2-Phen-oxy-1,2,4-triazolo[1,5-a]quinazol-in-5(4H)-one.

The triazoloquinazole ring system in the title compound, C(15)H(10)N(4)O(2) is approximately planar (r.m.s. deviation = 0.035 Å). The phenyl ring of the phen-oxy substitutent is aligned at 59.3 (1)° with respect to this ring system. In the crystal, two mol-ecules 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 = 278.27

Triclinic,

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[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.103

S = 1.03

2570 reflections

194 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.17 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: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812021782/bt5917sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812021782/bt5917Isup3.cml

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

C15H10N4O2	Z = 2
Mr = 278.27	F(000) = 288
Triclinic, P1	Dx = 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

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	Rint = 0.021
Detector resolution: 10.4041 pixels mm-1	θmax = 77.0°, θmin = 5.5°
ω scan	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −10→10
Tmin = 0.783, Tmax = 0.919	l = −16→16
10219 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)] = 0.035	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(Fo2) + (0.0596P)2 + 0.101P] where P = (Fo2 + 2Fc2)/3
2570 reflections	(Δ/σ)max = 0.001
194 parameters	Δρmax = 0.17 e Å−3
1 restraint	Δρmin = −0.17 e Å−3

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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)

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) .