1,3,5-Tris(pyridin-3-yl)-2,4-diaza-penta-1,4-diene.

In the solid state, the structure of the title compound, C(18)H(15)N(5), is stabilized by weak C-H⋯N interactions. Mol-ecules are arranged in layers parallel to the bc plane forming an inter-esting supra-molecular structure.

Related literature

For coordination polymers and supra­molecular structures, see: Itoh et al. (2005 ▶); Albrechet (2001 ▶); Leininger et al. (2000 ▶). For potential applications in catalysis, gas storage, chirality, optics, magnetism, nanotechnology and luminescence, see: James (2003 ▶); Kitagawa et al. (2004 ▶); Masaoka et al. (2001 ▶); Rarig et al. (2002 ▶); Yaghi et al. (2003 ▶); Wang et al. (2009 ▶). For the preparation of this class of compound, see: Larter et al. (1998 ▶); Lozinskaya et al. (2003 ▶); Bessonov et al. (2005 ▶); Fernandes et al. (2007 ▶).

Experimental

Crystal data

C18H15N5

M = 301.35

Monoclinic,

a = 5.7174 (11) Å

b = 8.0934 (10) Å

c = 16.972 (4) Å

β = 99.690 (18)°

V = 774.1 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.42 × 0.18 × 0.12 mm

Data collection

Bruker P4 diffractometer

3235 measured reflections

2874 independent reflections

1159 reflections with I > 2σ(I)

R int = 0.061

3 standard reflections every 97 reflections intensity decay: 11.5%

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.135

S = 0.98

2874 reflections

209 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.17 e Å−3

Data collection: XSCANS (Siemens, 1996 ▶); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXS97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812005909/rk2325sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005909/rk2325Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812005909/rk2325Isup3.cml

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

C18H15N5	F(000) = 316
Mr = 301.35	Dx = 1.293 Mg m−3
Monoclinic, Pc	Melting point = 388–390 K
Hall symbol: P -2yc	Mo Kα radiation, λ = 0.71073 Å
a = 5.7174 (11) Å	Cell parameters from 33 reflections
b = 8.0934 (10) Å	θ = 4.7–11.6°
c = 16.972 (4) Å	µ = 0.08 mm−1
β = 99.690 (18)°	T = 298 K
V = 774.1 (3) Å3	Neele, colourless
Z = 2	0.42 × 0.18 × 0.12 mm

Bruker P4 diffractometer	Rint = 0.061
Radiation source: fine-focus sealed tube	θmax = 30.0°, θmin = 2.4°
Graphite monochromator	h = −1→8
2θ/ω–scans	k = −1→11
3235 measured reflections	l = −23→23
2874 independent reflections	3 standard reflections every 97 reflections
1159 reflections with I > 2σ(I)	intensity decay: 11.5%

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.070	w = 1/[σ2(Fo2) + (0.0352P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.135	(Δ/σ)max < 0.001
S = 0.98	Δρmax = 0.17 e Å−3
2874 reflections	Δρmin = −0.17 e Å−3
209 parameters	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
2 restraints	Extinction coefficient: 0.019 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983)
Secondary atom site location: difference Fourier map

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
N3	0.3294 (7)	0.4546 (5)	0.0999 (2)	0.0434 (11)
C4	1.0463 (12)	0.2145 (8)	0.4651 (3)	0.0578 (18)
H4A	1.0947	0.1666	0.5150	0.069*
N2	0.6027 (8)	0.4678 (5)	0.2201 (2)	0.0408 (11)
C3	1.1993 (11)	0.2058 (7)	0.4105 (3)	0.0588 (18)
H3B	1.3474	0.1561	0.4235	0.071*
C7	0.5371 (9)	0.5446 (6)	0.1421 (3)	0.0413 (14)
H7A	0.6689	0.5367	0.1120	0.050*
C8	0.3369 (10)	0.4143 (6)	0.0281 (3)	0.0436 (14)
H8A	0.4684	0.4440	0.0057	0.052*
C16	0.2483 (11)	0.9366 (7)	0.1982 (3)	0.0486 (15)
H16A	0.1265	0.9714	0.2243	0.058*
N4	−0.0186 (9)	0.2211 (7)	−0.1527 (2)	0.0604 (15)
C2	1.1242 (10)	0.2739 (7)	0.3358 (3)	0.0481 (15)
H2B	1.2222	0.2715	0.2973	0.058*
C13	0.1481 (10)	0.2988 (7)	−0.1022 (3)	0.0497 (16)
H13A	0.2775	0.3410	−0.1223	0.060*
C14	0.4741 (10)	0.7230 (6)	0.1524 (3)	0.0402 (13)
C1	0.9022 (9)	0.3453 (7)	0.3190 (3)	0.0404 (14)
C12	−0.1994 (11)	0.1565 (7)	−0.1222 (3)	0.0587 (18)
H12A	−0.3174	0.1006	−0.1564	0.070*
C6	0.8136 (10)	0.4183 (7)	0.2402 (3)	0.0443 (15)
H6A	0.9172	0.4283	0.2037	0.053*
N1	0.8360 (8)	0.2859 (7)	0.4515 (2)	0.0638 (16)
C9	0.1421 (10)	0.3216 (7)	−0.0208 (3)	0.0411 (14)
C11	−0.2194 (10)	0.1688 (7)	−0.0427 (3)	0.0555 (17)
H11A	−0.3465	0.1201	−0.0238	0.067*
C10	−0.0493 (10)	0.2540 (7)	0.0083 (3)	0.0476 (15)
H10A	−0.0625	0.2662	0.0619	0.057*
C15	0.2938 (10)	0.7702 (7)	0.1923 (3)	0.0482 (15)
H15A	0.2052	0.6919	0.2145	0.058*
C18	0.5982 (12)	0.8483 (7)	0.1210 (3)	0.0558 (16)
H18A	0.7196	0.8174	0.0938	0.067*
C5	0.7697 (10)	0.3477 (7)	0.3793 (3)	0.0495 (15)
H5A	0.6207	0.3969	0.3683	0.059*
C17	0.3808 (11)	1.0503 (8)	0.1661 (3)	0.0627 (18)
H17A	0.3474	1.1617	0.1718	0.075*
N5	0.5548 (11)	1.0099 (6)	0.1272 (3)	0.0731 (18)

	U11	U22	U33	U12	U13	U23
N3	0.051 (3)	0.040 (3)	0.039 (2)	0.001 (3)	0.008 (2)	−0.001 (2)
C4	0.063 (5)	0.062 (5)	0.042 (3)	−0.010 (4)	−0.008 (3)	0.019 (3)
N2	0.050 (3)	0.039 (3)	0.033 (2)	0.000 (3)	0.005 (2)	0.001 (2)
C3	0.046 (4)	0.055 (4)	0.069 (4)	0.001 (4)	−0.008 (3)	0.007 (3)
C7	0.043 (4)	0.044 (3)	0.038 (3)	0.002 (3)	0.010 (3)	0.002 (3)
C8	0.049 (4)	0.041 (3)	0.041 (3)	−0.001 (3)	0.010 (3)	0.003 (3)
C16	0.060 (4)	0.041 (4)	0.049 (3)	0.002 (4)	0.019 (3)	−0.006 (3)
N4	0.061 (4)	0.073 (4)	0.044 (3)	0.011 (4)	0.000 (3)	−0.013 (3)
C2	0.042 (4)	0.057 (4)	0.046 (3)	0.002 (4)	0.010 (3)	−0.006 (3)
C13	0.050 (4)	0.060 (4)	0.038 (3)	0.014 (4)	0.006 (3)	0.000 (3)
C14	0.048 (4)	0.040 (3)	0.032 (3)	0.006 (4)	0.004 (3)	0.004 (3)
C1	0.039 (4)	0.043 (3)	0.037 (3)	−0.003 (3)	0.002 (3)	0.001 (3)
C12	0.059 (5)	0.054 (4)	0.057 (4)	0.006 (4)	−0.006 (3)	−0.016 (3)
C6	0.050 (4)	0.042 (3)	0.043 (3)	0.002 (3)	0.012 (3)	−0.005 (3)
N1	0.050 (4)	0.089 (4)	0.049 (3)	−0.004 (4)	−0.001 (3)	0.015 (3)
C9	0.048 (4)	0.037 (3)	0.038 (3)	0.009 (3)	0.007 (3)	−0.001 (3)
C11	0.051 (4)	0.057 (4)	0.058 (4)	0.002 (4)	0.009 (3)	−0.009 (3)
C10	0.057 (4)	0.047 (4)	0.039 (3)	0.008 (4)	0.007 (3)	−0.003 (3)
C15	0.056 (4)	0.048 (4)	0.042 (3)	−0.017 (4)	0.014 (3)	−0.002 (3)
C18	0.058 (4)	0.054 (4)	0.061 (3)	−0.001 (4)	0.028 (3)	−0.005 (3)
C5	0.041 (4)	0.059 (4)	0.048 (3)	0.000 (4)	0.007 (3)	0.004 (3)
C17	0.089 (6)	0.043 (4)	0.061 (3)	−0.001 (4)	0.026 (4)	−0.002 (3)
N5	0.101 (5)	0.050 (4)	0.080 (3)	−0.001 (4)	0.051 (4)	0.010 (3)

N3—C8	1.269 (5)	C13—C9	1.401 (6)
N3—C7	1.472 (6)	C13—H13A	0.9300
C4—N1	1.319 (7)	C14—C15	1.378 (7)
C4—C3	1.380 (8)	C14—C18	1.394 (7)
C4—H4A	0.9300	C1—C5	1.372 (7)
N2—C6	1.262 (6)	C1—C6	1.473 (7)
N2—C7	1.454 (6)	C12—C11	1.376 (7)
C3—C2	1.383 (7)	C12—H12A	0.9300
C3—H3B	0.9300	C6—H6A	0.9300
C7—C14	1.506 (6)	N1—C5	1.319 (6)
C7—H7A	0.9800	C9—C10	1.387 (7)
C8—C9	1.476 (7)	C11—C10	1.374 (7)
C8—H8A	0.9300	C11—H11A	0.9300
C16—C17	1.363 (7)	C10—H10A	0.9300
C16—C15	1.378 (7)	C15—H15A	0.9300
C16—H16A	0.9300	C18—N5	1.339 (7)
N4—C13	1.327 (7)	C18—H18A	0.9300
N4—C12	1.338 (8)	C5—H5A	0.9300
C2—C1	1.380 (7)	C17—N5	1.324 (7)
C2—H2B	0.9300	C17—H17A	0.9300
C8—N3—C7	116.0 (4)	C5—C1—C6	121.5 (5)
N1—C4—C3	124.5 (5)	C2—C1—C6	121.3 (5)
N1—C4—H4A	117.7	N4—C12—C11	123.2 (6)
C3—C4—H4A	117.7	N4—C12—H12A	118.4
C6—N2—C7	118.0 (4)	C11—C12—H12A	118.4
C4—C3—C2	117.5 (6)	N2—C6—C1	122.6 (5)
C4—C3—H3B	121.2	N2—C6—H6A	118.7
C2—C3—H3B	121.2	C1—C6—H6A	118.7
N2—C7—N3	107.1 (4)	C5—N1—C4	116.1 (5)
N2—C7—C14	109.5 (4)	C10—C9—C13	116.8 (5)
N3—C7—C14	110.0 (4)	C10—C9—C8	124.5 (5)
N2—C7—H7A	110.1	C13—C9—C8	118.7 (5)
N3—C7—H7A	110.1	C12—C11—C10	119.2 (6)
C14—C7—H7A	110.1	C12—C11—H11A	120.4
N3—C8—C9	121.7 (5)	C10—C11—H11A	120.4
N3—C8—H8A	119.1	C11—C10—C9	119.4 (5)
C9—C8—H8A	119.1	C11—C10—H10A	120.3
C17—C16—C15	120.4 (6)	C9—C10—H10A	120.3
C17—C16—H16A	119.8	C16—C15—C14	118.2 (5)
C15—C16—H16A	119.8	C16—C15—H15A	120.9
C13—N4—C12	117.0 (5)	C14—C15—H15A	120.9
C1—C2—C3	119.2 (5)	N5—C18—C14	124.5 (6)
C1—C2—H2B	120.4	N5—C18—H18A	117.7
C3—C2—H2B	120.4	C14—C18—H18A	117.7
N4—C13—C9	124.4 (5)	N1—C5—C1	125.4 (6)
N4—C13—H13A	117.8	N1—C5—H5A	117.3
C9—C13—H13A	117.8	C1—C5—H5A	117.3
C15—C14—C18	117.2 (5)	N5—C17—C16	123.2 (6)
C15—C14—C7	122.4 (5)	N5—C17—H17A	118.4
C18—C14—C7	120.3 (5)	C16—C17—H17A	118.4
C5—C1—C2	117.2 (5)	C17—N5—C18	116.4 (6)
N1—C4—C3—C2	−1.4 (9)	N4—C13—C9—C10	1.6 (8)
C6—N2—C7—N3	125.7 (5)	N4—C13—C9—C8	−178.4 (5)
C6—N2—C7—C14	−115.1 (5)	N3—C8—C9—C10	−7.8 (8)
C8—N3—C7—N2	−133.5 (5)	N3—C8—C9—C13	172.3 (5)
C8—N3—C7—C14	107.6 (5)	N4—C12—C11—C10	1.3 (9)
C7—N3—C8—C9	179.1 (4)	C12—C11—C10—C9	−1.8 (8)
C4—C3—C2—C1	−0.5 (8)	C13—C9—C10—C11	0.4 (7)
C12—N4—C13—C9	−2.2 (8)	C8—C9—C10—C11	−179.5 (5)
N2—C7—C14—C15	−59.2 (6)	C17—C16—C15—C14	−0.7 (8)
N3—C7—C14—C15	58.3 (6)	C18—C14—C15—C16	0.1 (7)
N2—C7—C14—C18	121.2 (5)	C7—C14—C15—C16	−179.6 (5)
N3—C7—C14—C18	−121.4 (5)	C15—C14—C18—N5	0.3 (9)
C3—C2—C1—C5	1.5 (8)	C7—C14—C18—N5	180.0 (6)
C3—C2—C1—C6	−179.6 (5)	C4—N1—C5—C1	−1.1 (9)
C13—N4—C12—C11	0.6 (9)	C2—C1—C5—N1	−0.7 (9)
C7—N2—C6—C1	177.3 (4)	C6—C1—C5—N1	−179.7 (6)
C5—C1—C6—N2	−9.1 (8)	C15—C16—C17—N5	0.9 (9)
C2—C1—C6—N2	171.9 (6)	C16—C17—N5—C18	−0.5 (9)
C3—C4—N1—C5	2.2 (9)	C14—C18—N5—C17	−0.1 (9)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18A···N1i	0.93	2.74	3.552 (7)	146
C17—H17A···N3ii	0.93	2.66	3.456 (7)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18A⋯N1i	0.93	2.74	3.552 (7)	146
C17—H17A⋯N3ii	0.93	2.66	3.456 (7)	144

Symmetry codes: (i) ; (ii) .