2-(5-{6-[5-(Pyrazin-2-yl)-1H-1,2,4-triazol-3-yl]pyridin-2-yl}-1H-1,2,4-triazol-3-yl)pyrazine.

In the title mol-ecule, C(17)H(11)N(11), the five rings are almost coplanar [maxium deviation 0.1949 (1) Å]. The dihedral angles between the two pyrazine rings and the two triazole rings are 1.52 (4) and 2.51 (5)°, respectively. The central pyridine ring forms dihedral angles of 5.57 (1) and 1.71 (1)° with the two triazole rings. The crystal packing consists of a three-dimensional network structure generated by inter-molecular N-H⋯N hydrogen bonds. The crystal structure is further consolidated by π-π stacking [centroid-to-centroid distances 3.599 (10) and 4.769 (13) Å].

Related literature

For the applications of compounds containing triazole subunits, see: Zhang et al. (2010 ▶); Fischer (2007 ▶); Ouellette et al. (2007 ▶). For a recent study, see: Xu et al. (2011 ▶). For the synthesis, see: Browne (1975 ▶); Klingele & Brooker (2004 ▶).

Experimental

Crystal data

C17H11N11

M = 369.37

Monoclinic,

a = 10.751 (2) Å

b = 13.721 (3) Å

c = 11.385 (2) Å

β = 102.57 (3)°

V = 1639.2 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.905, T max = 1.000

17628 measured reflections

3204 independent reflections

2896 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.125

S = 1.22

3204 reflections

259 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; 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 datablock(s) I, global. DOI: 10.1107/S1600536811034520/ng5216sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034520/ng5216Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811034520/ng5216Isup3.cml

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

C17H11N11	F(000) = 760
Mr = 369.37	Dx = 1.497 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4186 reflections
a = 10.751 (2) Å	θ = 1.9–27.1°
b = 13.721 (3) Å	µ = 0.10 mm−1
c = 11.385 (2) Å	T = 293 K
β = 102.57 (3)°	Prism, colourless
V = 1639.2 (6) Å3	0.20 × 0.20 × 0.20 mm
Z = 4

Bruker SMART APEX diffractometer	3204 independent reflections
Radiation source: fine-focus sealed tube	2896 reflections with I > 2σ(I)
graphite	Rint = 0.048
ω scans	θmax = 26.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −13→13
Tmin = 0.905, Tmax = 1.000	k = −16→16
17628 measured reflections	l = −13→14

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.22	w = 1/[σ2(Fo2) + (0.042P)2 + 0.4894P] where P = (Fo2 + 2Fc2)/3
3204 reflections	(Δ/σ)max < 0.001
259 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.18 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
N7	0.80331 (17)	0.04695 (12)	0.48120 (15)	0.0328 (4)
N3	0.65636 (17)	0.55996 (12)	0.51910 (15)	0.0338 (4)
N6	0.74831 (16)	0.30212 (12)	0.54161 (15)	0.0324 (4)
N1	0.67651 (19)	0.77043 (13)	0.71611 (16)	0.0429 (5)
N4	0.73685 (19)	0.56738 (13)	0.71244 (16)	0.0391 (5)
H35	0.764 (2)	0.5883 (17)	0.791 (2)	0.047*
N5	0.75302 (19)	0.47317 (13)	0.68211 (16)	0.0412 (5)
C19	0.9825 (2)	−0.15553 (16)	0.66349 (19)	0.0382 (5)
H19	1.0142	−0.1196	0.7328	0.046*
C1	0.90635 (19)	−0.10896 (14)	0.56482 (18)	0.0308 (5)
N9	0.91344 (18)	0.04313 (13)	0.67510 (16)	0.0401 (5)
C2	0.64501 (19)	0.72112 (15)	0.61304 (18)	0.0308 (5)
C3	0.6795 (2)	0.61778 (15)	0.61474 (18)	0.0311 (5)
N8	0.86523 (18)	0.13308 (13)	0.64512 (17)	0.0387 (5)
H34	0.887 (2)	0.1853 (17)	0.702 (2)	0.046*
C4	0.87349 (19)	−0.00581 (14)	0.57292 (18)	0.0307 (5)
N13	0.86310 (17)	−0.15592 (13)	0.46165 (16)	0.0365 (4)
N12	1.01117 (18)	−0.24929 (13)	0.66175 (17)	0.0412 (5)
C7	0.6963 (2)	0.38491 (14)	0.48938 (18)	0.0311 (5)
C8	0.8012 (2)	0.13480 (15)	0.52990 (18)	0.0307 (5)
C9	0.7024 (2)	0.47236 (14)	0.56489 (18)	0.0318 (5)
C10	0.6893 (2)	0.22266 (16)	0.34824 (19)	0.0368 (5)
H10	0.6895	0.1666	0.3023	0.044*
C23	0.6418 (3)	0.86407 (17)	0.7106 (2)	0.0495 (6)
H23	0.6623	0.9015	0.7802	0.059*
C12	0.74258 (19)	0.22300 (14)	0.47064 (18)	0.0306 (5)
C18	0.8945 (2)	−0.25062 (16)	0.4604 (2)	0.0406 (6)
H18	0.8673	−0.2861	0.3899	0.049*
N2	0.54644 (19)	0.85860 (14)	0.50318 (17)	0.0447 (5)
C13	0.9652 (2)	−0.29676 (16)	0.5592 (2)	0.0410 (6)
H13	0.9816	−0.3631	0.5548	0.049*
C14	0.6359 (2)	0.30832 (16)	0.2967 (2)	0.0393 (5)
H14	0.5992	0.3110	0.2149	0.047*
C15	0.5771 (2)	0.90720 (17)	0.6064 (2)	0.0468 (6)
H15	0.5541	0.9724	0.6081	0.056*
C16	0.6376 (2)	0.38988 (15)	0.36799 (19)	0.0363 (5)
H16	0.5999	0.4476	0.3352	0.044*
C22	0.5812 (2)	0.76535 (16)	0.5078 (2)	0.0396 (5)
H22	0.5619	0.7285	0.4377	0.048*

	U11	U22	U33	U12	U13	U23
N7	0.0419 (10)	0.0238 (9)	0.0304 (9)	0.0030 (8)	0.0026 (8)	0.0000 (7)
N3	0.0461 (11)	0.0226 (9)	0.0304 (9)	0.0026 (8)	0.0033 (8)	−0.0003 (7)
N6	0.0418 (10)	0.0226 (9)	0.0314 (9)	0.0008 (8)	0.0049 (8)	−0.0015 (7)
N1	0.0583 (12)	0.0295 (10)	0.0348 (10)	0.0045 (9)	−0.0030 (9)	−0.0043 (8)
N4	0.0593 (13)	0.0247 (10)	0.0288 (10)	0.0048 (9)	−0.0001 (9)	−0.0029 (8)
N5	0.0619 (13)	0.0242 (10)	0.0334 (10)	0.0060 (9)	0.0013 (9)	−0.0006 (8)
C19	0.0474 (13)	0.0293 (12)	0.0336 (12)	−0.0008 (10)	−0.0007 (10)	0.0024 (9)
C1	0.0340 (11)	0.0257 (11)	0.0312 (11)	−0.0026 (9)	0.0034 (9)	−0.0002 (8)
N9	0.0505 (11)	0.0277 (10)	0.0363 (10)	0.0023 (8)	−0.0033 (9)	−0.0028 (8)
C2	0.0363 (11)	0.0246 (11)	0.0305 (11)	0.0020 (9)	0.0048 (9)	0.0004 (8)
C3	0.0376 (11)	0.0258 (11)	0.0281 (11)	0.0016 (9)	0.0032 (9)	0.0000 (8)
N8	0.0518 (12)	0.0241 (10)	0.0359 (11)	0.0015 (8)	0.0002 (9)	−0.0050 (8)
C4	0.0373 (12)	0.0230 (10)	0.0300 (11)	−0.0009 (9)	0.0032 (9)	0.0004 (8)
N13	0.0445 (11)	0.0278 (10)	0.0345 (10)	0.0011 (8)	0.0025 (8)	−0.0006 (8)
N12	0.0453 (11)	0.0314 (11)	0.0427 (11)	0.0023 (9)	0.0003 (9)	0.0073 (9)
C7	0.0372 (11)	0.0244 (11)	0.0307 (11)	−0.0010 (9)	0.0052 (9)	0.0010 (8)
C8	0.0367 (11)	0.0248 (10)	0.0299 (11)	−0.0012 (9)	0.0056 (9)	−0.0023 (8)
C9	0.0401 (12)	0.0230 (10)	0.0302 (11)	0.0009 (9)	0.0030 (9)	0.0005 (8)
C10	0.0468 (13)	0.0270 (12)	0.0355 (12)	0.0001 (10)	0.0068 (10)	−0.0055 (9)
C23	0.0717 (17)	0.0291 (13)	0.0412 (13)	0.0063 (12)	−0.0017 (12)	−0.0085 (10)
C12	0.0358 (11)	0.0239 (11)	0.0317 (11)	−0.0007 (9)	0.0065 (9)	−0.0023 (8)
C18	0.0488 (13)	0.0291 (12)	0.0399 (13)	0.0030 (10)	0.0004 (11)	−0.0065 (10)
N2	0.0603 (13)	0.0323 (11)	0.0390 (11)	0.0109 (9)	0.0051 (10)	0.0030 (8)
C13	0.0437 (13)	0.0267 (12)	0.0493 (14)	0.0019 (10)	0.0031 (11)	0.0021 (10)
C14	0.0501 (14)	0.0348 (13)	0.0297 (12)	−0.0002 (10)	0.0018 (10)	0.0000 (9)
C15	0.0606 (16)	0.0272 (12)	0.0493 (14)	0.0089 (11)	0.0049 (12)	−0.0014 (11)
C16	0.0470 (13)	0.0261 (11)	0.0333 (12)	0.0014 (10)	0.0031 (10)	0.0022 (9)
C22	0.0515 (14)	0.0296 (12)	0.0354 (12)	0.0064 (10)	0.0041 (11)	−0.0025 (9)

N7—C8	1.329 (2)	N8—H34	0.96 (2)
N7—C4	1.357 (3)	N13—C18	1.343 (3)
N3—C3	1.326 (2)	N12—C13	1.334 (3)
N3—C9	1.360 (2)	C7—C16	1.390 (3)
N6—C7	1.346 (2)	C7—C9	1.469 (3)
N6—C12	1.347 (2)	C8—C12	1.460 (3)
N1—C2	1.333 (3)	C10—C14	1.381 (3)
N1—C23	1.336 (3)	C10—C12	1.387 (3)
N4—C3	1.340 (3)	C10—H10	0.9300
N4—N5	1.359 (2)	C23—C15	1.372 (3)
N4—H35	0.92 (2)	C23—H23	0.9300
N5—C9	1.327 (3)	C18—C13	1.368 (3)
C19—N12	1.324 (3)	C18—H18	0.9300
C19—C1	1.393 (3)	N2—C15	1.329 (3)
C19—H19	0.9300	N2—C22	1.331 (3)
C1—N13	1.332 (3)	C13—H13	0.9300
C1—C4	1.467 (3)	C14—C16	1.380 (3)
N9—C4	1.331 (3)	C14—H14	0.9300
N9—N8	1.353 (2)	C15—H15	0.9300
C2—C22	1.384 (3)	C16—H16	0.9300
C2—C3	1.465 (3)	C22—H22	0.9300
N8—C8	1.342 (3)
C8—N7—C4	102.71 (16)	N7—C8—C12	127.14 (18)
C3—N3—C9	103.07 (16)	N8—C8—C12	122.96 (18)
C7—N6—C12	117.06 (17)	N5—C9—N3	114.43 (18)
C2—N1—C23	115.61 (19)	N5—C9—C7	123.46 (18)
C3—N4—N5	109.94 (17)	N3—C9—C7	122.10 (18)
C3—N4—H35	129.4 (15)	C14—C10—C12	117.8 (2)
N5—N4—H35	120.7 (15)	C14—C10—H10	121.1
C9—N5—N4	102.49 (17)	C12—C10—H10	121.1
N12—C19—C1	122.1 (2)	N1—C23—C15	122.6 (2)
N12—C19—H19	118.9	N1—C23—H23	118.7
C1—C19—H19	118.9	C15—C23—H23	118.7
N13—C1—C19	121.37 (19)	N6—C12—C10	124.10 (19)
N13—C1—C4	118.67 (18)	N6—C12—C8	115.60 (18)
C19—C1—C4	119.95 (18)	C10—C12—C8	120.26 (18)
C4—N9—N8	101.92 (17)	N13—C18—C13	122.4 (2)
N1—C2—C22	121.49 (19)	N13—C18—H18	118.8
N1—C2—C3	117.69 (18)	C13—C18—H18	118.8
C22—C2—C3	120.82 (18)	C15—N2—C22	115.70 (19)
N3—C3—N4	110.06 (18)	N12—C13—C18	121.8 (2)
N3—C3—C2	124.49 (18)	N12—C13—H13	119.1
N4—C3—C2	125.44 (18)	C18—C13—H13	119.1
C8—N8—N9	110.45 (17)	C16—C14—C10	119.3 (2)
C8—N8—H34	129.9 (14)	C16—C14—H14	120.4
N9—N8—H34	119.3 (14)	C10—C14—H14	120.4
N9—C4—N7	115.03 (18)	N2—C15—C23	122.0 (2)
N9—C4—C1	120.37 (18)	N2—C15—H15	119.0
N7—C4—C1	124.60 (17)	C23—C15—H15	119.0
C1—N13—C18	115.89 (18)	C14—C16—C7	119.3 (2)
C19—N12—C13	116.37 (19)	C14—C16—H16	120.3
N6—C7—C16	122.38 (19)	C7—C16—H16	120.3
N6—C7—C9	118.00 (18)	N2—C22—C2	122.5 (2)
C16—C7—C9	119.62 (18)	N2—C22—H22	118.7
N7—C8—N8	109.88 (18)	C2—C22—H22	118.7

D—H···A	D—H	H···A	D···A	D—H···A
N8—H34···N12i	0.96 (2)	1.92 (2)	2.817 (3)	155 (2)
N4—H35···N13ii	0.92 (2)	2.21 (2)	3.113 (3)	167 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N8—H34⋯N12i	0.96 (2)	1.92 (2)	2.817 (3)	155 (2)
N4—H35⋯N13ii	0.92 (2)	2.21 (2)	3.113 (3)	167 (2)

Symmetry codes: (i) ; (ii) .