 (3)
N3	0.68915 (11)	0.7516 (3)	0.45394 (7)	0.0160 (3)
O1	0.55197 (9)	0.4218 (3)	0.36566 (7)	0.0217 (3)
C1	0.65417 (13)	0.4007 (3)	0.36022 (9)	0.0159 (3)
C2	0.71312 (13)	0.2152 (3)	0.31034 (9)	0.0153 (3)
C3	0.64945 (13)	0.0467 (4)	0.26154 (9)	0.0183 (3)
H3	0.5691	0.0533	0.2616	0.022*
C4	0.70332 (14)	−0.1282 (4)	0.21351 (9)	0.0196 (3)
H4	0.6602	−0.2429	0.1806	0.024*
C5	0.82196 (14)	−0.1368 (3)	0.21325 (9)	0.0192 (3)
H5	0.8589	−0.2560	0.1796	0.023*
C6	0.88539 (13)	0.0261 (3)	0.26135 (9)	0.0179 (3)
H6	0.9657	0.0173	0.2609	0.021*
C7	0.83228 (13)	0.2050 (3)	0.31091 (9)	0.0149 (3)
C8	0.84595 (12)	0.5289 (3)	0.40102 (8)	0.0149 (3)
C9	0.77423 (13)	0.8644 (3)	0.48930 (9)	0.0152 (3)
C10	0.61018 (14)	1.1556 (4)	0.55743 (10)	0.0211 (3)
H10A	0.5903	1.2965	0.5938	0.032*
H10B	0.5762	0.9854	0.5730	0.032*
H10C	0.5815	1.2041	0.5062	0.032*

	U11	U22	U33	U12	U13	U23
S1	0.01263 (19)	0.0180 (2)	0.0204 (2)	−0.00013 (13)	−0.00028 (14)	−0.00389 (14)
S2	0.0170 (2)	0.0176 (2)	0.0151 (2)	0.00105 (14)	−0.00022 (14)	−0.00248 (14)
N1	0.0136 (6)	0.0176 (7)	0.0167 (6)	0.0001 (5)	0.0003 (5)	−0.0019 (5)
N2	0.0124 (6)	0.0179 (7)	0.0133 (6)	0.0031 (5)	0.0007 (5)	−0.0011 (5)
N3	0.0161 (6)	0.0180 (7)	0.0139 (6)	0.0031 (5)	0.0001 (5)	−0.0018 (5)
O1	0.0118 (5)	0.0294 (7)	0.0239 (6)	0.0024 (5)	−0.0007 (4)	−0.0067 (5)
C1	0.0148 (7)	0.0191 (7)	0.0138 (7)	0.0014 (6)	−0.0011 (6)	−0.0006 (6)
C2	0.0151 (7)	0.0176 (7)	0.0131 (7)	0.0011 (6)	−0.0001 (5)	0.0006 (6)
C3	0.0146 (7)	0.0227 (8)	0.0176 (7)	0.0013 (7)	−0.0018 (6)	−0.0009 (6)
C4	0.0190 (8)	0.0219 (8)	0.0177 (8)	0.0007 (6)	−0.0041 (6)	−0.0031 (6)
C5	0.0204 (8)	0.0207 (8)	0.0166 (7)	0.0037 (6)	0.0012 (6)	−0.0032 (6)
C6	0.0135 (7)	0.0206 (8)	0.0195 (7)	0.0022 (6)	0.0013 (6)	−0.0013 (6)
C7	0.0149 (7)	0.0160 (7)	0.0139 (7)	−0.0004 (6)	0.0001 (5)	0.0017 (6)
C8	0.0127 (7)	0.0159 (7)	0.0160 (7)	−0.0008 (6)	−0.0005 (5)	0.0023 (6)
C9	0.0155 (7)	0.0160 (7)	0.0141 (7)	0.0019 (6)	0.0005 (5)	0.0014 (6)
C10	0.0178 (7)	0.0261 (9)	0.0194 (8)	0.0048 (7)	0.0015 (6)	−0.0032 (7)

S1—C8	1.7473 (16)	C2—C7	1.409 (2)
S1—C9	1.7542 (16)	C3—C4	1.378 (2)
S2—C9	1.7378 (16)	C3—H3	0.9500
S2—C10	1.8091 (17)	C4—C5	1.403 (2)
N1—C8	1.286 (2)	C4—H4	0.9500
N1—C7	1.393 (2)	C5—C6	1.378 (2)
N2—C8	1.3840 (18)	C5—H5	0.9500
N2—N3	1.3866 (18)	C6—C7	1.403 (2)
N2—C1	1.409 (2)	C6—H6	0.9500
N3—C9	1.296 (2)	C10—H10A	0.9800
O1—C1	1.2186 (19)	C10—H10B	0.9800
C1—C2	1.461 (2)	C10—H10C	0.9800
C2—C3	1.403 (2)
C8—S1—C9	88.48 (7)	C6—C5—H5	119.7
C9—S2—C10	100.19 (8)	C4—C5—H5	119.7
C8—N1—C7	114.96 (13)	C5—C6—C7	120.47 (14)
C8—N2—N3	117.51 (13)	C5—C6—H6	119.8
C8—N2—C1	122.09 (13)	C7—C6—H6	119.8
N3—N2—C1	120.37 (12)	N1—C7—C6	118.30 (14)
C9—N3—N2	108.78 (13)	N1—C7—C2	122.93 (14)
O1—C1—N2	121.69 (14)	C6—C7—C2	118.77 (14)
O1—C1—C2	126.16 (15)	N1—C8—N2	127.10 (14)
N2—C1—C2	112.15 (13)	N1—C8—S1	124.55 (12)
C3—C2—C7	120.23 (14)	N2—C8—S1	108.35 (11)
C3—C2—C1	119.08 (14)	N3—C9—S2	124.42 (12)
C7—C2—C1	120.69 (14)	N3—C9—S1	116.88 (12)
C4—C3—C2	120.06 (15)	S2—C9—S1	118.69 (9)
C4—C3—H3	120.0	S2—C10—H10A	109.5
C2—C3—H3	120.0	S2—C10—H10B	109.5
C3—C4—C5	119.90 (15)	H10A—C10—H10B	109.5
C3—C4—H4	120.0	S2—C10—H10C	109.5
C5—C4—H4	120.0	H10A—C10—H10C	109.5
C6—C5—C4	120.56 (15)	H10B—C10—H10C	109.5
C8—N2—N3—C9	−0.24 (19)	C3—C2—C7—N1	−179.16 (15)
C1—N2—N3—C9	177.60 (13)	C1—C2—C7—N1	0.9 (2)
C8—N2—C1—O1	176.66 (15)	C3—C2—C7—C6	0.7 (2)
N3—N2—C1—O1	−1.1 (2)	C1—C2—C7—C6	−179.20 (15)
C8—N2—C1—C2	−3.1 (2)	C7—N1—C8—N2	0.4 (2)
N3—N2—C1—C2	179.13 (13)	C7—N1—C8—S1	179.87 (11)
O1—C1—C2—C3	1.9 (3)	N3—N2—C8—N1	−179.87 (15)
N2—C1—C2—C3	−178.30 (14)	C1—N2—C8—N1	2.3 (2)
O1—C1—C2—C7	−178.17 (16)	N3—N2—C8—S1	0.61 (17)
N2—C1—C2—C7	1.6 (2)	C1—N2—C8—S1	−177.18 (12)
C7—C2—C3—C4	−0.5 (2)	C9—S1—C8—N1	179.88 (15)
C1—C2—C3—C4	179.44 (15)	C9—S1—C8—N2	−0.59 (11)
C2—C3—C4—C5	−0.3 (3)	N2—N3—C9—S2	178.77 (11)
C3—C4—C5—C6	0.8 (3)	N2—N3—C9—S1	−0.27 (17)
C4—C5—C6—C7	−0.5 (3)	C10—S2—C9—N3	0.76 (16)
C8—N1—C7—C6	178.13 (15)	C10—S2—C9—S1	179.79 (10)
C8—N1—C7—C2	−2.0 (2)	C8—S1—C9—N3	0.53 (13)
C5—C6—C7—N1	179.67 (15)	C8—S1—C9—S2	−178.57 (10)
C5—C6—C7—C2	−0.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O1i	0.98	2.32	3.170 (2)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯O1i	0.98	2.32	3.170 (2)	145

Symmetry code: (i) .