2-Eth-oxy-5-methylbis[1,2,4]triazolo[1,5-a:4',3'-c]quinazoline.

The title compound, C(13)H(12)N(6)O, is a functionalized ditriazoloquinazoline with substituted eth-oxy and methyl groups attached at the 2-position of each triazole spacer. The fused-ring system is essentially planar [r.m.s. deviation = 0.016 (2) Å]. In the crystal, a weak C-H⋯N hydrogen bond connects the mol-ecules into a chain along [101].

Related literature

For the biological activity of quinazoline derviatives, see: Alagarsamy et al. (2005 ▶, 2007 ▶). For our study of the chemical and pharmacological properties of triazolo quinazoline deriv­atives, see: Al-Salahi (2009 ▶); Al-Salahi et al. (2010 ▶, 2011 ▶); Berezank et al. (2008a ▶,b ▶). For related structures, see: El-Tombary et al. (1999 ▶).

Experimental

Crystal data

C13H12N6O

M = 268.29

Monoclinic,

a = 7.4121 (11) Å

b = 19.240 (3) Å

c = 9.3096 (14) Å

β = 109.051 (2)°

V = 1254.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 153 K

0.43 × 0.21 × 0.05 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.959, T max = 0.995

2851 measured reflections

2851 independent reflections

1817 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.134

S = 0.91

2851 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.24 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: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811052810/is5002sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811052810/is5002Isup2.hkl

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

C13H12N6O	F(000) = 560
Mr = 268.29	Dx = 1.420 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 210 reflections
a = 7.4121 (11) Å	θ = 1.2–27.0°
b = 19.240 (3) Å	µ = 0.10 mm−1
c = 9.3096 (14) Å	T = 153 K
β = 109.051 (2)°	Plate, colourless
V = 1254.9 (3) Å3	0.43 × 0.21 × 0.05 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	2851 independent reflections
Radiation source: fine-focus sealed tube	1817 reflections with I > 2σ(I)
graphite	Rint = 0.053
ω scan	θmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −9→9
Tmin = 0.959, Tmax = 0.995	k = −24→24
2851 measured reflections	l = 0→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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134	H-atom parameters constrained
S = 0.91	w = 1/[σ2(Fo2) + (0.072P)2] where P = (Fo2 + 2Fc2)/3
2851 reflections	(Δ/σ)max = 0.044
183 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.24 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
O1	0.26808 (18)	0.12586 (7)	0.60062 (14)	0.0292 (4)
N5	−0.0311 (2)	0.21218 (8)	0.29706 (16)	0.0243 (4)
N3	0.0101 (2)	0.33173 (8)	0.34526 (16)	0.0244 (4)
N4	0.1812 (2)	0.23979 (8)	0.52010 (16)	0.0233 (4)
N6	0.0364 (2)	0.14887 (8)	0.36339 (16)	0.0265 (4)
N1	−0.0267 (3)	0.44495 (9)	0.32026 (18)	0.0375 (4)
N2	−0.1545 (2)	0.41376 (9)	0.18987 (18)	0.0360 (4)
C6	−0.1751 (3)	0.22080 (10)	0.1548 (2)	0.0263 (5)
C1	−0.2270 (3)	0.28941 (10)	0.10826 (19)	0.0273 (5)
C8	0.0587 (2)	0.26359 (10)	0.39243 (19)	0.0223 (4)
C11	0.1609 (2)	0.16942 (10)	0.49439 (19)	0.0232 (4)
C5	−0.2620 (3)	0.16363 (11)	0.0665 (2)	0.0322 (5)
H5	−0.2268	0.1175	0.1003	0.039*
C7	−0.1306 (3)	0.34608 (11)	0.20684 (19)	0.0276 (5)
C4	−0.4021 (3)	0.17661 (12)	−0.0729 (2)	0.0379 (6)
H4	−0.4620	0.1386	−0.1356	0.045*
C3	−0.4562 (3)	0.24455 (12)	−0.1222 (2)	0.0379 (6)
H3	−0.5523	0.2522	−0.2174	0.045*
C9	0.0698 (3)	0.39608 (10)	0.4119 (2)	0.0292 (5)
C2	−0.3704 (3)	0.30040 (12)	−0.0332 (2)	0.0349 (5)
H2	−0.4079	0.3464	−0.0671	0.042*
C10	0.2187 (3)	0.40648 (10)	0.5633 (2)	0.0336 (5)
H10A	0.2326	0.4562	0.5868	0.050*
H10B	0.3407	0.3877	0.5610	0.050*
H10C	0.1805	0.3823	0.6414	0.050*
C12	0.2394 (3)	0.05207 (10)	0.5604 (2)	0.0371 (5)
H12A	0.2652	0.0432	0.4642	0.045*
H12B	0.1059	0.0386	0.5465	0.045*
C13	0.3737 (3)	0.01071 (11)	0.6867 (2)	0.0439 (6)
H13A	0.5055	0.0238	0.6983	0.066*
H13B	0.3556	−0.0389	0.6628	0.066*
H13C	0.3479	0.0202	0.7816	0.066*

	U11	U22	U33	U12	U13	U23
O1	0.0254 (7)	0.0221 (8)	0.0340 (7)	0.0003 (6)	0.0013 (6)	−0.0025 (6)
N5	0.0207 (8)	0.0270 (10)	0.0242 (8)	−0.0019 (7)	0.0060 (6)	−0.0033 (7)
N3	0.0219 (8)	0.0257 (10)	0.0265 (8)	0.0020 (7)	0.0092 (7)	0.0015 (7)
N4	0.0174 (8)	0.0253 (10)	0.0263 (8)	−0.0008 (7)	0.0059 (7)	−0.0020 (7)
N6	0.0241 (8)	0.0264 (10)	0.0272 (8)	−0.0008 (7)	0.0061 (7)	−0.0031 (7)
N1	0.0416 (11)	0.0319 (11)	0.0399 (10)	0.0074 (9)	0.0147 (8)	0.0028 (8)
N2	0.0360 (10)	0.0366 (12)	0.0348 (9)	0.0086 (9)	0.0108 (8)	0.0047 (8)
C6	0.0185 (9)	0.0407 (13)	0.0216 (9)	−0.0026 (9)	0.0091 (7)	−0.0014 (9)
C1	0.0190 (9)	0.0404 (13)	0.0248 (9)	0.0005 (9)	0.0100 (8)	0.0021 (8)
C8	0.0169 (9)	0.0267 (11)	0.0249 (9)	−0.0012 (8)	0.0092 (8)	−0.0029 (8)
C11	0.0179 (9)	0.0252 (11)	0.0264 (9)	−0.0011 (8)	0.0073 (7)	−0.0038 (8)
C5	0.0256 (10)	0.0441 (14)	0.0282 (10)	−0.0102 (10)	0.0107 (8)	−0.0060 (9)
C7	0.0226 (10)	0.0359 (13)	0.0258 (9)	0.0068 (9)	0.0099 (8)	0.0062 (9)
C4	0.0254 (11)	0.0629 (17)	0.0263 (10)	−0.0151 (11)	0.0097 (9)	−0.0098 (10)
C3	0.0200 (10)	0.0670 (17)	0.0250 (10)	−0.0045 (11)	0.0050 (8)	0.0011 (10)
C9	0.0296 (11)	0.0266 (12)	0.0350 (10)	0.0017 (9)	0.0153 (9)	−0.0033 (9)
C2	0.0220 (10)	0.0553 (15)	0.0281 (10)	0.0034 (10)	0.0092 (9)	0.0076 (10)
C10	0.0338 (12)	0.0270 (12)	0.0394 (11)	−0.0031 (10)	0.0110 (9)	−0.0077 (9)
C12	0.0357 (12)	0.0240 (12)	0.0473 (12)	−0.0033 (10)	0.0076 (10)	−0.0056 (10)
C13	0.0462 (14)	0.0250 (13)	0.0560 (14)	0.0026 (10)	0.0106 (11)	0.0014 (10)

O1—C11	1.341 (2)	C5—C4	1.395 (3)
O1—C12	1.466 (2)	C5—H5	0.9500
N5—C8	1.351 (2)	C4—C3	1.400 (3)
N5—N6	1.383 (2)	C4—H4	0.9500
N5—C6	1.414 (2)	C3—C2	1.379 (3)
N3—C9	1.391 (2)	C3—H3	0.9500
N3—C8	1.392 (2)	C9—C10	1.493 (3)
N3—C7	1.395 (2)	C2—H2	0.9500
N4—C8	1.320 (2)	C10—H10A	0.9800
N4—C11	1.375 (2)	C10—H10B	0.9800
N6—C11	1.327 (2)	C10—H10C	0.9800
N1—C9	1.313 (2)	C12—C13	1.497 (3)
N1—N2	1.407 (2)	C12—H12A	0.9900
N2—C7	1.317 (3)	C12—H12B	0.9900
C6—C5	1.398 (3)	C13—H13A	0.9800
C6—C1	1.403 (3)	C13—H13B	0.9800
C1—C2	1.412 (3)	C13—H13C	0.9800
C1—C7	1.454 (3)
C11—O1—C12	114.54 (14)	C5—C4—H4	119.4
C8—N5—N6	108.83 (14)	C3—C4—H4	119.4
C8—N5—C6	126.11 (16)	C2—C3—C4	120.26 (19)
N6—N5—C6	125.03 (15)	C2—C3—H3	119.9
C9—N3—C8	133.29 (16)	C4—C3—H3	119.9
C9—N3—C7	105.59 (16)	N1—C9—N3	108.74 (17)
C8—N3—C7	121.08 (16)	N1—C9—C10	126.52 (18)
C8—N4—C11	100.42 (14)	N3—C9—C10	124.74 (17)
C11—N6—N5	100.92 (14)	C3—C2—C1	120.2 (2)
C9—N1—N2	108.99 (16)	C3—C2—H2	119.9
C7—N2—N1	106.98 (15)	C1—C2—H2	119.9
C5—C6—C1	122.08 (18)	C9—C10—H10A	109.5
C5—C6—N5	121.37 (18)	C9—C10—H10B	109.5
C1—C6—N5	116.54 (16)	H10A—C10—H10B	109.5
C6—C1—C2	118.41 (18)	C9—C10—H10C	109.5
C6—C1—C7	118.80 (16)	H10A—C10—H10C	109.5
C2—C1—C7	122.79 (19)	H10B—C10—H10C	109.5
N4—C8—N5	112.61 (16)	O1—C12—C13	108.09 (16)
N4—C8—N3	129.94 (16)	O1—C12—H12A	110.1
N5—C8—N3	117.45 (16)	C13—C12—H12A	110.1
N6—C11—O1	123.95 (17)	O1—C12—H12B	110.1
N6—C11—N4	117.22 (16)	C13—C12—H12B	110.1
O1—C11—N4	118.83 (15)	H12A—C12—H12B	108.4
C4—C5—C6	117.8 (2)	C12—C13—H13A	109.5
C4—C5—H5	121.1	C12—C13—H13B	109.5
C6—C5—H5	121.1	H13A—C13—H13B	109.5
N2—C7—N3	109.70 (17)	C12—C13—H13C	109.5
N2—C7—C1	130.31 (17)	H13A—C13—H13C	109.5
N3—C7—C1	119.98 (17)	H13B—C13—H13C	109.5
C5—C4—C3	121.25 (19)
C8—N5—N6—C11	0.41 (17)	C8—N4—C11—O1	178.70 (15)
C6—N5—N6—C11	−177.68 (15)	C1—C6—C5—C4	1.1 (3)
C9—N1—N2—C7	−0.1 (2)	N5—C6—C5—C4	−179.63 (15)
C8—N5—C6—C5	−178.46 (16)	N1—N2—C7—N3	−0.09 (19)
N6—N5—C6—C5	−0.7 (3)	N1—N2—C7—C1	178.94 (18)
C8—N5—C6—C1	0.9 (2)	C9—N3—C7—N2	0.26 (19)
N6—N5—C6—C1	178.64 (15)	C8—N3—C7—N2	178.22 (14)
C5—C6—C1—C2	−0.6 (3)	C9—N3—C7—C1	−178.89 (15)
N5—C6—C1—C2	−179.99 (15)	C8—N3—C7—C1	−0.9 (2)
C5—C6—C1—C7	179.69 (16)	C6—C1—C7—N2	−179.24 (17)
N5—C6—C1—C7	0.3 (2)	C2—C1—C7—N2	1.1 (3)
C11—N4—C8—N5	0.72 (18)	C6—C1—C7—N3	−0.3 (2)
C11—N4—C8—N3	180.00 (16)	C2—C1—C7—N3	−179.94 (15)
N6—N5—C8—N4	−0.8 (2)	C6—C5—C4—C3	−0.9 (3)
C6—N5—C8—N4	177.30 (15)	C5—C4—C3—C2	0.2 (3)
N6—N5—C8—N3	179.86 (13)	N2—N1—C9—N3	0.3 (2)
C6—N5—C8—N3	−2.1 (2)	N2—N1—C9—C10	−179.39 (17)
C9—N3—C8—N4	0.1 (3)	C8—N3—C9—N1	−177.93 (16)
C7—N3—C8—N4	−177.21 (17)	C7—N3—C9—N1	−0.3 (2)
C9—N3—C8—N5	179.34 (16)	C8—N3—C9—C10	1.8 (3)
C7—N3—C8—N5	2.0 (2)	C7—N3—C9—C10	179.35 (16)
N5—N6—C11—O1	−179.07 (15)	C4—C3—C2—C1	0.2 (3)
N5—N6—C11—N4	0.04 (19)	C6—C1—C2—C3	0.0 (3)
C12—O1—C11—N6	0.7 (2)	C7—C1—C2—C3	179.65 (17)
C12—O1—C11—N4	−178.38 (14)	C11—O1—C12—C13	177.76 (15)
C8—N4—C11—N6	−0.47 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N4i	0.95	2.60	3.533 (2)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯N4i	0.95	2.60	3.533 (2)	166

Symmetry code: (i) .