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

Deng, S.-H.; Wang, H.-M.; Chen, P.; Ma, J.-K.; Cao, F.-J.

doi:10.1107/S160053680904118X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Pages o2730-o2731

https://doi.org/10.1107/S160053680904118X

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

Shou-Heng Deng,^a Hong-Mei Wang,^b ^* Ping Chen,^a Jun-Kai Ma ^b and Feng-Jun Cao ^a

^aCenter of Oncology, People's Hospital affiliated with the YunYang Medical College, Shi Yan 442000, People's Republic of China, and ^bInstitute of Medicinal Chemistry, Yunyang Medical College, Shiyan 442000, People's Republic of China
^*Correspondence e-mail: zengken@126.com

(Received 30 September 2009; accepted 9 October 2009; online 17 October 2009)

In the title compound, C₂₀H₁₉N₅O₂, all atoms of the 1,2,3-triazolo[4,5-d]pyrimidine ring system are essentially coplanar [maximum deviation = 0.015 (2) Å], indicating the existence of a conjugate system in which each carbon and nitrogen atom is sp² hybridized and ten π electrons (three from carbon atoms and seven from nitrogen atoms) constitute an aromatic heterocycle. The ring system forms dihedral angles of 68.37 (10) and 71.57 (9)° with the phenyl rings. The crystal packing is stabilized by van der Waals interactions and intermolecular C—H⋯π interactions.

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, Deng, Qu & Wang (2009 ); Zeng, Deng, Chen et al. (2009 ); Zeng, Liu et al. (2009 ).

Experimental

Crystal data

C₂₀H₁₉N₅O₂
M_r = 361.40
Monoclinic, P 2₁ /c
a = 9.4585 (13) Å
b = 9.0846 (12) Å
c = 21.992 (3) Å
β = 100.523 (2)°
V = 1858.0 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.16 × 0.13 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.986, T_max = 0.991
10907 measured reflections
3655 independent reflections
3079 reflections with I > 2σ(I)
R_int = 0.074

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.167
S = 1.14
3655 reflections
246 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯Cgⁱ	0.96	2.75	3.696 (3)	171
Symmetry code: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ . Cg is the centroid of the C15–C20 phenyl ring.

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/S160053680904118X/rz2370sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053680904118X/rz2370Isup2.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), 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 derivatives of 8-azaguanine via aza-Wittig reaction of beta-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 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; Maldonado et al., 2006; Zeng, Deng, Qu et al., 2009; Zeng, Deng, Chen et al., 2009; Zeng, Liu et al., 2009; Wang et al., 2008; Xiao & Shi, 2007; Chen & Shi, 2007), all atoms in the 1,2,3-triazolo[4,5-d]pyrimidine ring system are essentially coplanar (maximum deviation 0.015 (2)Å for atom N2), indicating that the 1,2,3-triazolo[4,5-d]pyrimidine moiety is a conjugate system, in which each carbon and nitrogen atom is sp² hybridized and ten π electrons (three from carbon atoms and seven from nitrogen atoms) constitute an aromatic heterocycle (Li et al., 2004). The dihedral angles it forms with the C4–C9 and C15–C20 phenyl rings are 68.37 (10) and 71.57 (9)°, respectively.

The crystal packing is stabilized mainly by van der Waals interactions, no intermolecular hydrogen bonds or π–π stacking interactions being observed. One of the methyl H atoms is involved in a contact to the centroid (Cg) of the C15/C20 phenyl ring (C13–H13A···Cg = 2.75 Å), which may be considered as a C—H···π interaction.

Related literature top

For the biological activity of 8-azaguanine derivatives, see: 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, Deng, Qu & Wang (2009); Zeng, Deng, Chen et al. (2009); Zeng, Liu et al. (2009).

Experimental top

To a solution of carbodiimide in CH₂Cl₂/CH₃CN (1:4 v/v, 15 ml) prepared according to the literature method (Wang et al., 2006), was added phenol (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 75%; m.p. 405 K). Elemental analysis: calculated for C₂₀H₁₉N₅O₂: C, 66.47; H, 5.30; N, 19.38%. Found: C, 65.67; H, 5.56; N, 18.92%. 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

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: SHELXTL97 (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.

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

Crystal data top

C₂₀H₁₉N₅O₂	F(000) = 760
M_r = 361.40	D_x = 1.292 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3682 reflections
a = 9.4585 (13) Å	θ = 2.4–25.1°
b = 9.0846 (12) Å	µ = 0.09 mm⁻¹
c = 21.992 (3) Å	T = 298 K
β = 100.523 (2)°	Block, colourless
V = 1858.0 (4) Å³	0.16 × 0.13 × 0.10 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3655 independent reflections
Radiation source: fine-focus sealed tube	3079 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.074
φ and ω scans	θ_max = 26.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→11
T_min = 0.986, T_max = 0.991	k = −11→11
10907 measured reflections	l = −27→27

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.167	H-atom parameters constrained
S = 1.14	w = 1/[σ²(F_o²) + (0.0685P)² + 0.418P] where P = (F_o² + 2F_c²)/3
3655 reflections	(Δ/σ)_max = 0.001
246 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₂₀H₁₉N₅O₂	V = 1858.0 (4) Å³
M_r = 361.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.4585 (13) Å	µ = 0.09 mm⁻¹
b = 9.0846 (12) Å	T = 298 K
c = 21.992 (3) Å	0.16 × 0.13 × 0.10 mm
β = 100.523 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3655 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3079 reflections with I > 2σ(I)
T_min = 0.986, T_max = 0.991	R_int = 0.074
10907 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	0 restraints
wR(F²) = 0.167	H-atom parameters constrained
S = 1.14	Δρ_max = 0.19 e Å⁻³
3655 reflections	Δρ_min = −0.31 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	0.3436 (2)	0.4731 (2)	0.22493 (9)	0.0422 (5)
C2	0.3377 (2)	0.4926 (2)	0.28596 (9)	0.0400 (5)
C3	0.4595 (3)	0.3594 (3)	0.38253 (11)	0.0615 (6)
H3A	0.4907	0.2579	0.3884	0.074*
H3B	0.3730	0.3701	0.4000	0.074*
C4	0.5747 (2)	0.4573 (2)	0.41799 (10)	0.0486 (5)
C5	0.5893 (3)	0.6038 (3)	0.40342 (11)	0.0616 (6)
H5	0.5277	0.6448	0.3699	0.074*
C6	0.6935 (3)	0.6893 (3)	0.43782 (12)	0.0697 (7)
H6	0.7016	0.7878	0.4276	0.084*
C7	0.7851 (4)	0.6317 (3)	0.48672 (12)	0.0810 (9)
H7	0.8549	0.6906	0.5103	0.097*
C8	0.7738 (4)	0.4858 (4)	0.50106 (13)	0.0974 (11)
H8	0.8373	0.4450	0.5340	0.117*
C9	0.6685 (3)	0.3994 (3)	0.46668 (12)	0.0751 (8)
H9	0.6614	0.3006	0.4768	0.090*
C10	0.2657 (2)	0.5691 (2)	0.17917 (9)	0.0435 (5)
C11	0.1931 (2)	0.6823 (2)	0.26940 (9)	0.0409 (5)
C12	0.0995 (3)	0.7849 (3)	0.16396 (10)	0.0594 (6)
H12	0.1186	0.7635	0.1225	0.071*
C13	−0.0597 (3)	0.7597 (3)	0.16099 (13)	0.0810 (9)
H13A	−0.0837	0.6606	0.1478	0.121*
H13B	−0.1133	0.8274	0.1321	0.121*
H13C	−0.0831	0.7751	0.2012	0.121*
C14	0.1452 (4)	0.9438 (3)	0.17780 (15)	0.0853 (9)
H14A	0.1002	0.9807	0.2105	0.128*
H14B	0.1163	1.0025	0.1414	0.128*
H14C	0.2478	0.9483	0.1903	0.128*
C15	0.1523 (3)	0.8427 (2)	0.34770 (9)	0.0479 (5)
C16	0.0476 (3)	0.8378 (3)	0.38311 (12)	0.0635 (7)
H16	−0.0422	0.7977	0.3677	0.076*
C17	0.0788 (4)	0.8938 (3)	0.44193 (13)	0.0838 (10)
H17	0.0090	0.8917	0.4667	0.101*
C18	0.2099 (4)	0.9524 (3)	0.46459 (11)	0.0810 (10)
H18	0.2297	0.9888	0.5048	0.097*
C19	0.3141 (3)	0.9579 (3)	0.42792 (12)	0.0723 (8)
H19	0.4035	0.9991	0.4432	0.087*
C20	0.2849 (3)	0.9021 (3)	0.36845 (10)	0.0591 (6)
H20	0.3538	0.9049	0.3432	0.071*
N1	0.4331 (2)	0.3583 (2)	0.21950 (10)	0.0601 (5)
N2	0.4819 (2)	0.3075 (2)	0.27476 (11)	0.0633 (6)
N3	0.42351 (19)	0.38878 (19)	0.31642 (8)	0.0488 (5)
N4	0.26237 (18)	0.59583 (19)	0.31105 (7)	0.0444 (4)
N5	0.18677 (18)	0.67677 (18)	0.20678 (7)	0.0411 (4)
O1	0.26306 (19)	0.56707 (19)	0.12390 (7)	0.0635 (5)
O2	0.11490 (17)	0.79269 (18)	0.28643 (6)	0.0572 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0411 (11)	0.0384 (10)	0.0493 (11)	−0.0012 (8)	0.0138 (9)	−0.0112 (8)
C2	0.0374 (10)	0.0343 (9)	0.0487 (11)	0.0003 (8)	0.0094 (9)	−0.0007 (8)
C3	0.0607 (15)	0.0502 (13)	0.0711 (16)	0.0003 (11)	0.0051 (12)	0.0202 (11)
C4	0.0540 (13)	0.0454 (11)	0.0475 (12)	0.0092 (10)	0.0123 (10)	0.0075 (9)
C5	0.0682 (16)	0.0488 (13)	0.0632 (15)	0.0028 (12)	0.0000 (12)	0.0114 (11)
C6	0.091 (2)	0.0526 (14)	0.0628 (16)	−0.0057 (14)	0.0072 (14)	0.0002 (11)
C7	0.106 (2)	0.0769 (19)	0.0526 (15)	−0.0154 (17)	−0.0042 (15)	−0.0061 (13)
C8	0.125 (3)	0.089 (2)	0.0612 (17)	−0.006 (2)	−0.0294 (18)	0.0158 (15)
C9	0.100 (2)	0.0570 (15)	0.0616 (15)	0.0009 (15)	−0.0032 (15)	0.0169 (12)
C10	0.0478 (12)	0.0438 (11)	0.0403 (11)	−0.0039 (9)	0.0115 (9)	−0.0117 (8)
C11	0.0415 (11)	0.0433 (11)	0.0387 (10)	0.0057 (9)	0.0089 (8)	−0.0045 (8)
C12	0.0767 (17)	0.0649 (15)	0.0354 (11)	0.0199 (13)	0.0073 (11)	0.0058 (10)
C13	0.0683 (18)	0.0792 (18)	0.0812 (19)	0.0162 (15)	−0.0237 (15)	−0.0102 (15)
C14	0.095 (2)	0.0628 (17)	0.103 (2)	0.0139 (16)	0.0296 (18)	0.0320 (16)
C15	0.0629 (14)	0.0431 (11)	0.0394 (11)	0.0186 (10)	0.0133 (10)	−0.0029 (8)
C16	0.0803 (18)	0.0497 (13)	0.0690 (15)	0.0098 (12)	0.0361 (14)	−0.0083 (11)
C17	0.137 (3)	0.0626 (17)	0.0659 (18)	0.0074 (19)	0.0572 (19)	−0.0088 (14)
C18	0.152 (3)	0.0538 (15)	0.0372 (12)	0.0233 (18)	0.0171 (17)	−0.0061 (11)
C19	0.093 (2)	0.0560 (15)	0.0598 (15)	0.0115 (14)	−0.0083 (14)	−0.0043 (12)
C20	0.0656 (16)	0.0636 (15)	0.0489 (13)	0.0154 (13)	0.0126 (11)	0.0025 (11)
N1	0.0563 (12)	0.0541 (11)	0.0707 (13)	0.0107 (9)	0.0138 (10)	−0.0194 (10)
N2	0.0584 (13)	0.0452 (11)	0.0843 (15)	0.0133 (9)	0.0081 (11)	−0.0134 (10)
N3	0.0466 (10)	0.0381 (9)	0.0604 (11)	0.0049 (8)	0.0063 (8)	0.0010 (8)
N4	0.0486 (10)	0.0474 (10)	0.0387 (9)	0.0117 (8)	0.0121 (7)	0.0014 (7)
N5	0.0456 (10)	0.0428 (9)	0.0350 (8)	0.0036 (7)	0.0079 (7)	−0.0024 (7)
O1	0.0826 (12)	0.0719 (11)	0.0383 (8)	0.0049 (9)	0.0172 (8)	−0.0126 (7)
O2	0.0638 (10)	0.0664 (10)	0.0401 (8)	0.0306 (8)	0.0057 (7)	−0.0096 (7)

Geometric parameters (Å, º) top

C1—N1	1.362 (3)	C12—N5	1.500 (3)
C1—C2	1.365 (3)	C12—C13	1.513 (4)
C1—C10	1.430 (3)	C12—C14	1.521 (4)
C2—N3	1.341 (2)	C12—H12	0.9800
C2—N4	1.355 (2)	C13—H13A	0.9600
C3—N3	1.456 (3)	C13—H13B	0.9600
C3—C4	1.509 (3)	C13—H13C	0.9600
C3—H3A	0.9700	C14—H14A	0.9600
C3—H3B	0.9700	C14—H14B	0.9600
C4—C9	1.365 (3)	C14—H14C	0.9600
C4—C5	1.382 (3)	C15—C20	1.365 (3)
C5—C6	1.369 (3)	C15—C16	1.367 (3)
C5—H5	0.9300	C15—O2	1.405 (2)
C6—C7	1.356 (4)	C16—C17	1.371 (4)
C6—H6	0.9300	C16—H16	0.9300
C7—C8	1.371 (4)	C17—C18	1.358 (5)
C7—H7	0.9300	C17—H17	0.9300
C8—C9	1.380 (4)	C18—C19	1.383 (4)
C8—H8	0.9300	C18—H18	0.9300
C9—H9	0.9300	C19—C20	1.383 (3)
C10—O1	1.211 (2)	C19—H19	0.9300
C10—N5	1.431 (2)	C20—H20	0.9300
C11—N4	1.291 (2)	N1—N2	1.303 (3)
C11—O2	1.339 (2)	N2—N3	1.369 (3)
C11—N5	1.368 (2)

N1—C1—C2	108.83 (19)	C14—C12—H12	106.3
N1—C1—C10	130.83 (19)	C12—C13—H13A	109.5
C2—C1—C10	120.31 (18)	C12—C13—H13B	109.5
N3—C2—N4	126.77 (18)	H13A—C13—H13B	109.5
N3—C2—C1	105.72 (17)	C12—C13—H13C	109.5
N4—C2—C1	127.51 (18)	H13A—C13—H13C	109.5
N3—C3—C4	115.02 (18)	H13B—C13—H13C	109.5
N3—C3—H3A	108.5	C12—C14—H14A	109.5
C4—C3—H3A	108.5	C12—C14—H14B	109.5
N3—C3—H3B	108.5	H14A—C14—H14B	109.5
C4—C3—H3B	108.5	C12—C14—H14C	109.5
H3A—C3—H3B	107.5	H14A—C14—H14C	109.5
C9—C4—C5	118.3 (2)	H14B—C14—H14C	109.5
C9—C4—C3	118.9 (2)	C20—C15—C16	122.6 (2)
C5—C4—C3	122.7 (2)	C20—C15—O2	120.2 (2)
C6—C5—C4	120.7 (2)	C16—C15—O2	117.0 (2)
C6—C5—H5	119.7	C15—C16—C17	118.2 (3)
C4—C5—H5	119.7	C15—C16—H16	120.9
C7—C6—C5	120.7 (2)	C17—C16—H16	120.9
C7—C6—H6	119.6	C18—C17—C16	121.1 (3)
C5—C6—H6	119.6	C18—C17—H17	119.5
C6—C7—C8	119.3 (3)	C16—C17—H17	119.5
C6—C7—H7	120.3	C17—C18—C19	120.0 (2)
C8—C7—H7	120.3	C17—C18—H18	120.0
C7—C8—C9	120.2 (3)	C19—C18—H18	120.0
C7—C8—H8	119.9	C20—C19—C18	119.8 (3)
C9—C8—H8	119.9	C20—C19—H19	120.1
C4—C9—C8	120.8 (2)	C18—C19—H19	120.1
C4—C9—H9	119.6	C15—C20—C19	118.3 (2)
C8—C9—H9	119.6	C15—C20—H20	120.9
O1—C10—C1	127.61 (19)	C19—C20—H20	120.9
O1—C10—N5	121.29 (19)	N2—N1—C1	108.03 (18)
C1—C10—N5	111.10 (16)	N1—N2—N3	108.40 (17)
N4—C11—O2	119.46 (17)	C2—N3—N2	109.02 (18)
N4—C11—N5	127.95 (18)	C2—N3—C3	129.62 (19)
O2—C11—N5	112.58 (16)	N2—N3—C3	121.34 (19)
N5—C12—C13	110.9 (2)	C11—N4—C2	111.65 (16)
N5—C12—C14	113.1 (2)	C11—N5—C10	121.45 (16)
C13—C12—C14	113.3 (2)	C11—N5—C12	121.72 (16)
N5—C12—H12	106.3	C10—N5—C12	116.81 (16)
C13—C12—H12	106.3	C11—O2—C15	117.06 (15)

N1—C1—C2—N3	−0.2 (2)	N4—C2—N3—N2	−179.02 (19)
C10—C1—C2—N3	−178.61 (18)	C1—C2—N3—N2	0.4 (2)
N1—C1—C2—N4	179.23 (19)	N4—C2—N3—C3	−0.5 (3)
C10—C1—C2—N4	0.8 (3)	C1—C2—N3—C3	178.9 (2)
N3—C3—C4—C9	−145.0 (2)	N1—N2—N3—C2	−0.5 (2)
N3—C3—C4—C5	35.3 (3)	N1—N2—N3—C3	−179.14 (19)
C9—C4—C5—C6	−1.3 (4)	C4—C3—N3—C2	−80.8 (3)
C3—C4—C5—C6	178.5 (2)	C4—C3—N3—N2	97.6 (2)
C4—C5—C6—C7	0.3 (4)	O2—C11—N4—C2	−178.81 (18)
C5—C6—C7—C8	0.9 (5)	N5—C11—N4—C2	1.8 (3)
C6—C7—C8—C9	−1.2 (6)	N3—C2—N4—C11	178.18 (19)
C5—C4—C9—C8	1.0 (4)	C1—C2—N4—C11	−1.1 (3)
C3—C4—C9—C8	−178.8 (3)	N4—C11—N5—C10	−2.1 (3)
C7—C8—C9—C4	0.2 (5)	O2—C11—N5—C10	178.45 (17)
N1—C1—C10—O1	0.3 (4)	N4—C11—N5—C12	179.2 (2)
C2—C1—C10—O1	178.4 (2)	O2—C11—N5—C12	−0.2 (3)
N1—C1—C10—N5	−178.9 (2)	O1—C10—N5—C11	−177.88 (19)
C2—C1—C10—N5	−0.8 (3)	C1—C10—N5—C11	1.4 (3)
C20—C15—C16—C17	−0.7 (4)	O1—C10—N5—C12	0.9 (3)
O2—C15—C16—C17	−176.3 (2)	C1—C10—N5—C12	−179.87 (18)
C15—C16—C17—C18	−0.1 (4)	C13—C12—N5—C11	−69.5 (3)
C16—C17—C18—C19	0.8 (4)	C14—C12—N5—C11	59.1 (3)
C17—C18—C19—C20	−0.8 (4)	C13—C12—N5—C10	111.8 (2)
C16—C15—C20—C19	0.7 (3)	C14—C12—N5—C10	−119.6 (2)
O2—C15—C20—C19	176.16 (19)	N4—C11—O2—C15	22.9 (3)
C18—C19—C20—C15	0.1 (4)	N5—C11—O2—C15	−157.54 (18)
C2—C1—N1—N2	−0.1 (2)	C20—C15—O2—C11	62.1 (3)
C10—C1—N1—N2	178.1 (2)	C16—C15—O2—C11	−122.2 (2)
C1—N1—N2—N3	0.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···Cgⁱ	0.96	2.75	3.696 (3)	171

Symmetry code: (i) −x, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₉N₅O₂
M_r	361.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	9.4585 (13), 9.0846 (12), 21.992 (3)
β (°)	100.523 (2)
V (Å³)	1858.0 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.16 × 0.13 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.986, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	10907, 3655, 3079
R_int	0.074
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.167, 1.14
No. of reflections	3655
No. of parameters	246
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.31

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL97 (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···Cgⁱ	0.96	2.75	3.696 (3)	171

Symmetry code: (i) −x, y−1/2, −z+1/2.

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 No. Q20092401, B20092412), the Public Health Department of Hubei of China (grant No. QJX200842), the Shiyan Municipal Science and Technology Bureau (grant No. 20061835) and the Yunyang Medical College (grant Nos. 2008CXZ02, 2007ZQB19).

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