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

In the title compound, C(21)H(21)N(5)O(2), the triazolopyrimidine ring system is essentially planar [maximum displacement = 0.021 (4) Å] and forms dihedral angles of 41.17 (9) and 67.99 (8)° with the phenyl and benzene rings, respectively. The n-butyl side chains is disordered over two positions with an ccupancy ratio of 0.77:0.23. An intra-molecular C-H⋯O hydrogen-bonding inter-action stabilizes the mol-ecular conformation. In the crystal, mol-ecules are linked by inter-molecular C-H⋯O and C-H⋯N hydrogen bonds into a three-dimensional network. In addition, π-π stacking inter-actions involving the triazole and pyrimidine rings of adjacent mol-ecules are observed, with centroid-centroid distances of 3.545 (1) Å.

Related literature

For the synthesis and 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 ▶); 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 et al. (2007 ▶); Wang et al. (2006 ▶, 2008 ▶); Zeng et al. (2006 ▶, 2009 ▶).

Experimental

Crystal data

C21H21N5O2

M = 375.43

Monoclinic,

a = 11.0954 (10) Å

b = 16.4478 (15) Å

c = 11.3484 (11) Å

β = 107.643 (1)°

V = 1973.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.983, T max = 0.985

20458 measured reflections

3876 independent reflections

2663 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.182

S = 1.08

3876 reflections

293 parameters

11 restraints

H-atom parameters constrained

Δρmax = 0.56 e Å−3

Δρmin = −0.24 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: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681004300X/rz2502sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681004300X/rz2502Isup2.hkl

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

C21H21N5O2	F(000) = 792
Mr = 375.43	Dx = 1.263 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6350 reflections
a = 11.0954 (10) Å	θ = 2.3–25.8°
b = 16.4478 (15) Å	µ = 0.09 mm−1
c = 11.3484 (11) Å	T = 298 K
β = 107.643 (1)°	Block, colourless
V = 1973.6 (3) Å3	0.20 × 0.20 × 0.20 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3876 independent reflections
Radiation source: fine-focus sealed tube	2663 reflections with I > 2σ(I)
graphite	Rint = 0.055
φ and ω scans	θmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.983, Tmax = 0.985	k = −20→20
20458 measured reflections	l = −13→13

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.182	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.1122P)2 + 0.0419P] where P = (Fo2 + 2Fc2)/3
3876 reflections	(Δ/σ)max < 0.001
293 parameters	Δρmax = 0.56 e Å−3
11 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	Occ. (<1)
C1	0.42419 (17)	0.24051 (13)	0.45138 (17)	0.0654 (5)
C2	0.5223 (2)	0.26001 (14)	0.5541 (2)	0.0797 (6)
H2	0.5810	0.2208	0.5936	0.096*
C3	0.5326 (2)	0.33854 (15)	0.5978 (2)	0.0904 (7)
H3	0.5980	0.3523	0.6682	0.108*
C4	0.4468 (3)	0.39682 (15)	0.5381 (3)	0.0909 (7)
H4	0.4543	0.4499	0.5677	0.109*
C5	0.3502 (2)	0.37608 (16)	0.4348 (3)	0.0923 (7)
H5	0.2922	0.4154	0.3942	0.111*
C6	0.3380 (2)	0.29824 (14)	0.3907 (2)	0.0764 (6)
H6	0.2723	0.2845	0.3205	0.092*
C7	0.49373 (17)	0.10245 (12)	0.39629 (16)	0.0616 (5)
C8	0.42311 (18)	0.03487 (12)	0.34748 (17)	0.0659 (5)
C9	0.4821 (2)	−0.03604 (13)	0.31905 (17)	0.0681 (5)
C10	0.67331 (18)	0.04538 (13)	0.39924 (17)	0.0670 (5)
C11	0.6857 (6)	−0.0970 (5)	0.3246 (5)	0.0795 (18)	0.77
H11A	0.6320	−0.1448	0.3109	0.095*	0.77
H11B	0.7589	−0.1073	0.3956	0.095*	0.77
C12	0.7294 (5)	−0.0808 (4)	0.2082 (5)	0.138 (2)	0.77
H12A	0.7829	−0.0328	0.2238	0.166*	0.77
H12B	0.7810	−0.1263	0.1980	0.166*	0.77
C13	0.6379 (6)	−0.0699 (3)	0.1027 (5)	0.149 (2)	0.77
H13A	0.6006	−0.0168	0.1050	0.179*	0.77
H13B	0.5726	−0.1101	0.0979	0.179*	0.77
C14	0.6776 (10)	−0.0757 (5)	−0.0175 (6)	0.142 (4)	0.77
H14A	0.7472	−0.0395	−0.0114	0.213*	0.77
H14B	0.6074	−0.0606	−0.0874	0.213*	0.77
H14C	0.7026	−0.1304	−0.0279	0.213*	0.77
C11'	0.704 (2)	−0.0825 (18)	0.3141 (15)	0.104 (10)	0.23
H11C	0.7847	−0.0555	0.3291	0.125*	0.23
H11D	0.7168	−0.1296	0.3679	0.125*	0.23
C12'	0.6617 (12)	−0.1107 (8)	0.1849 (10)	0.081 (3)	0.23
H12C	0.6172	−0.1610	0.1880	0.097*	0.23
H12D	0.5967	−0.0720	0.1431	0.097*	0.23
C13'	0.7276 (11)	−0.1267 (7)	0.0973 (8)	0.104 (4)	0.23
H13C	0.8104	−0.1024	0.1329	0.125*	0.23
H13D	0.7414	−0.1850	0.1015	0.125*	0.23
C14'	0.695 (2)	−0.1081 (15)	−0.0281 (18)	0.101 (6)	0.23
H14D	0.6086	−0.1234	−0.0676	0.152*	0.23
H14E	0.7492	−0.1374	−0.0650	0.152*	0.23
H14F	0.7046	−0.0508	−0.0381	0.152*	0.23
C15	0.87510 (18)	0.10857 (13)	0.4721 (2)	0.0717 (6)
C16	0.9372 (2)	0.14531 (16)	0.4005 (2)	0.0856 (7)
H16	0.9238	0.1289	0.3191	0.103*
C17	1.0212 (2)	0.20782 (16)	0.4509 (2)	0.0895 (7)
H17	1.0632	0.2338	0.4020	0.107*
C18	1.04316 (19)	0.23192 (14)	0.5710 (2)	0.0809 (6)
C19	0.9782 (2)	0.19289 (17)	0.6399 (2)	0.0904 (7)
H19	0.9913	0.2088	0.7215	0.108*
C20	0.8938 (2)	0.13042 (16)	0.5914 (2)	0.0865 (7)
H20	0.8511	0.1042	0.6396	0.104*
C21	1.1367 (3)	0.29832 (18)	0.6258 (3)	0.1124 (9)
H21A	1.2173	0.2847	0.6163	0.169*
H21B	1.1449	0.3040	0.7121	0.169*
H21C	1.1074	0.3486	0.5840	0.169*
N1	0.40888 (13)	0.15838 (10)	0.40749 (14)	0.0651 (4)
N2	0.28911 (15)	0.12506 (12)	0.36653 (17)	0.0760 (5)
N3	0.29856 (15)	0.05057 (12)	0.33090 (16)	0.0763 (5)
N4	0.61476 (15)	−0.02544 (10)	0.34970 (14)	0.0686 (5)
N5	0.62063 (14)	0.11114 (10)	0.42446 (15)	0.0660 (4)
O1	0.43198 (15)	−0.09929 (10)	0.27448 (15)	0.0877 (5)
O2	0.79833 (13)	0.04150 (9)	0.41997 (15)	0.0840 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0492 (10)	0.0861 (14)	0.0599 (11)	0.0031 (9)	0.0152 (8)	0.0080 (10)
C2	0.0634 (12)	0.0853 (15)	0.0760 (14)	0.0001 (11)	−0.0002 (10)	0.0097 (11)
C3	0.0771 (15)	0.0954 (17)	0.0843 (15)	−0.0114 (13)	0.0029 (12)	0.0014 (13)
C4	0.0866 (17)	0.0855 (15)	0.1014 (19)	−0.0009 (13)	0.0299 (14)	0.0018 (13)
C5	0.0803 (16)	0.0996 (18)	0.0938 (18)	0.0185 (13)	0.0215 (13)	0.0128 (14)
C6	0.0601 (12)	0.0930 (16)	0.0707 (13)	0.0125 (10)	0.0115 (10)	0.0046 (11)
C7	0.0500 (10)	0.0810 (12)	0.0489 (10)	−0.0003 (9)	0.0079 (7)	0.0085 (8)
C8	0.0558 (11)	0.0851 (13)	0.0507 (10)	−0.0027 (9)	0.0068 (8)	0.0085 (9)
C9	0.0658 (12)	0.0824 (14)	0.0495 (10)	−0.0053 (10)	0.0074 (8)	0.0065 (9)
C10	0.0532 (11)	0.0879 (14)	0.0570 (11)	0.0019 (10)	0.0121 (8)	0.0019 (10)
C11	0.075 (2)	0.086 (3)	0.076 (3)	0.011 (3)	0.020 (2)	−0.004 (2)
C12	0.111 (4)	0.156 (5)	0.147 (5)	−0.007 (3)	0.038 (4)	−0.070 (4)
C13	0.205 (6)	0.147 (4)	0.114 (3)	0.064 (4)	0.077 (4)	0.047 (3)
C14	0.200 (8)	0.147 (7)	0.095 (4)	−0.014 (5)	0.069 (4)	0.014 (4)
C11'	0.129 (17)	0.097 (15)	0.105 (15)	−0.015 (10)	0.064 (12)	−0.019 (10)
C12'	0.077 (7)	0.097 (8)	0.069 (7)	−0.011 (6)	0.022 (6)	−0.018 (6)
C13'	0.115 (10)	0.090 (7)	0.097 (9)	0.002 (7)	0.015 (7)	−0.010 (6)
C14'	0.090 (10)	0.108 (15)	0.106 (12)	−0.014 (9)	0.030 (8)	0.001 (9)
C15	0.0446 (10)	0.0929 (14)	0.0758 (13)	0.0081 (10)	0.0154 (9)	−0.0068 (11)
C16	0.0669 (13)	0.1198 (18)	0.0734 (14)	0.0020 (13)	0.0264 (11)	−0.0123 (13)
C17	0.0689 (14)	0.1146 (18)	0.0916 (17)	−0.0009 (13)	0.0341 (12)	−0.0005 (14)
C18	0.0544 (11)	0.0949 (15)	0.0930 (16)	0.0076 (11)	0.0217 (11)	−0.0096 (12)
C19	0.0702 (14)	0.127 (2)	0.0742 (14)	−0.0021 (13)	0.0221 (11)	−0.0188 (13)
C20	0.0644 (13)	0.1234 (19)	0.0741 (15)	−0.0102 (13)	0.0247 (11)	−0.0068 (13)
C21	0.0855 (18)	0.119 (2)	0.133 (2)	−0.0136 (16)	0.0334 (17)	−0.0260 (18)
N1	0.0459 (8)	0.0832 (11)	0.0604 (9)	0.0038 (8)	0.0072 (7)	0.0055 (8)
N2	0.0471 (9)	0.0998 (13)	0.0749 (11)	−0.0033 (8)	0.0091 (8)	0.0027 (9)
N3	0.0534 (10)	0.0983 (13)	0.0695 (10)	−0.0053 (9)	0.0072 (8)	0.0046 (9)
N4	0.0641 (10)	0.0817 (11)	0.0557 (9)	0.0031 (8)	0.0118 (7)	0.0001 (8)
N5	0.0480 (9)	0.0836 (11)	0.0630 (9)	0.0007 (8)	0.0116 (7)	0.0018 (8)
O1	0.0859 (11)	0.0879 (11)	0.0802 (10)	−0.0134 (8)	0.0117 (8)	−0.0049 (8)
O2	0.0526 (8)	0.1000 (11)	0.0981 (11)	0.0020 (7)	0.0209 (7)	−0.0187 (8)

C1—C2	1.370 (3)	C14—H14B	0.9600
C1—C6	1.375 (3)	C14—H14C	0.9600
C1—N1	1.432 (3)	C11'—C12'	1.473 (10)
C2—C3	1.376 (3)	C11'—N4	1.502 (10)
C2—H2	0.9300	C11'—H11C	0.9700
C3—C4	1.376 (3)	C11'—H11D	0.9700
C3—H3	0.9300	C12'—C13'	1.426 (9)
C4—C5	1.371 (4)	C12'—H12C	0.9700
C4—H4	0.9300	C12'—H12D	0.9700
C5—C6	1.366 (3)	C13'—C14'	1.39 (2)
C5—H5	0.9300	C13'—H13C	0.9700
C6—H6	0.9300	C13'—H13D	0.9700
C7—N1	1.349 (2)	C14'—H14D	0.9600
C7—N5	1.354 (2)	C14'—H14E	0.9600
C7—C8	1.376 (3)	C14'—H14F	0.9600
C8—N3	1.362 (3)	C15—C20	1.355 (3)
C8—C9	1.422 (3)	C15—C16	1.356 (3)
C9—O1	1.215 (2)	C15—O2	1.410 (3)
C9—N4	1.416 (3)	C16—C17	1.389 (3)
C10—N5	1.302 (3)	C16—H16	0.9300
C10—O2	1.336 (2)	C17—C18	1.369 (3)
C10—N4	1.369 (3)	C17—H17	0.9300
C11—N4	1.491 (4)	C18—C19	1.373 (3)
C11—C12	1.562 (8)	C18—C21	1.505 (3)
C11—H11A	0.9700	C19—C20	1.387 (3)
C11—H11B	0.9700	C19—H19	0.9300
C12—C13	1.326 (6)	C20—H20	0.9300
C12—H12A	0.9700	C21—H21A	0.9600
C12—H12B	0.9700	C21—H21B	0.9600
C13—C14	1.559 (7)	C21—H21C	0.9600
C13—H13A	0.9700	N1—N2	1.381 (2)
C13—H13B	0.9700	N2—N3	1.304 (3)
C14—H14A	0.9600
C2—C1—C6	121.1 (2)	C13'—C12'—H12C	104.1
C2—C1—N1	119.77 (18)	C11'—C12'—H12C	104.1
C6—C1—N1	119.07 (18)	C13'—C12'—H12D	104.1
C1—C2—C3	118.9 (2)	C11'—C12'—H12D	104.1
C1—C2—H2	120.5	H12C—C12'—H12D	105.5
C3—C2—H2	120.5	C14'—C13'—C12'	130.0 (14)
C4—C3—C2	120.5 (2)	C14'—C13'—H13C	104.8
C4—C3—H3	119.8	C12'—C13'—H13C	104.8
C2—C3—H3	119.8	C14'—C13'—H13D	104.8
C5—C4—C3	119.5 (2)	C12'—C13'—H13D	104.8
C5—C4—H4	120.2	H13C—C13'—H13D	105.8
C3—C4—H4	120.2	C13'—C14'—H14D	109.5
C6—C5—C4	120.8 (2)	C13'—C14'—H14E	109.5
C6—C5—H5	119.6	H14D—C14'—H14E	109.5
C4—C5—H5	119.6	C13'—C14'—H14F	109.5
C5—C6—C1	119.1 (2)	H14D—C14'—H14F	109.5
C5—C6—H6	120.4	H14E—C14'—H14F	109.5
C1—C6—H6	120.4	C20—C15—C16	121.9 (2)
N1—C7—N5	127.68 (18)	C20—C15—O2	121.1 (2)
N1—C7—C8	105.08 (17)	C16—C15—O2	116.70 (19)
N5—C7—C8	127.23 (19)	C15—C16—C17	118.9 (2)
N3—C8—C7	109.43 (18)	C15—C16—H16	120.6
N3—C8—C9	129.96 (19)	C17—C16—H16	120.6
C7—C8—C9	120.58 (19)	C18—C17—C16	121.3 (2)
O1—C9—N4	121.2 (2)	C18—C17—H17	119.4
O1—C9—C8	127.7 (2)	C16—C17—H17	119.4
N4—C9—C8	111.04 (18)	C17—C18—C19	117.8 (2)
N5—C10—O2	120.81 (18)	C17—C18—C21	120.9 (2)
N5—C10—N4	127.48 (18)	C19—C18—C21	121.3 (2)
O2—C10—N4	111.70 (18)	C18—C19—C20	121.9 (2)
N4—C11—C12	110.1 (5)	C18—C19—H19	119.0
N4—C11—H11A	109.6	C20—C19—H19	119.0
C12—C11—H11A	109.6	C15—C20—C19	118.2 (2)
N4—C11—H11B	109.6	C15—C20—H20	120.9
C12—C11—H11B	109.6	C19—C20—H20	120.9
H11A—C11—H11B	108.2	C18—C21—H21A	109.5
C13—C12—C11	115.9 (5)	C18—C21—H21B	109.5
C13—C12—H12A	108.3	H21A—C21—H21B	109.5
C11—C12—H12A	108.3	C18—C21—H21C	109.5
C13—C12—H12B	108.3	H21A—C21—H21C	109.5
C11—C12—H12B	108.3	H21B—C21—H21C	109.5
H12A—C12—H12B	107.4	C7—N1—N2	108.99 (17)
C12—C13—C14	116.1 (6)	C7—N1—C1	131.55 (16)
C12—C13—H13A	108.3	N2—N1—C1	119.47 (15)
C14—C13—H13A	108.3	N3—N2—N1	108.51 (16)
C12—C13—H13B	108.3	N2—N3—C8	107.99 (16)
C14—C13—H13B	108.3	C10—N4—C9	122.28 (17)
H13A—C13—H13B	107.4	C10—N4—C11	122.6 (4)
C12'—C11'—N4	115.4 (11)	C9—N4—C11	115.2 (4)
C12'—C11'—H11C	108.4	C10—N4—C11'	111.9 (13)
N4—C11'—H11C	108.4	C9—N4—C11'	125.1 (12)
C12'—C11'—H11D	108.4	C11—N4—C11'	13.6 (18)
N4—C11'—H11D	108.4	C10—N5—C7	111.38 (17)
H11C—C11'—H11D	107.5	C10—O2—C15	119.97 (16)
C13'—C12'—C11'	132.7 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O2	0.97	2.50	3.048 (5)	116
C2—H2···O1i	0.93	2.53	3.230 (3)	133
C3—H3···N2ii	0.93	2.61	3.535 (2)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯O2	0.97	2.50	3.048 (5)	116
C2—H2⋯O1i	0.93	2.53	3.230 (3)	133
C3—H3⋯N2ii	0.93	2.61	3.535 (2)	174

Symmetry codes: (i) ; (ii) .