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

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

doi:10.1107/S1600536810045575

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Pages o3140-o3141

https://doi.org/10.1107/S1600536810045575

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

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

^aInstitute of Medicinal Chemistry, Hubei Medical Univesity, 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: meirwang@126.com

(Received 23 October 2010; accepted 6 November 2010; online 13 November 2010)

In the title compound, C₁₈H₂₃N₅O₂, the triazolopyrimidine ring system is essentially planar, with a maximum displacement of 0.032 (2) Å, and forms a dihedral angle of 87.59 (15)° with the phenyl ring. In the crystal, molecules are linked by intermolecular C—H⋯O hydrogen bonds and C—H⋯π interactions into chains parallel to the c axis.

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 ); 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 & Shi (2007 ); Wang et al. (2006 , 2008 ); Zeng et al. (2006 , 2009 ).

Experimental

Crystal data

C₁₈H₂₃N₅O₂
M_r = 341.41
Orthorhombic, P b c n
a = 28.328 (6) Å
b = 14.818 (3) Å
c = 8.7995 (16) Å
V = 3693.7 (12) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.19 × 0.15 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.984, T_max = 0.992
18673 measured reflections
3346 independent reflections
2842 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.080
wR(F²) = 0.173
S = 1.21
3346 reflections
228 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1ⁱ	0.93	2.43	3.259 (4)	148
C15—H15B⋯Cg1ⁱ	0.97	2.94	3.711 (3)	137
Symmetry code: (i) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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: ORTEP-3 for Windows (Farrugia, 1999 ) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810045575/rz2509sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810045575/rz2509Isup2.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; Zeng et al., 2010), 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, Ding's group has been engaged in the preparation of derivatives of 8-azaguanine via aza-Wittig reaction of β-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 β-ethoxycarbonyl iminophosphorane with alphalic isocyanate, and structurally characterized in this context.

In the title compound (Fig. 1), bond lengths and angles within the triazolopyrimidinone 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 & Shi, 2007; Chen & Shi, 2006), the triazolopyrimidine ring system is essentially planar, with a maximum displacement of 0.032 (2) Å for atom N4, and forms dihedral angles of 87.59 (15)° with the C1–C6 phenyl ring. In the crystal packing, molecules are linked by intermolecular C—H···O hydrogen bonds and C—H···π interactions (Table 1) into chains parallel to the c axis.

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); 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 & Shi (2007); Wang et al. (2006, 2008); Zeng et al. (2006, 2009).

Experimental top

To the solution of carbodiimide prepared according to Zeng et al. (2006) in a mixed solvent (CH₂Cl₂/PrOH,1:4 v/v, 15 ml) was added a fresh prepared solution of Na/PrOH (0.1 g/2 ml). After stirring the reaction mixture for 6 h, the solvent was removed under reduced pressure and the residue was recrystallized from EtOH to give the title compound in 75% yield (m. p. 464 K). Elemental analysis: calculated for C₁₄H₁₅N₅O₂: C, 63.32; H, 6.79; N, 20.51%. Found: C, 62.75; H, 6.98; N, 20.22%. Crystals suitable for X-ray diffraction study were obtained by recrystallization from EtOH and dichloromethane (1:3 v/v) at room temperature.

Structure description 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); 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 & Shi (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: ORTEP-3 for Windows (Farrugia, 1999) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level. H-atoms are represented by circles of arbitrary size.

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

Crystal data top

C₁₈H₂₃N₅O₂	D_x = 1.228 Mg m⁻³
M_r = 341.41	Melting point: 364 K
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 3955 reflections
a = 28.328 (6) Å	θ = 2.6–23.4°
b = 14.818 (3) Å	µ = 0.08 mm⁻¹
c = 8.7995 (16) Å	T = 298 K
V = 3693.7 (12) Å³	Block, colourless
Z = 8	0.19 × 0.15 × 0.10 mm
F(000) = 1456

Data collection top

Bruker SMART CCD area-detector diffractometer	3346 independent reflections
Radiation source: fine-focus sealed tube	2842 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
φ and ω scans	θ_max = 25.3°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −34→29
T_min = 0.984, T_max = 0.992	k = −17→17
18673 measured reflections	l = −10→7

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)] = 0.080	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.173	H-atom parameters constrained
S = 1.21	w = 1/[σ²(F_o²) + (0.0532P)² + 2.6669P] where P = (F_o² + 2F_c²)/3
3346 reflections	(Δ/σ)_max < 0.001
228 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₈H₂₃N₅O₂	V = 3693.7 (12) Å³
M_r = 341.41	Z = 8
Orthorhombic, Pbcn	Mo Kα radiation
a = 28.328 (6) Å	µ = 0.08 mm⁻¹
b = 14.818 (3) Å	T = 298 K
c = 8.7995 (16) Å	0.19 × 0.15 × 0.10 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3346 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2842 reflections with I > 2σ(I)
T_min = 0.984, T_max = 0.992	R_int = 0.041
18673 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.080	0 restraints
wR(F²) = 0.173	H-atom parameters constrained
S = 1.21	Δρ_max = 0.30 e Å⁻³
3346 reflections	Δρ_min = −0.15 e Å⁻³
228 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	0.13547 (10)	0.44798 (18)	0.0088 (3)	0.0454 (7)
C2	0.11879 (15)	0.3707 (2)	0.0781 (4)	0.0689 (10)
H2	0.1388	0.3363	0.1387	0.083*
C3	0.07250 (19)	0.3444 (3)	0.0577 (5)	0.0900 (14)
H3	0.0613	0.2929	0.1062	0.108*
C4	0.04300 (15)	0.3936 (4)	−0.0333 (6)	0.0967 (15)
H4	0.0120	0.3752	−0.0487	0.116*
C5	0.05947 (13)	0.4692 (3)	−0.1007 (5)	0.0814 (12)
H5	0.0394	0.5033	−0.1616	0.098*
C6	0.10505 (11)	0.4963 (2)	−0.0807 (4)	0.0581 (8)
H6	0.1157	0.5485	−0.1286	0.070*
C7	0.18567 (11)	0.4789 (2)	0.0285 (4)	0.0674 (10)
H7A	0.1902	0.5352	−0.0259	0.081*
H7B	0.1917	0.4902	0.1354	0.081*
C8	0.25650 (9)	0.37249 (17)	0.0422 (3)	0.0413 (6)
C9	0.27483 (10)	0.31471 (18)	−0.0642 (3)	0.0424 (6)
C10	0.31511 (10)	0.26037 (18)	−0.0287 (3)	0.0443 (7)
C11	0.30961 (10)	0.33995 (18)	0.2144 (3)	0.0420 (6)
C12	0.30873 (12)	0.4007 (2)	0.4643 (3)	0.0628 (9)
H12A	0.2781	0.3761	0.4915	0.075*
H12B	0.3042	0.4616	0.4263	0.075*
C13	0.34015 (14)	0.4018 (3)	0.5988 (4)	0.0742 (10)
H13A	0.3245	0.4351	0.6792	0.089*
H13B	0.3441	0.3402	0.6339	0.089*
C14	0.38675 (18)	0.4409 (4)	0.5757 (6)	0.131 (2)
H14A	0.4045	0.4035	0.5076	0.197*
H14B	0.4029	0.4449	0.6714	0.197*
H14C	0.3836	0.5002	0.5330	0.197*
C15	0.37466 (10)	0.2295 (2)	0.1713 (3)	0.0516 (8)
H15A	0.3775	0.1745	0.1123	0.062*
H15B	0.3705	0.2127	0.2769	0.062*
C16	0.42007 (11)	0.2843 (3)	0.1552 (4)	0.0685 (10)
H16A	0.4163	0.3403	0.2108	0.082*
H16B	0.4455	0.2509	0.2031	0.082*
C17	0.43453 (13)	0.3064 (3)	−0.0027 (5)	0.0896 (13)
H17A	0.4092	0.3391	−0.0525	0.108*
H17B	0.4397	0.2509	−0.0586	0.108*
C18	0.47925 (15)	0.3631 (4)	−0.0072 (7)	0.1249 (19)
H18A	0.4741	0.4185	0.0467	0.187*
H18B	0.4873	0.3762	−0.1109	0.187*
H18C	0.5046	0.3304	0.0396	0.187*
N1	0.21950 (8)	0.41208 (15)	−0.0277 (3)	0.0508 (6)
N2	0.21576 (10)	0.37955 (17)	−0.1729 (3)	0.0577 (7)
N3	0.24886 (9)	0.32053 (17)	−0.1946 (3)	0.0537 (7)
N4	0.33234 (8)	0.28021 (15)	0.1193 (2)	0.0417 (6)
N5	0.27266 (8)	0.38784 (15)	0.1849 (3)	0.0430 (6)
O1	0.33434 (8)	0.20431 (16)	−0.1081 (2)	0.0664 (7)
O2	0.33084 (7)	0.34506 (14)	0.3490 (2)	0.0531 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0575 (18)	0.0412 (15)	0.0375 (15)	0.0103 (13)	−0.0086 (13)	−0.0097 (12)
C2	0.108 (3)	0.053 (2)	0.0456 (18)	0.009 (2)	−0.0091 (19)	−0.0024 (15)
C3	0.115 (4)	0.068 (3)	0.087 (3)	−0.027 (3)	0.036 (3)	−0.010 (2)
C4	0.058 (2)	0.099 (3)	0.133 (4)	−0.009 (2)	0.016 (3)	−0.038 (3)
C5	0.055 (2)	0.085 (3)	0.105 (3)	0.015 (2)	−0.020 (2)	−0.006 (2)
C6	0.0590 (19)	0.0582 (18)	0.0572 (19)	0.0091 (16)	−0.0092 (16)	0.0052 (15)
C7	0.066 (2)	0.0520 (19)	0.085 (2)	0.0146 (16)	−0.0294 (19)	−0.0257 (18)
C8	0.0412 (15)	0.0374 (14)	0.0452 (16)	−0.0057 (12)	−0.0025 (12)	−0.0010 (12)
C9	0.0454 (16)	0.0429 (15)	0.0390 (15)	−0.0034 (13)	−0.0016 (12)	−0.0010 (12)
C10	0.0472 (16)	0.0444 (15)	0.0413 (16)	−0.0007 (13)	0.0087 (13)	−0.0003 (13)
C11	0.0429 (15)	0.0421 (14)	0.0409 (15)	−0.0011 (13)	0.0029 (12)	0.0021 (12)
C12	0.068 (2)	0.076 (2)	0.0448 (18)	0.0197 (18)	0.0019 (15)	−0.0107 (16)
C13	0.089 (3)	0.081 (2)	0.053 (2)	0.009 (2)	−0.0058 (19)	−0.0148 (18)
C14	0.098 (4)	0.184 (6)	0.112 (4)	−0.033 (4)	−0.004 (3)	−0.051 (4)
C15	0.0522 (18)	0.0529 (17)	0.0495 (17)	0.0156 (14)	0.0040 (14)	0.0069 (14)
C16	0.0506 (19)	0.086 (2)	0.069 (2)	0.0180 (18)	0.0039 (16)	0.0131 (19)
C17	0.067 (2)	0.113 (3)	0.089 (3)	0.002 (2)	0.017 (2)	0.018 (3)
C18	0.079 (3)	0.148 (5)	0.148 (5)	−0.014 (3)	0.030 (3)	0.038 (4)
N1	0.0492 (14)	0.0432 (13)	0.0601 (16)	0.0056 (11)	−0.0176 (12)	−0.0115 (12)
N2	0.0653 (17)	0.0535 (15)	0.0543 (16)	0.0024 (14)	−0.0215 (13)	−0.0074 (13)
N3	0.0568 (15)	0.0554 (15)	0.0489 (15)	0.0000 (13)	−0.0086 (12)	−0.0075 (12)
N4	0.0414 (13)	0.0439 (12)	0.0397 (12)	0.0042 (10)	0.0042 (10)	0.0027 (10)
N5	0.0430 (13)	0.0439 (13)	0.0423 (13)	0.0047 (11)	−0.0054 (10)	−0.0054 (10)
O1	0.0752 (15)	0.0695 (14)	0.0544 (13)	0.0225 (12)	0.0036 (11)	−0.0173 (12)
O2	0.0539 (12)	0.0661 (13)	0.0393 (11)	0.0165 (10)	−0.0054 (9)	−0.0067 (9)

Geometric parameters (Å, º) top

C1—C6	1.370 (4)	C12—O2	1.450 (3)
C1—C2	1.381 (4)	C12—C13	1.481 (5)
C1—C7	1.504 (4)	C12—H12A	0.9700
C2—C3	1.380 (6)	C12—H12B	0.9700
C2—H2	0.9300	C13—C14	1.456 (6)
C3—C4	1.368 (6)	C13—H13A	0.9700
C3—H3	0.9300	C13—H13B	0.9700
C4—C5	1.350 (6)	C14—H14A	0.9600
C4—H4	0.9300	C14—H14B	0.9600
C5—C6	1.364 (5)	C14—H14C	0.9600
C5—H5	0.9300	C15—N4	1.486 (3)
C6—H6	0.9300	C15—C16	1.528 (4)
C7—N1	1.464 (4)	C15—H15A	0.9700
C7—H7A	0.9700	C15—H15B	0.9700
C7—H7B	0.9700	C16—C17	1.485 (5)
C8—N1	1.350 (3)	C16—H16A	0.9700
C8—N5	1.356 (3)	C16—H16B	0.9700
C8—C9	1.371 (4)	C17—C18	1.521 (6)
C9—N3	1.366 (4)	C17—H17A	0.9700
C9—C10	1.431 (4)	C17—H17B	0.9700
C10—O1	1.215 (3)	C18—H18A	0.9600
C10—N4	1.421 (3)	C18—H18B	0.9600
C11—N5	1.291 (3)	C18—H18C	0.9600
C11—O2	1.331 (3)	N1—N2	1.369 (3)
C11—N4	1.378 (3)	N2—N3	1.296 (3)

C6—C1—C2	118.2 (3)	C12—C13—H13A	108.3
C6—C1—C7	120.1 (3)	C14—C13—H13B	108.3
C2—C1—C7	121.7 (3)	C12—C13—H13B	108.3
C3—C2—C1	120.1 (4)	H13A—C13—H13B	107.4
C3—C2—H2	119.9	C13—C14—H14A	109.5
C1—C2—H2	119.9	C13—C14—H14B	109.5
C4—C3—C2	120.4 (4)	H14A—C14—H14B	109.5
C4—C3—H3	119.8	C13—C14—H14C	109.5
C2—C3—H3	119.8	H14A—C14—H14C	109.5
C5—C4—C3	119.2 (4)	H14B—C14—H14C	109.5
C5—C4—H4	120.4	N4—C15—C16	112.5 (2)
C3—C4—H4	120.4	N4—C15—H15A	109.1
C4—C5—C6	121.0 (4)	C16—C15—H15A	109.1
C4—C5—H5	119.5	N4—C15—H15B	109.1
C6—C5—H5	119.5	C16—C15—H15B	109.1
C5—C6—C1	121.0 (3)	H15A—C15—H15B	107.8
C5—C6—H6	119.5	C17—C16—C15	115.9 (3)
C1—C6—H6	119.5	C17—C16—H16A	108.3
N1—C7—C1	111.9 (2)	C15—C16—H16A	108.3
N1—C7—H7A	109.2	C17—C16—H16B	108.3
C1—C7—H7A	109.2	C15—C16—H16B	108.3
N1—C7—H7B	109.2	H16A—C16—H16B	107.4
C1—C7—H7B	109.2	C16—C17—C18	112.1 (4)
H7A—C7—H7B	107.9	C16—C17—H17A	109.2
N1—C8—N5	127.7 (2)	C18—C17—H17A	109.2
N1—C8—C9	104.8 (2)	C16—C17—H17B	109.2
N5—C8—C9	127.5 (3)	C18—C17—H17B	109.2
N3—C9—C8	109.3 (2)	H17A—C17—H17B	107.9
N3—C9—C10	130.4 (3)	C17—C18—H18A	109.5
C8—C9—C10	120.3 (2)	C17—C18—H18B	109.5
O1—C10—N4	121.0 (3)	H18A—C18—H18B	109.5
O1—C10—C9	128.1 (3)	C17—C18—H18C	109.5
N4—C10—C9	110.9 (2)	H18A—C18—H18C	109.5
N5—C11—O2	120.9 (2)	H18B—C18—H18C	109.5
N5—C11—N4	127.6 (2)	C8—N1—N2	109.4 (2)
O2—C11—N4	111.5 (2)	C8—N1—C7	130.4 (3)
O2—C12—C13	107.8 (3)	N2—N1—C7	120.2 (2)
O2—C12—H12A	110.1	N3—N2—N1	108.6 (2)
C13—C12—H12A	110.1	N2—N3—C9	108.0 (2)
O2—C12—H12B	110.1	C11—N4—C10	121.9 (2)
C13—C12—H12B	110.1	C11—N4—C15	121.0 (2)
H12A—C12—H12B	108.5	C10—N4—C15	117.0 (2)
C14—C13—C12	116.0 (4)	C11—N5—C8	111.6 (2)
C14—C13—H13A	108.3	C11—O2—C12	117.4 (2)

C6—C1—C2—C3	−0.7 (5)	C1—C7—N1—C8	−125.7 (3)
C7—C1—C2—C3	179.9 (3)	C1—C7—N1—N2	53.6 (4)
C1—C2—C3—C4	1.2 (6)	C8—N1—N2—N3	0.7 (3)
C2—C3—C4—C5	−1.3 (6)	C7—N1—N2—N3	−178.8 (3)
C3—C4—C5—C6	0.8 (7)	N1—N2—N3—C9	−0.6 (3)
C4—C5—C6—C1	−0.3 (6)	C8—C9—N3—N2	0.4 (3)
C2—C1—C6—C5	0.2 (5)	C10—C9—N3—N2	−179.7 (3)
C7—C1—C6—C5	179.7 (3)	N5—C11—N4—C10	−3.3 (4)
C6—C1—C7—N1	−118.6 (3)	O2—C11—N4—C10	177.3 (2)
C2—C1—C7—N1	60.9 (4)	N5—C11—N4—C15	−179.7 (3)
N1—C8—C9—N3	0.0 (3)	O2—C11—N4—C15	0.9 (3)
N5—C8—C9—N3	−178.7 (3)	O1—C10—N4—C11	−176.4 (3)
N1—C8—C9—C10	−179.9 (2)	C9—C10—N4—C11	4.2 (3)
N5—C8—C9—C10	1.4 (4)	O1—C10—N4—C15	0.1 (4)
N3—C9—C10—O1	−2.5 (5)	C9—C10—N4—C15	−179.2 (2)
C8—C9—C10—O1	177.3 (3)	C16—C15—N4—C11	−83.6 (3)
N3—C9—C10—N4	176.8 (3)	C16—C15—N4—C10	99.8 (3)
C8—C9—C10—N4	−3.4 (3)	O2—C11—N5—C8	−179.8 (2)
O2—C12—C13—C14	62.4 (5)	N4—C11—N5—C8	0.8 (4)
N4—C15—C16—C17	−65.6 (4)	N1—C8—N5—C11	−178.3 (3)
C15—C16—C17—C18	178.4 (3)	C9—C8—N5—C11	0.1 (4)
N5—C8—N1—N2	178.3 (3)	N5—C11—O2—C12	4.8 (4)
C9—C8—N1—N2	−0.4 (3)	N4—C11—O2—C12	−175.8 (2)
N5—C8—N1—C7	−2.4 (5)	C13—C12—O2—C11	−175.7 (3)
C9—C8—N1—C7	179.0 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1ⁱ	0.93	2.43	3.259 (4)	148
C15—H15B···Cg1ⁱ	0.97	2.94	3.711 (3)	137

Symmetry code: (i) −x+1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₃N₅O₂
M_r	341.41
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	298
a, b, c (Å)	28.328 (6), 14.818 (3), 8.7995 (16)
V (Å³)	3693.7 (12)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.19 × 0.15 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.984, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	18673, 3346, 2842
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.080, 0.173, 1.21
No. of reflections	3346
No. of parameters	228
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.15

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1ⁱ	0.93	2.43	3.259 (4)	148.4
C15—H15B···Cg1ⁱ	0.97	2.94	3.711 (3)	137

Symmetry code: (i) −x+1/2, −y+1/2, z+1/2.

Acknowledgements

We gratefully acknowledge the financial support for 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, B20102103) and the Shiyan Municipal Science and Technology Bureau (grant No. 20061835).

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