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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o3195.
Published online 2009 November 25. doi:  10.1107/S1600536809048168
PMCID: PMC2971826

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

Abstract

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 [triangle]). For the biological activity of 8-aza­purines, see: Shiokawa et al. (1986 [triangle]); Slusarkchyk & Zahler (1989 [triangle]); Subramanian & Gerwick (1989 [triangle]); Vince & Hua (1990 [triangle]); Yamamoto et al. (1994 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o3195-scheme1.jpg

Experimental

Crystal data

  • C13H12ClN7
  • M r = 301.75
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o3195-efi1.jpg
  • 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[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.109
  • S = 1.03
  • 5052 reflections
  • 384 parameters
  • 22 restraints
  • H-atom parameters constrained
  • Δρmax = 0.35 e Å−3
  • Δρmin = −0.36 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

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

Acknowledgments

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

supplementary crystallographic information

Comment

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.

Experimental

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).

Refinement

H atoms were placed in calculated positions, with C—H distances in the range 0.93–0.97 Å and N—H distances of 0.86 Å, and included in the final cycles of refinement using a riding-model approximation, with Uiso(H) = 1.2–1.5Ueq(carrier atom). A rotating group model was used for the methyl groups. Disorder was noted in the C24-C26 vinyl substituent in that two positions were resolved for the C25 atom. From refinement, the major component had a site occupancy factor = 0.539 (4).

Figures

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.

Crystal data

C13H12ClN7Z = 4
Mr = 301.75F(000) = 624
Triclinic, P1Dx = 1.436 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.2845 (7) ÅCell parameters from 5848 reflections
b = 13.2684 (12) Åθ = 2.8–28.2°
c = 14.7069 (14) ŵ = 0.28 mm1
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

Bruker SMART APEX CCD area-detector diffractometer4277 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.015
graphiteθmax = 25.5°, θmin = 2.8°
[var phi] and ω scansh = −8→8
10116 measured reflectionsk = −15→16
5052 independent reflectionsl = −17→17

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.109w = 1/[σ2(Fo2) + (0.0474P)2 + 0.5781P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
5052 reflectionsΔρmax = 0.35 e Å3
384 parametersΔρmin = −0.36 e Å3
22 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.050 (2)

Special details

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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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 andgoodness of fit S are based on F2, conventional R-factors R are basedon F, with F set to zero for negative F2. The threshold expression ofF2 > σ(F2) is used only for calculating R-factors(gt) etc. and isnot relevant to the choice of reflections for refinement. R-factors basedon 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)

xyzUiso*/UeqOcc. (<1)
C240.7964 (4)0.39425 (19)0.67973 (16)0.0710 (7)0.539 (4)
H24A0.90020.42880.69130.085*0.539 (4)
H24B0.68440.42650.71590.085*0.539 (4)
C250.8281 (6)0.2896 (3)0.7111 (3)0.0666 (9)0.539 (4)
H250.93410.25200.68140.080*0.539 (4)
C260.7319 (5)0.2418 (3)0.7732 (2)0.1002 (10)0.539 (4)
H26A0.62390.27470.80580.120*0.539 (4)
H26B0.76920.17380.78640.120*0.539 (4)
C24'0.7964 (4)0.39425 (19)0.67973 (16)0.0710 (7)0.461 (4)
H24C0.92790.37560.68400.085*0.461 (4)
H24D0.76000.45930.70860.085*0.461 (4)
C25'0.6943 (8)0.3207 (4)0.7325 (3)0.0666 (9)0.461 (4)
H25'0.56590.33850.73630.080*0.461 (4)
C26'0.7319 (5)0.2418 (3)0.7732 (2)0.1002 (10)0.461 (4)
H26C0.85610.21590.77460.120*0.461 (4)
H26D0.63680.20680.80340.120*0.461 (4)
C10.7678 (2)1.00162 (12)0.51743 (12)0.0346 (4)
C20.7015 (2)1.02006 (12)0.42960 (12)0.0360 (4)
C30.7187 (3)0.83395 (13)0.43489 (14)0.0448 (4)
H30.69960.77740.40400.054*
C40.8029 (2)0.90450 (12)0.55236 (12)0.0362 (4)
C50.9108 (3)0.83866 (14)0.70333 (13)0.0457 (4)
H5A1.02530.85100.72520.055*
H5B0.93090.77190.67680.055*
C60.5880 (3)0.80588 (16)0.77284 (13)0.0493 (5)
H60.58020.77580.71790.059*
C70.7544 (3)0.84151 (13)0.78275 (12)0.0406 (4)
C80.7665 (3)0.88164 (17)0.86595 (15)0.0588 (5)
H80.87700.90470.87630.071*
C90.6143 (3)0.88762 (18)0.93401 (15)0.0639 (6)
H90.61930.91400.99100.077*
C100.4556 (3)0.85311 (15)0.91408 (13)0.0511 (5)
C110.6112 (3)0.92790 (16)0.30226 (13)0.0484 (5)
H11A0.52760.98990.29600.058*
H11B0.54010.87110.30010.058*
C120.7634 (3)0.9228 (2)0.22394 (16)0.0681 (6)
H120.84530.97190.21930.082*
C130.7911 (4)0.8556 (3)0.1618 (2)0.1080 (12)
H13A0.71210.80530.16410.130*
H13B0.89020.85730.11440.130*
C140.7367 (2)0.51225 (13)0.45004 (13)0.0407 (4)
C150.7607 (3)0.51058 (14)0.54603 (13)0.0434 (4)
C160.7703 (3)0.32703 (15)0.52893 (15)0.0523 (5)
H160.78160.26380.55890.063*
C170.7361 (2)0.42382 (13)0.40561 (13)0.0398 (4)
C180.7094 (3)0.39121 (15)0.23947 (14)0.0514 (5)
H18A0.59960.41680.21140.062*
H18B0.69600.32200.26110.062*
C191.0541 (3)0.40537 (14)0.18782 (14)0.0499 (5)
H191.06500.41720.24860.060*
C200.8801 (3)0.39059 (13)0.16747 (13)0.0440 (4)
C210.8673 (3)0.37205 (16)0.07674 (14)0.0549 (5)
H210.75300.36180.05980.066*
C221.0239 (3)0.36883 (17)0.01182 (15)0.0608 (6)
H221.01840.3558−0.04930.073*
C231.1885 (3)0.38548 (15)0.04051 (15)0.0546 (5)
Cl10.25485 (10)0.86518 (6)0.99613 (4)0.0824 (2)
Cl21.39020 (10)0.38267 (5)−0.04027 (5)0.0812 (2)
N10.7805 (2)0.81572 (11)0.51360 (11)0.0446 (4)
N20.6786 (2)0.92572 (11)0.39244 (10)0.0399 (3)
N30.6629 (2)1.10214 (11)0.38456 (11)0.0450 (4)
H3A0.67661.15910.40690.054*
N40.86503 (19)0.91590 (10)0.63304 (10)0.0384 (3)
N50.8663 (2)1.01637 (11)0.64796 (10)0.0412 (4)
N60.8078 (2)1.06876 (11)0.57735 (10)0.0386 (3)
N70.4377 (2)0.81185 (14)0.83706 (11)0.0541 (4)
N80.7516 (2)0.32692 (11)0.44197 (12)0.0503 (4)
N90.7752 (2)0.40853 (12)0.58091 (11)0.0487 (4)
N100.7707 (3)0.58234 (13)0.59890 (12)0.0575 (5)
H10A0.76180.64400.57770.069*
N110.7175 (2)0.45313 (11)0.31812 (11)0.0451 (4)
N120.7058 (3)0.55636 (12)0.30882 (12)0.0545 (4)
N130.7175 (3)0.59204 (12)0.38966 (12)0.0515 (4)
N141.2090 (2)0.40379 (13)0.12549 (12)0.0551 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C240.0985 (19)0.0654 (15)0.0573 (14)−0.0258 (13)−0.0265 (13)0.0029 (11)
C250.065 (2)0.079 (2)0.0500 (19)0.0091 (18)−0.0045 (17)0.0038 (16)
C260.150 (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)
C10.0295 (8)0.0307 (8)0.0413 (9)−0.0047 (6)0.0045 (7)−0.0034 (7)
C20.0276 (8)0.0352 (9)0.0432 (10)−0.0045 (6)0.0037 (7)−0.0052 (7)
C30.0447 (10)0.0334 (9)0.0554 (12)−0.0065 (7)0.0007 (8)−0.0110 (8)
C40.0312 (8)0.0321 (8)0.0428 (10)−0.0045 (6)0.0042 (7)−0.0023 (7)
C50.0446 (10)0.0416 (10)0.0485 (11)−0.0001 (8)−0.0046 (8)0.0060 (8)
C60.0538 (11)0.0573 (12)0.0388 (10)−0.0159 (9)−0.0041 (8)−0.0049 (9)
C70.0466 (10)0.0334 (9)0.0414 (10)−0.0049 (7)−0.0070 (8)0.0050 (7)
C80.0591 (13)0.0651 (14)0.0568 (13)−0.0206 (10)−0.0102 (10)−0.0094 (10)
C90.0783 (15)0.0719 (15)0.0449 (12)−0.0233 (12)−0.0028 (11)−0.0168 (10)
C100.0619 (12)0.0475 (11)0.0421 (11)−0.0126 (9)0.0040 (9)0.0009 (9)
C110.0442 (10)0.0509 (11)0.0512 (11)−0.0049 (8)−0.0076 (8)−0.0114 (9)
C120.0555 (13)0.1005 (19)0.0509 (13)−0.0218 (12)−0.0025 (10)−0.0115 (12)
C130.0756 (18)0.169 (3)0.0780 (19)−0.0095 (19)0.0080 (15)−0.055 (2)
C140.0416 (9)0.0328 (9)0.0478 (10)−0.0046 (7)−0.0048 (8)−0.0076 (8)
C150.0442 (10)0.0377 (9)0.0494 (11)−0.0077 (8)−0.0063 (8)−0.0065 (8)
C160.0639 (13)0.0353 (10)0.0589 (13)−0.0094 (9)−0.0093 (10)−0.0001 (9)
C170.0397 (9)0.0332 (9)0.0464 (11)−0.0049 (7)−0.0040 (8)−0.0070 (7)
C180.0596 (12)0.0466 (11)0.0516 (12)−0.0104 (9)−0.0122 (9)−0.0133 (9)
C190.0639 (13)0.0438 (11)0.0448 (11)−0.0080 (9)−0.0150 (9)−0.0042 (8)
C200.0581 (11)0.0306 (9)0.0455 (11)−0.0040 (8)−0.0139 (9)−0.0054 (7)
C210.0660 (13)0.0504 (12)0.0518 (12)−0.0074 (10)−0.0178 (10)−0.0096 (9)
C220.0794 (16)0.0599 (13)0.0441 (12)−0.0061 (11)−0.0110 (11)−0.0102 (10)
C230.0660 (13)0.0419 (11)0.0532 (13)−0.0013 (9)−0.0040 (10)0.0004 (9)
Cl10.0861 (5)0.0912 (5)0.0643 (4)−0.0290 (4)0.0286 (3)−0.0165 (3)
Cl20.0782 (4)0.0853 (5)0.0717 (4)−0.0018 (3)0.0105 (3)0.0013 (3)
N10.0481 (9)0.0305 (8)0.0540 (10)−0.0051 (6)−0.0016 (7)−0.0038 (7)
N20.0381 (8)0.0369 (8)0.0441 (8)−0.0049 (6)−0.0014 (6)−0.0074 (6)
N30.0471 (9)0.0364 (8)0.0506 (9)−0.0031 (7)−0.0054 (7)−0.0007 (7)
N40.0371 (8)0.0338 (7)0.0424 (8)−0.0049 (6)0.0010 (6)0.0006 (6)
N50.0408 (8)0.0376 (8)0.0442 (9)−0.0071 (6)0.0002 (6)−0.0029 (7)
N60.0379 (8)0.0336 (7)0.0431 (8)−0.0062 (6)0.0008 (6)−0.0028 (6)
N70.0555 (10)0.0642 (11)0.0438 (9)−0.0203 (8)0.0004 (8)−0.0022 (8)
N80.0652 (11)0.0330 (8)0.0537 (10)−0.0085 (7)−0.0071 (8)−0.0074 (7)
N90.0599 (10)0.0410 (9)0.0482 (9)−0.0128 (7)−0.0117 (8)−0.0012 (7)
N100.0796 (12)0.0424 (9)0.0541 (10)−0.0111 (8)−0.0146 (9)−0.0116 (8)
N110.0544 (9)0.0351 (8)0.0473 (9)−0.0064 (7)−0.0082 (7)−0.0094 (7)
N120.0752 (12)0.0367 (9)0.0527 (10)−0.0044 (8)−0.0139 (9)−0.0055 (7)
N130.0693 (11)0.0337 (8)0.0525 (10)−0.0035 (7)−0.0124 (8)−0.0076 (7)
N140.0595 (11)0.0495 (10)0.0570 (11)−0.0068 (8)−0.0114 (9)0.0004 (8)

Geometric parameters (Å, °)

C24—C251.445 (5)C11—H11B0.9700
C24—N91.485 (3)C12—C131.283 (4)
C24—H24A0.9700C12—H120.9300
C24—H24B0.9700C13—H13A0.9300
C25—C261.265 (5)C13—H13B0.9300
C25—H250.9300C14—N131.357 (2)
C26—H26A0.9300C14—C171.370 (2)
C26—H26B0.9300C14—C151.446 (3)
C25'—H25'0.9300C15—N101.272 (2)
C1—N61.366 (2)C15—N91.423 (2)
C1—C41.373 (2)C16—N81.305 (3)
C1—C21.443 (2)C16—N91.360 (2)
C2—N31.271 (2)C16—H160.9300
C2—N21.426 (2)C17—N111.348 (2)
C3—N11.303 (3)C17—N81.367 (2)
C3—N21.361 (2)C18—N111.461 (2)
C3—H30.9300C18—C201.512 (3)
C4—N41.350 (2)C18—H18A0.9700
C4—N11.369 (2)C18—H18B0.9700
C5—N41.465 (2)C19—N141.346 (3)
C5—C71.509 (3)C19—C201.383 (3)
C5—H5A0.9700C19—H190.9300
C5—H5B0.9700C20—C211.386 (3)
C6—N71.337 (3)C21—C221.377 (3)
C6—C71.383 (3)C21—H210.9300
C6—H60.9300C22—C231.372 (3)
C7—C81.375 (3)C22—H220.9300
C8—C91.380 (3)C23—N141.317 (3)
C8—H80.9300C23—Cl21.750 (2)
C9—C101.368 (3)N3—H3A0.8600
C9—H90.9300N4—N51.362 (2)
C10—N71.310 (3)N5—N61.315 (2)
C10—Cl11.753 (2)N10—H10A0.8600
C11—N21.477 (2)N11—N121.364 (2)
C11—C121.478 (3)N12—N131.318 (2)
C11—H11A0.9700
C25—C24—N9114.8 (2)H13A—C13—H13B120.0
C25—C24—H24A108.6N13—C14—C17109.22 (16)
N9—C24—H24A108.6N13—C14—C15129.91 (16)
C25—C24—H24B108.6C17—C14—C15120.84 (16)
N9—C24—H24B108.6N10—C15—N9119.50 (18)
H24A—C24—H24B107.6N10—C15—C14130.94 (18)
C26—C25—C24129.2 (4)N9—C15—C14109.56 (15)
C26—C25—H25115.4N8—C16—N9127.79 (18)
C24—C25—H25115.4N8—C16—H16116.1
C25—C26—H26A120.0N9—C16—H16116.1
C25—C26—H26B120.0N11—C17—N8127.49 (16)
H26A—C26—H26B120.0N11—C17—C14104.94 (15)
N6—C1—C4109.19 (15)N8—C17—C14127.56 (17)
N6—C1—C2129.88 (15)N11—C18—C20113.36 (16)
C4—C1—C2120.92 (15)N11—C18—H18A108.9
N3—C2—N2119.22 (16)C20—C18—H18A108.9
N3—C2—C1131.28 (16)N11—C18—H18B108.9
N2—C2—C1109.50 (14)C20—C18—H18B108.9
N1—C3—N2127.88 (17)H18A—C18—H18B107.7
N1—C3—H3116.1N14—C19—C20124.30 (18)
N2—C3—H3116.1N14—C19—H19117.8
N4—C4—N1127.68 (16)C20—C19—H19117.8
N4—C4—C1104.78 (15)C19—C20—C21116.96 (19)
N1—C4—C1127.53 (17)C19—C20—C18122.96 (17)
N4—C5—C7110.31 (14)C21—C20—C18120.06 (18)
N4—C5—H5A109.6C22—C21—C20119.9 (2)
C7—C5—H5A109.6C22—C21—H21120.0
N4—C5—H5B109.6C20—C21—H21120.0
C7—C5—H5B109.6C23—C22—C21117.6 (2)
H5A—C5—H5B108.1C23—C22—H22121.2
N7—C6—C7124.30 (18)C21—C22—H22121.2
N7—C6—H6117.8N14—C23—C22125.2 (2)
C7—C6—H6117.8N14—C23—Cl2115.96 (17)
C8—C7—C6117.12 (18)C22—C23—Cl2118.84 (17)
C8—C7—C5122.66 (18)C3—N1—C4110.65 (15)
C6—C7—C5120.18 (17)C3—N2—C2123.51 (15)
C7—C8—C9119.8 (2)C3—N2—C11118.39 (15)
C7—C8—H8120.1C2—N2—C11118.09 (15)
C9—C8—H8120.1C2—N3—H3A119.3
C10—C9—C8117.16 (19)C4—N4—N5110.08 (14)
C10—C9—H9121.4C4—N4—C5129.06 (15)
C8—C9—H9121.4N5—N4—C5120.63 (15)
N7—C10—C9125.59 (19)N6—N5—N4107.99 (14)
N7—C10—Cl1115.58 (16)N5—N6—C1107.95 (14)
C9—C10—Cl1118.82 (16)C10—N7—C6115.93 (17)
N2—C11—C12113.26 (16)C16—N8—C17110.70 (16)
N2—C11—H11A108.9C16—N9—C15123.52 (17)
C12—C11—H11A108.9C16—N9—C24120.41 (17)
N2—C11—H11B108.9C15—N9—C24116.08 (16)
C12—C11—H11B108.9C15—N10—H10A119.3
H11A—C11—H11B107.7C17—N11—N12109.97 (14)
C13—C12—C11124.9 (3)C17—N11—C18129.37 (16)
C13—C12—H12117.5N12—N11—C18120.66 (16)
C11—C12—H12117.5N13—N12—N11107.63 (15)
C12—C13—H13A120.0N12—N13—C14108.23 (15)
C12—C13—H13B120.0C23—N14—C19116.03 (18)
N9—C24—C25—C26−120.5 (5)N3—C2—N2—C110.2 (2)
N6—C1—C2—N30.1 (3)C1—C2—N2—C11179.95 (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—C289.2 (2)
C4—C1—C2—N21.3 (2)N1—C4—N4—N5−179.62 (15)
N6—C1—C4—N4−0.42 (17)C1—C4—N4—N50.66 (17)
C2—C1—C4—N4178.88 (14)N1—C4—N4—C5−5.2 (3)
N6—C1—C4—N1179.86 (15)C1—C4—N4—C5175.05 (15)
C2—C1—C4—N1−0.8 (3)C7—C5—N4—C4−101.8 (2)
N7—C6—C7—C82.9 (3)C7—C5—N4—N572.1 (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—C672.5 (2)N4—N5—N6—C10.39 (17)
C6—C7—C8—C9−1.9 (3)C4—C1—N6—N50.02 (18)
C5—C7—C8—C9176.1 (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—N72.4 (4)Cl1—C10—N7—C6177.57 (15)
C8—C9—C10—Cl1−176.73 (18)C7—C6—N7—C10−1.2 (3)
N2—C11—C12—C13123.7 (3)N9—C16—N8—C17−0.1 (3)
N13—C14—C15—N10−0.3 (4)N11—C17—N8—C16179.08 (19)
C17—C14—C15—N10177.7 (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—C24179.6 (2)
N13—C14—C17—N110.4 (2)N10—C15—N9—C16−178.4 (2)
C15—C14—C17—N11−178.00 (16)C14—C15—N9—C161.2 (3)
N13—C14—C17—N8−179.76 (18)N10—C15—N9—C241.6 (3)
C15—C14—C17—N81.9 (3)C14—C15—N9—C24−178.73 (18)
N14—C19—C20—C210.7 (3)C25—C24—N9—C165.5 (4)
N14—C19—C20—C18179.01 (18)C25—C24—N9—C15−174.5 (3)
N11—C18—C20—C1927.4 (3)N8—C17—N11—N12179.79 (18)
N11—C18—C20—C21−154.32 (18)C14—C17—N11—N12−0.3 (2)
C19—C20—C21—C220.1 (3)N8—C17—N11—C18−0.3 (3)
C18—C20—C21—C22−178.26 (19)C14—C17—N11—C18179.60 (18)
C20—C21—C22—C23−0.6 (3)C20—C18—N11—C17−110.6 (2)
C21—C22—C23—N140.4 (3)C20—C18—N11—N1269.3 (2)
C21—C22—C23—Cl2−179.65 (16)C17—N11—N12—N130.2 (2)
N2—C3—N1—C40.0 (3)C18—N11—N12—N13−179.76 (17)
N4—C4—N1—C3−179.58 (17)N11—N12—N13—C140.1 (2)
C1—C4—N1—C30.1 (2)C17—C14—N13—N12−0.3 (2)
N1—C3—N2—C20.6 (3)C15—C14—N13—N12177.90 (19)
N1—C3—N2—C11179.45 (18)C22—C23—N14—C190.3 (3)
N3—C2—N2—C3179.06 (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, °)

D—H···AD—HH···AD···AD—H···A
N10—H10A···N10.862.443.292 (3)173
N3—H3A···N8i0.862.453.299 (2)169
C11—H11A···N30.972.412.749 (2)100
C19—H19···N110.932.592.909 (3)101
C3—H3···N130.932.463.309 (2)151
C11—H11A···Cg4ii0.972.873.446 (2)119
C24—H24A···Cg1iii0.972.993.851 (3)149

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2573).

References

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  • 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.
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