6-Allyl-3-(6-chloro-3-pyridylmeth­yl)-6,7-dihydro-3H-1,2,3-triazolo[4,5-d]pyrimidin-7-imine

Pan, D.-F.; Xu, J.; Ma, J.-K.; Luo, H.; Ma, Z.

doi:10.1107/S1600536809048168

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3195

doi:10.1107/S1600536809048168

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6-Allyl-3-(6-chloro-3-pyridylmethyl)-6,7-dihydro-3H-1,2,3-triazolo[4,5-d]pyrimidin-7-imine

Dong-Feng Pan,^a Jing Xu,^b Jun-Kai Ma,^b ^* Hong Luo ^b and Zuan Ma ^b

^aDepartment of Oncology, Renmin Hospital, Yunyang Medical College, Shiyan, 442000, People's Republic of China, and ^bInstitute of Medicinal Chemistry, Yunyang Medical College, Shiyan, 442000, People's Republic of China
^*Correspondence e-mail: youtianya@126.com

(Received 12 November 2009; accepted 13 November 2009; online 25 November 2009)

The title compound, C₁₃H₁₂ClN₇, crystallizes with two independent molecules in the asymmetric unit, each with similar geometries. The dihedral angles between the triazole and pyrimidine rings are 0.45 (9) and 1.00 (10)° in the two molecules. A number of N—H⋯N hydrogen bonds co-operate with C–H⋯N contacts, forming a supramolecular array in the ab plane. C—H⋯π interactions are also present. One of the vinyl groups was found to be disordered so that the C(H)=CH₂ atoms were resolved over two positions with the major component having a site occupancy factor of 0.539 (4).

Related literature

For general background to 8-azapurine derivatives, see: Albert (1986 ). For the biological activity of 8-azapurines, see: Shiokawa et al. (1986 ); Slusarkchyk & Zahler (1989 ); Subramanian & Gerwick (1989 ); Vince & Hua (1990 ); Yamamoto et al. (1994 ).

Experimental

Crystal data

C₁₃H₁₂ClN₇
M_r = 301.75
Triclinic, $[P \overline 1]$
a = 7.2845 (7) Å
b = 13.2684 (12) Å
c = 14.7069 (14) Å
α = 87.351 (1)°
β = 81.752 (1)°
γ = 82.917 (1)°
V = 1395.4 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 296 K
0.48 × 0.46 × 0.43 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: none
10116 measured reflections
5052 independent reflections
4277 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.109
S = 1.03
5052 reflections
384 parameters
22 restraints
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N10—H10A⋯N1	0.86	2.44	3.292 (3)	173
N3—H3A⋯N8ⁱ	0.86	2.45	3.299 (2)	169
C11—H11A⋯N3	0.97	2.41	2.749 (2)	100
C19—H19⋯N11	0.93	2.59	2.909 (3)	101
C3—H3⋯N13	0.93	2.46	3.309 (2)	151
C11—H11A⋯Cg4ⁱⁱ	0.97	2.87	3.446 (2)	119
C24—H24A⋯Cg1ⁱⁱⁱ	0.97	2.99	3.851 (3)	149
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y+2, -z+1; (iii) -x+2, -y+1, -z+1. Cg4 and Cg1 are the centroids of the N4–N6/C1/C4 and N11–N13/C14/C17C4 rings, respectively.

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809048168/tk2573sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809048168/tk2573Isup2.hkl

checkCIF report

Comment top

1,2,3-Triazolo[4,5-d]pyrimidines, i.e. 8-azapurines (Albert, 1986), have attracted attention because some of these derivatives exhibit anti-viral (Slusarkchyk & Zahler, 1989), anti-tumour (Slusarkchyk & Zahler, 1989; Vince & Hua, 1990), and herbicidal activities (Subramanian & Gerwick, 1989). Neonicotinoid insecticides, as nicotinic acetylcholine receptor inhibitors, have also attracted increasing attention because of their low toxicity, wide range of activities, and high potency (Shiokawa et al., 1986). It has been found that most biologically active nicotinic compounds contain the 3-aminomethylpyridine group (Yamamoto et al., 1994). Herein, we report the crystal structure of (I), Fig. 1, which was synthesized by introducing pyridine rings into a 1,2,3-triazolo[4,5-d]pyrimidine framework.

Several N—H···N hydrogen bonding contacts, together with C—H···N and C—H···π interactions, lead to the formation of supramolecular arrays in the ab plane, Table 1 and Fig. 2. In addition π—π stacking interactions stabilize the crystal structure, with the shortest centroid-centroid distance of 3.412 (1) Å occurring between centrosymmetrically related planes through the (N4–N6, C1, C4) rings, symmetry operation: 2-x, 1-y, 1-z.

Related literature top

For general background to 8-azapurine derivatives, see: Albert (1986). For the biological activity of 8-azapurines, see: Shiokawa et al. (1986); Slusarkchyk & Zahler (1989); Subramanian & Gerwick (1989); Vince & Hua (1990); Yamamoto et al. (1994). Cg4 and Cg1 are the centroids of the N4–N6/C1/C4 and N11–N13/C14/C17C4

rings, respectively.

Experimental top

Allylamine (1 mmol) in anhydrous acetonitrile (4 ml) was added dropwise to a solution of ethyl-N-3-((6-chloropyridin-3-yl)methyl)-5-cyano-3H-1,2,3- triazol-4-yl-formimidate (1 mmol) in anhydrous acetonitrile (8 ml) at room temperature. The mixture was stirred until the reaction was complete (by thin layer chromatography) and the solution concentrated under vacuum. The residue was recrystallized from anhydrous ethanol to give (I) (yield 87%). Colourless crystals were grown from a dichloromethane and petroleum ether (1:3 v/v) solution of (I).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structures of the two independent molecules in (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. A view of a supramolecular layer in (I). Hydrogen bonds are shown as dashed lines.

6-Allyl-3-(6-chloro-3-pyridylmethyl)-6,7-dihydro-3H-1,2,3- triazolo[4,5-d]pyrimidin-7-imine top

Crystal data top

C₁₃H₁₂ClN₇	Z = 4
M_r = 301.75	F(000) = 624
Triclinic, P1	D_x = 1.436 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2845 (7) Å	Cell parameters from 5848 reflections
b = 13.2684 (12) Å	θ = 2.8–28.2°
c = 14.7069 (14) Å	µ = 0.28 mm⁻¹
α = 87.351 (1)°	T = 296 K
β = 81.752 (1)°	Block, colorless
γ = 82.917 (1)°	0.48 × 0.46 × 0.43 mm
V = 1395.4 (2) Å³

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4277 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.015
Graphite monochromator	θ_max = 25.5°, θ_min = 2.8°
ϕ and ω scans	h = −8→8
10116 measured reflections	k = −15→16
5052 independent reflections	l = −17→17

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.109	w = 1/[σ²(F_o²) + (0.0474P)² + 0.5781P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
5052 reflections	Δρ_max = 0.35 e Å⁻³
384 parameters	Δρ_min = −0.36 e Å⁻³
22 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.050 (2)

Crystal data top

C₁₃H₁₂ClN₇	γ = 82.917 (1)°
M_r = 301.75	V = 1395.4 (2) Å³
Triclinic, P1	Z = 4
a = 7.2845 (7) Å	Mo Kα radiation
b = 13.2684 (12) Å	µ = 0.28 mm⁻¹
c = 14.7069 (14) Å	T = 296 K
α = 87.351 (1)°	0.48 × 0.46 × 0.43 mm
β = 81.752 (1)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4277 reflections with I > 2σ(I)
10116 measured reflections	R_int = 0.015
5052 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	22 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 1.03	Δρ_max = 0.35 e Å⁻³
5052 reflections	Δρ_min = −0.36 e Å⁻³
384 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)
C24	0.7964 (4)	0.39425 (19)	0.67973 (16)	0.0710 (7)	0.539 (4)
H24A	0.9002	0.4288	0.6913	0.085*	0.539 (4)
H24B	0.6844	0.4265	0.7159	0.085*	0.539 (4)
C25	0.8281 (6)	0.2896 (3)	0.7111 (3)	0.0666 (9)	0.539 (4)
H25	0.9341	0.2520	0.6814	0.080*	0.539 (4)
C26	0.7319 (5)	0.2418 (3)	0.7732 (2)	0.1002 (10)	0.539 (4)
H26A	0.6239	0.2747	0.8058	0.120*	0.539 (4)
H26B	0.7692	0.1738	0.7864	0.120*	0.539 (4)
C24'	0.7964 (4)	0.39425 (19)	0.67973 (16)	0.0710 (7)	0.461 (4)
H24C	0.9279	0.3756	0.6840	0.085*	0.461 (4)
H24D	0.7600	0.4593	0.7086	0.085*	0.461 (4)
C25'	0.6943 (8)	0.3207 (4)	0.7325 (3)	0.0666 (9)	0.461 (4)
H25'	0.5659	0.3385	0.7363	0.080*	0.461 (4)
C26'	0.7319 (5)	0.2418 (3)	0.7732 (2)	0.1002 (10)	0.461 (4)
H26C	0.8561	0.2159	0.7746	0.120*	0.461 (4)
H26D	0.6368	0.2068	0.8034	0.120*	0.461 (4)
C1	0.7678 (2)	1.00162 (12)	0.51743 (12)	0.0346 (4)
C2	0.7015 (2)	1.02006 (12)	0.42960 (12)	0.0360 (4)
C3	0.7187 (3)	0.83395 (13)	0.43489 (14)	0.0448 (4)
H3	0.6996	0.7774	0.4040	0.054*
C4	0.8029 (2)	0.90450 (12)	0.55236 (12)	0.0362 (4)
C5	0.9108 (3)	0.83866 (14)	0.70333 (13)	0.0457 (4)
H5A	1.0253	0.8510	0.7252	0.055*
H5B	0.9309	0.7719	0.6768	0.055*
C6	0.5880 (3)	0.80588 (16)	0.77284 (13)	0.0493 (5)
H6	0.5802	0.7758	0.7179	0.059*
C7	0.7544 (3)	0.84151 (13)	0.78275 (12)	0.0406 (4)
C8	0.7665 (3)	0.88164 (17)	0.86595 (15)	0.0588 (5)
H8	0.8770	0.9047	0.8763	0.071*
C9	0.6143 (3)	0.88762 (18)	0.93401 (15)	0.0639 (6)
H9	0.6193	0.9140	0.9910	0.077*
C10	0.4556 (3)	0.85311 (15)	0.91408 (13)	0.0511 (5)
C11	0.6112 (3)	0.92790 (16)	0.30226 (13)	0.0484 (5)
H11A	0.5276	0.9899	0.2960	0.058*
H11B	0.5401	0.8711	0.3001	0.058*
C12	0.7634 (3)	0.9228 (2)	0.22394 (16)	0.0681 (6)
H12	0.8453	0.9719	0.2193	0.082*
C13	0.7911 (4)	0.8556 (3)	0.1618 (2)	0.1080 (12)
H13A	0.7121	0.8053	0.1641	0.130*
H13B	0.8902	0.8573	0.1144	0.130*
C14	0.7367 (2)	0.51225 (13)	0.45004 (13)	0.0407 (4)
C15	0.7607 (3)	0.51058 (14)	0.54603 (13)	0.0434 (4)
C16	0.7703 (3)	0.32703 (15)	0.52893 (15)	0.0523 (5)
H16	0.7816	0.2638	0.5589	0.063*
C17	0.7361 (2)	0.42382 (13)	0.40561 (13)	0.0398 (4)
C18	0.7094 (3)	0.39121 (15)	0.23947 (14)	0.0514 (5)
H18A	0.5996	0.4168	0.2114	0.062*
H18B	0.6960	0.3220	0.2611	0.062*
C19	1.0541 (3)	0.40537 (14)	0.18782 (14)	0.0499 (5)
H19	1.0650	0.4172	0.2486	0.060*
C20	0.8801 (3)	0.39059 (13)	0.16747 (13)	0.0440 (4)
C21	0.8673 (3)	0.37205 (16)	0.07674 (14)	0.0549 (5)
H21	0.7530	0.3618	0.0598	0.066*
C22	1.0239 (3)	0.36883 (17)	0.01182 (15)	0.0608 (6)
H22	1.0184	0.3558	−0.0493	0.073*
C23	1.1885 (3)	0.38548 (15)	0.04051 (15)	0.0546 (5)
Cl1	0.25485 (10)	0.86518 (6)	0.99613 (4)	0.0824 (2)
Cl2	1.39020 (10)	0.38267 (5)	−0.04027 (5)	0.0812 (2)
N1	0.7805 (2)	0.81572 (11)	0.51360 (11)	0.0446 (4)
N2	0.6786 (2)	0.92572 (11)	0.39244 (10)	0.0399 (3)
N3	0.6629 (2)	1.10214 (11)	0.38456 (11)	0.0450 (4)
H3A	0.6766	1.1591	0.4069	0.054*
N4	0.86503 (19)	0.91590 (10)	0.63304 (10)	0.0384 (3)
N5	0.8663 (2)	1.01637 (11)	0.64796 (10)	0.0412 (4)
N6	0.8078 (2)	1.06876 (11)	0.57735 (10)	0.0386 (3)
N7	0.4377 (2)	0.81185 (14)	0.83706 (11)	0.0541 (4)
N8	0.7516 (2)	0.32692 (11)	0.44197 (12)	0.0503 (4)
N9	0.7752 (2)	0.40853 (12)	0.58091 (11)	0.0487 (4)
N10	0.7707 (3)	0.58234 (13)	0.59890 (12)	0.0575 (5)
H10A	0.7618	0.6440	0.5777	0.069*
N11	0.7175 (2)	0.45313 (11)	0.31812 (11)	0.0451 (4)
N12	0.7058 (3)	0.55636 (12)	0.30882 (12)	0.0545 (4)
N13	0.7175 (3)	0.59204 (12)	0.38966 (12)	0.0515 (4)
N14	1.2090 (2)	0.40379 (13)	0.12549 (12)	0.0551 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C24	0.0985 (19)	0.0654 (15)	0.0573 (14)	−0.0258 (13)	−0.0265 (13)	0.0029 (11)
C25	0.065 (2)	0.079 (2)	0.0500 (19)	0.0091 (18)	−0.0045 (17)	0.0038 (16)
C26	0.150 (3)	0.093 (2)	0.0610 (17)	−0.037 (2)	−0.0126 (18)	0.0071 (16)
C24'	0.0985 (19)	0.0654 (15)	0.0573 (14)	−0.0258 (13)	−0.0265 (13)	0.0029 (11)
C25'	0.065 (2)	0.079 (2)	0.0500 (19)	0.0091 (18)	−0.0045 (17)	0.0038 (16)
C26'	0.150 (3)	0.093 (2)	0.0610 (17)	−0.037 (2)	−0.0126 (18)	0.0071 (16)
C1	0.0295 (8)	0.0307 (8)	0.0413 (9)	−0.0047 (6)	0.0045 (7)	−0.0034 (7)
C2	0.0276 (8)	0.0352 (9)	0.0432 (10)	−0.0045 (6)	0.0037 (7)	−0.0052 (7)
C3	0.0447 (10)	0.0334 (9)	0.0554 (12)	−0.0065 (7)	0.0007 (8)	−0.0110 (8)
C4	0.0312 (8)	0.0321 (8)	0.0428 (10)	−0.0045 (6)	0.0042 (7)	−0.0023 (7)
C5	0.0446 (10)	0.0416 (10)	0.0485 (11)	−0.0001 (8)	−0.0046 (8)	0.0060 (8)
C6	0.0538 (11)	0.0573 (12)	0.0388 (10)	−0.0159 (9)	−0.0041 (8)	−0.0049 (9)
C7	0.0466 (10)	0.0334 (9)	0.0414 (10)	−0.0049 (7)	−0.0070 (8)	0.0050 (7)
C8	0.0591 (13)	0.0651 (14)	0.0568 (13)	−0.0206 (10)	−0.0102 (10)	−0.0094 (10)
C9	0.0783 (15)	0.0719 (15)	0.0449 (12)	−0.0233 (12)	−0.0028 (11)	−0.0168 (10)
C10	0.0619 (12)	0.0475 (11)	0.0421 (11)	−0.0126 (9)	0.0040 (9)	0.0009 (9)
C11	0.0442 (10)	0.0509 (11)	0.0512 (11)	−0.0049 (8)	−0.0076 (8)	−0.0114 (9)
C12	0.0555 (13)	0.1005 (19)	0.0509 (13)	−0.0218 (12)	−0.0025 (10)	−0.0115 (12)
C13	0.0756 (18)	0.169 (3)	0.0780 (19)	−0.0095 (19)	0.0080 (15)	−0.055 (2)
C14	0.0416 (9)	0.0328 (9)	0.0478 (10)	−0.0046 (7)	−0.0048 (8)	−0.0076 (8)
C15	0.0442 (10)	0.0377 (9)	0.0494 (11)	−0.0077 (8)	−0.0063 (8)	−0.0065 (8)
C16	0.0639 (13)	0.0353 (10)	0.0589 (13)	−0.0094 (9)	−0.0093 (10)	−0.0001 (9)
C17	0.0397 (9)	0.0332 (9)	0.0464 (11)	−0.0049 (7)	−0.0040 (8)	−0.0070 (7)
C18	0.0596 (12)	0.0466 (11)	0.0516 (12)	−0.0104 (9)	−0.0122 (9)	−0.0133 (9)
C19	0.0639 (13)	0.0438 (11)	0.0448 (11)	−0.0080 (9)	−0.0150 (9)	−0.0042 (8)
C20	0.0581 (11)	0.0306 (9)	0.0455 (11)	−0.0040 (8)	−0.0139 (9)	−0.0054 (7)
C21	0.0660 (13)	0.0504 (12)	0.0518 (12)	−0.0074 (10)	−0.0178 (10)	−0.0096 (9)
C22	0.0794 (16)	0.0599 (13)	0.0441 (12)	−0.0061 (11)	−0.0110 (11)	−0.0102 (10)
C23	0.0660 (13)	0.0419 (11)	0.0532 (13)	−0.0013 (9)	−0.0040 (10)	0.0004 (9)
Cl1	0.0861 (5)	0.0912 (5)	0.0643 (4)	−0.0290 (4)	0.0286 (3)	−0.0165 (3)
Cl2	0.0782 (4)	0.0853 (5)	0.0717 (4)	−0.0018 (3)	0.0105 (3)	0.0013 (3)
N1	0.0481 (9)	0.0305 (8)	0.0540 (10)	−0.0051 (6)	−0.0016 (7)	−0.0038 (7)
N2	0.0381 (8)	0.0369 (8)	0.0441 (8)	−0.0049 (6)	−0.0014 (6)	−0.0074 (6)
N3	0.0471 (9)	0.0364 (8)	0.0506 (9)	−0.0031 (7)	−0.0054 (7)	−0.0007 (7)
N4	0.0371 (8)	0.0338 (7)	0.0424 (8)	−0.0049 (6)	0.0010 (6)	0.0006 (6)
N5	0.0408 (8)	0.0376 (8)	0.0442 (9)	−0.0071 (6)	0.0002 (6)	−0.0029 (7)
N6	0.0379 (8)	0.0336 (7)	0.0431 (8)	−0.0062 (6)	0.0008 (6)	−0.0028 (6)
N7	0.0555 (10)	0.0642 (11)	0.0438 (9)	−0.0203 (8)	0.0004 (8)	−0.0022 (8)
N8	0.0652 (11)	0.0330 (8)	0.0537 (10)	−0.0085 (7)	−0.0071 (8)	−0.0074 (7)
N9	0.0599 (10)	0.0410 (9)	0.0482 (9)	−0.0128 (7)	−0.0117 (8)	−0.0012 (7)
N10	0.0796 (12)	0.0424 (9)	0.0541 (10)	−0.0111 (8)	−0.0146 (9)	−0.0116 (8)
N11	0.0544 (9)	0.0351 (8)	0.0473 (9)	−0.0064 (7)	−0.0082 (7)	−0.0094 (7)
N12	0.0752 (12)	0.0367 (9)	0.0527 (10)	−0.0044 (8)	−0.0139 (9)	−0.0055 (7)
N13	0.0693 (11)	0.0337 (8)	0.0525 (10)	−0.0035 (7)	−0.0124 (8)	−0.0076 (7)
N14	0.0595 (11)	0.0495 (10)	0.0570 (11)	−0.0068 (8)	−0.0114 (9)	0.0004 (8)

Geometric parameters (Å, º) top

C24—C25	1.445 (5)	C11—H11B	0.9700
C24—N9	1.485 (3)	C12—C13	1.283 (4)
C24—H24A	0.9700	C12—H12	0.9300
C24—H24B	0.9700	C13—H13A	0.9300
C25—C26	1.265 (5)	C13—H13B	0.9300
C25—H25	0.9300	C14—N13	1.357 (2)
C26—H26A	0.9300	C14—C17	1.370 (2)
C26—H26B	0.9300	C14—C15	1.446 (3)
C25'—H25'	0.9300	C15—N10	1.272 (2)
C1—N6	1.366 (2)	C15—N9	1.423 (2)
C1—C4	1.373 (2)	C16—N8	1.305 (3)
C1—C2	1.443 (2)	C16—N9	1.360 (2)
C2—N3	1.271 (2)	C16—H16	0.9300
C2—N2	1.426 (2)	C17—N11	1.348 (2)
C3—N1	1.303 (3)	C17—N8	1.367 (2)
C3—N2	1.361 (2)	C18—N11	1.461 (2)
C3—H3	0.9300	C18—C20	1.512 (3)
C4—N4	1.350 (2)	C18—H18A	0.9700
C4—N1	1.369 (2)	C18—H18B	0.9700
C5—N4	1.465 (2)	C19—N14	1.346 (3)
C5—C7	1.509 (3)	C19—C20	1.383 (3)
C5—H5A	0.9700	C19—H19	0.9300
C5—H5B	0.9700	C20—C21	1.386 (3)
C6—N7	1.337 (3)	C21—C22	1.377 (3)
C6—C7	1.383 (3)	C21—H21	0.9300
C6—H6	0.9300	C22—C23	1.372 (3)
C7—C8	1.375 (3)	C22—H22	0.9300
C8—C9	1.380 (3)	C23—N14	1.317 (3)
C8—H8	0.9300	C23—Cl2	1.750 (2)
C9—C10	1.368 (3)	N3—H3A	0.8600
C9—H9	0.9300	N4—N5	1.362 (2)
C10—N7	1.310 (3)	N5—N6	1.315 (2)
C10—Cl1	1.753 (2)	N10—H10A	0.8600
C11—N2	1.477 (2)	N11—N12	1.364 (2)
C11—C12	1.478 (3)	N12—N13	1.318 (2)
C11—H11A	0.9700

C25—C24—N9	114.8 (2)	H13A—C13—H13B	120.0
C25—C24—H24A	108.6	N13—C14—C17	109.22 (16)
N9—C24—H24A	108.6	N13—C14—C15	129.91 (16)
C25—C24—H24B	108.6	C17—C14—C15	120.84 (16)
N9—C24—H24B	108.6	N10—C15—N9	119.50 (18)
H24A—C24—H24B	107.6	N10—C15—C14	130.94 (18)
C26—C25—C24	129.2 (4)	N9—C15—C14	109.56 (15)
C26—C25—H25	115.4	N8—C16—N9	127.79 (18)
C24—C25—H25	115.4	N8—C16—H16	116.1
C25—C26—H26A	120.0	N9—C16—H16	116.1
C25—C26—H26B	120.0	N11—C17—N8	127.49 (16)
H26A—C26—H26B	120.0	N11—C17—C14	104.94 (15)
N6—C1—C4	109.19 (15)	N8—C17—C14	127.56 (17)
N6—C1—C2	129.88 (15)	N11—C18—C20	113.36 (16)
C4—C1—C2	120.92 (15)	N11—C18—H18A	108.9
N3—C2—N2	119.22 (16)	C20—C18—H18A	108.9
N3—C2—C1	131.28 (16)	N11—C18—H18B	108.9
N2—C2—C1	109.50 (14)	C20—C18—H18B	108.9
N1—C3—N2	127.88 (17)	H18A—C18—H18B	107.7
N1—C3—H3	116.1	N14—C19—C20	124.30 (18)
N2—C3—H3	116.1	N14—C19—H19	117.8
N4—C4—N1	127.68 (16)	C20—C19—H19	117.8
N4—C4—C1	104.78 (15)	C19—C20—C21	116.96 (19)
N1—C4—C1	127.53 (17)	C19—C20—C18	122.96 (17)
N4—C5—C7	110.31 (14)	C21—C20—C18	120.06 (18)
N4—C5—H5A	109.6	C22—C21—C20	119.9 (2)
C7—C5—H5A	109.6	C22—C21—H21	120.0
N4—C5—H5B	109.6	C20—C21—H21	120.0
C7—C5—H5B	109.6	C23—C22—C21	117.6 (2)
H5A—C5—H5B	108.1	C23—C22—H22	121.2
N7—C6—C7	124.30 (18)	C21—C22—H22	121.2
N7—C6—H6	117.8	N14—C23—C22	125.2 (2)
C7—C6—H6	117.8	N14—C23—Cl2	115.96 (17)
C8—C7—C6	117.12 (18)	C22—C23—Cl2	118.84 (17)
C8—C7—C5	122.66 (18)	C3—N1—C4	110.65 (15)
C6—C7—C5	120.18 (17)	C3—N2—C2	123.51 (15)
C7—C8—C9	119.8 (2)	C3—N2—C11	118.39 (15)
C7—C8—H8	120.1	C2—N2—C11	118.09 (15)
C9—C8—H8	120.1	C2—N3—H3A	119.3
C10—C9—C8	117.16 (19)	C4—N4—N5	110.08 (14)
C10—C9—H9	121.4	C4—N4—C5	129.06 (15)
C8—C9—H9	121.4	N5—N4—C5	120.63 (15)
N7—C10—C9	125.59 (19)	N6—N5—N4	107.99 (14)
N7—C10—Cl1	115.58 (16)	N5—N6—C1	107.95 (14)
C9—C10—Cl1	118.82 (16)	C10—N7—C6	115.93 (17)
N2—C11—C12	113.26 (16)	C16—N8—C17	110.70 (16)
N2—C11—H11A	108.9	C16—N9—C15	123.52 (17)
C12—C11—H11A	108.9	C16—N9—C24	120.41 (17)
N2—C11—H11B	108.9	C15—N9—C24	116.08 (16)
C12—C11—H11B	108.9	C15—N10—H10A	119.3
H11A—C11—H11B	107.7	C17—N11—N12	109.97 (14)
C13—C12—C11	124.9 (3)	C17—N11—C18	129.37 (16)
C13—C12—H12	117.5	N12—N11—C18	120.66 (16)
C11—C12—H12	117.5	N13—N12—N11	107.63 (15)
C12—C13—H13A	120.0	N12—N13—C14	108.23 (15)
C12—C13—H13B	120.0	C23—N14—C19	116.03 (18)

N9—C24—C25—C26	−120.5 (5)	N3—C2—N2—C11	0.2 (2)
N6—C1—C2—N3	0.1 (3)	C1—C2—N2—C11	179.95 (14)
C4—C1—C2—N3	−179.05 (17)	C12—C11—N2—C3	−89.6 (2)
N6—C1—C2—N2	−179.57 (15)	C12—C11—N2—C2	89.2 (2)
C4—C1—C2—N2	1.3 (2)	N1—C4—N4—N5	−179.62 (15)
N6—C1—C4—N4	−0.42 (17)	C1—C4—N4—N5	0.66 (17)
C2—C1—C4—N4	178.88 (14)	N1—C4—N4—C5	−5.2 (3)
N6—C1—C4—N1	179.86 (15)	C1—C4—N4—C5	175.05 (15)
C2—C1—C4—N1	−0.8 (3)	C7—C5—N4—C4	−101.8 (2)
N7—C6—C7—C8	2.9 (3)	C7—C5—N4—N5	72.1 (2)
N7—C6—C7—C5	−175.14 (18)	C4—N4—N5—N6	−0.68 (18)
N4—C5—C7—C8	−105.4 (2)	C5—N4—N5—N6	−175.62 (14)
N4—C5—C7—C6	72.5 (2)	N4—N5—N6—C1	0.39 (17)
C6—C7—C8—C9	−1.9 (3)	C4—C1—N6—N5	0.02 (18)
C5—C7—C8—C9	176.1 (2)	C2—C1—N6—N5	−179.19 (15)
C7—C8—C9—C10	−0.5 (3)	C9—C10—N7—C6	−1.6 (3)
C8—C9—C10—N7	2.4 (4)	Cl1—C10—N7—C6	177.57 (15)
C8—C9—C10—Cl1	−176.73 (18)	C7—C6—N7—C10	−1.2 (3)
N2—C11—C12—C13	123.7 (3)	N9—C16—N8—C17	−0.1 (3)
N13—C14—C15—N10	−0.3 (4)	N11—C17—N8—C16	179.08 (19)
C17—C14—C15—N10	177.7 (2)	C14—C17—N8—C16	−0.8 (3)
N13—C14—C15—N9	−179.85 (18)	N8—C16—N9—C15	−0.3 (3)
C17—C14—C15—N9	−1.9 (2)	N8—C16—N9—C24	179.6 (2)
N13—C14—C17—N11	0.4 (2)	N10—C15—N9—C16	−178.4 (2)
C15—C14—C17—N11	−178.00 (16)	C14—C15—N9—C16	1.2 (3)
N13—C14—C17—N8	−179.76 (18)	N10—C15—N9—C24	1.6 (3)
C15—C14—C17—N8	1.9 (3)	C14—C15—N9—C24	−178.73 (18)
N14—C19—C20—C21	0.7 (3)	C25—C24—N9—C16	5.5 (4)
N14—C19—C20—C18	179.01 (18)	C25—C24—N9—C15	−174.5 (3)
N11—C18—C20—C19	27.4 (3)	N8—C17—N11—N12	179.79 (18)
N11—C18—C20—C21	−154.32 (18)	C14—C17—N11—N12	−0.3 (2)
C19—C20—C21—C22	0.1 (3)	N8—C17—N11—C18	−0.3 (3)
C18—C20—C21—C22	−178.26 (19)	C14—C17—N11—C18	179.60 (18)
C20—C21—C22—C23	−0.6 (3)	C20—C18—N11—C17	−110.6 (2)
C21—C22—C23—N14	0.4 (3)	C20—C18—N11—N12	69.3 (2)
C21—C22—C23—Cl2	−179.65 (16)	C17—N11—N12—N13	0.2 (2)
N2—C3—N1—C4	0.0 (3)	C18—N11—N12—N13	−179.76 (17)
N4—C4—N1—C3	−179.58 (17)	N11—N12—N13—C14	0.1 (2)
C1—C4—N1—C3	0.1 (2)	C17—C14—N13—N12	−0.3 (2)
N1—C3—N2—C2	0.6 (3)	C15—C14—N13—N12	177.90 (19)
N1—C3—N2—C11	179.45 (18)	C22—C23—N14—C19	0.3 (3)
N3—C2—N2—C3	179.06 (16)	Cl2—C23—N14—C19	−179.61 (14)
C1—C2—N2—C3	−1.2 (2)	C20—C19—N14—C23	−0.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N10—H10A···N1	0.86	2.44	3.292 (3)	173
N3—H3A···N8ⁱ	0.86	2.45	3.299 (2)	169
C11—H11A···N3	0.97	2.41	2.749 (2)	100
C19—H19···N11	0.93	2.59	2.909 (3)	101
C3—H3···N13	0.93	2.46	3.309 (2)	151
C11—H11A···Cg4ⁱⁱ	0.97	2.87	3.446 (2)	119
C24—H24A···Cg1ⁱⁱⁱ	0.97	2.99	3.851 (3)	149

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

Experimental details

Crystal data
Chemical formula	C₁₃H₁₂ClN₇
M_r	301.75
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.2845 (7), 13.2684 (12), 14.7069 (14)
α, β, γ (°)	87.351 (1), 81.752 (1), 82.917 (1)
V (Å³)	1395.4 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.48 × 0.46 × 0.43

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10116, 5052, 4277
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.109, 1.03
No. of reflections	5052
No. of parameters	384
No. of restraints	22
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.36

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N10—H10A···N1	0.86	2.44	3.292 (3)	173
N3—H3A···N8ⁱ	0.86	2.45	3.299 (2)	169.0
C11—H11A···N3	0.97	2.41	2.749 (2)	100
C19—H19···N11	0.93	2.59	2.909 (3)	101
C3—H3···N13	0.93	2.46	3.309 (2)	151
C11—H11A···Cg4ⁱⁱ	0.97	2.87	3.446 (2)	119
C24—H24A···Cg1ⁱⁱⁱ	0.97	2.99	3.851 (3)	149

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

Acknowledgements

The authors gratefully acknowledge financial support of this work by Yunyang Medical College (grant No. 2007ZQB24).

References

Albert, A. (1986). Adv. Heterocycl. Chem. 39, 117–180. CrossRef CAS Web of Science Google Scholar
Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shiokawa, K., Tsubo, S. & Moriya, K. (1986). EP Patent 192 060. Google Scholar
Slusarkchyk, W. A. & Zahler, R. (1989). EP Patent 335–355. Google Scholar
Subramanian, M. V. & Gerwick, B. C. (1989). Inhibition of Acetolacetate Synthase by Triazolopyrimidines, in Biocatalysis in Agricultural Biotechnology, edited by J. R. Whitaker & P. E. Sonnet. ACS Symposium Series No. 389, pp. 277–288. Washington, DC, USA: American Chemical Society. Google Scholar
Vince, R. & Hua, M. (1990). US Patent 4 931 559. Google Scholar
Yamamoto, I., Yabita, G., Tomizawa, M. & Hissasomi, A. (1994). J. Pestic. Sci. 19, 335–339. Google Scholar

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Volume 65| Part 12| December 2009| Page o3195

doi:10.1107/S1600536809048168

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

6-Allyl-3-(6-chloro-3-pyridylmeth­yl)-6,7-di­hydro-3H-1,2,3-triazolo[4,5-d]pyrimidin-7-imine

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

6-Allyl-3-(6-chloro-3-pyridylmethyl)-6,7-dihydro-3H-1,2,3-triazolo[4,5-d]pyrimidin-7-imine