6-Benzyl-3-[(6-chloro­pyridin-3-yl)meth­yl]-6,7-dihydro-3H-1,2,3-triazolo[4,5-d]pyrimidin-7-imine

Dong-Feng Pan; Xiao-Bao Chen; Hai-Tao Gao; Chun Feng; Ping Chen

doi:10.1107/S1600536811047568

. 2011 Nov 16;67(Pt 12):o3326. doi: 10.1107/S1600536811047568

6-Benzyl-3-[(6-chloropyridin-3-yl)methyl]-6,7-dihydro-3H-1,2,3-triazolo[4,5-d]pyrimidin-7-imine

Dong-Feng Pan ^a, Xiao-Bao Chen ^b, Hai-Tao Gao ^b, Chun Feng ^b, Ping Chen ^a,^*

PMCID: PMC3238975 PMID: 22199824

Abstract

The title compound, C₁₇H₁₄ClN₇, crystallizes with two independent molecules in the asymmetric unit. Intermolecular N—H⋯N and C—H⋯N hydrogen bonds contribute to the stability of the crystal structure. In addition, weak C—H⋯π and π–π stacking [centroid–centroid distances of 3.699 (8) and 3.699 (6) Å] interactions are observed.

Related literature

For the biological activity of 1,2,3-triazoles, see: Santana et al. (2002 ▶); Zhao et al. (2005 ▶).

Experimental

Crystal data

C₁₇H₁₄ClN₇
M _r = 351.80
Triclinic,
a = 6.1090 (7) Å
b = 8.9537 (11) Å
c = 31.292 (4) Å
α = 83.141 (1)°
β = 88.896 (1)°
γ = 75.184 (1)°
V = 1642.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 296 K
0.47 × 0.39 × 0.21 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T _min = 0.892, T _max = 0.950
12520 measured reflections
6071 independent reflections
4578 reflections with I > 2σ(I)
R _int = 0.018

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.123
S = 1.03
6071 reflections
451 parameters
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.52 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT-Plus (Bruker, 2000 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811047568/bt5710sup1.cif

e-67-o3326-sup1.cif^{(29KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811047568/bt5710Isup2.hkl

e-67-o3326-Isup2.hkl^{(297.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811047568/bt5710Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 and Cg4 are the centroids of the N2–N4/C8/C7 and C12–C17 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N14—H14A⋯N5ⁱ	0.86	2.60	3.457 (3)	173
N7—H7A⋯N12ⁱⁱ	0.86	2.53	3.389 (3)	174
C5—H5⋯N14ⁱⁱⁱ	0.93	2.58	3.506 (3)	177
C10—H10⋯N11ⁱⁱⁱ	0.93	2.42	3.240 (3)	147
C27—H27⋯N4^iv	0.93	2.36	3.191 (3)	149
C23—H23A⋯Cg4^v	0.97	2.58	3.509 (3)	160
C28—H28B⋯Cg1	0.97	2.93	3.506 (3)	120

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) .

Acknowledgments

The authors are grateful to the Hubei University of Medicine Education Committee (grant No. 2009QJ12) for financial support and acknowledge the Sophisticated Analytical Instrument Facility, Central China Normal University, Whuhan, for the data collection.

supplementary crystallographic information

Comment

Neonicotinoids are a promising class of insecticides with excellent chemical and biological properties. 1,2,3-Triazoles have also received much attention because of their wide range of applications and biological activities such as anti-HIV and antimicrobial agents (Santana et al., 2002; Zhao et al., 2005). We report here the crystal structure of (I) (Fig. 1, Table 1), which was synthesized by introducing a pyridine ring into a 1,2,3-triazolo[4,5-d]pyrimidine molecular framework.

Significant intremolecular N—H···N and intramolecular C—H···N contribute strongly to the stability of the molecular configuration (Table 1). The crystal structure (Fig. 2) is stabilized by weak intermolecular C—H···π hydrogen bonds (Table 1) and by π— π stacking interactions with centroid-centroid separations of 3.699 (8) and 3.699 (6) Å for Cg3···Cg6ⁱ and Cg6···Cg3ⁱⁱ, respectively, where Cg3 and Cg6 are the centroids of rings N5/C7—C9/N6/C10 and N9—N11/C25—C24, respectively [symmetry code: (i) X, 1+Y, Z, (ii) 3X, -1+Y, Z,].

Experimental

To a solution of ethyl N-3-((6-chloropyridin-3-yl)methyl)-5-cyano-3H- 1,2,3-triazol-4-ylformimidate (2 mmol) in anhydrous acetonitrile (15 ml) was added dropwise benzylamine (2 mmol) in anhydrous acetonitrile (6 ml) at room temperature. The mixture was stirred at room temperature until the reaction finished (monitored by thin layer chromatography),the solid was filtered and recrystallized from anhydrous acetonitrile to give the title compound(yield 83%). A colourless crystal grown from anhydrous acetonitrile was selected for X-ray structure analysis.