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

In the title compound, C(19)H(16)ClN(5)O(2), the triazolopyrimidine ring system is essentially planar, with a maximum displacement of 0.021 (4) Å, and forms dihedral angles of 1.09 (9) and 87.74 (9)° with the phenyl and benzene rings, respectively. Short intra-molecular C-H⋯O and C-H⋯N hydrogen-bonding inter-actions occur within the molecule. In the crystal structure, mol-ecules are linked by inter-molecular C-H⋯O hydrogen bonds into chains parallel to the b axis. In addition, π-π stacking inter-actions involving the triazole and pyrimidine rings of adjacent mol-ecules are observed, with centroid-centroid distances of 3.600 (3) Å.

Related literature

For 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: 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

C19H16ClN5O2

M = 381.82

Monoclinic,

a = 16.8429 (3) Å

b = 11.7890 (2) Å

c = 18.8309 (3) Å

β = 91.737 (2)°

V = 3737.36 (11) Å3

Z = 8

Mo Kα radiation

μ = 0.23 mm−1

T = 298 K

0.26 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.943, T max = 0.978

10890 measured reflections

3290 independent reflections

2697 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.082

wR(F 2) = 0.188

S = 1.20

3290 reflections

246 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.27 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/S160053680903788X/rz2362sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680903788X/rz2362Isup2.hkl

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

C19H16ClN5O2	F(000) = 1584
Mr = 381.82	Dx = 1.357 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2541 reflections
a = 16.8429 (3) Å	θ = 2.4–22.6°
b = 11.7890 (2) Å	µ = 0.23 mm−1
c = 18.8309 (3) Å	T = 298 K
β = 91.737 (2)°	Block, colourless
V = 3737.36 (11) Å3	0.26 × 0.20 × 0.10 mm
Z = 8

Bruker SMART CCD area-detector diffractometer	3290 independent reflections
Radiation source: fine-focus sealed tube	2697 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→19
Tmin = 0.943, Tmax = 0.978	k = −11→14
10890 measured reflections	l = −22→22

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)] = 0.082	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.188	H-atom parameters constrained
S = 1.20	w = 1/[σ2(Fo2) + (0.064P)2 + 5.7684P] where P = (Fo2 + 2Fc2)/3
3290 reflections	(Δ/σ)max < 0.001
246 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.27 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	−0.09358 (19)	0.1023 (3)	0.18512 (17)	0.0439 (8)
C2	−0.1566 (2)	0.0468 (3)	0.2139 (2)	0.0642 (11)
H2	−0.1984	0.0882	0.2319	0.077*
C3	−0.1583 (3)	−0.0702 (3)	0.2161 (2)	0.0737 (12)
H3	−0.2009	−0.1075	0.2360	0.088*
C4	−0.0973 (3)	−0.1310 (3)	0.1891 (2)	0.0689 (12)
H4	−0.0982	−0.2099	0.1903	0.083*
C5	−0.0348 (3)	−0.0757 (3)	0.1601 (2)	0.0673 (11)
H5	0.0067	−0.1175	0.1417	0.081*
C6	−0.0322 (2)	0.0415 (3)	0.1578 (2)	0.0560 (10)
H6	0.0105	0.0785	0.1379	0.067*
C7	−0.06815 (19)	0.4035 (3)	0.17494 (18)	0.0453 (8)
C8	−0.03822 (18)	0.2986 (3)	0.16141 (16)	0.0397 (7)
C9	0.0704 (2)	0.3664 (3)	0.11400 (18)	0.0462 (8)
C10	−0.0258 (2)	0.5037 (3)	0.15489 (19)	0.0510 (9)
C11	0.16545 (19)	0.2430 (3)	0.06917 (19)	0.0476 (8)
C12	0.2136 (2)	0.1916 (3)	0.1182 (2)	0.0666 (11)
H12	0.2299	0.2299	0.1592	0.080*
C13	0.2380 (3)	0.0818 (4)	0.1064 (2)	0.0727 (12)
H13	0.2708	0.0449	0.1396	0.087*
C14	0.2136 (2)	0.0283 (3)	0.0458 (2)	0.0618 (11)
C15	0.1683 (3)	0.0821 (4)	−0.0042 (2)	0.0762 (13)
H15	0.1541	0.0454	−0.0465	0.091*
C16	0.1431 (2)	0.1920 (4)	0.0077 (2)	0.0687 (11)
H16	0.1114	0.2299	−0.0260	0.082*
C17	0.1015 (2)	0.5730 (3)	0.1032 (2)	0.0568 (10)
H17	0.1501	0.5378	0.0864	0.068*
C18	0.1260 (3)	0.6448 (4)	0.1659 (3)	0.0860 (14)
H18A	0.0816	0.6893	0.1804	0.129*
H18B	0.1685	0.6943	0.1530	0.129*
H18C	0.1436	0.5968	0.2044	0.129*
C19	0.0657 (3)	0.6376 (4)	0.0409 (3)	0.0867 (14)
H19A	0.0589	0.5875	0.0010	0.130*
H19B	0.1005	0.6987	0.0287	0.130*
H19C	0.0151	0.6678	0.0534	0.130*
Cl1	0.24101 (10)	−0.11289 (10)	0.03223 (8)	0.1080 (6)
N1	−0.09221 (15)	0.2236 (2)	0.18491 (14)	0.0435 (7)
N2	−0.15423 (17)	0.2844 (3)	0.21305 (17)	0.0555 (8)
N3	−0.13910 (18)	0.3917 (3)	0.20656 (17)	0.0562 (8)
N4	0.03181 (15)	0.2756 (2)	0.13053 (15)	0.0451 (7)
N5	0.04809 (16)	0.4770 (2)	0.12434 (15)	0.0470 (7)
O1	−0.04809 (17)	0.6008 (2)	0.16009 (17)	0.0747 (9)
O2	0.14044 (14)	0.35551 (19)	0.08206 (14)	0.0595 (7)

	U11	U22	U33	U12	U13	U23
C1	0.0430 (18)	0.0388 (19)	0.0495 (19)	0.0002 (15)	−0.0048 (15)	−0.0037 (15)
C2	0.058 (2)	0.051 (2)	0.084 (3)	−0.0023 (19)	0.011 (2)	−0.005 (2)
C3	0.084 (3)	0.048 (2)	0.091 (3)	−0.017 (2)	0.020 (3)	−0.002 (2)
C4	0.095 (3)	0.034 (2)	0.077 (3)	−0.002 (2)	−0.004 (2)	0.0014 (19)
C5	0.073 (3)	0.042 (2)	0.087 (3)	0.013 (2)	0.003 (2)	−0.003 (2)
C6	0.053 (2)	0.041 (2)	0.074 (3)	0.0024 (17)	0.0059 (18)	0.0014 (18)
C7	0.0420 (18)	0.0389 (19)	0.055 (2)	0.0124 (15)	0.0036 (15)	−0.0041 (15)
C8	0.0373 (17)	0.0401 (19)	0.0417 (17)	0.0047 (14)	0.0002 (14)	−0.0037 (14)
C9	0.0433 (19)	0.042 (2)	0.053 (2)	0.0054 (15)	0.0015 (15)	0.0000 (16)
C10	0.055 (2)	0.0335 (19)	0.064 (2)	0.0098 (16)	−0.0051 (17)	−0.0073 (16)
C11	0.0412 (18)	0.041 (2)	0.062 (2)	0.0016 (15)	0.0164 (16)	0.0024 (17)
C12	0.075 (3)	0.056 (2)	0.069 (3)	0.010 (2)	−0.004 (2)	−0.010 (2)
C13	0.081 (3)	0.069 (3)	0.069 (3)	0.029 (2)	0.000 (2)	0.008 (2)
C14	0.066 (2)	0.051 (2)	0.070 (3)	0.0115 (19)	0.026 (2)	0.001 (2)
C15	0.085 (3)	0.074 (3)	0.070 (3)	0.008 (2)	−0.001 (2)	−0.025 (2)
C16	0.066 (3)	0.070 (3)	0.070 (3)	0.024 (2)	−0.006 (2)	−0.006 (2)
C17	0.057 (2)	0.0365 (19)	0.077 (3)	−0.0035 (17)	0.0037 (19)	0.0052 (18)
C18	0.091 (3)	0.068 (3)	0.098 (3)	−0.026 (3)	−0.012 (3)	0.003 (3)
C19	0.098 (4)	0.073 (3)	0.089 (3)	−0.009 (3)	−0.005 (3)	0.020 (3)
Cl1	0.1354 (12)	0.0544 (8)	0.1367 (12)	0.0263 (7)	0.0429 (10)	−0.0117 (7)
N1	0.0396 (15)	0.0378 (15)	0.0533 (16)	0.0061 (12)	0.0041 (12)	−0.0042 (12)
N2	0.0470 (17)	0.0483 (19)	0.072 (2)	0.0101 (14)	0.0133 (15)	0.0009 (15)
N3	0.0543 (18)	0.0444 (19)	0.071 (2)	0.0108 (14)	0.0119 (15)	−0.0055 (15)
N4	0.0434 (16)	0.0315 (15)	0.0606 (17)	0.0021 (12)	0.0067 (13)	0.0009 (13)
N5	0.0459 (16)	0.0328 (15)	0.0624 (18)	0.0066 (12)	0.0040 (13)	−0.0031 (13)
O1	0.0739 (19)	0.0358 (15)	0.116 (2)	0.0105 (13)	0.0193 (17)	−0.0094 (14)
O2	0.0534 (15)	0.0370 (14)	0.0896 (19)	0.0029 (11)	0.0258 (13)	0.0010 (12)

C1—C6	1.371 (5)	C11—C12	1.353 (5)
C1—C2	1.372 (5)	C11—O2	1.414 (4)
C1—N1	1.431 (4)	C12—C13	1.378 (6)
C2—C3	1.380 (5)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.357 (6)
C3—C4	1.365 (6)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.352 (6)
C4—C5	1.366 (6)	C14—Cl1	1.749 (4)
C4—H4	0.9300	C15—C16	1.384 (6)
C5—C6	1.383 (5)	C15—H15	0.9300
C5—H5	0.9300	C16—H16	0.9300
C6—H6	0.9300	C17—C18	1.500 (6)
C7—N3	1.358 (4)	C17—N5	1.506 (4)
C7—C8	1.362 (4)	C17—C19	1.509 (6)
C7—C10	1.436 (5)	C17—H17	0.9800
C8—N1	1.352 (4)	C18—H18A	0.9600
C8—N4	1.358 (4)	C18—H18B	0.9600
C9—N4	1.296 (4)	C18—H18C	0.9600
C9—O2	1.346 (4)	C19—H19A	0.9600
C9—N5	1.372 (4)	C19—H19B	0.9600
C10—O1	1.210 (4)	C19—H19C	0.9600
C10—N5	1.422 (4)	N1—N2	1.385 (4)
C11—C16	1.348 (5)	N2—N3	1.297 (4)
C6—C1—C2	120.0 (3)	C12—C13—H13	120.4
C6—C1—N1	120.6 (3)	C15—C14—C13	121.2 (4)
C2—C1—N1	119.4 (3)	C15—C14—Cl1	119.4 (3)
C1—C2—C3	120.4 (4)	C13—C14—Cl1	119.4 (3)
C1—C2—H2	119.8	C14—C15—C16	119.7 (4)
C3—C2—H2	119.8	C14—C15—H15	120.2
C4—C3—C2	119.8 (4)	C16—C15—H15	120.2
C4—C3—H3	120.1	C11—C16—C15	118.6 (4)
C2—C3—H3	120.1	C11—C16—H16	120.7
C3—C4—C5	119.8 (4)	C15—C16—H16	120.7
C3—C4—H4	120.1	C18—C17—N5	111.7 (3)
C5—C4—H4	120.1	C18—C17—C19	114.9 (4)
C4—C5—C6	120.9 (4)	N5—C17—C19	111.0 (3)
C4—C5—H5	119.5	C18—C17—H17	106.2
C6—C5—H5	119.5	N5—C17—H17	106.2
C1—C6—C5	119.1 (4)	C19—C17—H17	106.2
C1—C6—H6	120.5	C17—C18—H18A	109.5
C5—C6—H6	120.5	C17—C18—H18B	109.5
N3—C7—C8	109.0 (3)	H18A—C18—H18B	109.5
N3—C7—C10	130.5 (3)	C17—C18—H18C	109.5
C8—C7—C10	120.5 (3)	H18A—C18—H18C	109.5
N1—C8—N4	127.7 (3)	H18B—C18—H18C	109.5
N1—C8—C7	106.0 (3)	C17—C19—H19A	109.5
N4—C8—C7	126.3 (3)	C17—C19—H19B	109.5
N4—C9—O2	118.8 (3)	H19A—C19—H19B	109.5
N4—C9—N5	127.5 (3)	C17—C19—H19C	109.5
O2—C9—N5	113.7 (3)	H19A—C19—H19C	109.5
O1—C10—N5	121.3 (3)	H19B—C19—H19C	109.5
O1—C10—C7	126.9 (3)	C8—N1—N2	108.0 (3)
N5—C10—C7	111.8 (3)	C8—N1—C1	131.7 (3)
C16—C11—C12	122.1 (4)	N2—N1—C1	120.2 (3)
C16—C11—O2	119.3 (3)	N3—N2—N1	108.4 (3)
C12—C11—O2	118.6 (3)	N2—N3—C7	108.6 (3)
C11—C12—C13	119.1 (4)	C9—N4—C8	112.7 (3)
C11—C12—H12	120.4	C9—N5—C10	121.0 (3)
C13—C12—H12	120.4	C9—N5—C17	120.5 (3)
C14—C13—C12	119.2 (4)	C10—N5—C17	118.5 (3)
C14—C13—H13	120.4	C9—O2—C11	115.8 (3)
C6—C1—C2—C3	0.7 (6)	C6—C1—N1—C8	−0.1 (5)
N1—C1—C2—C3	−178.5 (4)	C2—C1—N1—C8	179.0 (3)
C1—C2—C3—C4	−0.6 (7)	C6—C1—N1—N2	−179.6 (3)
C2—C3—C4—C5	0.2 (7)	C2—C1—N1—N2	−0.4 (5)
C3—C4—C5—C6	0.1 (7)	C8—N1—N2—N3	0.4 (4)
C2—C1—C6—C5	−0.4 (5)	C1—N1—N2—N3	−180.0 (3)
N1—C1—C6—C5	178.7 (3)	N1—N2—N3—C7	−0.2 (4)
C4—C5—C6—C1	0.0 (6)	C8—C7—N3—N2	−0.1 (4)
N3—C7—C8—N1	0.3 (4)	C10—C7—N3—N2	178.8 (4)
C10—C7—C8—N1	−178.6 (3)	O2—C9—N4—C8	−179.1 (3)
N3—C7—C8—N4	−179.7 (3)	N5—C9—N4—C8	0.0 (5)
C10—C7—C8—N4	1.4 (5)	N1—C8—N4—C9	−179.9 (3)
N3—C7—C10—O1	−3.4 (6)	C7—C8—N4—C9	0.1 (5)
C8—C7—C10—O1	175.3 (4)	N4—C9—N5—C10	−1.6 (5)
N3—C7—C10—N5	178.6 (3)	O2—C9—N5—C10	177.5 (3)
C8—C7—C10—N5	−2.7 (5)	N4—C9—N5—C17	178.6 (3)
C16—C11—C12—C13	−2.7 (6)	O2—C9—N5—C17	−2.3 (4)
O2—C11—C12—C13	179.7 (3)	O1—C10—N5—C9	−175.3 (3)
C11—C12—C13—C14	0.4 (6)	C7—C10—N5—C9	2.8 (4)
C12—C13—C14—C15	2.5 (7)	O1—C10—N5—C17	4.4 (5)
C12—C13—C14—Cl1	−177.4 (3)	C7—C10—N5—C17	−177.4 (3)
C13—C14—C15—C16	−3.1 (7)	C18—C17—N5—C9	−119.2 (4)
Cl1—C14—C15—C16	176.8 (3)	C19—C17—N5—C9	111.3 (4)
C12—C11—C16—C15	2.2 (6)	C18—C17—N5—C10	61.1 (4)
O2—C11—C16—C15	179.8 (4)	C19—C17—N5—C10	−68.5 (4)
C14—C15—C16—C11	0.7 (7)	N4—C9—O2—C11	0.2 (5)
N4—C8—N1—N2	179.5 (3)	N5—C9—O2—C11	−179.0 (3)
C7—C8—N1—N2	−0.5 (3)	C16—C11—O2—C9	89.1 (4)
N4—C8—N1—C1	0.0 (6)	C12—C11—O2—C9	−93.2 (4)
C7—C8—N1—C1	−180.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O2	0.98	2.16	2.679 (4)	112
C6—H6···N4	0.93	2.36	3.013 (4)	127
C4—H4···O1i	0.93	2.46	3.317 (5)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯O2	0.98	2.16	2.679 (4)	112
C6—H6⋯N4	0.93	2.36	3.013 (4)	127
C4—H4⋯O1i	0.93	2.46	3.317 (5)	154

Symmetry code: (i) .