5-(Pyridin-2-yl)-3,3'-bi(1H-1,2,4-triazole).

In the title mol-ecule, C(9)H(7)N(7), the two triazole rings are twisted by an angle of 3.8 (5)°; the central triazole ring is twisted by 32.3 (6)° with respect to the pyridyl ring. The crystal packing consists of layers generated by inter-molecular N-H⋯N hydrogen bonds.

Related literature

For related structures, see: Mai et al. (2009 ▶); Zhang et al. (2010 ▶). For the synthesis, see: Potts (1960 ▶); Wiley & Hart (1953 ▶).

Experimental

Crystal data

C9H7N7

M = 213.22

Monoclinic,

a = 12.372 (3) Å

b = 7.5361 (15) Å

c = 10.007 (2) Å

β = 93.670 (4)°

V = 931.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.24 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.975, T max = 0.979

5150 measured reflections

1832 independent reflections

1072 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.156

S = 0.94

1832 reflections

154 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAIn class="Chemical">NT; 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/S1600536811027449/ng5195sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811027449/ng5195Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811027449/ng5195Isup3.cml

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

C9H7N7	F(000) = 440
Mr = 213.22	Dx = 1.521 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.372 (3) Å	Cell parameters from 6322 reflections
b = 7.5361 (15) Å	θ = 2.0–27.9°
c = 10.007 (2) Å	µ = 0.11 mm−1
β = 93.670 (4)°	T = 296 K
V = 931.1 (3) Å3	Block, colourless
Z = 4	0.24 × 0.20 × 0.20 mm

Bruker SMART APEX diffractometer	1832 independent reflections
Radiation source: fine-focus sealed tube	1072 reflections with I > 2σ(I)
graphite	Rint = 0.055
ω scan	θmax = 26.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→12
Tmin = 0.975, Tmax = 0.979	k = −9→9
5150 measured reflections	l = −12→12

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) = 0.156	w = 1/[σ2(Fo2) + (0.0843P)2] where P = (Fo2 + 2Fc2)/3
S = 0.94	(Δ/σ)max < 0.001
1832 reflections	Δρmax = 0.26 e Å−3
154 parameters	Δρmin = −0.22 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.018 (5)

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
N4	0.22980 (16)	0.2080 (3)	0.46400 (19)	0.0342 (6)
N6	0.23958 (18)	0.2161 (3)	0.6818 (2)	0.0370 (6)
N2	0.07056 (18)	−0.2247 (3)	0.2744 (2)	0.0394 (6)
N3	0.06963 (16)	−0.2067 (3)	0.4914 (2)	0.0367 (6)
N5	0.18243 (17)	0.0672 (3)	0.6502 (2)	0.0372 (6)
C1	0.1252 (2)	−0.0720 (3)	0.4381 (2)	0.0311 (6)
N1	0.12802 (17)	−0.0763 (3)	0.3067 (2)	0.0387 (6)
C2	0.26642 (19)	0.2993 (3)	0.5708 (2)	0.0329 (6)
C3	0.1792 (2)	0.0682 (3)	0.5182 (2)	0.0324 (6)
C4	0.0376 (2)	−0.2994 (3)	0.3838 (3)	0.0388 (7)
H4	−0.0028	−0.4034	0.3851	0.047*
N7	0.40073 (18)	0.4877 (3)	0.6744 (2)	0.0446 (6)
C5	0.4476 (2)	0.7649 (4)	0.5774 (3)	0.0543 (8)
H5	0.4900	0.8669	0.5828	0.065*
C6	0.3285 (2)	0.4650 (3)	0.5701 (2)	0.0343 (6)
C7	0.3123 (2)	0.5856 (3)	0.4680 (3)	0.0417 (7)
H7	0.2620	0.5636	0.3969	0.050*
C8	0.3724 (2)	0.7401 (4)	0.4729 (3)	0.0531 (8)
H8	0.3618	0.8257	0.4064	0.064*
C9	0.4592 (2)	0.6366 (4)	0.6738 (3)	0.0547 (8)
H9	0.5113	0.6543	0.7437	0.066*
H1	0.249 (2)	0.252 (4)	0.776 (4)	0.088 (11)*
H2	0.062 (2)	−0.262 (4)	0.179 (3)	0.081 (11)*

	U11	U22	U33	U12	U13	U23
N4	0.0456 (13)	0.0338 (12)	0.0232 (11)	0.0004 (10)	0.0025 (9)	−0.0019 (9)
N6	0.0522 (14)	0.0363 (13)	0.0222 (12)	−0.0021 (11)	0.0009 (10)	−0.0032 (10)
N2	0.0552 (15)	0.0364 (13)	0.0262 (13)	0.0000 (11)	−0.0009 (10)	−0.0045 (10)
N3	0.0461 (13)	0.0346 (13)	0.0291 (12)	−0.0022 (10)	−0.0010 (10)	0.0007 (9)
N5	0.0483 (14)	0.0354 (13)	0.0276 (12)	−0.0030 (10)	−0.0001 (10)	−0.0029 (9)
C1	0.0411 (15)	0.0302 (14)	0.0220 (13)	0.0052 (11)	0.0015 (11)	0.0005 (11)
N1	0.0539 (15)	0.0371 (13)	0.0248 (12)	−0.0014 (11)	0.0011 (10)	−0.0023 (9)
C2	0.0402 (15)	0.0325 (15)	0.0257 (14)	0.0036 (12)	0.0003 (11)	−0.0006 (11)
C3	0.0422 (15)	0.0304 (14)	0.0246 (13)	0.0019 (11)	0.0022 (11)	−0.0009 (11)
C4	0.0485 (17)	0.0348 (15)	0.0329 (15)	0.0001 (12)	−0.0002 (12)	−0.0018 (12)
N7	0.0514 (14)	0.0434 (14)	0.0379 (14)	−0.0093 (12)	−0.0042 (11)	−0.0014 (11)
C5	0.061 (2)	0.0467 (19)	0.056 (2)	−0.0133 (15)	0.0099 (16)	−0.0040 (16)
C6	0.0399 (15)	0.0334 (15)	0.0299 (14)	0.0039 (12)	0.0041 (11)	−0.0020 (11)
C7	0.0461 (17)	0.0409 (16)	0.0380 (16)	0.0001 (13)	0.0017 (12)	0.0001 (13)
C8	0.057 (2)	0.0426 (17)	0.060 (2)	0.0022 (15)	0.0098 (16)	0.0114 (16)
C9	0.057 (2)	0.058 (2)	0.0487 (19)	−0.0165 (16)	−0.0029 (15)	−0.0037 (16)

N4—C2	1.326 (3)	C2—C6	1.467 (3)
N4—C3	1.356 (3)	C4—H4	0.9300
N6—C2	1.336 (3)	N7—C9	1.336 (3)
N6—N5	1.353 (3)	N7—C6	1.341 (3)
N6—H1	0.98 (4)	C5—C9	1.366 (4)
N2—C4	1.319 (3)	C5—C8	1.368 (4)
N2—N1	1.353 (3)	C5—H5	0.9300
N2—H2	0.99 (3)	C6—C7	1.372 (4)
N3—C4	1.322 (3)	C7—C8	1.380 (4)
N3—C1	1.354 (3)	C7—H7	0.9300
N5—C3	1.319 (3)	C8—H8	0.9300
C1—N1	1.318 (3)	C9—H9	0.9300
C1—C3	1.461 (3)
C2—N4—C3	102.9 (2)	N2—C4—N3	111.0 (2)
C2—N6—N5	110.4 (2)	N2—C4—H4	124.5
C2—N6—H1	131 (2)	N3—C4—H4	124.5
N5—N6—H1	119 (2)	C9—N7—C6	115.9 (2)
C4—N2—N1	109.8 (2)	C9—C5—C8	118.6 (3)
C4—N2—H2	131.2 (19)	C9—C5—H5	120.7
N1—N2—H2	118.9 (19)	C8—C5—H5	120.7
C4—N3—C1	102.0 (2)	N7—C6—C7	123.6 (2)
C3—N5—N6	102.2 (2)	N7—C6—C2	115.3 (2)
N1—C1—N3	114.9 (2)	C7—C6—C2	121.1 (2)
N1—C1—C3	121.6 (2)	C6—C7—C8	118.7 (3)
N3—C1—C3	123.5 (2)	C6—C7—H7	120.7
C1—N1—N2	102.3 (2)	C8—C7—H7	120.7
N4—C2—N6	109.7 (2)	C5—C8—C7	118.7 (3)
N4—C2—C6	126.1 (2)	C5—C8—H8	120.6
N6—C2—C6	124.2 (2)	C7—C8—H8	120.6
N5—C3—N4	114.8 (2)	N7—C9—C5	124.5 (3)
N5—C3—C1	121.9 (2)	N7—C9—H9	117.8
N4—C3—C1	123.3 (2)	C5—C9—H9	117.8
C2—N6—N5—C3	0.7 (3)	N1—C1—C3—N4	4.1 (4)
C4—N3—C1—N1	0.6 (3)	N3—C1—C3—N4	−176.4 (2)
C4—N3—C1—C3	−179.1 (2)	N1—N2—C4—N3	0.5 (3)
N3—C1—N1—N2	−0.3 (3)	C1—N3—C4—N2	−0.6 (3)
C3—C1—N1—N2	179.4 (2)	C9—N7—C6—C7	−0.9 (4)
C4—N2—N1—C1	−0.2 (3)	C9—N7—C6—C2	178.9 (2)
C3—N4—C2—N6	0.6 (3)	N4—C2—C6—N7	−147.8 (3)
C3—N4—C2—C6	179.8 (2)	N6—C2—C6—N7	31.2 (3)
N5—N6—C2—N4	−0.9 (3)	N4—C2—C6—C7	32.0 (4)
N5—N6—C2—C6	180.0 (2)	N6—C2—C6—C7	−149.0 (2)
N6—N5—C3—N4	−0.3 (3)	N7—C6—C7—C8	−0.8 (4)
N6—N5—C3—C1	179.4 (2)	C2—C6—C7—C8	179.5 (2)
C2—N4—C3—N5	−0.2 (3)	C9—C5—C8—C7	−0.9 (5)
C2—N4—C3—C1	−179.9 (2)	C6—C7—C8—C5	1.7 (4)
N1—C1—C3—N5	−175.6 (2)	C6—N7—C9—C5	1.7 (4)
N3—C1—C3—N5	3.9 (4)	C8—C5—C9—N7	−0.9 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N6—H1···N4i	0.98 (4)	1.93 (4)	2.891 (3)	165 (3)
N2—H2···N3ii	0.99 (3)	1.90 (4)	2.878 (3)	167 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H1⋯N4i	0.98 (4)	1.93 (4)	2.891 (3)	165 (3)
N2—H2⋯N3ii	0.99 (3)	1.90 (4)	2.878 (3)	167 (3)

Symmetry codes: (i) ; (ii) .