4,4'-(1,2,4,5-Tetra-zine-3,6-di-yl)dibenzo-nitrile.

Mol-ecules of the title compound, C(16)H(8)N(6), lie on crystallographic inversion centres. A dihedral angle of 16.1 (1)° is formed between the central tetra-zine ring and the plane of each cyano-phenyl group. The mol-ecules form stacks along [100] with a perpendicular inter-planar separation of 3.25 (1) Å. C-H⋯N inter-actions are formed between mol-ecules in neighbouring stacks.

Related literature

For synthesis details, see: Spychała et al. (1994 ▶, 2000 ▶). For related structures and discussion, see: Higashi & Osaki (1981 ▶); Infantes et al. (2003 ▶).

Experimental

Crystal data

C16H8N6

M = 284.28

Monoclinic,

a = 4.8447 (5) Å

b = 12.1054 (12) Å

c = 11.6927 (11) Å

β = 94.363 (8)°

V = 683.75 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 291 K

0.45 × 0.2 × 0.1 mm

Data collection

Kuma KM-4-CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.925, T max = 0.991

5912 measured reflections

1768 independent reflections

1094 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.135

S = 1.06

1768 reflections

116 parameters

All H-atom parameters refined

Δρmax = 0.16 e Å−3

Δρmin = −0.13 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Stereochemical Workstation Operation Manual (Siemens, 1989 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809008599/bi2354sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809008599/bi2354Isup2.hkl

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

C16H8N6	F(000) = 292
Mr = 284.28	Dx = 1.381 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2059 reflections
a = 4.8447 (5) Å	θ = 2.4–29.6°
b = 12.1054 (12) Å	µ = 0.09 mm−1
c = 11.6927 (11) Å	T = 291 K
β = 94.363 (8)°	Block, orange
V = 683.75 (12) Å3	0.45 × 0.2 × 0.1 mm
Z = 2

Kuma KM-4-CCD diffractometer	1768 independent reflections
Radiation source: fine-focus sealed tube	1094 reflections with I > 2σ(I)
graphite	Rint = 0.017
Detector resolution: 8.1929 pixels mm-1	θmax = 29.7°, θmin = 3.4°
ω scans	h = −6→6
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −16→15
Tmin = 0.925, Tmax = 0.991	l = −15→14
5912 measured 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)] = 0.044	Hydrogen site location: difference Fourier map
wR(F2) = 0.135	All H-atom parameters refined
S = 1.06	w = 1/[σ2(Fo2) + (0.0683P)2 + 0.0311P] where P = (Fo2 + 2Fc2)/3
1768 reflections	(Δ/σ)max < 0.001
116 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.13 e Å−3

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
N1	−0.2003 (2)	0.01444 (9)	−0.08623 (10)	0.0532 (4)
N2	−0.0256 (2)	0.09630 (9)	−0.05942 (10)	0.0528 (4)
C3	0.1693 (2)	0.07922 (10)	0.02639 (10)	0.0418 (3)
C4	0.3614 (2)	0.17078 (10)	0.05676 (11)	0.0434 (3)
C5	0.3849 (3)	0.25828 (12)	−0.01845 (13)	0.0546 (4)
C6	0.5664 (3)	0.34327 (13)	0.00878 (14)	0.0596 (4)
C7	0.7235 (3)	0.34205 (12)	0.11308 (13)	0.0542 (4)
C8	0.7010 (3)	0.25569 (14)	0.18883 (14)	0.0626 (5)
C9	0.5218 (3)	0.16937 (13)	0.16039 (13)	0.0564 (4)
C10	0.9104 (3)	0.43269 (15)	0.14189 (14)	0.0682 (5)
N10	1.0547 (4)	0.50498 (14)	0.16340 (14)	0.0986 (6)
H6	0.588 (3)	0.4047 (13)	−0.0455 (16)	0.080 (5)*
H5	0.271 (3)	0.2606 (13)	−0.0895 (14)	0.065 (4)*
H8	0.811 (3)	0.2535 (13)	0.2601 (15)	0.078 (5)*
H9	0.509 (3)	0.1054 (14)	0.2128 (14)	0.076 (5)*

	U11	U22	U33	U12	U13	U23
N1	0.0548 (7)	0.0474 (7)	0.0549 (7)	−0.0081 (5)	−0.0131 (5)	0.0051 (5)
N2	0.0546 (7)	0.0469 (7)	0.0542 (7)	−0.0070 (5)	−0.0128 (5)	0.0056 (5)
C3	0.0429 (7)	0.0433 (7)	0.0388 (7)	−0.0019 (6)	0.0003 (5)	−0.0008 (5)
C4	0.0423 (7)	0.0441 (7)	0.0433 (7)	−0.0026 (6)	−0.0005 (5)	−0.0012 (6)
C5	0.0578 (8)	0.0545 (9)	0.0496 (8)	−0.0100 (7)	−0.0075 (6)	0.0061 (7)
C6	0.0670 (10)	0.0537 (9)	0.0572 (9)	−0.0152 (8)	−0.0005 (7)	0.0056 (7)
C7	0.0534 (8)	0.0538 (9)	0.0553 (9)	−0.0146 (7)	0.0033 (6)	−0.0068 (7)
C8	0.0640 (9)	0.0719 (10)	0.0494 (8)	−0.0190 (8)	−0.0114 (7)	0.0007 (8)
C9	0.0620 (9)	0.0566 (9)	0.0487 (8)	−0.0149 (7)	−0.0086 (7)	0.0060 (7)
C10	0.0749 (10)	0.0741 (11)	0.0554 (9)	−0.0259 (9)	0.0034 (8)	−0.0063 (8)
N10	0.1182 (13)	0.1029 (13)	0.0742 (11)	−0.0672 (11)	0.0037 (9)	−0.0105 (9)

N1—N2	1.3254 (14)	C6—C7	1.388 (2)
N1—C3i	1.3347 (17)	C6—H6	0.989 (17)
N2—C3	1.3403 (17)	C7—C8	1.380 (2)
C3—N1i	1.3347 (17)	C7—C10	1.446 (2)
C3—C4	1.4735 (17)	C8—C9	1.383 (2)
C4—C5	1.3869 (19)	C8—H8	0.955 (17)
C4—C9	1.3888 (18)	C9—H9	0.993 (17)
C5—C6	1.375 (2)	C10—N10	1.1360 (18)
C5—H5	0.962 (16)
N2—N1—C3i	117.81 (11)	C5—C6—H6	120.8 (10)
N1—N2—C3	117.55 (11)	C7—C6—H6	119.6 (10)
N1i—C3—N2	124.64 (11)	C8—C7—C6	120.49 (13)
N1i—C3—C4	117.94 (11)	C8—C7—C10	120.27 (13)
N2—C3—C4	117.42 (11)	C6—C7—C10	119.25 (14)
C5—C4—C9	119.68 (12)	C7—C8—C9	119.80 (14)
C5—C4—C3	120.17 (12)	C7—C8—H8	121.0 (10)
C9—C4—C3	120.15 (12)	C9—C8—H8	119.1 (10)
C6—C5—C4	120.43 (13)	C8—C9—C4	119.99 (14)
C6—C5—H5	119.6 (9)	C8—C9—H9	120.7 (10)
C4—C5—H5	120.0 (9)	C4—C9—H9	119.4 (10)
C5—C6—C7	119.60 (14)	N10—C10—C7	178.9 (2)
C3i—N1—N2—C3	−0.3 (2)	C4—C5—C6—C7	−1.0 (2)
N1—N2—C3—N1i	0.3 (2)	C5—C6—C7—C8	0.7 (2)
N1—N2—C3—C4	−179.39 (11)	C5—C6—C7—C10	−178.94 (15)
N1i—C3—C4—C5	164.01 (13)	C6—C7—C8—C9	0.4 (3)
N2—C3—C4—C5	−16.25 (19)	C10—C7—C8—C9	−179.95 (15)
N1i—C3—C4—C9	−15.40 (19)	C7—C8—C9—C4	−1.2 (3)
N2—C3—C4—C9	164.34 (13)	C5—C4—C9—C8	0.9 (2)
C9—C4—C5—C6	0.2 (2)	C3—C4—C9—C8	−179.71 (14)
C3—C4—C5—C6	−179.18 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···N10ii	0.989 (17)	2.539 (17)	3.370 (2)	141.6 (13)
C8—H8···N2iii	0.956 (17)	2.850 (17)	3.6106 (19)	137.2 (12)
C9—H9···N10iv	0.993 (17)	2.754 (17)	3.431 (2)	125.8 (12)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯N10i	0.989 (17)	2.539 (17)	3.370 (2)	141.6 (13)
C8—H8⋯N2ii	0.956 (17)	2.850 (17)	3.6106 (19)	137.2 (12)
C9—H9⋯N10iii	0.993 (17)	2.754 (17)	3.431 (2)	125.8 (12)

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