1-[3-(4-Methoxy-phen-yl)-6-methyl-1,6-dihydro-1,2,4,5-tetra-zin-1-yl]propanone.

In the title compound, C(13)H(16)N(4)O(2), the central tetra-zine ring adopts an unsymmetrical boat conformation with the two C atoms as flagpoles. This compound can be considered as having homoaromaticity.

Related literature

For the biological activity of 1,2,4,5-tetra­zine derivatives, see: Sauer (1996 ▶). For related structures, see: Jennison et al. (1986 ▶); Stam et al. (1982 ▶); Xu et al. (2010 ▶). For the structure–activity relationships of 1,6-dihydro-1,2,4,5-tetra­zine derivatives, see: Hu et al. (2004 ▶, 2005 ▶).

Experimental

Crystal data

C13H16N4O2

M = 260.30

Triclinic,

a = 8.345 (2) Å

b = 8.4898 (19) Å

c = 10.245 (3) Å

α = 113.232 (6)°

β = 99.820 (15)°

γ = 93.268 (11)°

V = 651.0 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 93 K

0.50 × 0.37 × 0.23 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer

6410 measured reflections

2920 independent reflections

2207 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.081

S = 1.00

2920 reflections

175 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810011165/ci5067sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011165/ci5067Isup2.hkl

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

C13H16N4O2	Z = 2
Mr = 260.30	F(000) = 276
Triclinic, P1	Dx = 1.328 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.345 (2) Å	Cell parameters from 1846 reflections
b = 8.4898 (19) Å	θ = 3.4–27.5°
c = 10.245 (3) Å	µ = 0.09 mm−1
α = 113.232 (6)°	T = 93 K
β = 99.820 (15)°	Prism, red
γ = 93.268 (11)°	0.50 × 0.37 × 0.23 mm
V = 651.0 (3) Å3

Rigaku AFC10/Saturn724+ diffractometer	2207 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.022
graphite	θmax = 27.5°, θmin = 3.4°
Detector resolution: 28.5714 pixels mm-1	h = −10→10
φ and ω scans	k = −11→11
6410 measured reflections	l = −13→12
2920 independent reflections

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0282P)2 + 0.16P] where P = (Fo2 + 2Fc2)/3
2920 reflections	(Δ/σ)max = 0.001
175 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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.

	x	y	z	Uiso*/Ueq
O1	1.03435 (11)	0.17376 (12)	0.48191 (9)	0.0240 (2)
O2	0.16763 (10)	0.73207 (11)	0.11227 (10)	0.0240 (2)
N1	0.33360 (12)	0.55086 (13)	0.15664 (11)	0.0189 (2)
N2	0.47200 (12)	0.53199 (13)	0.23910 (11)	0.0186 (2)
N3	0.47565 (13)	0.27926 (13)	0.02813 (11)	0.0209 (2)
N4	0.34190 (13)	0.29167 (14)	−0.04264 (11)	0.0224 (2)
C1	0.69924 (15)	0.41266 (16)	0.41273 (13)	0.0193 (3)
H1	0.6425	0.5041	0.4631	0.023*
C2	0.82340 (15)	0.36341 (16)	0.49081 (13)	0.0198 (3)
H2	0.8512	0.4207	0.5938	0.024*
C3	0.90723 (14)	0.22979 (16)	0.41785 (13)	0.0179 (3)
C4	0.86288 (15)	0.14452 (16)	0.26693 (13)	0.0213 (3)
H4	0.9183	0.0516	0.2169	0.026*
C5	0.73919 (15)	0.19411 (16)	0.18974 (13)	0.0198 (3)
H5	0.7102	0.1351	0.0869	0.024*
C6	0.65589 (14)	0.33049 (15)	0.26145 (13)	0.0166 (3)
C7	0.52322 (15)	0.38258 (16)	0.18025 (13)	0.0174 (3)
C8	0.23071 (15)	0.39564 (16)	0.04682 (13)	0.0197 (3)
H8	0.1475	0.4295	−0.0163	0.024*
C9	0.14232 (16)	0.29206 (17)	0.11103 (14)	0.0229 (3)
H9A	0.2213	0.2738	0.1846	0.027*
H9B	0.0908	0.1798	0.0339	0.027*
H9C	0.0577	0.3556	0.1561	0.027*
C10	0.29499 (15)	0.71638 (16)	0.18095 (13)	0.0188 (3)
C11	0.41530 (15)	0.86447 (16)	0.29536 (13)	0.0211 (3)
H11A	0.5256	0.8546	0.2720	0.025*
H11B	0.4215	0.8583	0.3906	0.025*
C12	0.36603 (17)	1.03756 (17)	0.30564 (15)	0.0267 (3)
H12A	0.3573	1.0429	0.2109	0.032*
H12B	0.4492	1.1311	0.3782	0.032*
H12C	0.2598	1.0506	0.3345	0.032*
C13	1.07827 (16)	0.24669 (18)	0.63702 (14)	0.0246 (3)
H13A	1.1083	0.3722	0.6737	0.030*
H13B	1.1719	0.1957	0.6680	0.030*
H13C	0.9848	0.2222	0.6757	0.030*

	U11	U22	U33	U12	U13	U23
O1	0.0227 (5)	0.0325 (5)	0.0196 (5)	0.0115 (4)	0.0026 (4)	0.0134 (4)
O2	0.0192 (5)	0.0280 (5)	0.0261 (5)	0.0064 (4)	0.0008 (4)	0.0134 (4)
N1	0.0169 (5)	0.0206 (5)	0.0185 (5)	0.0019 (4)	−0.0015 (4)	0.0094 (4)
N2	0.0166 (5)	0.0217 (5)	0.0192 (5)	0.0028 (4)	0.0004 (4)	0.0114 (4)
N3	0.0206 (6)	0.0244 (6)	0.0174 (5)	0.0031 (4)	0.0013 (4)	0.0094 (5)
N4	0.0210 (6)	0.0256 (6)	0.0195 (5)	0.0030 (5)	0.0004 (5)	0.0096 (5)
C1	0.0184 (6)	0.0202 (6)	0.0187 (6)	0.0047 (5)	0.0037 (5)	0.0073 (5)
C2	0.0205 (6)	0.0224 (6)	0.0151 (6)	0.0019 (5)	0.0014 (5)	0.0073 (5)
C3	0.0147 (6)	0.0219 (6)	0.0200 (6)	0.0027 (5)	0.0020 (5)	0.0123 (5)
C4	0.0239 (7)	0.0220 (6)	0.0199 (6)	0.0088 (5)	0.0065 (5)	0.0091 (5)
C5	0.0227 (7)	0.0210 (6)	0.0144 (6)	0.0033 (5)	0.0022 (5)	0.0066 (5)
C6	0.0147 (6)	0.0182 (6)	0.0181 (6)	0.0001 (5)	0.0017 (5)	0.0096 (5)
C7	0.0157 (6)	0.0207 (6)	0.0169 (6)	0.0007 (5)	0.0026 (5)	0.0094 (5)
C8	0.0173 (6)	0.0218 (6)	0.0180 (6)	0.0017 (5)	−0.0015 (5)	0.0083 (5)
C9	0.0200 (6)	0.0238 (7)	0.0237 (7)	0.0003 (5)	0.0008 (5)	0.0103 (5)
C10	0.0188 (6)	0.0232 (6)	0.0184 (6)	0.0053 (5)	0.0057 (5)	0.0118 (5)
C11	0.0212 (7)	0.0218 (7)	0.0209 (7)	0.0048 (5)	0.0024 (5)	0.0101 (5)
C12	0.0261 (7)	0.0213 (7)	0.0332 (8)	0.0049 (5)	0.0047 (6)	0.0120 (6)
C13	0.0222 (7)	0.0329 (7)	0.0200 (7)	0.0043 (6)	−0.0006 (5)	0.0141 (6)

O1—C3	1.3596 (14)	C5—C6	1.3995 (17)
O1—C13	1.4291 (15)	C5—H5	0.95
O2—C10	1.2155 (14)	C6—C7	1.4647 (16)
N1—N2	1.3669 (14)	C8—C9	1.5160 (17)
N1—C10	1.3941 (16)	C8—H8	1.00
N1—C8	1.4531 (15)	C9—H9A	0.98
N2—C7	1.3044 (16)	C9—H9B	0.98
N3—N4	1.2571 (14)	C9—H9C	0.98
N3—C7	1.4236 (16)	C10—C11	1.5015 (17)
N4—C8	1.4917 (16)	C11—C12	1.5169 (17)
C1—C2	1.3852 (17)	C11—H11A	0.99
C1—C6	1.3952 (17)	C11—H11B	0.99
C1—H1	0.95	C12—H12A	0.98
C2—C3	1.3911 (17)	C12—H12B	0.98
C2—H2	0.95	C12—H12C	0.98
C3—C4	1.3939 (17)	C13—H13A	0.98
C4—C5	1.3791 (17)	C13—H13B	0.98
C4—H4	0.95	C13—H13C	0.98
C3—O1—C13	118.23 (10)	N1—C8—H8	108.9
N2—N1—C10	119.47 (10)	N4—C8—H8	108.9
N2—N1—C8	118.20 (10)	C9—C8—H8	108.9
C10—N1—C8	122.32 (10)	C8—C9—H9A	109.5
C7—N2—N1	113.70 (10)	C8—C9—H9B	109.5
N4—N3—C7	120.02 (11)	H9A—C9—H9B	109.5
N3—N4—C8	115.25 (10)	C8—C9—H9C	109.5
C2—C1—C6	121.25 (12)	H9A—C9—H9C	109.5
C2—C1—H1	119.4	H9B—C9—H9C	109.5
C6—C1—H1	119.4	O2—C10—N1	119.15 (11)
C1—C2—C3	119.76 (11)	O2—C10—C11	124.57 (12)
C1—C2—H2	120.1	N1—C10—C11	116.27 (10)
C3—C2—H2	120.1	C10—C11—C12	111.53 (11)
O1—C3—C2	125.16 (11)	C10—C11—H11A	109.3
O1—C3—C4	115.33 (11)	C12—C11—H11A	109.3
C2—C3—C4	119.50 (11)	C10—C11—H11B	109.3
C5—C4—C3	120.48 (12)	C12—C11—H11B	109.3
C5—C4—H4	119.8	H11A—C11—H11B	108.0
C3—C4—H4	119.8	C11—C12—H12A	109.5
C4—C5—C6	120.64 (11)	C11—C12—H12B	109.5
C4—C5—H5	119.7	H12A—C12—H12B	109.5
C6—C5—H5	119.7	C11—C12—H12C	109.5
C1—C6—C5	118.35 (11)	H12A—C12—H12C	109.5
C1—C6—C7	120.72 (11)	H12B—C12—H12C	109.5
C5—C6—C7	120.91 (11)	O1—C13—H13A	109.5
N2—C7—N3	121.12 (11)	O1—C13—H13B	109.5
N2—C7—C6	121.13 (11)	H13A—C13—H13B	109.5
N3—C7—C6	116.68 (11)	O1—C13—H13C	109.5
N1—C8—N4	106.07 (9)	H13A—C13—H13C	109.5
N1—C8—C9	112.98 (10)	H13B—C13—H13C	109.5
N4—C8—C9	110.99 (10)
C10—N1—N2—C7	−159.83 (10)	N4—N3—C7—C6	164.47 (10)
C8—N1—N2—C7	20.73 (14)	C1—C6—C7—N2	18.43 (17)
C7—N3—N4—C8	−9.80 (16)	C5—C6—C7—N2	−163.36 (11)
C6—C1—C2—C3	0.09 (18)	C1—C6—C7—N3	−173.30 (11)
C13—O1—C3—C2	5.43 (17)	C5—C6—C7—N3	4.91 (16)
C13—O1—C3—C4	−175.44 (11)	N2—N1—C8—N4	−52.33 (13)
C1—C2—C3—O1	177.78 (11)	C10—N1—C8—N4	128.25 (11)
C1—C2—C3—C4	−1.32 (18)	N2—N1—C8—C9	69.47 (13)
O1—C3—C4—C5	−177.85 (11)	C10—N1—C8—C9	−109.95 (13)
C2—C3—C4—C5	1.33 (18)	N3—N4—C8—N1	45.04 (13)
C3—C4—C5—C6	−0.12 (18)	N3—N4—C8—C9	−78.02 (13)
C2—C1—C6—C5	1.10 (17)	N2—N1—C10—O2	−176.38 (11)
C2—C1—C6—C7	179.36 (11)	C8—N1—C10—O2	3.04 (17)
C4—C5—C6—C1	−1.09 (17)	N2—N1—C10—C11	2.16 (16)
C4—C5—C6—C7	−179.34 (11)	C8—N1—C10—C11	−178.43 (10)
N1—N2—C7—N3	20.73 (16)	O2—C10—C11—C12	−5.10 (17)
N1—N2—C7—C6	−171.53 (10)	N1—C10—C11—C12	176.46 (11)
N4—N3—C7—N2	−27.26 (17)