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

In the title compound, C(18)H(23)N(5)O(2), the triazolopyrimidine ring system is essentially planar, with a maximum displacement of 0.032 (2) Å, and forms a dihedral angle of 87.59 (15)° with the phenyl ring. In the crystal, mol-ecules are linked by inter-molecular C-H⋯O hydrogen bonds and C-H⋯π inter-actions into chains parallel to the c axis.

Related literature

For the biological activity of 8-aza­n class="Chemical">guanine 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 ▶); Zeng et al. (2010 ▶). 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 et al. (2006 ▶, 2009 ▶).

Experimental

Crystal data

C18H23N5O2

M = 341.41

Orthorhombic,

a = 28.328 (6) Å

b = 14.818 (3) Å

c = 8.7995 (16) Å

V = 3693.7 (12) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.19 × 0.15 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.984, T max = 0.992

18673 measured reflections

3346 independent reflections

2842 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.080

wR(F 2) = 0.173

S = 1.21

3346 reflections

228 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1999 ▶) and PLATON (Spek, 2009) ▶; software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810045575/rz2509sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045575/rz2509Isup2.hkl

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

C18H23N5O2	Dx = 1.228 Mg m−3
Mr = 341.41	Melting point: 364 K
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 3955 reflections
a = 28.328 (6) Å	θ = 2.6–23.4°
b = 14.818 (3) Å	µ = 0.08 mm−1
c = 8.7995 (16) Å	T = 298 K
V = 3693.7 (12) Å3	Block, colourless
Z = 8	0.19 × 0.15 × 0.10 mm
F(000) = 1456

Bruker SMART CCD area-detector diffractometer	3346 independent reflections
Radiation source: fine-focus sealed tube	2842 reflections with I > 2σ(I)
graphite	Rint = 0.041
φ and ω scans	θmax = 25.3°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −34→29
Tmin = 0.984, Tmax = 0.992	k = −17→17
18673 measured reflections	l = −10→7

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)] = 0.080	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.173	H-atom parameters constrained
S = 1.21	w = 1/[σ2(Fo2) + (0.0532P)2 + 2.6669P] where P = (Fo2 + 2Fc2)/3
3346 reflections	(Δ/σ)max < 0.001
228 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.15 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	0.13547 (10)	0.44798 (18)	0.0088 (3)	0.0454 (7)
C2	0.11879 (15)	0.3707 (2)	0.0781 (4)	0.0689 (10)
H2	0.1388	0.3363	0.1387	0.083*
C3	0.07250 (19)	0.3444 (3)	0.0577 (5)	0.0900 (14)
H3	0.0613	0.2929	0.1062	0.108*
C4	0.04300 (15)	0.3936 (4)	−0.0333 (6)	0.0967 (15)
H4	0.0120	0.3752	−0.0487	0.116*
C5	0.05947 (13)	0.4692 (3)	−0.1007 (5)	0.0814 (12)
H5	0.0394	0.5033	−0.1616	0.098*
C6	0.10505 (11)	0.4963 (2)	−0.0807 (4)	0.0581 (8)
H6	0.1157	0.5485	−0.1286	0.070*
C7	0.18567 (11)	0.4789 (2)	0.0285 (4)	0.0674 (10)
H7A	0.1902	0.5352	−0.0259	0.081*
H7B	0.1917	0.4902	0.1354	0.081*
C8	0.25650 (9)	0.37249 (17)	0.0422 (3)	0.0413 (6)
C9	0.27483 (10)	0.31471 (18)	−0.0642 (3)	0.0424 (6)
C10	0.31511 (10)	0.26037 (18)	−0.0287 (3)	0.0443 (7)
C11	0.30961 (10)	0.33995 (18)	0.2144 (3)	0.0420 (6)
C12	0.30873 (12)	0.4007 (2)	0.4643 (3)	0.0628 (9)
H12A	0.2781	0.3761	0.4915	0.075*
H12B	0.3042	0.4616	0.4263	0.075*
C13	0.34015 (14)	0.4018 (3)	0.5988 (4)	0.0742 (10)
H13A	0.3245	0.4351	0.6792	0.089*
H13B	0.3441	0.3402	0.6339	0.089*
C14	0.38675 (18)	0.4409 (4)	0.5757 (6)	0.131 (2)
H14A	0.4045	0.4035	0.5076	0.197*
H14B	0.4029	0.4449	0.6714	0.197*
H14C	0.3836	0.5002	0.5330	0.197*
C15	0.37466 (10)	0.2295 (2)	0.1713 (3)	0.0516 (8)
H15A	0.3775	0.1745	0.1123	0.062*
H15B	0.3705	0.2127	0.2769	0.062*
C16	0.42007 (11)	0.2843 (3)	0.1552 (4)	0.0685 (10)
H16A	0.4163	0.3403	0.2108	0.082*
H16B	0.4455	0.2509	0.2031	0.082*
C17	0.43453 (13)	0.3064 (3)	−0.0027 (5)	0.0896 (13)
H17A	0.4092	0.3391	−0.0525	0.108*
H17B	0.4397	0.2509	−0.0586	0.108*
C18	0.47925 (15)	0.3631 (4)	−0.0072 (7)	0.1249 (19)
H18A	0.4741	0.4185	0.0467	0.187*
H18B	0.4873	0.3762	−0.1109	0.187*
H18C	0.5046	0.3304	0.0396	0.187*
N1	0.21950 (8)	0.41208 (15)	−0.0277 (3)	0.0508 (6)
N2	0.21576 (10)	0.37955 (17)	−0.1729 (3)	0.0577 (7)
N3	0.24886 (9)	0.32053 (17)	−0.1946 (3)	0.0537 (7)
N4	0.33234 (8)	0.28021 (15)	0.1193 (2)	0.0417 (6)
N5	0.27266 (8)	0.38784 (15)	0.1849 (3)	0.0430 (6)
O1	0.33434 (8)	0.20431 (16)	−0.1081 (2)	0.0664 (7)
O2	0.33084 (7)	0.34506 (14)	0.3490 (2)	0.0531 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0575 (18)	0.0412 (15)	0.0375 (15)	0.0103 (13)	−0.0086 (13)	−0.0097 (12)
C2	0.108 (3)	0.053 (2)	0.0456 (18)	0.009 (2)	−0.0091 (19)	−0.0024 (15)
C3	0.115 (4)	0.068 (3)	0.087 (3)	−0.027 (3)	0.036 (3)	−0.010 (2)
C4	0.058 (2)	0.099 (3)	0.133 (4)	−0.009 (2)	0.016 (3)	−0.038 (3)
C5	0.055 (2)	0.085 (3)	0.105 (3)	0.015 (2)	−0.020 (2)	−0.006 (2)
C6	0.0590 (19)	0.0582 (18)	0.0572 (19)	0.0091 (16)	−0.0092 (16)	0.0052 (15)
C7	0.066 (2)	0.0520 (19)	0.085 (2)	0.0146 (16)	−0.0294 (19)	−0.0257 (18)
C8	0.0412 (15)	0.0374 (14)	0.0452 (16)	−0.0057 (12)	−0.0025 (12)	−0.0010 (12)
C9	0.0454 (16)	0.0429 (15)	0.0390 (15)	−0.0034 (13)	−0.0016 (12)	−0.0010 (12)
C10	0.0472 (16)	0.0444 (15)	0.0413 (16)	−0.0007 (13)	0.0087 (13)	−0.0003 (13)
C11	0.0429 (15)	0.0421 (14)	0.0409 (15)	−0.0011 (13)	0.0029 (12)	0.0021 (12)
C12	0.068 (2)	0.076 (2)	0.0448 (18)	0.0197 (18)	0.0019 (15)	−0.0107 (16)
C13	0.089 (3)	0.081 (2)	0.053 (2)	0.009 (2)	−0.0058 (19)	−0.0148 (18)
C14	0.098 (4)	0.184 (6)	0.112 (4)	−0.033 (4)	−0.004 (3)	−0.051 (4)
C15	0.0522 (18)	0.0529 (17)	0.0495 (17)	0.0156 (14)	0.0040 (14)	0.0069 (14)
C16	0.0506 (19)	0.086 (2)	0.069 (2)	0.0180 (18)	0.0039 (16)	0.0131 (19)
C17	0.067 (2)	0.113 (3)	0.089 (3)	0.002 (2)	0.017 (2)	0.018 (3)
C18	0.079 (3)	0.148 (5)	0.148 (5)	−0.014 (3)	0.030 (3)	0.038 (4)
N1	0.0492 (14)	0.0432 (13)	0.0601 (16)	0.0056 (11)	−0.0176 (12)	−0.0115 (12)
N2	0.0653 (17)	0.0535 (15)	0.0543 (16)	0.0024 (14)	−0.0215 (13)	−0.0074 (13)
N3	0.0568 (15)	0.0554 (15)	0.0489 (15)	0.0000 (13)	−0.0086 (12)	−0.0075 (12)
N4	0.0414 (13)	0.0439 (12)	0.0397 (12)	0.0042 (10)	0.0042 (10)	0.0027 (10)
N5	0.0430 (13)	0.0439 (13)	0.0423 (13)	0.0047 (11)	−0.0054 (10)	−0.0054 (10)
O1	0.0752 (15)	0.0695 (14)	0.0544 (13)	0.0225 (12)	0.0036 (11)	−0.0173 (12)
O2	0.0539 (12)	0.0661 (13)	0.0393 (11)	0.0165 (10)	−0.0054 (9)	−0.0067 (9)

C1—C6	1.370 (4)	C12—O2	1.450 (3)
C1—C2	1.381 (4)	C12—C13	1.481 (5)
C1—C7	1.504 (4)	C12—H12A	0.9700
C2—C3	1.380 (6)	C12—H12B	0.9700
C2—H2	0.9300	C13—C14	1.456 (6)
C3—C4	1.368 (6)	C13—H13A	0.9700
C3—H3	0.9300	C13—H13B	0.9700
C4—C5	1.350 (6)	C14—H14A	0.9600
C4—H4	0.9300	C14—H14B	0.9600
C5—C6	1.364 (5)	C14—H14C	0.9600
C5—H5	0.9300	C15—N4	1.486 (3)
C6—H6	0.9300	C15—C16	1.528 (4)
C7—N1	1.464 (4)	C15—H15A	0.9700
C7—H7A	0.9700	C15—H15B	0.9700
C7—H7B	0.9700	C16—C17	1.485 (5)
C8—N1	1.350 (3)	C16—H16A	0.9700
C8—N5	1.356 (3)	C16—H16B	0.9700
C8—C9	1.371 (4)	C17—C18	1.521 (6)
C9—N3	1.366 (4)	C17—H17A	0.9700
C9—C10	1.431 (4)	C17—H17B	0.9700
C10—O1	1.215 (3)	C18—H18A	0.9600
C10—N4	1.421 (3)	C18—H18B	0.9600
C11—N5	1.291 (3)	C18—H18C	0.9600
C11—O2	1.331 (3)	N1—N2	1.369 (3)
C11—N4	1.378 (3)	N2—N3	1.296 (3)
C6—C1—C2	118.2 (3)	C12—C13—H13A	108.3
C6—C1—C7	120.1 (3)	C14—C13—H13B	108.3
C2—C1—C7	121.7 (3)	C12—C13—H13B	108.3
C3—C2—C1	120.1 (4)	H13A—C13—H13B	107.4
C3—C2—H2	119.9	C13—C14—H14A	109.5
C1—C2—H2	119.9	C13—C14—H14B	109.5
C4—C3—C2	120.4 (4)	H14A—C14—H14B	109.5
C4—C3—H3	119.8	C13—C14—H14C	109.5
C2—C3—H3	119.8	H14A—C14—H14C	109.5
C5—C4—C3	119.2 (4)	H14B—C14—H14C	109.5
C5—C4—H4	120.4	N4—C15—C16	112.5 (2)
C3—C4—H4	120.4	N4—C15—H15A	109.1
C4—C5—C6	121.0 (4)	C16—C15—H15A	109.1
C4—C5—H5	119.5	N4—C15—H15B	109.1
C6—C5—H5	119.5	C16—C15—H15B	109.1
C5—C6—C1	121.0 (3)	H15A—C15—H15B	107.8
C5—C6—H6	119.5	C17—C16—C15	115.9 (3)
C1—C6—H6	119.5	C17—C16—H16A	108.3
N1—C7—C1	111.9 (2)	C15—C16—H16A	108.3
N1—C7—H7A	109.2	C17—C16—H16B	108.3
C1—C7—H7A	109.2	C15—C16—H16B	108.3
N1—C7—H7B	109.2	H16A—C16—H16B	107.4
C1—C7—H7B	109.2	C16—C17—C18	112.1 (4)
H7A—C7—H7B	107.9	C16—C17—H17A	109.2
N1—C8—N5	127.7 (2)	C18—C17—H17A	109.2
N1—C8—C9	104.8 (2)	C16—C17—H17B	109.2
N5—C8—C9	127.5 (3)	C18—C17—H17B	109.2
N3—C9—C8	109.3 (2)	H17A—C17—H17B	107.9
N3—C9—C10	130.4 (3)	C17—C18—H18A	109.5
C8—C9—C10	120.3 (2)	C17—C18—H18B	109.5
O1—C10—N4	121.0 (3)	H18A—C18—H18B	109.5
O1—C10—C9	128.1 (3)	C17—C18—H18C	109.5
N4—C10—C9	110.9 (2)	H18A—C18—H18C	109.5
N5—C11—O2	120.9 (2)	H18B—C18—H18C	109.5
N5—C11—N4	127.6 (2)	C8—N1—N2	109.4 (2)
O2—C11—N4	111.5 (2)	C8—N1—C7	130.4 (3)
O2—C12—C13	107.8 (3)	N2—N1—C7	120.2 (2)
O2—C12—H12A	110.1	N3—N2—N1	108.6 (2)
C13—C12—H12A	110.1	N2—N3—C9	108.0 (2)
O2—C12—H12B	110.1	C11—N4—C10	121.9 (2)
C13—C12—H12B	110.1	C11—N4—C15	121.0 (2)
H12A—C12—H12B	108.5	C10—N4—C15	117.0 (2)
C14—C13—C12	116.0 (4)	C11—N5—C8	111.6 (2)
C14—C13—H13A	108.3	C11—O2—C12	117.4 (2)
C6—C1—C2—C3	−0.7 (5)	C1—C7—N1—C8	−125.7 (3)
C7—C1—C2—C3	179.9 (3)	C1—C7—N1—N2	53.6 (4)
C1—C2—C3—C4	1.2 (6)	C8—N1—N2—N3	0.7 (3)
C2—C3—C4—C5	−1.3 (6)	C7—N1—N2—N3	−178.8 (3)
C3—C4—C5—C6	0.8 (7)	N1—N2—N3—C9	−0.6 (3)
C4—C5—C6—C1	−0.3 (6)	C8—C9—N3—N2	0.4 (3)
C2—C1—C6—C5	0.2 (5)	C10—C9—N3—N2	−179.7 (3)
C7—C1—C6—C5	179.7 (3)	N5—C11—N4—C10	−3.3 (4)
C6—C1—C7—N1	−118.6 (3)	O2—C11—N4—C10	177.3 (2)
C2—C1—C7—N1	60.9 (4)	N5—C11—N4—C15	−179.7 (3)
N1—C8—C9—N3	0.0 (3)	O2—C11—N4—C15	0.9 (3)
N5—C8—C9—N3	−178.7 (3)	O1—C10—N4—C11	−176.4 (3)
N1—C8—C9—C10	−179.9 (2)	C9—C10—N4—C11	4.2 (3)
N5—C8—C9—C10	1.4 (4)	O1—C10—N4—C15	0.1 (4)
N3—C9—C10—O1	−2.5 (5)	C9—C10—N4—C15	−179.2 (2)
C8—C9—C10—O1	177.3 (3)	C16—C15—N4—C11	−83.6 (3)
N3—C9—C10—N4	176.8 (3)	C16—C15—N4—C10	99.8 (3)
C8—C9—C10—N4	−3.4 (3)	O2—C11—N5—C8	−179.8 (2)
O2—C12—C13—C14	62.4 (5)	N4—C11—N5—C8	0.8 (4)
N4—C15—C16—C17	−65.6 (4)	N1—C8—N5—C11	−178.3 (3)
C15—C16—C17—C18	178.4 (3)	C9—C8—N5—C11	0.1 (4)
N5—C8—N1—N2	178.3 (3)	N5—C11—O2—C12	4.8 (4)
C9—C8—N1—N2	−0.4 (3)	N4—C11—O2—C12	−175.8 (2)
N5—C8—N1—C7	−2.4 (5)	C13—C12—O2—C11	−175.7 (3)
C9—C8—N1—C7	179.0 (3)

Cg1 is the centroid of the the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1i	0.93	2.43	3.259 (4)	148
C15—H15B···Cg1i	0.97	2.94	3.711 (3)	137

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1i	0.93	2.43	3.259 (4)	148
C15—H15B⋯Cg1i	0.97	2.94	3.711 (3)	137

Symmetry code: (i) .