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

Xu, Z.; Sun, Y.; Wang, Q.

doi:10.1107/S1600536811034520

organic compounds

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Volume 67| Part 9| September 2011| Page o2457

doi:10.1107/S1600536811034520

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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

Zhouqing Xu,^a Yanchun Sun ^b and Qiang Wang ^a ^*

^aDepartment of Physical Chemistry, Henan Polytechnic University, Jiao Zuo 454000, People's Republic of China, and ^bDepartment of Medicine, Hebi College of Vocation and Technology, He Bi 458030, People's Republic of China
^*Correspondence e-mail: wangqiang@hpu.edu.cn

(Received 18 August 2011; accepted 22 August 2011; online 27 August 2011)

In the title molecule, C₁₇H₁₁N₁₁, 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 intermolecular 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_r = 369.37
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.064
wR(F²) = 0.125
S = 1.22
3204 reflections
259 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.18 e Å⁻³

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) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811034520/ng5216sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811034520/ng5216Isup3.cml

checkCIF report

Comment top

Compounds containing triazole subunits have been intensively studied owing to diverse biological properties and also to the ease of complexation (Zhang et al., 2010; Fischer, 2007; Ouellette et al., 2007). In continuation with a recent study (Xu et al., 2011), we report the title compound (Scheme I), 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.

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 (Fig. 1). The crystal packing consists of a three-dimensional net structure generated by intermolecular N—H···N hydrogen bonds. The crystal structure is further consolidated by π–π stacking [centroid–centroid distances = 3.599 (10) and 4.769 (13) Å].

Related literature top

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 top

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 was prepared according to Browne (1975) and Klingele & Brooker (2004). The crystals suitable for crystallographic analysis were grown by recrystallization from DMF and ethanol solution as colorless prism.

Computing details top

Data collection: APEX2 (Bruker, 2003); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines, viewed down the a axis.

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 top

Crystal data top

C₁₇H₁₁N₁₁	F(000) = 760
M_r = 369.37	D_x = 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

Data collection top

Bruker SMART APEX diffractometer	3204 independent reflections
Radiation source: fine-focus sealed tube	2896 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
ω scans	θ_max = 26.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −13→13
T_min = 0.905, T_max = 1.000	k = −16→16
17628 measured reflections	l = −13→14

Refinement top

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(F_o²) + (0.042P)² + 0.4894P] where P = (F_o² + 2F_c²)/3
3204 reflections	(Δ/σ)_max < 0.001
259 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₇H₁₁N₁₁	V = 1639.2 (6) Å³
M_r = 369.37	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.751 (2) Å	µ = 0.10 mm⁻¹
b = 13.721 (3) Å	T = 293 K
c = 11.385 (2) Å	0.20 × 0.20 × 0.20 mm
β = 102.57 (3)°

Data collection top

Bruker SMART APEX diffractometer	3204 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2896 reflections with I > 2σ(I)
T_min = 0.905, T_max = 1.000	R_int = 0.048
17628 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.22	Δρ_max = 0.17 e Å⁻³
3204 reflections	Δρ_min = −0.18 e Å⁻³
259 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) −x+2, y+1/2, −z+3/2; (ii) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₁N₁₁
M_r	369.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	10.751 (2), 13.721 (3), 11.385 (2)
β (°)	102.57 (3)
V (Å³)	1639.2 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.905, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	17628, 3204, 2896
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.125, 1.22
No. of reflections	3204
No. of parameters	259
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.18

Computer programs: APEX2 (Bruker, 2003), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) −x+2, y+1/2, −z+3/2; (ii) x, −y+1/2, z+1/2.

Acknowledgements

This work was supported by the Natural Science Research Programme of the Education Department of Henan Province (grant No. 2011 A150015), the Henan Polytechnic University Foundation for Youth (grant No. P051102) and the Henan Polytechnic University Foundation for Doctoral Teachers (grant No. B2010-65). The authors thank Dr D. Zhao for assistance with the data analysis.

References

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Volume 67| Part 9| September 2011| Page o2457

doi:10.1107/S1600536811034520

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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