6-Isopropyl-5-meth-oxy-3-phenyl-3H-1,2,3-triazolo[4,5-d]pyrimidin-7(6H)-one.

In the title compound, C(14)H(15)N(5)O(2), the whole mol-ecule apart from the terminal C atoms of the isopropyl group is located on a crystallographic mirror plane. An intra-molecular C-H⋯N hydrogen-bonding inter-action may stabilize the mol-ecular conformation. The crystal packing features weak slipped π-π inter-actions between the pyrimidine and the phenyl rings of symmetry-related mol-ecules [centroid-centroid distance = 3.746 (1)Å, slippage of 1.574 Å].

Related literature

Fpr the biological activity of 8-aza­guanine derivatives, see: Roblin et al. (1945 ▶); Ding et al. (2004 ▶); Mitchell et al. (1950 ▶); Levine et al. (1963 ▶); Montgomery et al. (1962 ▶); Yamamoto et al. (1967 ▶); Bariana (1971 ▶); Holland et al. (1975 ▶). For related structures, see: Chen & Shi (2006 ▶); Ferguson et al. (1998 ▶); Li et al. (2004 ▶); Maldonado et al. (2006 ▶); Wang et al. (2006 ▶); Xiao & Shi (2007 ▶); Zeng et al. (2006 ▶, 2009 ▶); Zhao, Hu et al. (2005 ▶); Zhao, Wang & Ding (2005 ▶); Zhao, Xie et al. (2005 ▶).

Experimental

Crystal data

C14H15N5O2

M = 285.31

Orthorhombic,

a = 14.921 (2) Å

b = 6.7989 (11) Å

c = 13.839 (2) Å

V = 1404.0 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.16 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ▶) T min = 0.985, T max = 0.991

7422 measured reflections

1418 independent reflections

1045 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.185

S = 1.07

1418 reflections

125 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAIn class="Chemical">NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810041978/dn2610sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810041978/dn2610Isup2.hkl

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

C14H15N5O2	F(000) = 600
Mr = 285.31	Dx = 1.350 Mg m−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 982 reflections
a = 14.921 (2) Å	θ = 2.9–20.5°
b = 6.7989 (11) Å	µ = 0.10 mm−1
c = 13.839 (2) Å	T = 298 K
V = 1404.0 (4) Å3	Block, colourless
Z = 4	0.16 × 0.12 × 0.10 mm

Bruker SMART CCD area-detector diffractometer	1418 independent reflections
Radiation source: fine-focus sealed tube	1045 reflections with I > 2σ(I)
graphite	Rint = 0.039
φ and ω scans	θmax = 25.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	h = −17→18
Tmin = 0.985, Tmax = 0.991	k = −8→8
7422 measured reflections	l = −13→16

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.185	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0883P)2 + 0.4734P] where P = (Fo2 + 2Fc2)/3
1418 reflections	(Δ/σ)max < 0.001
125 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.36483 (19)	0.2500	0.3850 (3)	0.1092 (13)
O2	0.24610 (18)	0.2500	0.6874 (2)	0.0829 (9)
N1	0.06296 (18)	0.2500	0.41475 (18)	0.0507 (7)
N2	0.0868 (3)	0.2500	0.3193 (2)	0.0843 (12)
N3	0.1730 (3)	0.2500	0.3126 (2)	0.0908 (12)
N4	0.14519 (17)	0.2500	0.5659 (2)	0.0495 (7)
N5	0.30395 (19)	0.2500	0.5368 (3)	0.0629 (9)
C1	−0.0298 (2)	0.2500	0.4402 (2)	0.0462 (8)
C2	−0.0554 (2)	0.2500	0.5362 (2)	0.0546 (9)
H2	−0.0124	0.2500	0.5848	0.065*
C3	−0.1452 (2)	0.2500	0.5591 (3)	0.0599 (10)
H3	−0.1626	0.2500	0.6236	0.072*
C4	−0.2092 (3)	0.2500	0.4886 (3)	0.0630 (10)
H4	−0.2697	0.2500	0.5049	0.076*
C5	−0.1835 (3)	0.2500	0.3938 (3)	0.0672 (11)
H5	−0.2270	0.2500	0.3457	0.081*
C6	−0.0949 (3)	0.2500	0.3683 (3)	0.0580 (10)
H6	−0.0783	0.2500	0.3035	0.070*
C7	0.1382 (2)	0.2500	0.4688 (2)	0.0464 (8)
C8	0.2070 (2)	0.2500	0.4039 (3)	0.0608 (10)
C9	0.2979 (3)	0.2500	0.4346 (3)	0.0721 (11)
C10	0.2277 (2)	0.2500	0.5942 (3)	0.0589 (9)
C11	0.3973 (3)	0.2500	0.5789 (4)	0.0879 (14)
H11	0.4338	0.2500	0.5200	0.105*
C12	0.4225 (2)	0.0624 (6)	0.6212 (3)	0.1210 (15)
H12A	0.4861	0.0599	0.6319	0.181*
H12B	0.4063	−0.0421	0.5780	0.181*
H12C	0.3919	0.0454	0.6816	0.181*
C13	0.1714 (3)	0.2500	0.7534 (3)	0.1016 (17)
H13A	0.1933	0.2500	0.8186	0.152*
H13B	0.1356	0.1347	0.7427	0.152*	0.50
H13C	0.1356	0.3653	0.7427	0.152*	0.50

	U11	U22	U33	U12	U13	U23
O1	0.0561 (19)	0.156 (3)	0.115 (3)	0.000	0.0314 (18)	0.000
O2	0.0545 (17)	0.125 (3)	0.0687 (18)	0.000	−0.0150 (14)	0.000
N1	0.0539 (18)	0.0584 (17)	0.0399 (14)	0.000	0.0009 (13)	0.000
N2	0.075 (2)	0.131 (3)	0.0470 (19)	0.000	0.0067 (17)	0.000
N3	0.074 (3)	0.142 (4)	0.056 (2)	0.000	0.0142 (18)	0.000
N4	0.0419 (16)	0.0507 (16)	0.0559 (18)	0.000	−0.0071 (12)	0.000
N5	0.0365 (16)	0.0593 (19)	0.093 (2)	0.000	−0.0019 (15)	0.000
C1	0.050 (2)	0.0395 (17)	0.0485 (19)	0.000	−0.0052 (15)	0.000
C2	0.043 (2)	0.066 (2)	0.055 (2)	0.000	−0.0077 (16)	0.000
C3	0.052 (2)	0.065 (2)	0.063 (2)	0.000	0.0000 (17)	0.000
C4	0.047 (2)	0.060 (2)	0.082 (3)	0.000	−0.0074 (19)	0.000
C5	0.054 (2)	0.064 (2)	0.083 (3)	0.000	−0.030 (2)	0.000
C6	0.067 (3)	0.056 (2)	0.051 (2)	0.000	−0.0148 (18)	0.000
C7	0.048 (2)	0.0419 (18)	0.0497 (19)	0.000	−0.0003 (15)	0.000
C8	0.050 (2)	0.072 (2)	0.060 (2)	0.000	0.0094 (17)	0.000
C9	0.060 (3)	0.078 (3)	0.078 (3)	0.000	0.016 (2)	0.000
C10	0.055 (2)	0.055 (2)	0.067 (2)	0.000	−0.0120 (19)	0.000
C11	0.045 (2)	0.086 (3)	0.133 (4)	0.000	−0.013 (2)	0.000
C12	0.082 (2)	0.118 (3)	0.163 (4)	0.011 (2)	−0.034 (2)	0.043 (3)
C13	0.079 (3)	0.172 (5)	0.054 (2)	0.000	−0.016 (2)	0.000

O1—C9	1.212 (5)	C3—H3	0.9300
O2—C10	1.319 (4)	C4—C5	1.367 (6)
O2—C13	1.441 (5)	C4—H4	0.9300
N1—C7	1.350 (4)	C5—C6	1.369 (5)
N1—N2	1.368 (4)	C5—H5	0.9300
N1—C1	1.428 (4)	C6—H6	0.9300
N2—N3	1.290 (5)	C7—C8	1.364 (5)
N3—C8	1.360 (5)	C8—C9	1.421 (5)
N4—C10	1.293 (4)	C11—C12i	1.453 (4)
N4—C7	1.348 (4)	C11—C12	1.453 (4)
N5—C10	1.387 (5)	C11—H11	0.9800
N5—C9	1.418 (5)	C12—H12A	0.9600
N5—C11	1.510 (5)	C12—H12B	0.9600
C1—C2	1.382 (5)	C12—H12C	0.9600
C1—C6	1.391 (4)	C13—H13A	0.9600
C2—C3	1.377 (5)	C13—H13B	0.9600
C2—H2	0.9300	C13—H13C	0.9600
C3—C4	1.365 (5)
C10—O2—C13	117.3 (3)	N4—C7—C8	126.8 (3)
C7—N1—N2	108.6 (3)	N1—C7—C8	105.1 (3)
C7—N1—C1	132.0 (3)	N3—C8—C7	109.4 (3)
N2—N1—C1	119.4 (3)	N3—C8—C9	129.3 (4)
N3—N2—N1	109.2 (3)	C7—C8—C9	121.4 (4)
N2—N3—C8	107.8 (3)	O1—C9—N5	120.8 (4)
C10—N4—C7	112.0 (3)	O1—C9—C8	128.1 (4)
C10—N5—C9	121.2 (3)	N5—C9—C8	111.1 (3)
C10—N5—C11	122.4 (4)	N4—C10—O2	119.6 (3)
C9—N5—C11	116.4 (3)	N4—C10—N5	127.5 (4)
C2—C1—C6	119.6 (3)	O2—C10—N5	112.9 (3)
C2—C1—N1	120.4 (3)	C12i—C11—C12	122.8 (5)
C6—C1—N1	120.0 (3)	C12i—C11—N5	113.2 (2)
C3—C2—C1	119.4 (3)	C12—C11—N5	113.2 (2)
C3—C2—H2	120.3	C12i—C11—H11	101.0
C1—C2—H2	120.3	C12—C11—H11	101.0
C4—C3—C2	121.1 (4)	N5—C11—H11	101.0
C4—C3—H3	119.5	C11—C12—H12A	109.5
C2—C3—H3	119.5	C11—C12—H12B	109.5
C3—C4—C5	119.3 (4)	H12A—C12—H12B	109.5
C3—C4—H4	120.3	C11—C12—H12C	109.5
C5—C4—H4	120.3	H12A—C12—H12C	109.5
C4—C5—C6	121.2 (3)	H12B—C12—H12C	109.5
C4—C5—H5	119.4	O2—C13—H13A	109.5
C6—C5—H5	119.4	O2—C13—H13B	109.5
C5—C6—C1	119.4 (3)	H13A—C13—H13B	109.5
C5—C6—H6	120.3	O2—C13—H13C	109.5
C1—C6—H6	120.3	H13A—C13—H13C	109.5
N4—C7—N1	128.1 (3)	H13B—C13—H13C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N4	0.93	2.37	3.021 (4)	127
C6—H6···N2	0.93	2.47	2.794 (5)	100
C11—H11···O1	0.98	2.13	2.727 (7)	117
C12—H12C···O2	0.96	2.58	3.065 (5)	111

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯N4	0.93	2.37	3.021 (4)	127