2-[1-(1-Naphth-yl)-1H-1,2,3-triazol-4-yl]pyridine.

In the crystal structure of the title compound, C(17)H(12)N(4), the angle between the naphthalene and 1H-1,2,3-triazole ring systems is 71.02 (4)° and that between the pyridine and triazole rings is 8.30 (9)°.

Related literature

For related literature on the synthesis of polypyridyl ligands and 1,2,3-triazole-containing compounds, see: Marin et al. (2007 ▶); Winter et al. (2007 ▶); Balzani et al. (1996 ▶); Newkome et al. (2004 ▶); Chan et al. (2004 ▶); Rostovtsev et al. (2002 ▶); Kolb et al. (2001 ▶). The synthesis of the title compound is reported in Happ et al. (2009 ▶). For related crystal structures, see: Obata et al. (2008 ▶); Schweinfurth et al. (2008 ▶); Schulze et al. (2009 ▶); Li et al. (2007 ▶); Richardson et al. (2008 ▶); Angell & Burgess (2007 ▶).

Experimental

Crystal data

C17H12N4

M = 272.31

Orthorhombic,

a = 11.6378 (4) Å

b = 9.3228 (4) Å

c = 25.0592 (9) Å

V = 2718.84 (18) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.63 × 0.18 × 0.07 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008a ▶) T min = 0.950, T max = 0.994

14517 measured reflections

2391 independent reflections

1934 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.120

S = 1.01

2391 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b ▶); molecular graphics: CARINE (Boudias & Monceau, 1998 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008b ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680901407X/wn2322sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901407X/wn2322Isup2.hkl

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

C17H12N4	Dx = 1.330 Mg m−3
Mr = 272.31	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 4456 reflections
a = 11.6378 (4) Å	θ = 2.4–20.9°
b = 9.3228 (4) Å	µ = 0.08 mm−1
c = 25.0592 (9) Å	T = 296 K
V = 2718.84 (18) Å3	Stick, colourless
Z = 8	0.63 × 0.18 × 0.07 mm
F(000) = 1136

Bruker Kappa APEXII diffractometer	2391 independent reflections
Radiation source: fine-focus sealed tube	1934 reflections with I > 2σ(I)
graphite	Rint = 0.027
ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	h = −13→13
Tmin = 0.950, Tmax = 0.994	k = −10→11
14517 measured reflections	l = −28→29

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0842P)2 + 0.1848P] where P = (Fo2 + 2Fc2)/3
2391 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.14 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
N1	0.20019 (9)	0.39250 (12)	0.37942 (4)	0.0428 (3)
N2	0.31490 (10)	0.36728 (14)	0.37933 (5)	0.0509 (3)
N3	0.35790 (10)	0.43998 (13)	0.33925 (5)	0.0489 (3)
C4	0.27219 (11)	0.51071 (14)	0.31370 (5)	0.0403 (3)
C5	0.17170 (12)	0.48053 (15)	0.33923 (5)	0.0450 (4)
H5	0.0987	0.5139	0.3306	0.054*
N6	0.19978 (11)	0.66666 (14)	0.24668 (5)	0.0530 (4)
C7	0.29352 (12)	0.60832 (15)	0.26887 (5)	0.0411 (3)
C8	0.40394 (13)	0.64153 (17)	0.25220 (5)	0.0495 (4)
H8	0.4672	0.5971	0.2678	0.059*
C9	0.41850 (15)	0.74114 (18)	0.21229 (6)	0.0590 (4)
H9	0.4918	0.7662	0.2008	0.071*
C10	0.32349 (16)	0.80283 (19)	0.18976 (7)	0.0635 (5)
H10	0.3310	0.8711	0.1629	0.076*
C11	0.21677 (15)	0.76197 (19)	0.20758 (7)	0.0619 (5)
H11	0.1526	0.8030	0.1915	0.074*
C12	0.12717 (11)	0.32768 (14)	0.41875 (5)	0.0420 (3)
C13	0.13387 (11)	0.37575 (14)	0.47248 (5)	0.0405 (3)
C14	0.20520 (12)	0.48862 (16)	0.48997 (6)	0.0482 (4)
H14	0.2525	0.5357	0.4657	0.058*
C15	0.20518 (14)	0.52911 (18)	0.54222 (7)	0.0573 (4)
H15	0.2519	0.6044	0.5532	0.069*
C16	0.13572 (14)	0.4588 (2)	0.57950 (6)	0.0607 (4)
H16	0.1381	0.4860	0.6152	0.073*
C17	0.06506 (14)	0.35138 (18)	0.56387 (6)	0.0552 (4)
H17	0.0187	0.3060	0.5890	0.066*
C18	0.06071 (12)	0.30717 (15)	0.50993 (5)	0.0445 (4)
C19	−0.01489 (14)	0.19830 (16)	0.49262 (7)	0.0554 (4)
H19	−0.0625	0.1532	0.5173	0.066*
C20	−0.01924 (15)	0.15834 (17)	0.44059 (7)	0.0587 (4)
H20	−0.0703	0.0872	0.4298	0.070*
C21	0.05301 (13)	0.22392 (16)	0.40296 (6)	0.0523 (4)
H21	0.0500	0.1963	0.3673	0.063*

	U11	U22	U33	U12	U13	U23
N1	0.0377 (6)	0.0483 (6)	0.0423 (6)	0.0049 (5)	0.0060 (5)	0.0034 (5)
N2	0.0405 (7)	0.0621 (8)	0.0501 (7)	0.0109 (6)	0.0055 (5)	0.0043 (6)
N3	0.0401 (7)	0.0593 (8)	0.0472 (7)	0.0042 (6)	0.0065 (5)	−0.0002 (6)
C4	0.0378 (7)	0.0452 (7)	0.0378 (7)	0.0007 (6)	0.0040 (5)	−0.0052 (6)
C5	0.0374 (7)	0.0524 (8)	0.0451 (8)	0.0036 (6)	0.0028 (6)	0.0066 (6)
N6	0.0468 (8)	0.0585 (8)	0.0536 (8)	0.0012 (6)	0.0035 (5)	0.0076 (6)
C7	0.0415 (8)	0.0447 (7)	0.0371 (7)	−0.0040 (6)	0.0043 (5)	−0.0063 (6)
C8	0.0425 (9)	0.0630 (9)	0.0429 (8)	−0.0055 (7)	0.0058 (6)	−0.0039 (6)
C9	0.0571 (10)	0.0706 (10)	0.0493 (9)	−0.0173 (8)	0.0161 (7)	−0.0035 (8)
C10	0.0792 (12)	0.0613 (10)	0.0500 (9)	−0.0061 (9)	0.0136 (8)	0.0087 (8)
C11	0.0632 (11)	0.0660 (10)	0.0566 (10)	0.0047 (8)	0.0022 (8)	0.0104 (8)
C12	0.0403 (7)	0.0404 (7)	0.0454 (8)	0.0062 (6)	0.0061 (6)	0.0045 (6)
C13	0.0383 (8)	0.0397 (7)	0.0437 (7)	0.0086 (6)	0.0013 (5)	0.0054 (6)
C14	0.0421 (8)	0.0502 (8)	0.0524 (9)	0.0010 (6)	0.0019 (6)	0.0040 (7)
C15	0.0517 (9)	0.0619 (10)	0.0581 (9)	0.0027 (7)	−0.0055 (7)	−0.0072 (8)
C16	0.0589 (10)	0.0774 (11)	0.0459 (9)	0.0123 (9)	−0.0010 (7)	−0.0057 (8)
C17	0.0543 (9)	0.0658 (10)	0.0455 (8)	0.0103 (8)	0.0089 (7)	0.0093 (7)
C18	0.0427 (8)	0.0440 (8)	0.0469 (8)	0.0088 (6)	0.0070 (6)	0.0089 (6)
C19	0.0540 (9)	0.0483 (8)	0.0639 (10)	−0.0024 (7)	0.0152 (7)	0.0106 (7)
C20	0.0588 (10)	0.0460 (8)	0.0713 (11)	−0.0111 (7)	0.0087 (8)	−0.0034 (8)
C21	0.0562 (9)	0.0477 (9)	0.0529 (9)	0.0017 (7)	0.0047 (7)	−0.0053 (6)

N1—C5	1.3408 (17)	C12—C21	1.355 (2)
N1—N2	1.3556 (16)	C12—C13	1.4212 (19)
N1—C12	1.4348 (17)	C13—C14	1.410 (2)
N2—N3	1.3110 (16)	C13—C18	1.4195 (19)
N3—C4	1.3563 (18)	C14—C15	1.363 (2)
C4—C5	1.3623 (19)	C14—H14	0.9300
C4—C7	1.4669 (19)	C15—C16	1.398 (2)
C5—H5	0.9300	C15—H15	0.9300
N6—C11	1.337 (2)	C16—C17	1.354 (2)
N6—C7	1.3398 (19)	C16—H16	0.9300
C7—C8	1.386 (2)	C17—C18	1.414 (2)
C8—C9	1.375 (2)	C17—H17	0.9300
C8—H8	0.9300	C18—C19	1.411 (2)
C9—C10	1.368 (2)	C19—C20	1.357 (2)
C9—H9	0.9300	C19—H19	0.9300
C10—C11	1.374 (2)	C20—C21	1.403 (2)
C10—H10	0.9300	C20—H20	0.9300
C11—H11	0.9300	C21—H21	0.9300
C5—N1—N2	110.40 (11)	C13—C12—N1	119.05 (12)
C5—N1—C12	128.86 (11)	C14—C13—C12	124.20 (12)
N2—N1—C12	120.75 (11)	C14—C13—C18	118.92 (13)
N3—N2—N1	106.70 (11)	C12—C13—C18	116.84 (13)
N2—N3—C4	109.41 (11)	C15—C14—C13	120.35 (14)
N3—C4—C5	108.01 (12)	C15—C14—H14	119.8
N3—C4—C7	122.59 (12)	C13—C14—H14	119.8
C5—C4—C7	129.27 (12)	C14—C15—C16	120.81 (16)
N1—C5—C4	105.48 (12)	C14—C15—H15	119.6
N1—C5—H5	127.3	C16—C15—H15	119.6
C4—C5—H5	127.3	C17—C16—C15	120.30 (15)
C11—N6—C7	116.96 (13)	C17—C16—H16	119.9
N6—C7—C8	122.62 (13)	C15—C16—H16	119.9
N6—C7—C4	115.59 (12)	C16—C17—C18	120.93 (14)
C8—C7—C4	121.75 (13)	C16—C17—H17	119.5
C9—C8—C7	118.96 (15)	C18—C17—H17	119.5
C9—C8—H8	120.5	C19—C18—C17	121.72 (13)
C7—C8—H8	120.5	C19—C18—C13	119.63 (13)
C10—C9—C8	118.97 (15)	C17—C18—C13	118.64 (14)
C10—C9—H9	120.5	C20—C19—C18	121.07 (14)
C8—C9—H9	120.5	C20—C19—H19	119.5
C9—C10—C11	118.68 (16)	C18—C19—H19	119.5
C9—C10—H10	120.7	C19—C20—C21	120.23 (15)
C11—C10—H10	120.7	C19—C20—H20	119.9
N6—C11—C10	123.78 (16)	C21—C20—H20	119.9
N6—C11—H11	118.1	C12—C21—C20	119.76 (14)
C10—C11—H11	118.1	C12—C21—H21	120.1
C21—C12—C13	122.44 (13)	C20—C21—H21	120.1
C21—C12—N1	118.51 (13)
C5—N1—N2—N3	0.24 (15)	C5—N1—C12—C13	−109.53 (16)
C12—N1—N2—N3	179.90 (12)	N2—N1—C12—C13	70.88 (16)
N1—N2—N3—C4	−0.21 (15)	C21—C12—C13—C14	−176.38 (14)
N2—N3—C4—C5	0.12 (16)	N1—C12—C13—C14	2.65 (19)
N2—N3—C4—C7	176.41 (12)	C21—C12—C13—C18	1.60 (19)
N2—N1—C5—C4	−0.16 (15)	N1—C12—C13—C18	−179.37 (12)
C12—N1—C5—C4	−179.79 (13)	C12—C13—C14—C15	179.13 (13)
N3—C4—C5—N1	0.03 (16)	C18—C13—C14—C15	1.2 (2)
C7—C4—C5—N1	−175.93 (13)	C13—C14—C15—C16	0.7 (2)
C11—N6—C7—C8	−1.1 (2)	C14—C15—C16—C17	−1.7 (2)
C11—N6—C7—C4	176.54 (13)	C15—C16—C17—C18	0.6 (2)
N3—C4—C7—N6	177.95 (12)	C16—C17—C18—C19	−178.08 (14)
C5—C4—C7—N6	−6.6 (2)	C16—C17—C18—C13	1.3 (2)
N3—C4—C7—C8	−4.4 (2)	C14—C13—C18—C19	177.22 (13)
C5—C4—C7—C8	171.04 (14)	C12—C13—C18—C19	−0.87 (18)
N6—C7—C8—C9	1.8 (2)	C14—C13—C18—C17	−2.18 (19)
C4—C7—C8—C9	−175.67 (13)	C12—C13—C18—C17	179.73 (12)
C7—C8—C9—C10	−0.9 (2)	C17—C18—C19—C20	179.09 (14)
C8—C9—C10—C11	−0.5 (3)	C13—C18—C19—C20	−0.3 (2)
C7—N6—C11—C10	−0.5 (3)	C18—C19—C20—C21	0.8 (2)
C9—C10—C11—N6	1.3 (3)	C13—C12—C21—C20	−1.1 (2)
C5—N1—C12—C21	69.54 (19)	N1—C12—C21—C20	179.83 (13)
N2—N1—C12—C21	−110.05 (15)	C19—C20—C21—C12	−0.1 (2)