3-Benzyl-6-isopropyl-5-phen-oxy-3H-1,2,3-triazolo[4,5-d]pyrimidin-7(6H)-one.

In the title compound, C(20)H(19)N(5)O(2), all atoms of the 1,2,3-triazolo[4,5-d]pyrimidine ring system are essentially coplanar [maximum deviation = 0.015 (2) Å], indicating the existence of a conjugate system in which each carbon and nitrogen atom is sp(2) hybridized and ten π electrons (three from carbon atoms and seven from nitrogen atoms) constitute an aromatic heterocycle. The ring system forms dihedral angles of 68.37 (10) and 71.57 (9)° with the phenyl rings. The crystal packing is stabilized by van der Waals inter-actions and intermolecular C-H⋯π interactions.

Related literature

For the biological activity of 8-<span class="Chemical">aza­<span class="Chemical">guanine derivatives, see: Roblin et al. (1945 ▶); <span class="Gene">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: Ferguson et al. (1998 ▶); Li et al. (2004 ▶); Zhao, Xie et al. (2005 ▶); Zhao, Hu et al. (2005 ▶); Zhao, Wang & Ding (2005 ▶); Chen & Shi (2006 ▶); Maldonado et al. (2006 ▶); Xiao & Shi (2007 ▶); Wang et al. (2006 ▶, 2008 ▶); Zeng, Deng, Qu & Wang (2009 ▶); Zeng, Deng, Chen et al. (2009 ▶); Zeng, Liu et al. (2009 ▶).

Experimental

Crystal data

<span class="Chemical">C20H19N5O2

M = 361.40

Monoclinic,

a = 9.4585 (13) Å

b = 9.0846 (12) Å

c = 21.992 (3) Å

β = 100.523 (2)°

V = 1858.0 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.16 × 0.13 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.986, T max = 0.991

10907 measured reflections

3655 independent reflections

3079 reflections with I > 2σ(I)

R int = 0.074

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.167

S = 1.14

3655 reflections

246 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.31 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: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680904118X/rz2370sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680904118X/rz2370Isup2.hkl

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

C20H19N5O2	F(000) = 760
Mr = 361.40	Dx = 1.292 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3682 reflections
a = 9.4585 (13) Å	θ = 2.4–25.1°
b = 9.0846 (12) Å	µ = 0.09 mm−1
c = 21.992 (3) Å	T = 298 K
β = 100.523 (2)°	Block, colourless
V = 1858.0 (4) Å3	0.16 × 0.13 × 0.10 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3655 independent reflections
Radiation source: fine-focus sealed tube	3079 reflections with I > 2σ(I)
graphite	Rint = 0.074
φ and ω scans	θmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→11
Tmin = 0.986, Tmax = 0.991	k = −11→11
10907 measured reflections	l = −27→27

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.167	H-atom parameters constrained
S = 1.14	w = 1/[σ2(Fo2) + (0.0685P)2 + 0.418P] where P = (Fo2 + 2Fc2)/3
3655 reflections	(Δ/σ)max = 0.001
246 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.31 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
C1	0.3436 (2)	0.4731 (2)	0.22493 (9)	0.0422 (5)
C2	0.3377 (2)	0.4926 (2)	0.28596 (9)	0.0400 (5)
C3	0.4595 (3)	0.3594 (3)	0.38253 (11)	0.0615 (6)
H3A	0.4907	0.2579	0.3884	0.074*
H3B	0.3730	0.3701	0.4000	0.074*
C4	0.5747 (2)	0.4573 (2)	0.41799 (10)	0.0486 (5)
C5	0.5893 (3)	0.6038 (3)	0.40342 (11)	0.0616 (6)
H5	0.5277	0.6448	0.3699	0.074*
C6	0.6935 (3)	0.6893 (3)	0.43782 (12)	0.0697 (7)
H6	0.7016	0.7878	0.4276	0.084*
C7	0.7851 (4)	0.6317 (3)	0.48672 (12)	0.0810 (9)
H7	0.8549	0.6906	0.5103	0.097*
C8	0.7738 (4)	0.4858 (4)	0.50106 (13)	0.0974 (11)
H8	0.8373	0.4450	0.5340	0.117*
C9	0.6685 (3)	0.3994 (3)	0.46668 (12)	0.0751 (8)
H9	0.6614	0.3006	0.4768	0.090*
C10	0.2657 (2)	0.5691 (2)	0.17917 (9)	0.0435 (5)
C11	0.1931 (2)	0.6823 (2)	0.26940 (9)	0.0409 (5)
C12	0.0995 (3)	0.7849 (3)	0.16396 (10)	0.0594 (6)
H12	0.1186	0.7635	0.1225	0.071*
C13	−0.0597 (3)	0.7597 (3)	0.16099 (13)	0.0810 (9)
H13A	−0.0837	0.6606	0.1478	0.121*
H13B	−0.1133	0.8274	0.1321	0.121*
H13C	−0.0831	0.7751	0.2012	0.121*
C14	0.1452 (4)	0.9438 (3)	0.17780 (15)	0.0853 (9)
H14A	0.1002	0.9807	0.2105	0.128*
H14B	0.1163	1.0025	0.1414	0.128*
H14C	0.2478	0.9483	0.1903	0.128*
C15	0.1523 (3)	0.8427 (2)	0.34770 (9)	0.0479 (5)
C16	0.0476 (3)	0.8378 (3)	0.38311 (12)	0.0635 (7)
H16	−0.0422	0.7977	0.3677	0.076*
C17	0.0788 (4)	0.8938 (3)	0.44193 (13)	0.0838 (10)
H17	0.0090	0.8917	0.4667	0.101*
C18	0.2099 (4)	0.9524 (3)	0.46459 (11)	0.0810 (10)
H18	0.2297	0.9888	0.5048	0.097*
C19	0.3141 (3)	0.9579 (3)	0.42792 (12)	0.0723 (8)
H19	0.4035	0.9991	0.4432	0.087*
C20	0.2849 (3)	0.9021 (3)	0.36845 (10)	0.0591 (6)
H20	0.3538	0.9049	0.3432	0.071*
N1	0.4331 (2)	0.3583 (2)	0.21950 (10)	0.0601 (5)
N2	0.4819 (2)	0.3075 (2)	0.27476 (11)	0.0633 (6)
N3	0.42351 (19)	0.38878 (19)	0.31642 (8)	0.0488 (5)
N4	0.26237 (18)	0.59583 (19)	0.31105 (7)	0.0444 (4)
N5	0.18677 (18)	0.67677 (18)	0.20678 (7)	0.0411 (4)
O1	0.26306 (19)	0.56707 (19)	0.12390 (7)	0.0635 (5)
O2	0.11490 (17)	0.79269 (18)	0.28643 (6)	0.0572 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0411 (11)	0.0384 (10)	0.0493 (11)	−0.0012 (8)	0.0138 (9)	−0.0112 (8)
C2	0.0374 (10)	0.0343 (9)	0.0487 (11)	0.0003 (8)	0.0094 (9)	−0.0007 (8)
C3	0.0607 (15)	0.0502 (13)	0.0711 (16)	0.0003 (11)	0.0051 (12)	0.0202 (11)
C4	0.0540 (13)	0.0454 (11)	0.0475 (12)	0.0092 (10)	0.0123 (10)	0.0075 (9)
C5	0.0682 (16)	0.0488 (13)	0.0632 (15)	0.0028 (12)	0.0000 (12)	0.0114 (11)
C6	0.091 (2)	0.0526 (14)	0.0628 (16)	−0.0057 (14)	0.0072 (14)	0.0002 (11)
C7	0.106 (2)	0.0769 (19)	0.0526 (15)	−0.0154 (17)	−0.0042 (15)	−0.0061 (13)
C8	0.125 (3)	0.089 (2)	0.0612 (17)	−0.006 (2)	−0.0294 (18)	0.0158 (15)
C9	0.100 (2)	0.0570 (15)	0.0616 (15)	0.0009 (15)	−0.0032 (15)	0.0169 (12)
C10	0.0478 (12)	0.0438 (11)	0.0403 (11)	−0.0039 (9)	0.0115 (9)	−0.0117 (8)
C11	0.0415 (11)	0.0433 (11)	0.0387 (10)	0.0057 (9)	0.0089 (8)	−0.0045 (8)
C12	0.0767 (17)	0.0649 (15)	0.0354 (11)	0.0199 (13)	0.0073 (11)	0.0058 (10)
C13	0.0683 (18)	0.0792 (18)	0.0812 (19)	0.0162 (15)	−0.0237 (15)	−0.0102 (15)
C14	0.095 (2)	0.0628 (17)	0.103 (2)	0.0139 (16)	0.0296 (18)	0.0320 (16)
C15	0.0629 (14)	0.0431 (11)	0.0394 (11)	0.0186 (10)	0.0133 (10)	−0.0029 (8)
C16	0.0803 (18)	0.0497 (13)	0.0690 (15)	0.0098 (12)	0.0361 (14)	−0.0083 (11)
C17	0.137 (3)	0.0626 (17)	0.0659 (18)	0.0074 (19)	0.0572 (19)	−0.0088 (14)
C18	0.152 (3)	0.0538 (15)	0.0372 (12)	0.0233 (18)	0.0171 (17)	−0.0061 (11)
C19	0.093 (2)	0.0560 (15)	0.0598 (15)	0.0115 (14)	−0.0083 (14)	−0.0043 (12)
C20	0.0656 (16)	0.0636 (15)	0.0489 (13)	0.0154 (13)	0.0126 (11)	0.0025 (11)
N1	0.0563 (12)	0.0541 (11)	0.0707 (13)	0.0107 (9)	0.0138 (10)	−0.0194 (10)
N2	0.0584 (13)	0.0452 (11)	0.0843 (15)	0.0133 (9)	0.0081 (11)	−0.0134 (10)
N3	0.0466 (10)	0.0381 (9)	0.0604 (11)	0.0049 (8)	0.0063 (8)	0.0010 (8)
N4	0.0486 (10)	0.0474 (10)	0.0387 (9)	0.0117 (8)	0.0121 (7)	0.0014 (7)
N5	0.0456 (10)	0.0428 (9)	0.0350 (8)	0.0036 (7)	0.0079 (7)	−0.0024 (7)
O1	0.0826 (12)	0.0719 (11)	0.0383 (8)	0.0049 (9)	0.0172 (8)	−0.0126 (7)
O2	0.0638 (10)	0.0664 (10)	0.0401 (8)	0.0306 (8)	0.0057 (7)	−0.0096 (7)

C1—N1	1.362 (3)	C12—N5	1.500 (3)
C1—C2	1.365 (3)	C12—C13	1.513 (4)
C1—C10	1.430 (3)	C12—C14	1.521 (4)
C2—N3	1.341 (2)	C12—H12	0.9800
C2—N4	1.355 (2)	C13—H13A	0.9600
C3—N3	1.456 (3)	C13—H13B	0.9600
C3—C4	1.509 (3)	C13—H13C	0.9600
C3—H3A	0.9700	C14—H14A	0.9600
C3—H3B	0.9700	C14—H14B	0.9600
C4—C9	1.365 (3)	C14—H14C	0.9600
C4—C5	1.382 (3)	C15—C20	1.365 (3)
C5—C6	1.369 (3)	C15—C16	1.367 (3)
C5—H5	0.9300	C15—O2	1.405 (2)
C6—C7	1.356 (4)	C16—C17	1.371 (4)
C6—H6	0.9300	C16—H16	0.9300
C7—C8	1.371 (4)	C17—C18	1.358 (5)
C7—H7	0.9300	C17—H17	0.9300
C8—C9	1.380 (4)	C18—C19	1.383 (4)
C8—H8	0.9300	C18—H18	0.9300
C9—H9	0.9300	C19—C20	1.383 (3)
C10—O1	1.211 (2)	C19—H19	0.9300
C10—N5	1.431 (2)	C20—H20	0.9300
C11—N4	1.291 (2)	N1—N2	1.303 (3)
C11—O2	1.339 (2)	N2—N3	1.369 (3)
C11—N5	1.368 (2)
N1—C1—C2	108.83 (19)	C14—C12—H12	106.3
N1—C1—C10	130.83 (19)	C12—C13—H13A	109.5
C2—C1—C10	120.31 (18)	C12—C13—H13B	109.5
N3—C2—N4	126.77 (18)	H13A—C13—H13B	109.5
N3—C2—C1	105.72 (17)	C12—C13—H13C	109.5
N4—C2—C1	127.51 (18)	H13A—C13—H13C	109.5
N3—C3—C4	115.02 (18)	H13B—C13—H13C	109.5
N3—C3—H3A	108.5	C12—C14—H14A	109.5
C4—C3—H3A	108.5	C12—C14—H14B	109.5
N3—C3—H3B	108.5	H14A—C14—H14B	109.5
C4—C3—H3B	108.5	C12—C14—H14C	109.5
H3A—C3—H3B	107.5	H14A—C14—H14C	109.5
C9—C4—C5	118.3 (2)	H14B—C14—H14C	109.5
C9—C4—C3	118.9 (2)	C20—C15—C16	122.6 (2)
C5—C4—C3	122.7 (2)	C20—C15—O2	120.2 (2)
C6—C5—C4	120.7 (2)	C16—C15—O2	117.0 (2)
C6—C5—H5	119.7	C15—C16—C17	118.2 (3)
C4—C5—H5	119.7	C15—C16—H16	120.9
C7—C6—C5	120.7 (2)	C17—C16—H16	120.9
C7—C6—H6	119.6	C18—C17—C16	121.1 (3)
C5—C6—H6	119.6	C18—C17—H17	119.5
C6—C7—C8	119.3 (3)	C16—C17—H17	119.5
C6—C7—H7	120.3	C17—C18—C19	120.0 (2)
C8—C7—H7	120.3	C17—C18—H18	120.0
C7—C8—C9	120.2 (3)	C19—C18—H18	120.0
C7—C8—H8	119.9	C20—C19—C18	119.8 (3)
C9—C8—H8	119.9	C20—C19—H19	120.1
C4—C9—C8	120.8 (2)	C18—C19—H19	120.1
C4—C9—H9	119.6	C15—C20—C19	118.3 (2)
C8—C9—H9	119.6	C15—C20—H20	120.9
O1—C10—C1	127.61 (19)	C19—C20—H20	120.9
O1—C10—N5	121.29 (19)	N2—N1—C1	108.03 (18)
C1—C10—N5	111.10 (16)	N1—N2—N3	108.40 (17)
N4—C11—O2	119.46 (17)	C2—N3—N2	109.02 (18)
N4—C11—N5	127.95 (18)	C2—N3—C3	129.62 (19)
O2—C11—N5	112.58 (16)	N2—N3—C3	121.34 (19)
N5—C12—C13	110.9 (2)	C11—N4—C2	111.65 (16)
N5—C12—C14	113.1 (2)	C11—N5—C10	121.45 (16)
C13—C12—C14	113.3 (2)	C11—N5—C12	121.72 (16)
N5—C12—H12	106.3	C10—N5—C12	116.81 (16)
C13—C12—H12	106.3	C11—O2—C15	117.06 (15)
N1—C1—C2—N3	−0.2 (2)	N4—C2—N3—N2	−179.02 (19)
C10—C1—C2—N3	−178.61 (18)	C1—C2—N3—N2	0.4 (2)
N1—C1—C2—N4	179.23 (19)	N4—C2—N3—C3	−0.5 (3)
C10—C1—C2—N4	0.8 (3)	C1—C2—N3—C3	178.9 (2)
N3—C3—C4—C9	−145.0 (2)	N1—N2—N3—C2	−0.5 (2)
N3—C3—C4—C5	35.3 (3)	N1—N2—N3—C3	−179.14 (19)
C9—C4—C5—C6	−1.3 (4)	C4—C3—N3—C2	−80.8 (3)
C3—C4—C5—C6	178.5 (2)	C4—C3—N3—N2	97.6 (2)
C4—C5—C6—C7	0.3 (4)	O2—C11—N4—C2	−178.81 (18)
C5—C6—C7—C8	0.9 (5)	N5—C11—N4—C2	1.8 (3)
C6—C7—C8—C9	−1.2 (6)	N3—C2—N4—C11	178.18 (19)
C5—C4—C9—C8	1.0 (4)	C1—C2—N4—C11	−1.1 (3)
C3—C4—C9—C8	−178.8 (3)	N4—C11—N5—C10	−2.1 (3)
C7—C8—C9—C4	0.2 (5)	O2—C11—N5—C10	178.45 (17)
N1—C1—C10—O1	0.3 (4)	N4—C11—N5—C12	179.2 (2)
C2—C1—C10—O1	178.4 (2)	O2—C11—N5—C12	−0.2 (3)
N1—C1—C10—N5	−178.9 (2)	O1—C10—N5—C11	−177.88 (19)
C2—C1—C10—N5	−0.8 (3)	C1—C10—N5—C11	1.4 (3)
C20—C15—C16—C17	−0.7 (4)	O1—C10—N5—C12	0.9 (3)
O2—C15—C16—C17	−176.3 (2)	C1—C10—N5—C12	−179.87 (18)
C15—C16—C17—C18	−0.1 (4)	C13—C12—N5—C11	−69.5 (3)
C16—C17—C18—C19	0.8 (4)	C14—C12—N5—C11	59.1 (3)
C17—C18—C19—C20	−0.8 (4)	C13—C12—N5—C10	111.8 (2)
C16—C15—C20—C19	0.7 (3)	C14—C12—N5—C10	−119.6 (2)
O2—C15—C20—C19	176.16 (19)	N4—C11—O2—C15	22.9 (3)
C18—C19—C20—C15	0.1 (4)	N5—C11—O2—C15	−157.54 (18)
C2—C1—N1—N2	−0.1 (2)	C20—C15—O2—C11	62.1 (3)
C10—C1—N1—N2	178.1 (2)	C16—C15—O2—C11	−122.2 (2)
C1—N1—N2—N3	0.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···Cgi	0.96	2.75	3.696 (3)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯Cgi	0.96	2.75	3.696 (3)	171

Symmetry code: (i) . Cg is the centroid of the C15–C20 phenyl ring.