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Acta Crystallogr Sect E Struct Rep Online. 2009 September 1; 65(Pt 9): o2148.
Published online 2009 August 15. doi:  10.1107/S1600536809031341
PMCID: PMC2969890

6-Methyl-7,7,9-tripropargyl-7H-1,2,4-triazolo[4,3-b][1,2,4]triazepin-8(9H)-one

Abstract

The title compound, C15H13N5O, features a triazolyl ring fused with a seven-membered triazepinyl ring; the latter ring adopts a boat conformation (with the propargyl-bearing C atom as the prow and the fused-ring C/N atoms as the stern).

Related literature

Triazepines are a class of compounds used in the treatment of neuronal disorders. They are also the reacta­nts for the synthesis of other heterocyclic compounds; see, for example: Essassi et al. (1977 [triangle]); Richter & Sheefelot (1991 [triangle]).

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Object name is e-65-o2148-scheme1.jpg

Experimental

Crystal data

  • C15H13N5O
  • M r = 279.30
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2148-efi1.jpg
  • a = 7.6710 (2) Å
  • b = 8.2415 (2) Å
  • c = 12.9619 (3) Å
  • α = 108.510 (1)°
  • β = 90.659 (1)°
  • γ = 114.726 (1)°
  • V = 695.85 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 293 K
  • 0.3 × 0.3 × 0.3 mm

Data collection

  • Bruker APEX2 diffractometer
  • Absorption correction: none
  • 16879 measured reflections
  • 3187 independent reflections
  • 2577 reflections with I > 2σ(I)
  • R int = 0.026

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.129
  • S = 1.06
  • 3187 reflections
  • 191 parameters
  • H-atom parameters constrained
  • Δρmax = 0.33 e Å−3
  • Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [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: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809031341/xu2584sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809031341/xu2584Isup2.hkl

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

Acknowledgments

We thank Université Mohammed V-Agdal and the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

To a solution of 6-methyl-7H-[1,2,4]triazolo[4,3-b][1,2,4]triazepin-8(9H)-one (1 g, 6 mmol) in N,N-dimethylformamide (20 ml), potassium carbonate (1.26 g, 9 mmol), propargyl bromide (0.7 ml, 9 mmol) and a catalytic amount of tetrabutyammonium broide were added. The mixture was stirred for 12 h. After the completion of the reaction (as monitored by TLC), the solid material was removed by filtration and the solvent evaporated under vacuum. Dichloromethane (20 ml) was added and the solution filtered. The solvent was removed and the product purified by column chromatography (30% ethyl acetate/hexane) to afford colorless crystals in 15% yield; m.p. 463 K. The formulation was established by proton and carbon-13 NMR spectroscopy in DMSO-d6.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.93 to 0.97 Å) and were included in the refinement in the riding model approximation, with Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for the others.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of C15H13N5O at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C15H13N5OZ = 2
Mr = 279.30F(000) = 292
Triclinic, P1Dx = 1.333 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.6710 (2) ÅCell parameters from 6818 reflections
b = 8.2415 (2) Åθ = 2.8–32.3°
c = 12.9619 (3) ŵ = 0.09 mm1
α = 108.510 (1)°T = 293 K
β = 90.659 (1)°Block, colorless
γ = 114.726 (1)°0.3 × 0.3 × 0.3 mm
V = 695.85 (3) Å3

Data collection

Bruker APEX2 diffractometer2577 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
graphiteθmax = 27.5°, θmin = 1.7°
[var phi] and ω scansh = −9→9
16879 measured reflectionsk = −10→10
3187 independent reflectionsl = −16→16

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.0758P)2 + 0.0861P] where P = (Fo2 + 2Fc2)/3
3187 reflections(Δ/σ)max = 0.001
191 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = −0.26 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O10.30213 (18)0.47985 (14)0.37303 (8)0.0488 (3)
N10.07241 (16)−0.03916 (15)0.11746 (9)0.0346 (3)
N20.22767 (16)0.05768 (15)0.07150 (8)0.0323 (3)
N30.4030 (2)0.1070 (2)−0.05735 (10)0.0462 (3)
N40.46123 (19)0.28152 (18)0.02864 (10)0.0446 (3)
N50.35151 (17)0.38407 (15)0.19840 (9)0.0372 (3)
C10.31447 (19)0.35728 (17)0.29631 (11)0.0330 (3)
C20.28282 (18)0.16329 (17)0.30330 (10)0.0289 (3)
C30.09422 (18)0.01262 (17)0.22312 (10)0.0303 (3)
C4−0.0871 (2)−0.0827 (2)0.26582 (13)0.0475 (4)
H4A−0.1893−0.17480.20490.071*
H4B−0.12550.01140.30900.071*
H4C−0.0628−0.14610.31090.071*
C50.45567 (18)0.11327 (18)0.27425 (11)0.0317 (3)
H5A0.45020.01910.30550.038*
H5B0.44000.05600.19470.038*
C60.6465 (2)0.2779 (2)0.31450 (12)0.0412 (3)
C70.8004 (3)0.4075 (3)0.34405 (18)0.0702 (5)
H70.92330.51090.36760.084*
C80.2658 (2)0.18290 (19)0.42552 (11)0.0372 (3)
H8A0.37960.29440.47280.045*
H8B0.15250.20370.44310.045*
C90.2492 (2)0.0156 (2)0.44969 (11)0.0398 (3)
C100.2456 (2)−0.1166 (2)0.46867 (14)0.0512 (4)
H100.2427−0.22080.48360.061*
C110.2649 (2)−0.0213 (2)−0.03028 (11)0.0401 (3)
H110.1996−0.1499−0.07420.048*
C120.3531 (2)0.24704 (19)0.10322 (11)0.0343 (3)
C130.3765 (2)0.56697 (19)0.18940 (13)0.0451 (4)
H13A0.44270.67000.25930.054*
H13B0.45640.59330.13380.054*
C140.1885 (3)0.5585 (2)0.15971 (13)0.0482 (4)
C150.0358 (3)0.5466 (3)0.13320 (17)0.0655 (5)
H15−0.08530.53720.11220.079*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0733 (8)0.0385 (5)0.0407 (6)0.0331 (5)0.0150 (5)0.0102 (4)
N10.0306 (6)0.0390 (6)0.0356 (6)0.0150 (5)0.0058 (4)0.0157 (5)
N20.0347 (6)0.0390 (6)0.0276 (5)0.0190 (5)0.0069 (4)0.0138 (4)
N30.0575 (8)0.0644 (8)0.0371 (6)0.0405 (7)0.0202 (6)0.0246 (6)
N40.0528 (8)0.0531 (7)0.0458 (7)0.0315 (6)0.0235 (6)0.0285 (6)
N50.0478 (7)0.0324 (5)0.0395 (6)0.0214 (5)0.0155 (5)0.0180 (5)
C10.0355 (7)0.0307 (6)0.0346 (7)0.0165 (5)0.0079 (5)0.0114 (5)
C20.0318 (6)0.0302 (6)0.0278 (6)0.0156 (5)0.0082 (5)0.0116 (5)
C30.0293 (6)0.0325 (6)0.0341 (7)0.0158 (5)0.0069 (5)0.0152 (5)
C40.0324 (7)0.0619 (9)0.0511 (9)0.0162 (7)0.0116 (6)0.0301 (8)
C50.0315 (6)0.0366 (6)0.0311 (6)0.0180 (5)0.0071 (5)0.0132 (5)
C60.0358 (7)0.0486 (8)0.0410 (8)0.0188 (6)0.0084 (6)0.0182 (6)
C70.0408 (10)0.0661 (11)0.0781 (13)0.0050 (8)0.0039 (9)0.0197 (10)
C80.0454 (8)0.0416 (7)0.0290 (6)0.0224 (6)0.0112 (6)0.0138 (5)
C90.0400 (7)0.0508 (8)0.0310 (7)0.0195 (6)0.0083 (6)0.0183 (6)
C100.0515 (9)0.0566 (9)0.0538 (9)0.0225 (8)0.0074 (7)0.0319 (8)
C110.0478 (8)0.0517 (8)0.0295 (7)0.0313 (7)0.0066 (6)0.0129 (6)
C120.0390 (7)0.0390 (7)0.0361 (7)0.0224 (6)0.0122 (5)0.0204 (6)
C130.0548 (9)0.0323 (7)0.0539 (9)0.0186 (6)0.0167 (7)0.0236 (6)
C140.0677 (11)0.0368 (7)0.0506 (9)0.0289 (7)0.0161 (8)0.0208 (7)
C150.0762 (13)0.0636 (11)0.0728 (12)0.0435 (10)0.0109 (10)0.0274 (10)

Geometric parameters (Å, °)

O1—C11.2094 (15)C4—H4C0.9600
N1—C31.2845 (17)C5—C61.4583 (19)
N1—N21.3905 (15)C5—H5A0.9700
N2—C121.3630 (17)C5—H5B0.9700
N2—C111.3653 (17)C6—C71.165 (2)
N3—C111.293 (2)C7—H70.9300
N3—N41.3940 (18)C8—C91.4643 (19)
N4—C121.3035 (17)C8—H8A0.9700
N5—C11.3690 (17)C8—H8B0.9700
N5—C121.3874 (17)C9—C101.180 (2)
N5—C131.4808 (16)C10—H100.9300
C1—C21.5463 (16)C11—H110.9300
C2—C31.5357 (17)C13—C141.455 (2)
C2—C81.5532 (17)C13—H13A0.9700
C2—C51.5620 (17)C13—H13B0.9700
C3—C41.4957 (19)C14—C151.172 (3)
C4—H4A0.9600C15—H150.9300
C4—H4B0.9600
C3—N1—N2117.64 (11)C2—C5—H5A108.8
C12—N2—C11104.18 (11)C6—C5—H5B108.8
C12—N2—N1130.86 (11)C2—C5—H5B108.8
C11—N2—N1124.18 (11)H5A—C5—H5B107.7
C11—N3—N4107.51 (11)C7—C6—C5178.18 (18)
C12—N4—N3106.47 (12)C6—C7—H7180.0
C1—N5—C12124.97 (10)C9—C8—C2113.42 (11)
C1—N5—C13118.17 (11)C9—C8—H8A108.9
C12—N5—C13116.66 (11)C2—C8—H8A108.9
O1—C1—N5120.67 (11)C9—C8—H8B108.9
O1—C1—C2121.75 (12)C2—C8—H8B108.9
N5—C1—C2117.55 (10)H8A—C8—H8B107.7
C3—C2—C1106.03 (10)C10—C9—C8176.60 (16)
C3—C2—C8112.84 (10)C9—C10—H10180.0
C1—C2—C8105.71 (10)N3—C11—N2110.81 (13)
C3—C2—C5110.77 (10)N3—C11—H11124.6
C1—C2—C5113.58 (10)N2—C11—H11124.6
C8—C2—C5107.91 (10)N4—C12—N2111.01 (12)
N1—C3—C4113.98 (12)N4—C12—N5125.45 (12)
N1—C3—C2125.47 (11)N2—C12—N5123.34 (11)
C4—C3—C2120.51 (11)C14—C13—N5110.59 (12)
C3—C4—H4A109.5C14—C13—H13A109.5
C3—C4—H4B109.5N5—C13—H13A109.5
H4A—C4—H4B109.5C14—C13—H13B109.5
C3—C4—H4C109.5N5—C13—H13B109.5
H4A—C4—H4C109.5H13A—C13—H13B108.1
H4B—C4—H4C109.5C15—C14—C13178.00 (18)
C6—C5—C2113.64 (11)C14—C15—H15180.0
C6—C5—H5A108.8
C3—N1—N2—C12−40.63 (18)C1—C2—C5—C637.77 (15)
C3—N1—N2—C11151.13 (13)C8—C2—C5—C6−79.06 (13)
C11—N3—N4—C120.01 (16)C3—C2—C8—C968.72 (15)
C12—N5—C1—O1−174.64 (13)C1—C2—C8—C9−175.83 (11)
C13—N5—C1—O10.2 (2)C5—C2—C8—C9−53.99 (15)
C12—N5—C1—C23.4 (2)C2—C8—C9—C1072 (3)
C13—N5—C1—C2178.27 (11)N4—N3—C11—N2−0.81 (16)
O1—C1—C2—C3112.39 (14)C12—N2—C11—N31.25 (15)
N5—C1—C2—C3−65.67 (14)N1—N2—C11—N3172.10 (11)
O1—C1—C2—C8−7.63 (17)N3—N4—C12—N20.80 (15)
N5—C1—C2—C8174.31 (12)N3—N4—C12—N5−174.12 (12)
O1—C1—C2—C5−125.74 (14)C11—N2—C12—N4−1.25 (15)
N5—C1—C2—C556.20 (15)N1—N2—C12—N4−171.23 (12)
N2—N1—C3—C4173.10 (11)C11—N2—C12—N5173.80 (12)
N2—N1—C3—C2−4.67 (18)N1—N2—C12—N53.8 (2)
C1—C2—C3—N168.84 (15)C1—N5—C12—N4−148.84 (14)
C8—C2—C3—N1−175.91 (12)C13—N5—C12—N436.3 (2)
C5—C2—C3—N1−54.80 (16)C1—N5—C12—N236.8 (2)
C1—C2—C3—C4−108.79 (13)C13—N5—C12—N2−138.05 (13)
C8—C2—C3—C46.46 (16)C1—N5—C13—C14−84.87 (17)
C5—C2—C3—C4127.57 (13)C12—N5—C13—C1490.39 (15)
C3—C2—C5—C6156.96 (11)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2584).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2005). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Essassi, E. M., Lavergne, J. P. & Vialleffont, P. (1977). Tetrahedron, 33, 2807–2812.
  • Richter, P. & Sheefelot, U. (1991). Pharmazie, 46, 701–705. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.

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