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

Zeng, X.-H.; Liu, X.-L.; Deng, S.-H.; Chen, P.; Wang, H.-M.

doi:10.1107/S160053680903788X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Pages o2583-o2584

doi:10.1107/S160053680903788X

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

Xiao-Hua Zeng,^a Xiao-Ling Liu,^a Shou-Heng Deng,^b ^* Ping Chen ^b and Hong-Mei Wang ^a

^aInstitute of Medicinal Chemistry, YunYang Medical College, ShiYan 442000, People's Republic of China, and ^bCenter of Oncology, People's Hospital affiliated with YunYang Medical College, Shi Yan 442000, People's Republic of China
^*Correspondence e-mail: dengshouheng@yahoo.cn

(Received 10 September 2009; accepted 18 September 2009; online 30 September 2009)

In the title compound, C₁₉H₁₆ClN₅O₂, 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 intramolecular C—H⋯O and C—H⋯N hydrogen-bonding interactions occur within the molecule. In the crystal structure, molecules are linked by intermolecular C—H⋯O hydrogen bonds into chains parallel to the b axis. In addition, π–π stacking interactions involving the triazole and pyrimidine rings of adjacent molecules 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_r = 381.82
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.082
wR(F²) = 0.188
S = 1.20
3290 reflections
246 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.27 e Å⁻³

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) x, y-1, z.

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).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680903788X/rz2362sup1.cif

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

checkCIF report

Comment top

The derivatives of heterocycles containing the 8-azaguanine system, which are well known bioisosteres of guanine, are of great importance because of their remarkable biological properties. Some of these activities include antimicrobial or antifungal activities (Roblin et al., 1945; Ding et al., 2004), encephaloma cell inhibitor activity (Mitchell et al., 1950; Levine et al., 1963), antileukemie activity (Montgomery et al., 1962), hypersusceptibility inhibitor activity and acesodyne activity (Yamamoto et al., 1967; Bariana, 1971; Holland et al., 1975).

In recent years, we have been engaged in the preparation of the derivatives of 8-azaguanine via aza-Wittig reaction of /b-ethoxycarbonyl iminophosphorane with aromatic isocyanate (Zhao, Xie et al., 2005). As a continuation of our research for new biologically active heterocycles, the title compound was obtained from /b-ethoxycarbonyl iminophosphorane with alphalic isocyanate, and structurally characterized in this context.

In the title compound (Fig. 1), bond lengths and angles within the triazolopyrimidinone ring system are in good agreement with those observed for closely related structures (Zhao, Hu et al., 2005; Zhao, Wang & Ding, 2005). As reported for related compounds (Ferguson et al., 1998; Li et al., 2004; Maldonado et al., 2006; Zeng et al., 2006, 2009; Wang et al., 2006, 2008; Xiao et al., 2007; Chen & Shi, 2006), all ring atoms in the 1,2,3-triazolo[4,5-d]pyrimidine ring system are essentially coplanar (maximum deviation 0.021 (4) Å for atom C10), indicating that the moiety is a conjugate system. The dihedral angles it forms with the C1–C6 and C11–C16 phenyl and benzene rings are 1.09 (9) and 87.74 (9)°, respectively.

There exist two intramolecular C—H···O and C—H···N hydrogen bonding interactions (Table 1) stabilizing the molecular conformation. The crystal packing is stabilized by intermolecular C—H···O hydrogen bonds forming chains parallel to the b axis, and by π–π stacking interactions occurring between adjacent triazole and pyrimidine rings, with centroid-to-centroid distances of 3.600 (3) Å.

Related literature top

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 top

To the solution of carbodiimide in CH₂Cl₂/CH₃CN (1:4 v/v, 15 ml) prepared according to the literature method (Zeng et al., 2006), 4-chlorophenol (3 mmol) and excess K₂CO₃ were added, and the reaction mixture was stirred for 12 h. The solvent was removed under reduced pressure and the residue was recrystallized from EtOH to give the title compound (yield 92%; m.p. 459 K). Elemental analysis: calculated for C₁₉H₁₆ClN₅O₂: C, 59.77; H, 4.22; N, 18.34%. Found: C, 58.62; H, 4.48; N, 17.83%. Crystals suitable for single crystal X-ray diffraction analysis were obtained by slow evaporation of a hexane/dichloromethane (1:3 v/v) solution at room temperature.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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).

Figures top

Fig. 1. View of the molecule of showing the atom-labeling scheme. Displacement ellipsoids are drawn at 50% probability level. H-atoms are represented by circles of arbitrary size.

5-(4-Chlorophenoxy)-6-isopropyl-3-phenyl-3H-1,2,3- triazolo[4,5-d]pyrimidin-7(6H)-one top

Crystal data top

C₁₉H₁₆ClN₅O₂	F(000) = 1584
M_r = 381.82	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.064P)² + 5.7684P] where P = (F_o² + 2F_c²)/3
3290 reflections	(Δ/σ)_max < 0.001
246 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₉H₁₆ClN₅O₂	V = 3737.36 (11) Å³
M_r = 381.82	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 16.8429 (3) Å	µ = 0.23 mm⁻¹
b = 11.7890 (2) Å	T = 298 K
c = 18.8309 (3) Å	0.26 × 0.20 × 0.10 mm
β = 91.737 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3290 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2697 reflections with I > 2σ(I)
T_min = 0.943, T_max = 0.978	R_int = 0.030
10890 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.082	0 restraints
wR(F²) = 0.188	H-atom parameters constrained
S = 1.20	Δρ_max = 0.35 e Å⁻³
3290 reflections	Δρ_min = −0.27 e Å⁻³
246 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₆ClN₅O₂
M_r	381.82
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	16.8429 (3), 11.7890 (2), 18.8309 (3)
β (°)	91.737 (2)
V (Å³)	3737.36 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.26 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.943, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	10890, 3290, 2697
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.082, 0.188, 1.20
No. of reflections	3290
No. of parameters	246
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.27

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O2	0.98	2.16	2.679 (4)	111.7
C6—H6···N4	0.93	2.36	3.013 (4)	127.4
C4—H4···O1ⁱ	0.93	2.46	3.317 (5)	153.5

Symmetry code: (i) x, y−1, z.

Acknowledgements

We gratefully acknowledge financial support of this work by the National Basic Research Program of China (2003CB114400), the National Natural Science Foundation of China (20372023, 20102001), the Educational Commission of Hubei Province of China (grant Nos. B200624004, B20092412), the Shiyan Municipal Science and the Technology Bureau (grant No. 20061835) and Yunyang Medical College (grant Nos. 2007QDJ15, 2007ZQB19, 2007ZQB20).

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Volume 65| Part 10| October 2009| Pages o2583-o2584

doi:10.1107/S160053680903788X

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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