3,6-Di-4-pyridyl-1,4-dihydro-1,2,4,5-tetra-zine.

The mol-ecule of the title compound, C(12)H(10)N(6), which is V-shaped due to the boat conformation of the dihydro-tetra-zine ring, has crystallographic C(2) symmetry. The dihedral angle between the planes of the two pyridine rings is 31.57 (3)°. Mol-ecules are linked by weak N-H⋯N and C-H⋯N hydrogen bonds, forming a two-dimensional polymeric structure.

Related literature

For related structures, see: Bradford et al. (2004 ▶); Caira et al. (1976 ▶); Liou et al. (1996 ▶); Zachara et al. (2004 ▶); Rao & Hu (2005 ▶). For related literature on tetra­zines, see: Sauer (1996 ▶).

Experimental

Crystal data

C12H10N6

M = 238.26

Orthorhombic,

a = 11.2862 (18) Å

b = 14.481 (2) Å

c = 6.8864 (12) Å

V = 1125.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 (2) K

0.50 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.955, T max = 0.991

4214 measured reflections

1105 independent reflections

938 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.128

S = 1.08

1105 reflections

86 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SMART; data reduction: SAINT (Bruker, 2000 ▶); 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 I, global. DOI: 10.1107/S160053680801742X/gk2149sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680801742X/gk2149Isup2.hkl

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

C12H10N6	F000 = 496
Mr = 238.26	Dx = 1.406 Mg m−3
Orthorhombic, Pccn	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 820 reflections
a = 11.2862 (18) Å	θ = 2.5–28.0º
b = 14.481 (2) Å	µ = 0.09 mm−1
c = 6.8864 (12) Å	T = 293 (2) K
V = 1125.4 (3) Å3	Block, red
Z = 4	0.50 × 0.10 × 0.10 mm

Bruker SMART CCD area-detector diffractometer	1105 independent reflections
Radiation source: fine-focus sealed tube	938 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.032
Detector resolution: 0 pixels mm-1	θmax = 26.0º
T = 293(2) K	θmin = 2.8º
φ and ω scans	h = −13→10
Absorption correction: multi-scan(SADABS; Bruker, 2000)	k = −17→17
Tmin = 0.955, Tmax = 0.991	l = −3→8
4214 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.128	w = 1/[σ2(Fo2) + (0.0618P)2 + 0.3052P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
1105 reflections	Δρmax = 0.20 e Å−3
86 parameters	Δρmin = −0.14 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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 taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used 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 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
C1	0.56160 (17)	0.17370 (13)	0.1811 (4)	0.0589 (7)
H1A	0.5769	0.2351	0.1500	0.071*
C2	0.65246 (19)	0.11530 (16)	0.2327 (4)	0.0683 (8)
H2A	0.7286	0.1397	0.2370	0.082*
C3	0.52968 (17)	−0.00510 (13)	0.2686 (3)	0.0463 (5)
H3A	0.5172	−0.0671	0.2971	0.056*
C4	0.43215 (16)	0.04780 (12)	0.2202 (3)	0.0390 (5)
H4A	0.3571	0.0214	0.2176	0.047*
C5	0.44678 (15)	0.13961 (11)	0.1762 (3)	0.0322 (4)
C6	0.34693 (13)	0.20078 (11)	0.1238 (2)	0.0296 (4)
N1	0.63928 (15)	0.02634 (11)	0.2770 (3)	0.0526 (5)
N2	0.36287 (11)	0.28776 (9)	0.1283 (2)	0.0331 (4)
N3	0.26087 (12)	0.33789 (10)	0.0671 (2)	0.0332 (4)
H3B	0.2708 (17)	0.3931 (14)	0.097 (3)	0.047 (6)*

	U11	U22	U33	U12	U13	U23
C1	0.0310 (11)	0.0379 (11)	0.108 (2)	−0.0006 (8)	−0.0039 (11)	0.0119 (11)
C2	0.0282 (11)	0.0536 (13)	0.123 (2)	0.0004 (9)	−0.0073 (12)	0.0094 (14)
C3	0.0396 (13)	0.0355 (10)	0.0639 (14)	0.0077 (8)	−0.0012 (9)	0.0042 (9)
C4	0.0294 (10)	0.0324 (9)	0.0553 (12)	0.0011 (7)	−0.0008 (8)	0.0023 (8)
C5	0.0273 (9)	0.0314 (9)	0.0379 (9)	0.0025 (7)	0.0029 (7)	−0.0026 (7)
C6	0.0255 (9)	0.0272 (8)	0.0360 (9)	−0.0013 (6)	0.0027 (7)	−0.0009 (7)
N1	0.0357 (10)	0.0463 (10)	0.0756 (13)	0.0111 (7)	−0.0021 (8)	0.0028 (9)
N2	0.0238 (8)	0.0283 (7)	0.0471 (9)	0.0007 (6)	0.0036 (6)	0.0006 (6)
N3	0.0270 (8)	0.0239 (7)	0.0487 (9)	0.0011 (6)	0.0019 (6)	0.0030 (6)

C1—C2	1.376 (3)	C4—C5	1.374 (2)
C1—C5	1.387 (2)	C4—H4A	0.9300
C1—H1A	0.9300	C5—C6	1.478 (2)
C2—N1	1.332 (3)	C6—N2	1.273 (2)
C2—H2A	0.9300	C6—N3i	1.395 (2)
C3—N1	1.319 (2)	N2—N3	1.4249 (18)
C3—C4	1.382 (3)	N3—C6i	1.395 (2)
C3—H3A	0.9300	N3—H3B	0.83 (2)
C2—C1—C5	118.94 (18)	C4—C5—C1	116.82 (16)
C2—C1—H1A	120.5	C4—C5—C6	122.84 (15)
C5—C1—H1A	120.5	C1—C5—C6	120.33 (16)
N1—C2—C1	124.8 (2)	N2—C6—N3i	121.83 (14)
N1—C2—H2A	117.6	N2—C6—C5	118.64 (15)
C1—C2—H2A	117.6	N3i—C6—C5	119.51 (14)
N1—C3—C4	124.48 (18)	C3—N1—C2	115.36 (17)
N1—C3—H3A	117.8	C6—N2—N3	112.51 (13)
C4—C3—H3A	117.8	C6i—N3—N2	114.66 (12)
C5—C4—C3	119.61 (17)	C6i—N3—H3B	115.7 (14)
C5—C4—H4A	120.2	N2—N3—H3B	107.9 (14)
C3—C4—H4A	120.2

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···N1ii	0.83 (2)	2.35 (2)	3.142 (2)	159.8 (18)
C3—H3A···N2iii	0.93	2.55	3.312 (2)	139
C4—H4A···N1iv	0.93	2.55	3.475 (3)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3B⋯N1i	0.83 (2)	2.35 (2)	3.142 (2)	159.8 (18)
C3—H3A⋯N2ii	0.93	2.55	3.312 (2)	139
C4—H4A⋯N1iii	0.93	2.55	3.475 (3)	171

Symmetry codes: (i) ; (ii) ; (iii) .