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

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

doi:10.1107/S1600536812021782

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1808

doi:10.1107/S1600536812021782

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

Rashad Al-Salahi,^a Lolak Nabih,^b Mohamed Al-Omar ^a and Seik Weng Ng ^c,^d ^*

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, ^bDepartment of Chemistry, Institute of Pharmacy, University of Hamburg, Bundesstrasse 45, 20146 Hamburg, Germany, ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^dChemistry 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 triazoloquinazole ring system in the title compound, C₁₅H₁₀N₄O₂ is approximately planar (r.m.s. deviation = 0.035 Å). The phenyl ring of the phenoxy substitutent is aligned at 59.3 (1)° with respect to this ring system. In the crystal, two molecules are linked about a center of inversion by a pair of N—H⋯O hydrogen bonds, generating a dimer.

Related literature

The synthesis was based on theat of a similar compound; see: Al-Salahi & Geffken (2011 ).

Experimental

Crystal data

C₁₅H₁₀N₄O₂
M_r = 278.27
Triclinic, $[P \overline 1]$
a = 5.6985 (2) Å
b = 8.4328 (4) Å
c = 13.4322 (7) Å
α = 74.087 (4)°
β = 86.623 (4)°
γ = 89.284 (4)°
V = 619.66 (5) Å³
Z = 2
Cu Kα radiation
μ = 0.86 mm⁻¹
T = 294 K
0.30 × 0.30 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ) T_min = 0.783, T_max = 0.919
10219 measured reflections
2570 independent reflections
2408 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.103
S = 1.03
2570 reflections
194 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.88 (1)	1.90 (1)	2.775 (1)	174 (1)
Symmetry code: (i) -x+2, -y+1, -z+1.

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/S1600536812021782/bt5917sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812021782/bt5917Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812021782/bt5917Isup3.cml

checkCIF report

Comment top

The procedure for the synthesis of 2-(methylsulfanyl)-[1,2,4]triazolo[1,5-a]quinazolin-5-one uses dimethyl N-cyanodithioimidocarbonate as one of the reactants (Al-Salahi & Geffken, 2011). The title phenoxy-substituted analog (Scheme I) is obtained with diphenyl N-cyanodithioimidocarbonate instead. The triazoloquinazole fused-ring system of C₁₅H₁₀N₄O₂ is planar. The phenyl ring of the phenoxy substitutent is aligned at 59.3 (1) ° with respect to this ring system. Two molecules are linked about a center of inversion by N–H···O hydrogen bonds to generate a dimer (Table 1).

Related literature top

The synthesis was based on theat of a similar compound; 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 diphenyl N-cyanodithioimidocarbonate (10 mmol, 2.38 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-phenoxy-[1,2,4]triazolo[1,5-a]quinazolin-5-one. The procedure was based on that reported for 2-(methylsulfanyl)-[1,2,4]triazolo[1,5-a]quinazolin-5-one (Al-Salahi & Geffken, 2011).

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. Anitropic displacement ellipsoid plot (Barbour, 2001) of C₁₅H₁₀N₄O₂ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

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

Crystal data top

C₁₅H₁₀N₄O₂	Z = 2
M_r = 278.27	F(000) = 288
Triclinic, P1	D_x = 1.491 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 5.6985 (2) Å	Cell parameters from 6342 reflections
b = 8.4328 (4) Å	θ = 5.5–76.8°
c = 13.4322 (7) Å	µ = 0.86 mm⁻¹
α = 74.087 (4)°	T = 294 K
β = 86.623 (4)°	Prism, colorless
γ = 89.284 (4)°	0.30 × 0.30 × 0.10 mm
V = 619.66 (5) Å³

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2570 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2408 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.021
Detector resolution: 10.4041 pixels mm^-1	θ_max = 77.0°, θ_min = 5.5°
ω scan	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −10→10
T_min = 0.783, T_max = 0.919	l = −16→16
10219 measured reflections

Refinement top

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0596P)² + 0.101P] where P = (F_o² + 2F_c²)/3
2570 reflections	(Δ/σ)_max = 0.001
194 parameters	Δρ_max = 0.17 e Å⁻³
1 restraint	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₅H₁₀N₄O₂	γ = 89.284 (4)°
M_r = 278.27	V = 619.66 (5) Å³
Triclinic, P1	Z = 2
a = 5.6985 (2) Å	Cu Kα radiation
b = 8.4328 (4) Å	µ = 0.86 mm⁻¹
c = 13.4322 (7) Å	T = 294 K
α = 74.087 (4)°	0.30 × 0.30 × 0.10 mm
β = 86.623 (4)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2570 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	2408 reflections with I > 2σ(I)
T_min = 0.783, T_max = 0.919	R_int = 0.021
10219 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	1 restraint
wR(F²) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.17 e Å⁻³
2570 reflections	Δρ_min = −0.17 e Å⁻³
194 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.99321 (13)	0.65595 (10)	0.38673 (6)	0.0434 (2)
O2	0.05541 (15)	0.63656 (11)	0.73718 (7)	0.0575 (3)
N1	0.72791 (14)	0.61117 (11)	0.52356 (7)	0.0368 (2)
H1	0.815 (2)	0.5287 (14)	0.5565 (10)	0.052 (4)*
N2	0.39197 (14)	0.77669 (10)	0.51740 (7)	0.0357 (2)
N3	0.19077 (15)	0.78851 (11)	0.57764 (7)	0.0407 (2)
N4	0.42432 (15)	0.57551 (11)	0.66105 (7)	0.0392 (2)
C1	0.80686 (17)	0.69434 (12)	0.42497 (8)	0.0357 (2)
C2	0.65586 (18)	0.82833 (13)	0.36907 (8)	0.0371 (2)
C3	0.7175 (2)	0.91440 (15)	0.26696 (9)	0.0478 (3)
H3A	0.8541	0.8874	0.2340	0.057*
C4	0.5757 (2)	1.03986 (17)	0.21472 (10)	0.0559 (3)
H4	0.6164	1.0970	0.1463	0.067*
C5	0.3716 (2)	1.08128 (15)	0.26419 (10)	0.0509 (3)
H5	0.2790	1.1674	0.2285	0.061*
C6	0.30459 (19)	0.99747 (14)	0.36443 (9)	0.0423 (3)
H6	0.1673	1.0250	0.3967	0.051*
C7	0.44778 (18)	0.86996 (13)	0.41660 (8)	0.0354 (2)
C8	0.52273 (17)	0.64985 (12)	0.56919 (8)	0.0342 (2)
C9	0.22415 (18)	0.66579 (14)	0.66014 (8)	0.0400 (2)
C10	0.0660 (2)	0.49527 (15)	0.82080 (9)	0.0453 (3)
C11	−0.1218 (2)	0.38863 (17)	0.83833 (10)	0.0524 (3)
H11	−0.2437	0.4075	0.7934	0.063*
C12	−0.1261 (3)	0.25285 (19)	0.92387 (11)	0.0621 (4)
H12	−0.2514	0.1790	0.9366	0.075*
C13	0.0546 (3)	0.22606 (19)	0.99069 (11)	0.0664 (4)
H13	0.0512	0.1346	1.0482	0.080*
C14	0.2391 (3)	0.3353 (2)	0.97164 (11)	0.0663 (4)
H14	0.3603	0.3175	1.0169	0.080*
C15	0.2473 (2)	0.47089 (19)	0.88648 (11)	0.0567 (3)
H15	0.3729	0.5445	0.8736	0.068*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0337 (4)	0.0480 (4)	0.0435 (4)	0.0121 (3)	0.0022 (3)	−0.0057 (3)
O2	0.0464 (5)	0.0600 (5)	0.0506 (5)	0.0199 (4)	0.0148 (4)	0.0065 (4)
N1	0.0287 (4)	0.0391 (5)	0.0391 (5)	0.0091 (3)	−0.0027 (3)	−0.0053 (4)
N2	0.0288 (4)	0.0379 (5)	0.0377 (5)	0.0075 (3)	−0.0014 (3)	−0.0064 (4)
N3	0.0319 (4)	0.0454 (5)	0.0410 (5)	0.0097 (4)	0.0023 (4)	−0.0066 (4)
N4	0.0330 (4)	0.0414 (5)	0.0391 (5)	0.0073 (3)	0.0000 (4)	−0.0048 (4)
C1	0.0299 (5)	0.0376 (5)	0.0387 (5)	0.0045 (4)	−0.0023 (4)	−0.0091 (4)
C2	0.0323 (5)	0.0376 (5)	0.0395 (5)	0.0055 (4)	−0.0028 (4)	−0.0076 (4)
C3	0.0434 (6)	0.0502 (6)	0.0433 (6)	0.0114 (5)	0.0036 (5)	−0.0038 (5)
C4	0.0558 (7)	0.0581 (7)	0.0420 (6)	0.0153 (6)	0.0037 (5)	0.0044 (5)
C5	0.0482 (7)	0.0486 (6)	0.0481 (7)	0.0159 (5)	−0.0059 (5)	0.0000 (5)
C6	0.0356 (5)	0.0414 (6)	0.0461 (6)	0.0098 (4)	−0.0036 (4)	−0.0058 (5)
C7	0.0313 (5)	0.0357 (5)	0.0379 (5)	0.0035 (4)	−0.0036 (4)	−0.0077 (4)
C8	0.0280 (5)	0.0360 (5)	0.0377 (5)	0.0052 (4)	−0.0042 (4)	−0.0085 (4)
C9	0.0322 (5)	0.0442 (6)	0.0401 (5)	0.0066 (4)	0.0025 (4)	−0.0069 (4)
C10	0.0416 (6)	0.0515 (6)	0.0373 (6)	0.0114 (5)	0.0062 (4)	−0.0053 (5)
C11	0.0428 (6)	0.0679 (8)	0.0431 (6)	0.0044 (5)	0.0020 (5)	−0.0104 (6)
C12	0.0593 (8)	0.0625 (8)	0.0578 (8)	−0.0047 (6)	0.0123 (6)	−0.0082 (6)
C13	0.0724 (9)	0.0666 (9)	0.0466 (7)	0.0142 (7)	0.0078 (6)	0.0043 (6)
C14	0.0580 (8)	0.0876 (11)	0.0464 (7)	0.0160 (7)	−0.0100 (6)	−0.0061 (7)
C15	0.0468 (7)	0.0675 (8)	0.0525 (7)	0.0017 (6)	−0.0024 (5)	−0.0112 (6)

Geometric parameters (Å, º) top

O1—C1	1.2307 (12)	C4—C5	1.3938 (17)
O2—C9	1.3435 (13)	C4—H4	0.9300
O2—C10	1.3990 (14)	C5—C6	1.3721 (17)
N1—C8	1.3656 (13)	C5—H5	0.9300
N1—C1	1.3699 (13)	C6—C7	1.3947 (14)
N1—H1	0.878 (9)	C6—H6	0.9300
N2—C8	1.3477 (12)	C10—C15	1.3753 (18)
N2—N3	1.3824 (12)	C10—C11	1.3738 (18)
N2—C7	1.3874 (14)	C11—C12	1.3813 (19)
N3—C9	1.3139 (14)	C11—H11	0.9300
N4—C8	1.3164 (14)	C12—C13	1.382 (2)
N4—C9	1.3622 (13)	C12—H12	0.9300
C1—C2	1.4722 (14)	C13—C14	1.372 (2)
C2—C3	1.3910 (16)	C13—H13	0.9300
C2—C7	1.4000 (14)	C14—C15	1.377 (2)
C3—C4	1.3794 (17)	C14—H14	0.9300
C3—H3A	0.9300	C15—H15	0.9300

C9—O2—C10	119.95 (9)	N2—C7—C6	122.26 (10)
C8—N1—C1	122.69 (8)	N2—C7—C2	116.34 (9)
C8—N1—H1	120.6 (9)	C6—C7—C2	121.40 (10)
C1—N1—H1	116.7 (9)	N4—C8—N2	111.92 (9)
C8—N2—N3	109.16 (8)	N4—C8—N1	128.29 (9)
C8—N2—C7	123.88 (9)	N2—C8—N1	119.77 (9)
N3—N2—C7	126.79 (8)	N3—C9—O2	117.36 (9)
C9—N3—N2	100.32 (8)	N3—C9—N4	118.04 (9)
C8—N4—C9	100.54 (8)	O2—C9—N4	124.59 (10)
O1—C1—N1	120.70 (9)	C15—C10—C11	121.75 (12)
O1—C1—C2	123.08 (10)	C15—C10—O2	121.40 (12)
N1—C1—C2	116.22 (9)	C11—C10—O2	116.68 (11)
C3—C2—C7	118.94 (10)	C10—C11—C12	118.73 (12)
C3—C2—C1	120.02 (10)	C10—C11—H11	120.6
C7—C2—C1	121.04 (10)	C12—C11—H11	120.6
C4—C3—C2	119.93 (11)	C11—C12—C13	120.38 (14)
C4—C3—H3A	120.0	C11—C12—H12	119.8
C2—C3—H3A	120.0	C13—C12—H12	119.8
C3—C4—C5	120.17 (12)	C14—C13—C12	119.61 (13)
C3—C4—H4	119.9	C14—C13—H13	120.2
C5—C4—H4	119.9	C12—C13—H13	120.2
C6—C5—C4	121.30 (11)	C13—C14—C15	120.89 (13)
C6—C5—H5	119.4	C13—C14—H14	119.6
C4—C5—H5	119.4	C15—C14—H14	119.6
C5—C6—C7	118.26 (11)	C10—C15—C14	118.62 (13)
C5—C6—H6	120.9	C10—C15—H15	120.7
C7—C6—H6	120.9	C14—C15—H15	120.7

C8—N2—N3—C9	0.14 (11)	C9—N4—C8—N1	−177.91 (10)
C7—N2—N3—C9	175.59 (10)	N3—N2—C8—N4	−0.50 (12)
C8—N1—C1—O1	179.78 (9)	C7—N2—C8—N4	−176.12 (9)
C8—N1—C1—C2	−0.77 (15)	N3—N2—C8—N1	178.16 (8)
O1—C1—C2—C3	2.27 (17)	C7—N2—C8—N1	2.54 (16)
N1—C1—C2—C3	−177.17 (10)	C1—N1—C8—N4	177.01 (10)
O1—C1—C2—C7	−178.59 (10)	C1—N1—C8—N2	−1.40 (15)
N1—C1—C2—C7	1.98 (15)	N2—N3—C9—O2	−178.60 (10)
C7—C2—C3—C4	0.81 (19)	N2—N3—C9—N4	0.27 (13)
C1—C2—C3—C4	179.98 (12)	C10—O2—C9—N3	171.70 (11)
C2—C3—C4—C5	0.4 (2)	C10—O2—C9—N4	−7.09 (18)
C3—C4—C5—C6	−1.2 (2)	C8—N4—C9—N3	−0.55 (13)
C4—C5—C6—C7	0.7 (2)	C8—N4—C9—O2	178.22 (11)
C8—N2—C7—C6	178.15 (10)	C9—O2—C10—C15	63.17 (17)
N3—N2—C7—C6	3.32 (17)	C9—O2—C10—C11	−121.42 (12)
C8—N2—C7—C2	−1.29 (15)	C15—C10—C11—C12	−0.6 (2)
N3—N2—C7—C2	−176.12 (9)	O2—C10—C11—C12	−175.96 (11)
C5—C6—C7—N2	−178.86 (10)	C10—C11—C12—C13	0.5 (2)
C5—C6—C7—C2	0.55 (17)	C11—C12—C13—C14	0.0 (2)
C3—C2—C7—N2	178.15 (9)	C12—C13—C14—C15	−0.3 (2)
C1—C2—C7—N2	−1.00 (15)	C11—C10—C15—C14	0.2 (2)
C3—C2—C7—C6	−1.29 (17)	O2—C10—C15—C14	175.40 (12)
C1—C2—C7—C6	179.55 (10)	C13—C14—C15—C10	0.2 (2)
C9—N4—C8—N2	0.60 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.88 (1)	1.90 (1)	2.775 (1)	174 (1)

Symmetry code: (i) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₀N₄O₂
M_r	278.27
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	5.6985 (2), 8.4328 (4), 13.4322 (7)
α, β, γ (°)	74.087 (4), 86.623 (4), 89.284 (4)
V (Å³)	619.66 (5)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	0.86
Crystal size (mm)	0.30 × 0.30 × 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	0.783, 0.919
No. of measured, independent and observed [I > 2σ(I)] reflections	10219, 2570, 2408
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.632

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.103, 1.03
No. of reflections	2570
No. of parameters	194
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)	0.17, −0.17

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···O1ⁱ	0.88 (1)	1.901 (9)	2.775 (1)	174 (1)

Symmetry code: (i) −x+2, −y+1, −z+1.

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

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Al-Salahi, R. & Geffken, D. (2011). Synth. Commun. 41, 3512–3523. CAS Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar