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

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

doi:10.1107/S1600536812021757

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1805

doi:10.1107/S1600536812021757

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

Rashad Al-Salahi,^a Mohamed Al-Omar,^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 non-H atoms of the title compound, C₁₀H₈N₄OS, lie approximately in a common plane (r.m.s. deviation = 0.058 Å). In the crystal, two molecules 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_r = 232.26
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.030
wR(F²) = 0.089
S = 1.05
2052 reflections
151 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.21 e Å⁻³

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) -x, -y+1, -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/S1600536812021757/bt5914sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812021757/bt5914Isup3.cml

checkCIF report

Comment top

The title compound (Scheme I) was synthesized from 2-hydrazinobenzoic acid and dimethyl N-cyanoimidodithiocarbonate; further reactions on the inherent lactam unit yielded other derivatives (Al-Salahi & Geffken, 2011). The non-H atoms of C₁₀H₈N₄OS lie in a common plane (Fig. 1). Two molecules are linked across a center-of-inversion by N–H···N hydrogen bonds to form a dimer (Table 1). A related compound that has a benzyloxy group instead of the methylsulfanyl group also exists as a hydrogen-bonded dimer (Al-Salahi et al., 2011).

Related literature top

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

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 C₁₀H₈N₄OS at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

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

Crystal data top

C₁₀H₈N₄OS	F(000) = 480
M_r = 232.26	D_x = 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

Data collection top

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	R_int = 0.033
Detector resolution: 10.4041 pixels mm^-1	θ_max = 76.9°, θ_min = 4.3°
ω scan	h = −13→13
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −6→6
T_min = 0.439, T_max = 0.766	l = −23→23
15980 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) = 0.089	w = 1/[σ²(F_o²) + (0.0547P)² + 0.2828P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
2052 reflections	Δρ_max = 0.24 e Å⁻³
151 parameters	Δρ_min = −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)

Crystal data top

C₁₀H₈N₄OS	V = 976.76 (3) Å³
M_r = 232.26	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 10.4150 (1) Å	µ = 2.81 mm⁻¹
b = 5.0631 (1) Å	T = 294 K
c = 18.6564 (3) Å	0.35 × 0.15 × 0.10 mm
β = 96.857 (1)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2052 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	1996 reflections with I > 2σ(I)
T_min = 0.439, T_max = 0.766	R_int = 0.033
15980 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.24 e Å⁻³
2052 reflections	Δρ_min = −0.21 e Å⁻³
151 parameters

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

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₀H₈N₄OS
M_r	232.26
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	10.4150 (1), 5.0631 (1), 18.6564 (3)
β (°)	96.857 (1)
V (Å³)	976.76 (3)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	2.81
Crystal size (mm)	0.35 × 0.15 × 0.10

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.439, 0.766
No. of measured, independent and observed [I > 2σ(I)] reflections	15980, 2052, 1996
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.632

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.089, 1.05
No. of reflections	2052
No. of parameters	151
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.21

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

Symmetry code: (i) −x, −y+1, −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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