2-Benz-yloxy-1,2,4-triazolo[1,5-a]quinazolin-5(4H)-one.

The title compound, C(16)H(12)N(4)O(2), is a functionalized triazoloquinazoline with a substituted benz-yloxy group attached at the 2-position of a triazole spacer. The triazoloquinazoline fused-ring system is approximately planar (r.m.s. deviation = 0.016 Å) while the benzyl substituent is perpendicular to the ring system, making a dihedral angle of 65.29 (6)°. The phenyl ring of the benz-yloxy moiety is equally disordered over two sets of sites. A centrosymmetric N-H⋯N hydrogen bond connects mol-ecules into dimers.

Related literature

For the biological activity of related compounds, see: Francis et al. (1991 ▶, 1998) ▶; Kim et al. (1998 ▶); Geffken et al. (2008) ▶. For related structures, see: Al-Salahi (2009 ▶); Al-Salahi & Geffken (2010 ▶); Berezank et al. (2008a ▶,b ▶); Ongini et al. (2001 ▶).

Experimental

Crystal data

C16H12N4O2

M = 292.30

Monoclinic,

a = 5.0319 (15) Å

b = 28.207 (9) Å

c = 9.408 (3) Å

β = 99.503 (5)°

V = 1317.0 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 153 K

0.50 × 0.10 × 0.03 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.951, T max = 0.997

8172 measured reflections

2849 independent reflections

1679 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.098

S = 0.80

2849 reflections

236 parameters

6 restraints

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811024962/kp2309sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811024962/kp2309Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811024962/kp2309Isup3.cml

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

C16H12N4O2	Z = 4
Mr = 292.30	F(000) = 608
Monoclinic, P21/n	Dx = 1.474 Mg m−3
a = 5.0319 (15) Å	Mo Kα radiation, λ = 0.71073 Å
b = 28.207 (9) Å	µ = 0.10 mm−1
c = 9.408 (3) Å	T = 153 K
β = 99.503 (5)°	Needle, colourless
V = 1317.0 (7) Å3	0.50 × 0.10 × 0.03 mm

Bruker SMART APEX CCD area-detector diffractometer	2849 independent reflections
Radiation source: fine-focus sealed tube	1679 reflections with I > 2σ(I)
graphite	Rint = 0.053
ω scans	θmax = 27.0°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −6→6
Tmin = 0.951, Tmax = 0.997	k = −25→35
8172 measured reflections	l = −12→11

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H-atom parameters constrained
S = 0.80	w = 1/[σ2(Fo2) + (0.0347P)2 + 0.4968P] where P = (Fo2 + 2Fc2)/3
2849 reflections	(Δ/σ)max = 0.005
236 parameters	Δρmax = 0.20 e Å−3
6 restraints	Δρmin = −0.20 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.8828 (3)	1.12152 (5)	0.45128 (14)	0.0270 (4)
O2	0.8556 (3)	0.91207 (5)	0.83235 (14)	0.0245 (4)
N1	0.7916 (3)	1.04986 (6)	0.54486 (16)	0.0209 (4)
H1	0.6460	1.0465	0.4796	0.025*
N2	1.0822 (3)	1.01884 (6)	0.74430 (16)	0.0194 (4)
N3	1.1110 (3)	0.97886 (6)	0.83206 (17)	0.0231 (4)
N4	0.7304 (3)	0.97406 (6)	0.65836 (16)	0.0197 (4)
C1	1.2541 (4)	1.05801 (7)	0.7576 (2)	0.0195 (5)
C2	1.4809 (4)	1.06091 (7)	0.8647 (2)	0.0237 (5)
H2	1.5256	1.0359	0.9321	0.028*
C3	1.6386 (4)	1.10113 (7)	0.8700 (2)	0.0276 (5)
H3	1.7925	1.1039	0.9430	0.033*
C4	1.5772 (4)	1.13772 (8)	0.7708 (2)	0.0287 (5)
H4	1.6891	1.1650	0.7762	0.034*
C5	1.3524 (4)	1.13430 (7)	0.6640 (2)	0.0236 (5)
H5	1.3105	1.1592	0.5962	0.028*
C6	1.1870 (4)	1.09411 (7)	0.6560 (2)	0.0196 (5)
C7	0.9465 (4)	1.09086 (7)	0.5424 (2)	0.0203 (5)
C8	0.8573 (4)	1.01485 (7)	0.64452 (19)	0.0180 (4)
C9	0.8959 (4)	0.95440 (7)	0.7751 (2)	0.0193 (5)
C10	0.6230 (4)	0.88574 (7)	0.7619 (2)	0.0256 (5)
H10A	0.6238	0.8843	0.6568	0.031*
H10B	0.4553	0.9017	0.7779	0.031*
C11	0.6348 (4)	0.83661 (7)	0.8236 (2)	0.0225 (5)	0.496 (2)
C12	0.5451 (8)	0.79726 (15)	0.7427 (5)	0.0272 (11)	0.496 (2)
H12	0.4805	0.8018	0.6429	0.033*	0.496 (2)
C13	0.5427 (9)	0.75163 (15)	0.7968 (5)	0.0300 (12)	0.496 (2)
H13	0.4760	0.7261	0.7352	0.036*	0.496 (2)
C14	0.6311 (5)	0.74409 (8)	0.9305 (3)	0.0357 (6)	0.496 (2)
H14	0.6246	0.7126	0.9658	0.043*	0.496 (2)
C15	0.7393 (9)	0.78049 (16)	1.0299 (5)	0.0313 (12)	0.496 (2)
H15	0.8071	0.7737	1.1281	0.038*	0.496 (2)
C16	0.7399 (8)	0.82635 (15)	0.9751 (4)	0.0228 (10)	0.496 (2)
H16	0.8099	0.8515	1.0373	0.027*	0.496 (2)
C11'	0.6348 (4)	0.83661 (7)	0.8236 (2)	0.0225 (5)	0.504 (2)
C12'	0.3903 (8)	0.81776 (14)	0.8448 (4)	0.0242 (11)	0.504 (2)
H12'	0.2290	0.8358	0.8244	0.029*	0.504 (2)
C13'	0.3880 (9)	0.77136 (15)	0.8972 (4)	0.0281 (11)	0.504 (2)
H13'	0.2219	0.7576	0.9111	0.034*	0.504 (2)
C14'	0.6311 (5)	0.74409 (8)	0.9305 (3)	0.0357 (6)	0.504 (2)
H14'	0.6357	0.7137	0.9745	0.043*	0.504 (2)
C15'	0.8587 (10)	0.76532 (16)	0.8936 (5)	0.0408 (14)	0.504 (2)
H15'	1.0208	0.7474	0.9042	0.049*	0.504 (2)
C16'	0.8615 (9)	0.81179 (16)	0.8417 (5)	0.0357 (13)	0.504 (2)
H16'	1.0229	0.8253	0.8198	0.043*	0.504 (2)

	U11	U22	U33	U12	U13	U23
O1	0.0252 (8)	0.0249 (9)	0.0296 (8)	−0.0033 (7)	0.0001 (6)	0.0086 (7)
O2	0.0239 (8)	0.0186 (8)	0.0285 (8)	−0.0063 (7)	−0.0031 (6)	0.0045 (6)
N1	0.0183 (9)	0.0213 (10)	0.0217 (9)	−0.0006 (8)	−0.0007 (7)	0.0038 (7)
N2	0.0187 (9)	0.0168 (9)	0.0218 (9)	0.0002 (8)	0.0001 (7)	0.0019 (7)
N3	0.0256 (10)	0.0168 (9)	0.0259 (9)	−0.0018 (8)	0.0013 (7)	0.0034 (8)
N4	0.0186 (9)	0.0174 (9)	0.0224 (9)	−0.0001 (8)	0.0017 (7)	0.0013 (7)
C1	0.0188 (11)	0.0164 (11)	0.0240 (10)	−0.0016 (9)	0.0056 (8)	−0.0040 (9)
C2	0.0236 (12)	0.0235 (12)	0.0234 (11)	0.0021 (10)	0.0019 (9)	0.0018 (9)
C3	0.0264 (13)	0.0249 (12)	0.0287 (11)	−0.0038 (10)	−0.0034 (9)	−0.0035 (10)
C4	0.0268 (13)	0.0239 (12)	0.0341 (12)	−0.0074 (10)	0.0009 (10)	−0.0001 (10)
C5	0.0278 (12)	0.0174 (11)	0.0258 (11)	0.0013 (10)	0.0050 (9)	0.0007 (9)
C6	0.0189 (11)	0.0188 (11)	0.0217 (10)	0.0031 (9)	0.0055 (8)	−0.0017 (9)
C7	0.0193 (11)	0.0190 (12)	0.0237 (11)	0.0020 (9)	0.0071 (8)	0.0000 (9)
C8	0.0168 (11)	0.0185 (11)	0.0194 (10)	0.0022 (9)	0.0050 (8)	−0.0022 (9)
C9	0.0187 (11)	0.0168 (11)	0.0221 (10)	0.0006 (9)	0.0022 (8)	−0.0003 (9)
C10	0.0206 (12)	0.0254 (13)	0.0296 (11)	−0.0021 (10)	0.0007 (9)	−0.0018 (9)
C11	0.0184 (12)	0.0220 (12)	0.0280 (11)	−0.0004 (10)	0.0071 (8)	−0.0021 (9)
C12	0.027 (3)	0.023 (3)	0.030 (2)	0.003 (2)	−0.0003 (19)	0.0025 (19)
C13	0.027 (3)	0.020 (3)	0.041 (3)	−0.002 (2)	0.001 (2)	0.000 (2)
C14	0.0316 (15)	0.0226 (13)	0.0535 (16)	−0.0040 (11)	0.0088 (12)	0.0055 (11)
C15	0.036 (3)	0.029 (3)	0.029 (2)	0.001 (2)	0.007 (2)	0.006 (2)
C16	0.022 (2)	0.022 (2)	0.025 (2)	−0.0017 (19)	0.0085 (18)	0.0003 (18)
C11'	0.0184 (12)	0.0220 (12)	0.0280 (11)	−0.0004 (10)	0.0071 (8)	−0.0021 (9)
C12'	0.019 (2)	0.023 (3)	0.031 (2)	−0.0005 (19)	0.0057 (18)	−0.0009 (19)
C13'	0.030 (3)	0.026 (3)	0.029 (2)	−0.005 (2)	0.0084 (19)	0.002 (2)
C14'	0.0316 (15)	0.0226 (13)	0.0535 (16)	−0.0040 (11)	0.0088 (12)	0.0055 (11)
C15'	0.028 (3)	0.027 (3)	0.066 (3)	0.003 (2)	0.002 (2)	0.008 (2)
C16'	0.020 (3)	0.028 (3)	0.059 (3)	0.001 (2)	0.008 (2)	0.011 (2)

O1—C7	1.223 (2)	C6—C7	1.479 (3)
O2—C9	1.339 (2)	C10—C11	1.500 (3)
O2—C10	1.450 (2)	C10—H10A	0.9900
N1—C8	1.364 (2)	C10—H10B	0.9900
N1—C7	1.397 (2)	C11—C12	1.379 (5)
N1—H1	0.8800	C11—C16	1.465 (4)
N2—C8	1.351 (2)	C12—C13	1.385 (6)
N2—N3	1.391 (2)	C12—H12	0.9500
N2—C1	1.396 (2)	C13—C14	1.281 (5)
N3—C9	1.320 (2)	C13—H13	0.9500
N4—C8	1.333 (2)	C14—C15	1.435 (5)
N4—C9	1.380 (2)	C14—H14	0.9500
C1—C2	1.394 (3)	C15—C16	1.393 (6)
C1—C6	1.399 (3)	C15—H15	0.9500
C2—C3	1.381 (3)	C16—H16	0.9500
C2—H2	0.9500	C12'—C13'	1.399 (6)
C3—C4	1.392 (3)	C12'—H12'	0.9500
C3—H3	0.9500	C13'—H13'	0.9500
C4—C5	1.387 (3)	C15'—C16'	1.400 (6)
C4—H4	0.9500	C15'—H15'	0.9500
C5—C6	1.401 (3)	C16'—H16'	0.9500
C5—H5	0.9500
C9—O2—C10	115.94 (15)	N2—C8—N1	119.84 (18)
C8—N1—C7	122.56 (16)	N3—C9—O2	118.13 (17)
C8—N1—H1	118.7	N3—C9—N4	117.35 (18)
C7—N1—H1	118.7	O2—C9—N4	124.51 (17)
C8—N2—N3	109.78 (16)	O2—C10—C11	108.60 (16)
C8—N2—C1	124.32 (16)	O2—C10—H10A	110.0
N3—N2—C1	125.89 (16)	C11—C10—H10A	110.0
C9—N3—N2	100.65 (15)	O2—C10—H10B	110.0
C8—N4—C9	100.89 (16)	C11—C10—H10B	110.0
C2—C1—N2	122.16 (18)	H10A—C10—H10B	108.3
C2—C1—C6	121.80 (19)	C12—C11—C16	114.3 (3)
N2—C1—C6	116.03 (17)	C12—C11—C10	122.8 (2)
C3—C2—C1	118.12 (19)	C16—C11—C10	122.9 (2)
C3—C2—H2	120.9	C11—C12—C13	124.5 (4)
C1—C2—H2	120.9	C11—C12—H12	117.7
C2—C3—C4	121.51 (19)	C13—C12—H12	117.7
C2—C3—H3	119.2	C14—C13—C12	119.5 (4)
C4—C3—H3	119.2	C14—C13—H13	120.2
C5—C4—C3	119.9 (2)	C12—C13—H13	120.2
C5—C4—H4	120.1	C13—C14—C15	123.7 (3)
C3—C4—H4	120.1	C13—C14—H14	118.2
C4—C5—C6	120.09 (19)	C15—C14—H14	118.2
C4—C5—H5	120.0	C16—C15—C14	116.6 (4)
C6—C5—H5	120.0	C16—C15—H15	121.7
C1—C6—C5	118.57 (18)	C14—C15—H15	121.7
C1—C6—C7	121.65 (18)	C15—C16—C11	121.4 (4)
C5—C6—C7	119.78 (18)	C15—C16—H16	119.3
O1—C7—N1	120.98 (18)	C11—C16—H16	119.3
O1—C7—C6	123.46 (19)	C13'—C12'—H12'	121.0
N1—C7—C6	115.55 (17)	C12'—C13'—H13'	119.3
N4—C8—N2	111.34 (16)	C16'—C15'—H15'	118.4
N4—C8—N1	128.80 (17)	C15'—C16'—H16'	120.6

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N4i	0.88	2.19	3.058 (2)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N4i	0.88	2.19	3.058 (2)	169

Symmetry code: (i) .