2-Methyl­sulfonyl-1,2,4-triazolo[1,5-a]quinazolin-5(4H)-one

Abstract

The triazoloquinazoline fused-ring system of the title compound, C₁₀H₈N₄O₃S, is essentially planar (r.m.s. deviation = 0.027 Å). In the crystal, adjacent mol­ecules are linked by N—H⋯O_sulfon­yl hydrogen bonds, generating a helical chain running along the b axis.

Related literature  

For the synthesis of the precursor, see: Al-Salahi & Geffken (2011 ▶).

Experimental  

Crystal data  

• C₁₀H₈N₄O₃S

• M _r = 264.26

• Monoclinic,

• a = 9.6216 (2) Å

• b = 4.9206 (1) Å

• c = 12.1623 (3) Å

• β = 106.628 (2)°

• V = 551.73 (2) ų

• Z = 2

• Cu Kα radiation

• μ = 2.71 mm⁻¹

• T = 294 K

• 0.20 × 0.10 × 0.02 mm

Data collection  

• Agilent SuperNova Dual diffractometer with an Atlas detector

• Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) ▶ T _min = 0.613, T _max = 0.948

• 9640 measured reflections

• 2304 independent reflections

• 2237 reflections with I > 2σ(I)

• R _int = 0.025

Refinement  

• R[F ² > 2σ(F ²)] = 0.030

• wR(F ²) = 0.082

• S = 1.04

• 2304 reflections

• 168 parameters

• 1 restraint

• H atoms treated by a mixture of independent and constrained refinement

• Δρ_max = 0.15 e Å⁻³

• Δρ_min = −0.26 e Å⁻³

• Absolute structure: Flack (1983 ▶), 1007 Friedel pairs

• Flack parameter: 0.00 (2)

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 ▶).

Supplementary Material

Supplementary material file. DOI: 10.1107/S1600536812021769/bt5915Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.88 (1)	2.23 (1)	3.072 (2)	160 (3)

Symmetry code: (i) .

supplementary crystallographic information

Comment

2-(Methylsulfanyl)-[1,2,4]triazolo[1,5-a]quinazolin-5-one was synthesized from 2-hydrazinobenzoic acid and dimethyl N-cyanoimidodithiocarbonate; further reactions on the inherent lactam unit yielded other derivatives (Al-Salahi & Geffken, 2011). In the present study, this compound is oxided by hydrogen peroxide. The triazoloquinazoline fused-ring system of C₁₀H₈N₄O₃S (Scheme I, Fig. 1) is planar. Adjacent molecules are linked by an N–H···O_sulfonyl hydrogen bond to generate a helical chain running along the b-axis of the monoclinic unit cell (Fig. 2, Table 1).

Experimental

Under ice-cold conditions, 2-hydrazinobenzoic acid (10 mmol, 1.52 g) was added to a solution of dimethyl N-cyanodithioimidocarbonate (10 mmol, 1.46 g) in ethanol (20 ml). Triethylamine (30 mmol, 3.03 g) was added. The reaction mixture was stirred overnight at room temperature. Concentrated hydrochloric acid was added; the acidified mixture for heated for an hour. The mixture was poured into ice water; the solid that formed was collected and recrystallized from ethanol to give colorless crystals of 2-(methylsulfanyl)-[1,2,4]triazolo[1,5-a]quinazolin-5-one. The procedure was that reported earlier (Al-Salahi & Geffken, 2011).

To the boiling mixture of 2-methylsulfanyl-[1,2,4]triazolo[1,5-a]quinazolin-5-one (1 mmol, 0.23 g) in glacial acetic acid (5 ml) was added hydrogen peroxide. Colorless crystals of the oxidized product were obtained when the solution was allowed to cool.

Refinement

All H-atom were located in a difference Fourier map. Carbon-bound H-atoms were placed in calculated positions [C–H 0.93 to 0.96 Å, U_iso(H) 1.2–1.5U_eq(C)] and were included in the refinement in the riding model approximation.

The amino H-atom was refined isotropically with a distance restraint of N–H 0.88±0.01 Å.

Figures

Fig. 1.

Anisotropic displacement ellipsoid plot (Barbour, 2001) of C10H8N4O3S at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Fig. 2.

Hydrogen-bonded chain motif.

Crystal data

C10H8N4O3S	F(000) = 272
Mr = 264.26	Dx = 1.591 Mg m−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2yb	Cell parameters from 6133 reflections
a = 9.6216 (2) Å	θ = 3.8–76.5°
b = 4.9206 (1) Å	µ = 2.71 mm−1
c = 12.1623 (3) Å	T = 294 K
β = 106.628 (2)°	Plate, colorless
V = 551.73 (2) Å3	0.20 × 0.10 × 0.02 mm
Z = 2

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector	2304 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2237 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.025
Detector resolution: 10.4041 pixels mm-1	θmax = 76.7°, θmin = 3.8°
ω scan	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −6→6
Tmin = 0.613, Tmax = 0.948	l = −14→15
9640 measured reflections

Refinement

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) = 0.082	w = 1/[σ2(Fo2) + (0.0569P)2 + 0.056P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
2304 reflections	Δρmax = 0.15 e Å−3
168 parameters	Δρmin = −0.26 e Å−3
1 restraint	Absolute structure: Flack (1983), 1007 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.00 (2)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.24294 (4)	0.00109 (9)	0.18198 (3)	0.04202 (13)
O1	0.8628 (2)	0.7880 (6)	0.13678 (16)	0.0903 (8)
O2	0.24690 (17)	−0.1892 (3)	0.09276 (13)	0.0566 (4)
O3	0.23731 (18)	−0.0963 (4)	0.29138 (14)	0.0645 (4)
N1	0.67906 (18)	0.4984 (5)	0.12477 (13)	0.0542 (4)
H1	0.677 (3)	0.451 (7)	0.0548 (13)	0.086 (9)*
N2	0.56362 (13)	0.4813 (4)	0.27059 (11)	0.0354 (3)
N3	0.45055 (15)	0.3499 (3)	0.29552 (13)	0.0392 (3)
N4	0.47068 (16)	0.2190 (4)	0.12045 (12)	0.0436 (4)
C1	0.7743 (2)	0.6953 (5)	0.18009 (17)	0.0528 (5)
C2	0.75983 (17)	0.7852 (4)	0.29235 (15)	0.0396 (4)
C3	0.85191 (19)	0.9855 (5)	0.35516 (16)	0.0478 (4)
H3	0.9222	1.0634	0.3262	0.057*
C4	0.8387 (2)	1.0679 (4)	0.45993 (18)	0.0536 (5)
H4	0.8999	1.2021	0.5012	0.064*
C5	0.7349 (2)	0.9521 (5)	0.50437 (17)	0.0534 (5)
H5	0.7273	1.0095	0.5753	0.064*
C6	0.6429 (2)	0.7530 (5)	0.44484 (16)	0.0472 (4)
H6	0.5743	0.6733	0.4752	0.057*
C7	0.65534 (17)	0.6748 (3)	0.33865 (14)	0.0356 (3)
C8	0.57227 (18)	0.3991 (4)	0.16704 (14)	0.0389 (4)
C9	0.40156 (18)	0.2013 (4)	0.20289 (14)	0.0382 (4)
C10	0.1035 (2)	0.2349 (4)	0.12929 (18)	0.0500 (5)
H10A	0.0116	0.1442	0.1142	0.075*
H10B	0.1129	0.3136	0.0596	0.075*
H10C	0.1091	0.3755	0.1851	0.075*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
S1	0.0482 (2)	0.0365 (2)	0.0405 (2)	−0.01197 (18)	0.01137 (15)	0.00488 (17)
O1	0.0929 (13)	0.131 (2)	0.0609 (10)	−0.0698 (14)	0.0448 (10)	−0.0294 (12)
O2	0.0684 (9)	0.0428 (8)	0.0593 (9)	−0.0175 (7)	0.0197 (7)	−0.0074 (7)
O3	0.0741 (10)	0.0654 (10)	0.0541 (8)	−0.0176 (8)	0.0183 (7)	0.0194 (7)
N1	0.0573 (9)	0.0762 (11)	0.0343 (7)	−0.0280 (10)	0.0216 (6)	−0.0137 (9)
N2	0.0342 (6)	0.0410 (7)	0.0312 (6)	−0.0058 (6)	0.0100 (5)	−0.0011 (6)
N3	0.0387 (7)	0.0435 (8)	0.0372 (7)	−0.0075 (6)	0.0138 (6)	−0.0003 (6)
N4	0.0456 (8)	0.0505 (9)	0.0342 (7)	−0.0125 (7)	0.0107 (6)	−0.0036 (6)
C1	0.0521 (10)	0.0692 (14)	0.0385 (9)	−0.0229 (10)	0.0150 (8)	−0.0051 (9)
C2	0.0359 (8)	0.0446 (9)	0.0360 (8)	−0.0031 (7)	0.0064 (6)	0.0006 (7)
C3	0.0431 (8)	0.0498 (10)	0.0471 (9)	−0.0101 (9)	0.0073 (7)	−0.0003 (10)
C4	0.0515 (11)	0.0499 (13)	0.0516 (11)	−0.0093 (8)	0.0022 (9)	−0.0136 (8)
C5	0.0555 (10)	0.0585 (15)	0.0452 (9)	−0.0048 (10)	0.0126 (8)	−0.0181 (9)
C6	0.0476 (9)	0.0554 (12)	0.0412 (9)	−0.0052 (9)	0.0169 (7)	−0.0098 (9)
C7	0.0342 (7)	0.0369 (8)	0.0332 (7)	0.0004 (6)	0.0055 (6)	−0.0014 (6)
C8	0.0389 (8)	0.0471 (9)	0.0296 (8)	−0.0095 (7)	0.0079 (6)	−0.0017 (7)
C9	0.0392 (8)	0.0380 (8)	0.0360 (8)	−0.0059 (7)	0.0084 (6)	0.0027 (7)
C10	0.0407 (9)	0.0498 (11)	0.0585 (11)	−0.0090 (8)	0.0127 (8)	0.0067 (9)

Geometric parameters (Å, º)

S1—O3	1.4296 (16)	C1—C2	1.479 (3)
S1—O2	1.4421 (16)	C2—C7	1.395 (2)
S1—C10	1.744 (2)	C2—C3	1.397 (3)
S1—C9	1.7726 (17)	C3—C4	1.377 (3)
O1—C1	1.211 (2)	C3—H3	0.9300
N1—C8	1.364 (2)	C4—C5	1.387 (3)
N1—C1	1.370 (3)	C4—H4	0.9300
N1—H1	0.877 (10)	C5—C6	1.379 (3)
N2—C8	1.348 (2)	C5—H5	0.9300
N2—N3	1.3718 (19)	C6—C7	1.385 (2)
N2—C7	1.397 (2)	C6—H6	0.9300
N3—C9	1.312 (2)	C10—H10A	0.9600
N4—C8	1.321 (2)	C10—H10B	0.9600
N4—C9	1.355 (2)	C10—H10C	0.9600
O3—S1—O2	119.93 (11)	C3—C4—H4	119.8
O3—S1—C10	109.44 (11)	C5—C4—H4	119.8
O2—S1—C10	109.57 (10)	C6—C5—C4	120.88 (19)
O3—S1—C9	108.24 (9)	C6—C5—H5	119.6
O2—S1—C9	105.18 (9)	C4—C5—H5	119.6
C10—S1—C9	103.09 (9)	C5—C6—C7	118.24 (18)
C8—N1—C1	122.54 (16)	C5—C6—H6	120.9
C8—N1—H1	117 (2)	C7—C6—H6	120.9
C1—N1—H1	120 (2)	C6—C7—C2	122.18 (17)
C8—N2—N3	109.28 (14)	C6—C7—N2	122.22 (16)
C8—N2—C7	124.09 (14)	C2—C7—N2	115.60 (15)
N3—N2—C7	126.61 (13)	N4—C8—N2	111.47 (16)
C9—N3—N2	100.69 (13)	N4—C8—N1	128.56 (17)
C8—N4—C9	100.67 (15)	N2—C8—N1	119.95 (15)
O1—C1—N1	120.47 (19)	N3—C9—N4	117.88 (15)
O1—C1—C2	123.5 (2)	N3—C9—S1	121.05 (13)
N1—C1—C2	116.01 (16)	N4—C9—S1	120.94 (13)
C7—C2—C3	118.12 (18)	S1—C10—H10A	109.5
C7—C2—C1	121.66 (16)	S1—C10—H10B	109.5
C3—C2—C1	120.22 (17)	H10A—C10—H10B	109.5
C4—C3—C2	120.10 (18)	S1—C10—H10C	109.5
C4—C3—H3	119.9	H10A—C10—H10C	109.5
C2—C3—H3	119.9	H10B—C10—H10C	109.5
C3—C4—C5	120.47 (18)
C8—N2—N3—C9	−0.34 (19)	C8—N2—C7—C2	0.5 (2)
C7—N2—N3—C9	178.37 (16)	N3—N2—C7—C2	−178.05 (17)
C8—N1—C1—O1	−176.2 (3)	C9—N4—C8—N2	0.2 (2)
C8—N1—C1—C2	3.1 (3)	C9—N4—C8—N1	178.8 (2)
O1—C1—C2—C7	179.4 (3)	N3—N2—C8—N4	0.1 (2)
N1—C1—C2—C7	0.1 (3)	C7—N2—C8—N4	−178.68 (16)
O1—C1—C2—C3	−0.6 (4)	N3—N2—C8—N1	−178.63 (19)
N1—C1—C2—C3	−179.9 (2)	C7—N2—C8—N1	2.6 (3)
C7—C2—C3—C4	0.4 (3)	C1—N1—C8—N4	177.0 (2)
C1—C2—C3—C4	−179.7 (2)	C1—N1—C8—N2	−4.5 (3)
C2—C3—C4—C5	0.4 (3)	N2—N3—C9—N4	0.5 (2)
C3—C4—C5—C6	−0.1 (3)	N2—N3—C9—S1	−175.38 (13)
C4—C5—C6—C7	−1.0 (3)	C8—N4—C9—N3	−0.5 (2)
C5—C6—C7—C2	1.8 (3)	C8—N4—C9—S1	175.42 (14)
C5—C6—C7—N2	−177.84 (18)	O3—S1—C9—N3	−34.09 (18)
C3—C2—C7—C6	−1.5 (3)	O2—S1—C9—N3	−163.43 (15)
C1—C2—C7—C6	178.53 (19)	C10—S1—C9—N3	81.78 (17)
C3—C2—C7—N2	178.19 (17)	O3—S1—C9—N4	150.12 (17)
C1—C2—C7—N2	−1.8 (3)	O2—S1—C9—N4	20.79 (18)
C8—N2—C7—C6	−179.84 (18)	C10—S1—C9—N4	−94.00 (18)
N3—N2—C7—C6	1.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.88 (1)	2.23 (1)	3.072 (2)	160 (3)

Symmetry code: (i) −x+1, y+1/2, −z.