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

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

doi:10.1107/S160053681004300X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Pages o2990-o2991

https://doi.org/10.1107/S160053681004300X

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

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

^aInstitute of Medicinal Chemistry, Hubei Medical University, Shiyan 442000, People's Republic of China, and ^bCenter of Oncology, People's Hospital affiliated with Hubei Medical University, Shiyan 442000, People's Republic of China
^*Correspondence e-mail: zengken@126.com

(Received 9 October 2010; accepted 22 October 2010; online 31 October 2010)

In the title compound, C₂₁H₂₁N₅O₂, 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 intramolecular C—H⋯O hydrogen-bonding interaction stabilizes the molecular conformation. In the crystal, molecules are linked by intermolecular C—H⋯O and C—H⋯N hydrogen bonds into a three-dimensional network. In addition, π–π stacking interactions involving the triazole and pyrimidine rings of adjacent molecules 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_r = 375.43
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.054
wR(F²) = 0.182
S = 1.08
3876 reflections
293 parameters
11 restraints
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.24 e Å⁻³

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) -x+1, -y, -z+1; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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: https://doi.org/10.1107/S160053681004300X/rz2502sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681004300X/rz2502Isup2.hkl

checkCIF report

Comment top

The derivatives of heterocycles containing 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; Zeng et al., 2010), encephaloma cell inhibitor activity (Mitchell et al., 1950; Levine et al., 1963), antileukemic activity (Montgomery et al., 1962), hypersusceptibility inhibitor activity and acesodyne activity (Yamamoto et al., 1967; Bariana, 1971; Holland et al., 1975). In recent years, Ding's group has been engaged in the preparation of derivatives of 8-azaguanine via aza-Wittig reaction of beta-ethoxycarbonyl iminophosphoranes with aromatic isocyanates (Zhao, Xie et al., 2005). As a continuation of our research for new biologically active heterocycles, the title compound was obtained from beta-ethoxycarbonyl iminophosphorane with alphalic isocyanate, and structurally characterized in this context.

In the title compound (Fig. 1), bond lengths and angles within the triazolopyrimidinone moiety 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), the triazolopyrimidine ring system is essentially planar, with a maximum displacement of 0.021 (4) Å for atom C8, and forms dihedral angles of 41.17 (9) and 67.99 (8)° with the C1–C6 and C15–C20 rings, respectively. There exists an intramolecular C—H···O hydrogen bonding interaction stabilizing the molecular conformation. In the crystal packing, molecules are linked by intermolecular C—H···O and C—H···N hydrogen bonds (Table 1). In addition, π–π stacking interactions involving the triazole and pyrimidine rings of adjacent molecules are observed, with cenroid-to-centroid distances of 3.545 (1) Å.

Related literature top

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 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), was added 4-methylphenol (3 mmol) and excess K₂CO₃, 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 93%; m.p. 406 K). Elemental analysis: calculated for C₂₁H₂₁N₅O₂: C, 67.18; H, 5.64; N, 18.65%. Found: C, 66.62; H, 5.98; N, 18.13%. 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.

Structure description top

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).

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. The molecular structure of the title compound showing the atom-labeling scheme. Displacement ellipsoids are drawn at 50% probability level. H-atoms are represented by circles of arbitrary size. Only the major component of the disorder is shown.

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

Crystal data top

C₂₁H₂₁N₅O₂	F(000) = 792
M_r = 375.43	D_x = 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

Data collection top

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

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.182	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.1122P)² + 0.0419P] where P = (F_o² + 2F_c²)/3
3876 reflections	(Δ/σ)_max < 0.001
293 parameters	Δρ_max = 0.56 e Å⁻³
11 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₁H₂₁N₅O₂	V = 1973.6 (3) Å³
M_r = 375.43	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.0954 (10) Å	µ = 0.09 mm⁻¹
b = 16.4478 (15) Å	T = 298 K
c = 11.3484 (11) Å	0.20 × 0.20 × 0.20 mm
β = 107.643 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3876 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2663 reflections with I > 2σ(I)
T_min = 0.983, T_max = 0.985	R_int = 0.055
20458 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	11 restraints
wR(F²) = 0.182	H-atom parameters constrained
S = 1.08	Δρ_max = 0.56 e Å⁻³
3876 reflections	Δρ_min = −0.24 e Å⁻³
293 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	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y, −z+1; (ii) x+1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₁N₅O₂
M_r	375.43
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	11.0954 (10), 16.4478 (15), 11.3484 (11)
β (°)	107.643 (1)
V (Å³)	1973.6 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.983, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	20458, 3876, 2663
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.182, 1.08
No. of reflections	3876
No. of parameters	293
No. of restraints	11
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.24

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
C12—H12A···O2	0.97	2.50	3.048 (5)	115.7
C2—H2···O1ⁱ	0.93	2.53	3.230 (3)	132.6
C3—H3···N2ⁱⁱ	0.93	2.61	3.535 (2)	174

Symmetry codes: (i) −x+1, −y, −z+1; (ii) x+1/2, −y+1/2, z+1/2.

Acknowledgements

The authors 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 No. B200624004, B20092412), Shiyan Municipal Science and Technology Bureau (grant No. 20061835) and Yunyang Medical College (grant Nos. 2007QDJ15, 2007ZQB19, 2007ZQB20).

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Volume 66| Part 11| November 2010| Pages o2990-o2991

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

6-Butyl-5-(4-methyl­phen­­oxy)-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

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