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

Al-Salahi, R.; Marzouk, M.; Abbas, M.; Ng, S.W.

doi:10.1107/S1600536812021769

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1806

doi:10.1107/S1600536812021769

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

Rashad Al-Salahi,^a Mohamed Marzouk,^a Mohammed Abbas ^a and Seik Weng Ng ^b,^c ^*

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 10 May 2012; accepted 14 May 2012; online 19 May 2012)

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, P 2₁
a = 9.6216 (2) Å
b = 4.9206 (1) Å
c = 12.1623 (3) Å
β = 106.628 (2)°
V = 551.73 (2) Å³
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[F² > 2σ(F²)] = 0.030
wR(F²) = 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)

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) $[-x+1, y+{\script{1\over 2}}, -z]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812021769/bt5915sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812021769/bt5915Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812021769/bt5915Isup3.cml

checkCIF report

Comment top

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).

Related literature top

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

Experimental top

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.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); 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).

Figures top

	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.

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

Crystal data top

C₁₀H₈N₄O₃S	F(000) = 272
M_r = 264.26	D_x = 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 top

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	R_int = 0.025
Detector resolution: 10.4041 pixels mm^-1	θ_max = 76.7°, θ_min = 3.8°
ω scan	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −6→6
T_min = 0.613, T_max = 0.948	l = −14→15
9640 measured reflections

Refinement top

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(F_o²) + (0.0569P)² + 0.056P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
2304 reflections	Δρ_max = 0.15 e Å⁻³
168 parameters	Δρ_min = −0.26 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1007 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (2)

Crystal data top

C₁₀H₈N₄O₃S	V = 551.73 (2) Å³
M_r = 264.26	Z = 2
Monoclinic, P2₁	Cu Kα radiation
a = 9.6216 (2) Å	µ = 2.71 mm⁻¹
b = 4.9206 (1) Å	T = 294 K
c = 12.1623 (3) Å	0.20 × 0.10 × 0.02 mm
β = 106.628 (2)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2304 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	2237 reflections with I > 2σ(I)
T_min = 0.613, T_max = 0.948	R_int = 0.025
9640 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.082	Δρ_max = 0.15 e Å⁻³
S = 1.04	Δρ_min = −0.26 e Å⁻³
2304 reflections	Absolute structure: Flack (1983), 1007 Friedel pairs
168 parameters	Absolute structure parameter: 0.00 (2)
1 restraint

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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) top

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) top

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.

Experimental details

Crystal data
Chemical formula	C₁₀H₈N₄O₃S
M_r	264.26
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	294
a, b, c (Å)	9.6216 (2), 4.9206 (1), 12.1623 (3)
β (°)	106.628 (2)
V (Å³)	551.73 (2)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	2.71
Crystal size (mm)	0.20 × 0.10 × 0.02

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.613, 0.948
No. of measured, independent and observed [I > 2σ(I)] reflections	9640, 2304, 2237
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.631

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.082, 1.04
No. of reflections	2304
No. of parameters	168
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.26
Absolute structure	Flack (1983), 1007 Friedel pairs
Absolute structure parameter	0.00 (2)

Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

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.

Acknowledgements

We thank the Research Center of the College of Pharmacy College and Deanship of Scientific Research of King Saud University, and the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12) for supporting this study.

References

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