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

The title compound, C(12)H(15)N(5)O, features a triazolyl ring fused with a seven-membered triazepinyl ring; the latter ring adopts a boat conformation with the allyl-bearing C atom as the prow and the C and N fused-ring atoms as the stern.

Related literature

Triazepines are 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

C12H15N5O

M = 245.29

Monoclinic,

a = 7.4674 (3) Å

b = 8.3398 (3) Å

c = 20.2214 (6) Å

β = 95.174 (2)°

V = 1254.19 (8) Å3

Z = 4

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

11394 measured reflections

2435 independent reflections

1600 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.176

S = 1.03

2435 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.62 e Å−3

Δρmin = −0.31 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/S160053680903133X/xu2583sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680903133X/xu2583Isup2.hkl

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

C12H15N5O	F(000) = 520
Mr = 245.29	Dx = 1.299 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2666 reflections
a = 7.4674 (3) Å	θ = 2.6–23.2°
b = 8.3398 (3) Å	µ = 0.09 mm−1
c = 20.2214 (6) Å	T = 293 K
β = 95.174 (2)°	Block, colorless
V = 1254.19 (8) Å3	0.3 × 0.3 × 0.3 mm
Z = 4

Bruker APEXII diffractometer	1600 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.041
graphite	θmax = 25.9°, θmin = 2.0°
φ and ω scans	h = −9→9
11394 measured reflections	k = −10→10
2435 independent reflections	l = −22→24

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.176	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.1011P)2 + 0.1814P] where P = (Fo2 + 2Fc2)/3
2435 reflections	(Δ/σ)max = 0.001
164 parameters	Δρmax = 0.62 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.6016 (3)	0.9072 (2)	0.62240 (9)	0.0504 (5)
N1	0.6575 (3)	0.4291 (2)	0.67475 (9)	0.0372 (5)
N2	0.6714 (3)	0.4126 (2)	0.60624 (9)	0.0346 (5)
N3	0.7253 (3)	0.2937 (3)	0.51391 (10)	0.0486 (6)
N4	0.7390 (3)	0.4593 (3)	0.50437 (9)	0.0424 (6)
N5	0.7149 (3)	0.6893 (2)	0.57403 (9)	0.0360 (5)
C1	0.5941 (3)	0.7634 (3)	0.61190 (10)	0.0353 (6)
C2	0.4588 (3)	0.6533 (3)	0.63974 (10)	0.0328 (6)
H2	0.4112	0.5834	0.6033	0.039*
C3	0.3002 (3)	0.7447 (3)	0.66310 (12)	0.0460 (7)
H3A	0.3402	0.8057	0.7025	0.055*
H3B	0.2560	0.8200	0.6289	0.055*
C4	0.1488 (4)	0.6348 (4)	0.67861 (16)	0.0600 (8)
H4	0.1127	0.5587	0.6465	0.072*
C5	0.0662 (5)	0.6348 (5)	0.73019 (19)	0.0877 (12)
H5A	0.0969	0.7084	0.7639	0.105*
H5B	−0.0256	0.5613	0.7346	0.105*
C6	0.5616 (3)	0.5471 (3)	0.69075 (10)	0.0338 (6)
C7	0.5614 (4)	0.5818 (3)	0.76328 (11)	0.0480 (7)
H7A	0.6349	0.5044	0.7882	0.072*
H7B	0.4406	0.5759	0.7758	0.072*
H7C	0.6086	0.6874	0.7724	0.072*
C8	0.6870 (3)	0.2708 (3)	0.57428 (13)	0.0433 (6)
H8	0.6722	0.1707	0.5933	0.052*
C9	0.7056 (3)	0.5264 (3)	0.56022 (11)	0.0334 (6)
C10	0.8431 (3)	0.7867 (3)	0.53946 (12)	0.0449 (7)
H10A	0.9421	0.7191	0.5286	0.054*
H10B	0.8920	0.8704	0.5692	0.054*
C11	0.7587 (4)	0.8618 (3)	0.47735 (13)	0.0519 (7)
H11	0.6702	0.9388	0.4813	0.062*
C12	0.8000 (5)	0.8273 (4)	0.41876 (16)	0.0779 (11)
H12A	0.8880	0.7509	0.4130	0.093*
H12B	0.7420	0.8788	0.3820	0.093*

	U11	U22	U33	U12	U13	U23
O1	0.0657 (13)	0.0282 (11)	0.0585 (11)	−0.0048 (9)	0.0122 (9)	−0.0007 (8)
N1	0.0448 (12)	0.0352 (12)	0.0313 (10)	−0.0009 (10)	0.0013 (8)	0.0048 (8)
N2	0.0407 (12)	0.0290 (11)	0.0341 (10)	0.0007 (9)	0.0037 (8)	0.0025 (8)
N3	0.0564 (15)	0.0419 (14)	0.0482 (13)	0.0010 (11)	0.0084 (11)	−0.0081 (10)
N4	0.0485 (13)	0.0417 (13)	0.0376 (11)	−0.0001 (10)	0.0073 (9)	−0.0018 (9)
N5	0.0391 (12)	0.0314 (12)	0.0381 (10)	−0.0050 (9)	0.0063 (9)	0.0049 (8)
C1	0.0424 (15)	0.0303 (14)	0.0327 (12)	0.0003 (11)	−0.0005 (10)	0.0010 (10)
C2	0.0363 (13)	0.0296 (13)	0.0324 (12)	−0.0009 (10)	0.0016 (10)	0.0014 (9)
C3	0.0504 (17)	0.0422 (15)	0.0461 (14)	0.0071 (13)	0.0087 (12)	0.0053 (11)
C4	0.0377 (16)	0.081 (2)	0.0619 (18)	0.0146 (15)	0.0103 (13)	0.0091 (16)
C5	0.066 (2)	0.106 (3)	0.093 (3)	0.009 (2)	0.018 (2)	0.018 (2)
C6	0.0360 (14)	0.0328 (13)	0.0323 (12)	−0.0049 (11)	0.0018 (10)	0.0028 (10)
C7	0.0541 (17)	0.0556 (18)	0.0340 (13)	0.0011 (14)	0.0022 (11)	0.0019 (11)
C8	0.0489 (16)	0.0299 (14)	0.0510 (15)	0.0011 (12)	0.0038 (12)	−0.0002 (11)
C9	0.0323 (13)	0.0331 (14)	0.0342 (12)	−0.0008 (10)	0.0004 (9)	0.0016 (10)
C10	0.0443 (16)	0.0436 (16)	0.0475 (14)	−0.0111 (13)	0.0080 (12)	0.0063 (11)
C11	0.0567 (18)	0.0493 (18)	0.0519 (16)	−0.0001 (14)	0.0166 (13)	0.0142 (13)
C12	0.100 (3)	0.079 (3)	0.0560 (19)	0.009 (2)	0.0132 (18)	0.0164 (17)

O1—C1	1.218 (3)	C3—H3B	0.9700
N1—C6	1.276 (3)	C4—C5	1.259 (4)
N1—N2	1.405 (3)	C4—H4	0.9300
N2—C8	1.358 (3)	C5—H5A	0.9300
N2—C9	1.369 (3)	C5—H5B	0.9300
N3—C8	1.293 (3)	C6—C7	1.495 (3)
N3—N4	1.400 (3)	C7—H7A	0.9600
N4—C9	1.304 (3)	C7—H7B	0.9600
N5—C1	1.381 (3)	C7—H7C	0.9600
N5—C9	1.388 (3)	C8—H8	0.9300
N5—C10	1.479 (3)	C10—C11	1.491 (4)
C1—C2	1.511 (3)	C10—H10A	0.9700
C2—C6	1.514 (3)	C10—H10B	0.9700
C2—C3	1.519 (3)	C11—C12	1.283 (4)
C2—H2	0.9800	C11—H11	0.9300
C3—C4	1.510 (4)	C12—H12A	0.9300
C3—H3A	0.9700	C12—H12B	0.9300
C6—N1—N2	114.74 (18)	H5A—C5—H5B	120.0
C8—N2—C9	104.5 (2)	N1—C6—C7	116.6 (2)
C8—N2—N1	124.87 (19)	N1—C6—C2	122.7 (2)
C9—N2—N1	129.60 (19)	C7—C6—C2	120.7 (2)
C8—N3—N4	107.47 (19)	C6—C7—H7A	109.5
C9—N4—N3	106.37 (19)	C6—C7—H7B	109.5
C1—N5—C9	121.80 (19)	H7A—C7—H7B	109.5
C1—N5—C10	119.9 (2)	C6—C7—H7C	109.5
C9—N5—C10	117.75 (19)	H7A—C7—H7C	109.5
O1—C1—N5	121.0 (2)	H7B—C7—H7C	109.5
O1—C1—C2	123.7 (2)	N3—C8—N2	110.9 (2)
N5—C1—C2	115.2 (2)	N3—C8—H8	124.5
C1—C2—C6	107.12 (18)	N2—C8—H8	124.5
C1—C2—C3	112.1 (2)	N4—C9—N2	110.7 (2)
C6—C2—C3	116.29 (18)	N4—C9—N5	125.7 (2)
C1—C2—H2	106.9	N2—C9—N5	123.41 (19)
C6—C2—H2	106.9	N5—C10—C11	112.7 (2)
C3—C2—H2	106.9	N5—C10—H10A	109.0
C4—C3—C2	112.3 (2)	C11—C10—H10A	109.0
C4—C3—H3A	109.1	N5—C10—H10B	109.0
C2—C3—H3A	109.1	C11—C10—H10B	109.0
C4—C3—H3B	109.1	H10A—C10—H10B	107.8
C2—C3—H3B	109.1	C12—C11—C10	124.4 (3)
H3A—C3—H3B	107.9	C12—C11—H11	117.8
C5—C4—C3	127.1 (4)	C10—C11—H11	117.8
C5—C4—H4	116.4	C11—C12—H12A	120.0
C3—C4—H4	116.4	C11—C12—H12B	120.0
C4—C5—H5A	120.0	H12A—C12—H12B	120.0
C4—C5—H5B	120.0
C6—N1—N2—C8	−147.4 (2)	C1—C2—C6—C7	101.0 (2)
C6—N1—N2—C9	46.1 (3)	C3—C2—C6—C7	−25.3 (3)
C8—N3—N4—C9	−0.7 (3)	N4—N3—C8—N2	0.8 (3)
C9—N5—C1—O1	−178.4 (2)	C9—N2—C8—N3	−0.6 (3)
C10—N5—C1—O1	−6.7 (3)	N1—N2—C8—N3	−170.0 (2)
C9—N5—C1—C2	3.0 (3)	N3—N4—C9—N2	0.3 (3)
C10—N5—C1—C2	174.68 (19)	N3—N4—C9—N5	176.1 (2)
O1—C1—C2—C6	−110.7 (2)	C8—N2—C9—N4	0.2 (3)
N5—C1—C2—C6	67.9 (2)	N1—N2—C9—N4	168.8 (2)
O1—C1—C2—C3	18.0 (3)	C8—N2—C9—N5	−175.7 (2)
N5—C1—C2—C3	−163.40 (19)	N1—N2—C9—N5	−7.1 (4)
C1—C2—C3—C4	169.1 (2)	C1—N5—C9—N4	142.8 (2)
C6—C2—C3—C4	−67.2 (3)	C10—N5—C9—N4	−29.0 (3)
C2—C3—C4—C5	130.9 (3)	C1—N5—C9—N2	−41.9 (3)
N2—N1—C6—C7	−172.6 (2)	C10—N5—C9—N2	146.2 (2)
N2—N1—C6—C2	4.6 (3)	C1—N5—C10—C11	−78.4 (3)
C1—C2—C6—N1	−76.1 (3)	C9—N5—C10—C11	93.6 (3)
C3—C2—C6—N1	157.6 (2)	N5—C10—C11—C12	−114.4 (3)