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

The title compound, C(15)H(13)N(5)O, 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 ▶); Richter & Sheefelot (1991 ▶).

Experimental

Crystal data

C15H13N5O

M = 279.30

Triclinic,

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 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

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

C15H13N5O	Z = 2
Mr = 279.30	F(000) = 292
Triclinic, P1	Dx = 1.333 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6710 (2) Å	Cell parameters from 6818 reflections
b = 8.2415 (2) Å	θ = 2.8–32.3°
c = 12.9619 (3) Å	µ = 0.09 mm−1
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

Bruker APEX2 diffractometer	2577 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
graphite	θmax = 27.5°, θmin = 1.7°
φ and ω scans	h = −9→9
16879 measured reflections	k = −10→10
3187 independent reflections	l = −16→16

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0758P)2 + 0.0861P] where P = (Fo2 + 2Fc2)/3
3187 reflections	(Δ/σ)max = 0.001
191 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.30213 (18)	0.47985 (14)	0.37303 (8)	0.0488 (3)
N1	0.07241 (16)	−0.03916 (15)	0.11746 (9)	0.0346 (3)
N2	0.22767 (16)	0.05768 (15)	0.07150 (8)	0.0323 (3)
N3	0.4030 (2)	0.1070 (2)	−0.05735 (10)	0.0462 (3)
N4	0.46123 (19)	0.28152 (18)	0.02864 (10)	0.0446 (3)
N5	0.35151 (17)	0.38407 (15)	0.19840 (9)	0.0372 (3)
C1	0.31447 (19)	0.35728 (17)	0.29631 (11)	0.0330 (3)
C2	0.28282 (18)	0.16329 (17)	0.30330 (10)	0.0289 (3)
C3	0.09422 (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	−0.1748	0.2049	0.071*
H4B	−0.1255	0.0114	0.3090	0.071*
H4C	−0.0628	−0.1461	0.3109	0.071*
C5	0.45567 (18)	0.11327 (18)	0.27425 (11)	0.0317 (3)
H5A	0.4502	0.0191	0.3055	0.038*
H5B	0.4400	0.0560	0.1947	0.038*
C6	0.6465 (2)	0.2779 (2)	0.31450 (12)	0.0412 (3)
C7	0.8004 (3)	0.4075 (3)	0.34405 (18)	0.0702 (5)
H7	0.9233	0.5109	0.3676	0.084*
C8	0.2658 (2)	0.18290 (19)	0.42552 (11)	0.0372 (3)
H8A	0.3796	0.2944	0.4728	0.045*
H8B	0.1525	0.2037	0.4431	0.045*
C9	0.2492 (2)	0.0156 (2)	0.44969 (11)	0.0398 (3)
C10	0.2456 (2)	−0.1166 (2)	0.46867 (14)	0.0512 (4)
H10	0.2427	−0.2208	0.4836	0.061*
C11	0.2649 (2)	−0.0213 (2)	−0.03028 (11)	0.0401 (3)
H11	0.1996	−0.1499	−0.0742	0.048*
C12	0.3531 (2)	0.24704 (19)	0.10322 (11)	0.0343 (3)
C13	0.3765 (2)	0.56697 (19)	0.18940 (13)	0.0451 (4)
H13A	0.4427	0.6700	0.2593	0.054*
H13B	0.4564	0.5933	0.1338	0.054*
C14	0.1885 (3)	0.5585 (2)	0.15971 (13)	0.0482 (4)
C15	0.0358 (3)	0.5466 (3)	0.13320 (17)	0.0655 (5)
H15	−0.0853	0.5372	0.1122	0.079*

	U11	U22	U33	U12	U13	U23
O1	0.0733 (8)	0.0385 (5)	0.0407 (6)	0.0331 (5)	0.0150 (5)	0.0102 (4)
N1	0.0306 (6)	0.0390 (6)	0.0356 (6)	0.0150 (5)	0.0058 (4)	0.0157 (5)
N2	0.0347 (6)	0.0390 (6)	0.0276 (5)	0.0190 (5)	0.0069 (4)	0.0138 (4)
N3	0.0575 (8)	0.0644 (8)	0.0371 (6)	0.0405 (7)	0.0202 (6)	0.0246 (6)
N4	0.0528 (8)	0.0531 (7)	0.0458 (7)	0.0315 (6)	0.0235 (6)	0.0285 (6)
N5	0.0478 (7)	0.0324 (5)	0.0395 (6)	0.0214 (5)	0.0155 (5)	0.0180 (5)
C1	0.0355 (7)	0.0307 (6)	0.0346 (7)	0.0165 (5)	0.0079 (5)	0.0114 (5)
C2	0.0318 (6)	0.0302 (6)	0.0278 (6)	0.0156 (5)	0.0082 (5)	0.0116 (5)
C3	0.0293 (6)	0.0325 (6)	0.0341 (7)	0.0158 (5)	0.0069 (5)	0.0152 (5)
C4	0.0324 (7)	0.0619 (9)	0.0511 (9)	0.0162 (7)	0.0116 (6)	0.0301 (8)
C5	0.0315 (6)	0.0366 (6)	0.0311 (6)	0.0180 (5)	0.0071 (5)	0.0132 (5)
C6	0.0358 (7)	0.0486 (8)	0.0410 (8)	0.0188 (6)	0.0084 (6)	0.0182 (6)
C7	0.0408 (10)	0.0661 (11)	0.0781 (13)	0.0050 (8)	0.0039 (9)	0.0197 (10)
C8	0.0454 (8)	0.0416 (7)	0.0290 (6)	0.0224 (6)	0.0112 (6)	0.0138 (5)
C9	0.0400 (7)	0.0508 (8)	0.0310 (7)	0.0195 (6)	0.0083 (6)	0.0183 (6)
C10	0.0515 (9)	0.0566 (9)	0.0538 (9)	0.0225 (8)	0.0074 (7)	0.0319 (8)
C11	0.0478 (8)	0.0517 (8)	0.0295 (7)	0.0313 (7)	0.0066 (6)	0.0129 (6)
C12	0.0390 (7)	0.0390 (7)	0.0361 (7)	0.0224 (6)	0.0122 (5)	0.0204 (6)
C13	0.0548 (9)	0.0323 (7)	0.0539 (9)	0.0186 (6)	0.0167 (7)	0.0236 (6)
C14	0.0677 (11)	0.0368 (7)	0.0506 (9)	0.0289 (7)	0.0161 (8)	0.0208 (7)
C15	0.0762 (13)	0.0636 (11)	0.0728 (12)	0.0435 (10)	0.0109 (10)	0.0274 (10)

O1—C1	1.2094 (15)	C4—H4C	0.9600
N1—C3	1.2845 (17)	C5—C6	1.4583 (19)
N1—N2	1.3905 (15)	C5—H5A	0.9700
N2—C12	1.3630 (17)	C5—H5B	0.9700
N2—C11	1.3653 (17)	C6—C7	1.165 (2)
N3—C11	1.293 (2)	C7—H7	0.9300
N3—N4	1.3940 (18)	C8—C9	1.4643 (19)
N4—C12	1.3035 (17)	C8—H8A	0.9700
N5—C1	1.3690 (17)	C8—H8B	0.9700
N5—C12	1.3874 (17)	C9—C10	1.180 (2)
N5—C13	1.4808 (16)	C10—H10	0.9300
C1—C2	1.5463 (16)	C11—H11	0.9300
C2—C3	1.5357 (17)	C13—C14	1.455 (2)
C2—C8	1.5532 (17)	C13—H13A	0.9700
C2—C5	1.5620 (17)	C13—H13B	0.9700
C3—C4	1.4957 (19)	C14—C15	1.172 (3)
C4—H4A	0.9600	C15—H15	0.9300
C4—H4B	0.9600
C3—N1—N2	117.64 (11)	C2—C5—H5A	108.8
C12—N2—C11	104.18 (11)	C6—C5—H5B	108.8
C12—N2—N1	130.86 (11)	C2—C5—H5B	108.8
C11—N2—N1	124.18 (11)	H5A—C5—H5B	107.7
C11—N3—N4	107.51 (11)	C7—C6—C5	178.18 (18)
C12—N4—N3	106.47 (12)	C6—C7—H7	180.0
C1—N5—C12	124.97 (10)	C9—C8—C2	113.42 (11)
C1—N5—C13	118.17 (11)	C9—C8—H8A	108.9
C12—N5—C13	116.66 (11)	C2—C8—H8A	108.9
O1—C1—N5	120.67 (11)	C9—C8—H8B	108.9
O1—C1—C2	121.75 (12)	C2—C8—H8B	108.9
N5—C1—C2	117.55 (10)	H8A—C8—H8B	107.7
C3—C2—C1	106.03 (10)	C10—C9—C8	176.60 (16)
C3—C2—C8	112.84 (10)	C9—C10—H10	180.0
C1—C2—C8	105.71 (10)	N3—C11—N2	110.81 (13)
C3—C2—C5	110.77 (10)	N3—C11—H11	124.6
C1—C2—C5	113.58 (10)	N2—C11—H11	124.6
C8—C2—C5	107.91 (10)	N4—C12—N2	111.01 (12)
N1—C3—C4	113.98 (12)	N4—C12—N5	125.45 (12)
N1—C3—C2	125.47 (11)	N2—C12—N5	123.34 (11)
C4—C3—C2	120.51 (11)	C14—C13—N5	110.59 (12)
C3—C4—H4A	109.5	C14—C13—H13A	109.5
C3—C4—H4B	109.5	N5—C13—H13A	109.5
H4A—C4—H4B	109.5	C14—C13—H13B	109.5
C3—C4—H4C	109.5	N5—C13—H13B	109.5
H4A—C4—H4C	109.5	H13A—C13—H13B	108.1
H4B—C4—H4C	109.5	C15—C14—C13	178.00 (18)
C6—C5—C2	113.64 (11)	C14—C15—H15	180.0
C6—C5—H5A	108.8
C3—N1—N2—C12	−40.63 (18)	C1—C2—C5—C6	37.77 (15)
C3—N1—N2—C11	151.13 (13)	C8—C2—C5—C6	−79.06 (13)
C11—N3—N4—C12	0.01 (16)	C3—C2—C8—C9	68.72 (15)
C12—N5—C1—O1	−174.64 (13)	C1—C2—C8—C9	−175.83 (11)
C13—N5—C1—O1	0.2 (2)	C5—C2—C8—C9	−53.99 (15)
C12—N5—C1—C2	3.4 (2)	C2—C8—C9—C10	72 (3)
C13—N5—C1—C2	178.27 (11)	N4—N3—C11—N2	−0.81 (16)
O1—C1—C2—C3	112.39 (14)	C12—N2—C11—N3	1.25 (15)
N5—C1—C2—C3	−65.67 (14)	N1—N2—C11—N3	172.10 (11)
O1—C1—C2—C8	−7.63 (17)	N3—N4—C12—N2	0.80 (15)
N5—C1—C2—C8	174.31 (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—C5	56.20 (15)	N1—N2—C12—N4	−171.23 (12)
N2—N1—C3—C4	173.10 (11)	C11—N2—C12—N5	173.80 (12)
N2—N1—C3—C2	−4.67 (18)	N1—N2—C12—N5	3.8 (2)
C1—C2—C3—N1	68.84 (15)	C1—N5—C12—N4	−148.84 (14)
C8—C2—C3—N1	−175.91 (12)	C13—N5—C12—N4	36.3 (2)
C5—C2—C3—N1	−54.80 (16)	C1—N5—C12—N2	36.8 (2)
C1—C2—C3—C4	−108.79 (13)	C13—N5—C12—N2	−138.05 (13)
C8—C2—C3—C4	6.46 (16)	C1—N5—C13—C14	−84.87 (17)
C5—C2—C3—C4	127.57 (13)	C12—N5—C13—C14	90.39 (15)
C3—C2—C5—C6	156.96 (11)