Crystal structure of 2-[bis(1H-pyrazol-1-yl)meth-yl]pyridine.

The title compound, C12H11N5, was synthesized as a potential tridentate ligand to make catalytic metal complexes. The dihedral angle between the pyrazolyl rings is 67.9 (1)°. The most prominent feature in the crystal packing are C-H⋯N hydrogen-bonding inter-actions that link the mol-ecules into a supra-molecular tape along the b-axis direction.

Related literature

For the synthesis of the title compound, see: Park et al. (2015 ▸); Hoffmann et al. (2010 ▸). For metal complexes of the similar ligands, see: Anderson et al. (2000 ▸); Liu et al. (2011 ▸); Xiao et al. (2012 ▸). For potential applications of similar ligands in catalysis, see: Park et al. (2015 ▸); Zhang et al. (2009 ▸).

Experimental

Crystal data

C12H11N5

M = 225.26

Triclinic,

a = 7.5723 (3) Å

b = 8.6376 (3) Å

c = 9.7354 (5) Å

α = 97.539 (2)°

β = 106.123 (4)°

γ = 105.510 (5)°

V = 574.73 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 173 K

0.26 × 0.24 × 0.09 mm

Data collection

Bruker SMART CCD area-detector diffractometer

18045 measured reflections

2870 independent reflections

1813 reflections with I > 2σ(I)

R int = 0.089

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.123

S = 0.98

2870 reflections

153 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.26 e Å−3

Data collection: SMART (Bruker, 2002 ▸); cell refinement: SAINT (Bruker, 2002 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: publCIF (Westrip,2010 ▸).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989015013195/tk5373sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015013195/tk5373Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015013195/tk5373Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015013195/tk5373fig1.tif

Mol­ecular structure of the title compound, showing the atom-numbering scheme and 30% probability displacement ellipsoids.

Click here for additional data file.

b . DOI: 10.1107/S2056989015013195/tk5373fig2.tif

Part of the crystal structure of the title compound, showing supra­molecular tapes aligned along the b axis and sustained by C—H⋯N hydrogen bonds (dashed lines).

CCDC reference: 1411603

Additional supporting information: crystallographic information; 3D view; checkCIF report

C12H11N5	Z = 2
Mr = 225.26	F(000) = 236
Triclinic, P1	Dx = 1.302 Mg m−3
a = 7.5723 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.6376 (3) Å	Cell parameters from 2704 reflections
c = 9.7354 (5) Å	θ = 2.2–22.9°
α = 97.539 (2)°	µ = 0.09 mm−1
β = 106.123 (4)°	T = 173 K
γ = 105.510 (5)°	Plate, colourless
V = 574.73 (5) Å3	0.26 × 0.24 × 0.09 mm

Bruker SMART CCD area-detector diffractometer	Rint = 0.089
Radiation source: fine-focus sealed tube	θmax = 28.4°, θmin = 2.2°
φ and ω scans	h = −10→10
18045 measured reflections	k = −11→11
2870 independent reflections	l = −12→13
1813 reflections with I > 2σ(I)

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047	H-atom parameters constrained
wR(F2) = 0.123	w = 1/[σ2(Fo2) + (0.0585P)2] where P = (Fo2 + 2Fc2)/3
S = 0.98	(Δ/σ)max < 0.001
2870 reflections	Δρmax = 0.32 e Å−3
153 parameters	Δρmin = −0.26 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.

	x	y	z	Uiso*/Ueq
C1	0.2525 (2)	0.40769 (18)	0.78430 (15)	0.0249 (3)
H1	0.3386	0.3778	0.8644	0.030*
N2	0.05923 (18)	0.35498 (16)	0.79587 (13)	0.0289 (3)
N3	−0.09589 (19)	0.34989 (18)	0.68237 (15)	0.0373 (4)
C4	−0.2452 (3)	0.3038 (2)	0.7301 (2)	0.0421 (4)
H4	−0.3725	0.2901	0.6753	0.051*
C5	−0.1886 (3)	0.2781 (2)	0.8731 (2)	0.0488 (4)
H5	−0.2673	0.2452	0.9292	0.059*
C6	0.0106 (3)	0.3128 (2)	0.91191 (18)	0.0382 (4)
H6	0.0940	0.3078	1.0004	0.046*
N7	0.32364 (18)	0.58610 (15)	0.80514 (12)	0.0268 (3)
N8	0.50866 (18)	0.66766 (16)	0.89361 (13)	0.0311 (3)
C9	0.5303 (3)	0.8249 (2)	0.89025 (18)	0.0370 (4)
H9	0.6438	0.9111	0.9418	0.044*
C10	0.3645 (3)	0.8456 (2)	0.80116 (18)	0.0420 (5)
H10	0.3457	0.9437	0.7819	0.050*
C11	0.2343 (3)	0.6900 (2)	0.74763 (18)	0.0382 (4)
H11	0.1080	0.6612	0.6837	0.046*
C12	0.2556 (2)	0.31567 (18)	0.64180 (15)	0.0237 (3)
N13	0.24020 (19)	0.15718 (16)	0.64034 (14)	0.0323 (3)
C14	0.2372 (3)	0.0666 (2)	0.51714 (19)	0.0405 (4)
H14	0.2239	−0.0441	0.5137	0.049*
C15	0.2520 (3)	0.1246 (2)	0.3968 (2)	0.0456 (5)
H15	0.2493	0.0558	0.3138	0.055*
C16	0.2709 (3)	0.2866 (2)	0.40071 (18)	0.0421 (4)
H16	0.2829	0.3305	0.3202	0.050*
C17	0.2721 (2)	0.3854 (2)	0.52497 (16)	0.0326 (4)
H17	0.2837	0.4960	0.5294	0.039*

	U11	U22	U33	U12	U13	U23
C1	0.0240 (8)	0.0233 (8)	0.0262 (7)	0.0089 (6)	0.0048 (6)	0.0061 (6)
N2	0.0294 (8)	0.0300 (7)	0.0288 (7)	0.0111 (6)	0.0106 (6)	0.0055 (5)
N3	0.0264 (8)	0.0442 (9)	0.0416 (8)	0.0144 (7)	0.0078 (6)	0.0116 (7)
C4	0.0279 (9)	0.0368 (10)	0.0615 (12)	0.0103 (8)	0.0176 (8)	0.0040 (8)
C5	0.0579 (13)	0.0362 (10)	0.057	0.0060 (9)	0.0400 (8)	−0.0013 (9)
C6	0.0504 (12)	0.0311 (10)	0.0332 (9)	0.0075 (8)	0.0206 (8)	0.0036 (7)
N7	0.0300 (7)	0.0242 (7)	0.0237 (6)	0.0098 (6)	0.0043 (5)	0.0039 (5)
N8	0.0312 (8)	0.0285 (8)	0.0274 (7)	0.0044 (6)	0.0069 (6)	0.0018 (5)
C9	0.0483 (11)	0.0250 (9)	0.0334 (8)	0.0043 (8)	0.0155 (8)	0.0023 (7)
C10	0.0662 (13)	0.0265 (9)	0.0376 (9)	0.0196 (9)	0.0186 (9)	0.0082 (7)
C11	0.0457 (11)	0.0321 (9)	0.0368 (9)	0.0210 (8)	0.0053 (8)	0.0078 (7)
C12	0.0180 (8)	0.0244 (8)	0.0268 (7)	0.0076 (6)	0.0049 (6)	0.0029 (6)
N13	0.0332 (8)	0.0259 (7)	0.0347 (7)	0.0081 (6)	0.0103 (6)	0.0018 (6)
C14	0.0416 (11)	0.0320 (10)	0.0421 (10)	0.0088 (8)	0.0128 (8)	−0.0035 (8)
C15	0.0471 (12)	0.0455 (12)	0.0410 (10)	0.0153 (9)	0.0141 (8)	−0.0009 (8)
C16	0.0478 (11)	0.0506 (12)	0.0324 (9)	0.0205 (9)	0.0162 (8)	0.0076 (8)
C17	0.0371 (10)	0.0318 (9)	0.0321 (8)	0.0152 (8)	0.0119 (7)	0.0076 (7)

C1—N2	1.4527 (19)	C9—C10	1.384 (2)
C1—N7	1.4559 (18)	C9—H9	0.9300
C1—C12	1.515 (2)	C10—C11	1.368 (2)
C1—H1	0.9800	C10—H10	0.9300
N2—C6	1.346 (2)	C11—H11	0.9300
N2—N3	1.3570 (17)	C12—N13	1.3403 (19)
N3—C4	1.323 (2)	C12—C17	1.375 (2)
C4—C5	1.404 (3)	N13—C14	1.334 (2)
C4—H4	0.9300	C14—C15	1.354 (3)
C5—C6	1.386 (2)	C14—H14	0.9300
C5—H5	0.9300	C15—C16	1.362 (3)
C6—H6	0.9300	C15—H15	0.9300
N7—C11	1.3502 (19)	C16—C17	1.382 (2)
N7—N8	1.3578 (16)	C16—H16	0.9300
N8—C9	1.330 (2)	C17—H17	0.9300
N2—C1—N7	110.59 (12)	N8—C9—H9	123.9
N2—C1—C12	110.54 (12)	C10—C9—H9	123.9
N7—C1—C12	113.54 (12)	C11—C10—C9	104.88 (15)
N2—C1—H1	107.3	C11—C10—H10	127.6
N7—C1—H1	107.3	C9—C10—H10	127.6
C12—C1—H1	107.3	N7—C11—C10	107.06 (15)
C6—N2—N3	112.85 (14)	N7—C11—H11	126.5
C6—N2—C1	127.42 (13)	C10—C11—H11	126.5
N3—N2—C1	119.70 (12)	N13—C12—C17	122.77 (14)
C4—N3—N2	104.30 (14)	N13—C12—C1	113.00 (12)
N3—C4—C5	112.05 (16)	C17—C12—C1	124.22 (13)
N3—C4—H4	124.0	C14—N13—C12	116.65 (14)
C5—C4—H4	124.0	N13—C14—C15	124.63 (17)
C6—C5—C4	104.55 (16)	N13—C14—H14	117.7
C6—C5—H5	127.7	C15—C14—H14	117.7
C4—C5—H5	127.7	C14—C15—C16	118.08 (17)
N2—C6—C5	106.26 (15)	C14—C15—H15	121.0
N2—C6—H6	126.9	C16—C15—H15	121.0
C5—C6—H6	126.9	C15—C16—C17	119.63 (16)
C11—N7—N8	111.66 (13)	C15—C16—H16	120.2
C11—N7—C1	130.08 (13)	C17—C16—H16	120.2
N8—N7—C1	118.25 (11)	C12—C17—C16	118.22 (15)
C9—N8—N7	104.15 (13)	C12—C17—H17	120.9
N8—C9—C10	112.24 (15)	C16—C17—H17	120.9

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···N8i	0.98	2.45	3.3974 (18)	162
C10—H10···N13ii	0.93	2.60	3.496 (2)	161

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C1H1N8i	0.98	2.45	3.3974(18)	162
C10H10N13ii	0.93	2.60	3.496(2)	161

Symmetry codes: (i) ; (ii) .