5-(4-Hexyl-1H-1,2,3-triazol-1-yl)-2,1,3-benzoxadiazole.

The title compound, C(14)H(17)N(5)O, a 1,2,3-triazole derivative of benzoxadiazole (C(14)H(17)N(5)O), was synthesized via Cu-catal-ysed azide-alkyne cyclo-addition (CuAAC) from the corres-ponding n-octyne and 4-azido-benzoxadiazole. The benz-oxa-diazole and triazole rings show a roughly planar orientation [dihedral angle between the ring planes = 12.18 (5)°]. The alkane chain adopts a zigzag conformation, which deviates from the central triazole ring by 20.89 (6)°. These two torsion angles result in an overall twist to the structure, with a dihedral angle of 32.86 (7)° between the benzoxadiazole group and the hexyl chain. The crystal structure features C-H⋯N hydrogen bonds leading to chains propagating along [2-10] and offset parallel stacking inter-actions of the triazole and benzoxadiazole rings. The centroid of the extended π-system formed by the benzoxadiazole and triazole rings (14 atoms total) was calculated; the centroid-centroid distance was 4.179 Å, interplanar separation was 3.243 Å, and the resulting offset was 2.636 Å.

Related literature

For the synthesis of the title compound and related benz­oxa­diazole analogs, see: Key & Cairo (2011 ▶). For computational studies of the absorption and fluorescence properties of this series of compounds, see: Brown et al. (2012 ▶). For structures with 1-aryl-substituted 1,2,3-triazole rings, see: Costa et al. (2006 ▶). For the use of fluoro­phores as chemical or biological probes, see: Cairo et al. (2010 ▶); Lavis & Raines (2008 ▶). For related benzoxadiazole structures, see: Key et al. (2012a ▶,b ▶). For triazole-substituted coumarin derivatives, see: Key et al. (2009 ▶).

Experimental

Crystal data

C14H17N5O

M = 271.33

Triclinic,

a = 5.3604 (8) Å

b = 7.8585 (11) Å

c = 16.357 (2) Å

α = 87.4656 (17)°

β = 86.2519 (16)°

γ = 85.6240 (17)°

V = 685.04 (17) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 173 K

1.02 × 0.35 × 0.03 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.915, T max = 0.997

6114 measured reflections

3120 independent reflections

2568 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.099

S = 1.04

3120 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.22 e Å−3

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

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812041815/mw2081sup1.cif

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812041815/mw2081Isup2.cdx

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812041815/mw2081Isup3.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812041815/mw2081Isup4.cml

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

C14H17N5O	Z = 2
Mr = 271.33	F(000) = 288
Triclinic, P1	Dx = 1.315 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.3604 (8) Å	Cell parameters from 5179 reflections
b = 7.8585 (11) Å	θ = 2.5–27.5°
c = 16.357 (2) Å	µ = 0.09 mm−1
α = 87.4656 (17)°	T = 173 K
β = 86.2519 (16)°	Plate, colourless
γ = 85.6240 (17)°	1.02 × 0.35 × 0.03 mm
V = 685.04 (17) Å3

Bruker APEXII CCD diffractometer	3120 independent reflections
Radiation source: fine-focus sealed tube	2568 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.013
ω scans	θmax = 27.6°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −6→6
Tmin = 0.915, Tmax = 0.997	k = −10→10
6114 measured reflections	l = −21→21

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0495P)2 + 0.1216P] where P = (Fo2 + 2Fc2)/3
3120 reflections	(Δ/σ)max = 0.002
181 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.22 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
O	0.41878 (17)	0.07628 (11)	0.71631 (5)	0.0427 (2)
N1	0.2106 (2)	0.18420 (14)	0.73699 (6)	0.0420 (3)
N2	0.44587 (19)	0.04944 (13)	0.63299 (6)	0.0359 (2)
N3	−0.10674 (16)	0.28627 (11)	0.42563 (5)	0.0269 (2)
N4	−0.33882 (18)	0.36159 (13)	0.41382 (6)	0.0351 (2)
N5	−0.36564 (18)	0.36862 (13)	0.33489 (6)	0.0370 (2)
C1	0.1091 (2)	0.22446 (14)	0.66688 (7)	0.0316 (2)
C2	0.2550 (2)	0.14071 (13)	0.60238 (7)	0.0287 (2)
C3	0.1873 (2)	0.15961 (13)	0.51960 (6)	0.0278 (2)
H3	0.2835	0.1041	0.4763	0.033*
C4	−0.0229 (2)	0.26178 (13)	0.50634 (6)	0.0259 (2)
C5	−0.1709 (2)	0.34929 (13)	0.57088 (7)	0.0299 (2)
H5	−0.3147	0.4207	0.5575	0.036*
C6	−0.1098 (2)	0.33215 (14)	0.64981 (7)	0.0336 (3)
H6	−0.2082	0.3892	0.6921	0.040*
C7	0.0134 (2)	0.24553 (14)	0.35268 (6)	0.0284 (2)
H7	0.1772	0.1920	0.3437	0.034*
C8	−0.1520 (2)	0.29817 (14)	0.29511 (7)	0.0306 (2)
C9	−0.1308 (2)	0.29097 (17)	0.20385 (7)	0.0374 (3)
H9A	−0.2088	0.3989	0.1804	0.045*
H9B	−0.2280	0.1970	0.1878	0.045*
C10	0.1352 (2)	0.26410 (16)	0.16610 (7)	0.0343 (3)
H10A	0.2127	0.1538	0.1872	0.041*
H10B	0.2354	0.3561	0.1827	0.041*
C11	0.1402 (2)	0.26410 (15)	0.07277 (7)	0.0340 (3)
H11A	0.0493	0.1669	0.0568	0.041*
H11B	0.0490	0.3704	0.0526	0.041*
C12	0.4022 (2)	0.25125 (16)	0.03056 (7)	0.0340 (3)
H12A	0.4936	0.3484	0.0462	0.041*
H12B	0.4938	0.1447	0.0503	0.041*
C13	0.4010 (2)	0.25185 (16)	−0.06240 (7)	0.0379 (3)
H13A	0.3132	0.1529	−0.0781	0.045*
H13B	0.3055	0.3570	−0.0819	0.045*
C14	0.6621 (3)	0.24356 (19)	−0.10491 (8)	0.0466 (3)
H14A	0.6491	0.2458	−0.1644	0.056*
H14B	0.7560	0.1377	−0.0874	0.056*
H14C	0.7497	0.3418	−0.0903	0.056*

	U11	U22	U33	U12	U13	U23
O	0.0479 (5)	0.0486 (5)	0.0312 (4)	0.0037 (4)	−0.0081 (4)	−0.0020 (4)
N1	0.0476 (6)	0.0462 (6)	0.0318 (5)	0.0020 (5)	−0.0039 (5)	−0.0046 (4)
N2	0.0388 (6)	0.0387 (5)	0.0302 (5)	−0.0004 (4)	−0.0060 (4)	−0.0015 (4)
N3	0.0223 (4)	0.0292 (4)	0.0283 (5)	0.0012 (3)	0.0008 (3)	−0.0011 (3)
N4	0.0250 (5)	0.0441 (6)	0.0348 (5)	0.0057 (4)	−0.0011 (4)	−0.0015 (4)
N5	0.0283 (5)	0.0477 (6)	0.0336 (5)	0.0047 (4)	−0.0009 (4)	−0.0003 (4)
C1	0.0374 (6)	0.0312 (6)	0.0266 (5)	−0.0057 (5)	0.0007 (4)	−0.0031 (4)
C2	0.0288 (6)	0.0261 (5)	0.0314 (5)	−0.0036 (4)	−0.0010 (4)	−0.0007 (4)
C3	0.0275 (5)	0.0285 (5)	0.0272 (5)	−0.0017 (4)	0.0023 (4)	−0.0037 (4)
C4	0.0263 (5)	0.0259 (5)	0.0256 (5)	−0.0053 (4)	0.0007 (4)	−0.0010 (4)
C5	0.0279 (6)	0.0280 (5)	0.0328 (6)	0.0004 (4)	0.0040 (4)	−0.0028 (4)
C6	0.0378 (6)	0.0323 (6)	0.0299 (6)	−0.0016 (5)	0.0063 (5)	−0.0062 (4)
C7	0.0241 (5)	0.0334 (6)	0.0268 (5)	0.0008 (4)	0.0018 (4)	−0.0011 (4)
C8	0.0247 (5)	0.0354 (6)	0.0312 (6)	−0.0013 (4)	−0.0007 (4)	0.0013 (4)
C9	0.0299 (6)	0.0539 (7)	0.0275 (6)	0.0017 (5)	−0.0039 (4)	0.0031 (5)
C10	0.0313 (6)	0.0438 (7)	0.0271 (5)	0.0021 (5)	−0.0035 (4)	0.0002 (5)
C11	0.0325 (6)	0.0416 (6)	0.0272 (5)	0.0018 (5)	−0.0043 (4)	0.0010 (4)
C12	0.0333 (6)	0.0410 (6)	0.0274 (5)	0.0009 (5)	−0.0034 (4)	−0.0017 (4)
C13	0.0390 (7)	0.0468 (7)	0.0275 (6)	−0.0001 (5)	−0.0031 (5)	−0.0009 (5)
C14	0.0459 (8)	0.0612 (9)	0.0326 (6)	−0.0065 (6)	0.0041 (5)	−0.0064 (6)

O—N1	1.3821 (14)	C8—C9	1.4929 (15)
O—N2	1.3849 (12)	C9—C10	1.5195 (16)
N1—C1	1.3170 (15)	C9—H9A	0.9900
N2—C2	1.3173 (14)	C9—H9B	0.9900
N3—C7	1.3576 (13)	C10—C11	1.5251 (15)
N3—N4	1.3581 (13)	C10—H10A	0.9900
N3—C4	1.4227 (13)	C10—H10B	0.9900
N4—N5	1.3067 (13)	C11—C12	1.5223 (16)
N5—C8	1.3709 (14)	C11—H11A	0.9900
C1—C2	1.4257 (15)	C11—H11B	0.9900
C1—C6	1.4288 (16)	C12—C13	1.5207 (15)
C2—C3	1.4231 (15)	C12—H12A	0.9900
C3—C4	1.3563 (15)	C12—H12B	0.9900
C3—H3	0.9500	C13—C14	1.5200 (17)
C4—C5	1.4451 (15)	C13—H13A	0.9900
C5—C6	1.3511 (16)	C13—H13B	0.9900
C5—H5	0.9500	C14—H14A	0.9800
C6—H6	0.9500	C14—H14B	0.9800
C7—C8	1.3648 (15)	C14—H14C	0.9800
C7—H7	0.9500
N1—O—N2	112.30 (8)	C10—C9—H9A	108.5
C1—N1—O	104.60 (9)	C8—C9—H9B	108.5
C2—N2—O	104.44 (9)	C10—C9—H9B	108.5
C7—N3—N4	110.32 (9)	H9A—C9—H9B	107.5
C7—N3—C4	129.66 (9)	C9—C10—C11	111.55 (9)
N4—N3—C4	120.02 (9)	C9—C10—H10A	109.3
N5—N4—N3	107.10 (9)	C11—C10—H10A	109.3
N4—N5—C8	109.41 (9)	C9—C10—H10B	109.3
N1—C1—C2	109.28 (10)	C11—C10—H10B	109.3
N1—C1—C6	130.17 (11)	H10A—C10—H10B	108.0
C2—C1—C6	120.55 (10)	C12—C11—C10	114.34 (9)
N2—C2—C3	129.02 (10)	C12—C11—H11A	108.7
N2—C2—C1	109.39 (10)	C10—C11—H11A	108.7
C3—C2—C1	121.58 (10)	C12—C11—H11B	108.7
C4—C3—C2	115.86 (9)	C10—C11—H11B	108.7
C4—C3—H3	122.1	H11A—C11—H11B	107.6
C2—C3—H3	122.1	C13—C12—C11	113.10 (9)
C3—C4—N3	119.77 (9)	C13—C12—H12A	109.0
C3—C4—C5	123.22 (10)	C11—C12—H12A	109.0
N3—C4—C5	117.01 (9)	C13—C12—H12B	109.0
C6—C5—C4	121.65 (10)	C11—C12—H12B	109.0
C6—C5—H5	119.2	H12A—C12—H12B	107.8
C4—C5—H5	119.2	C14—C13—C12	113.29 (10)
C5—C6—C1	117.13 (10)	C14—C13—H13A	108.9
C5—C6—H6	121.4	C12—C13—H13A	108.9
C1—C6—H6	121.4	C14—C13—H13B	108.9
N3—C7—C8	105.12 (9)	C12—C13—H13B	108.9
N3—C7—H7	127.4	H13A—C13—H13B	107.7
C8—C7—H7	127.4	C13—C14—H14A	109.5
C7—C8—N5	108.05 (10)	C13—C14—H14B	109.5
C7—C8—C9	131.26 (10)	H14A—C14—H14B	109.5
N5—C8—C9	120.69 (10)	C13—C14—H14C	109.5
C8—C9—C10	115.02 (9)	H14A—C14—H14C	109.5
C8—C9—H9A	108.5	H14B—C14—H14C	109.5
N2—O—N1—C1	−0.10 (12)	C7—N3—C4—C5	167.55 (10)
N1—O—N2—C2	0.04 (12)	N4—N3—C4—C5	−12.02 (14)
C7—N3—N4—N5	−0.01 (12)	C3—C4—C5—C6	−1.06 (17)
C4—N3—N4—N5	179.64 (9)	N3—C4—C5—C6	178.83 (10)
N3—N4—N5—C8	0.00 (13)	C4—C5—C6—C1	0.44 (16)
O—N1—C1—C2	0.11 (12)	N1—C1—C6—C5	−179.58 (12)
O—N1—C1—C6	−179.94 (11)	C2—C1—C6—C5	0.36 (16)
O—N2—C2—C3	−179.31 (10)	N4—N3—C7—C8	0.01 (12)
O—N2—C2—C1	0.03 (12)	C4—N3—C7—C8	−179.59 (10)
N1—C1—C2—N2	−0.09 (13)	N3—C7—C8—N5	−0.01 (12)
C6—C1—C2—N2	179.96 (10)	N3—C7—C8—C9	179.38 (12)
N1—C1—C2—C3	179.30 (10)	N4—N5—C8—C7	0.01 (13)
C6—C1—C2—C3	−0.65 (16)	N4—N5—C8—C9	−179.46 (10)
N2—C2—C3—C4	179.35 (11)	C7—C8—C9—C10	−18.02 (19)
C1—C2—C3—C4	0.08 (15)	N5—C8—C9—C10	161.30 (11)
C2—C3—C4—N3	−179.14 (9)	C8—C9—C10—C11	−178.16 (10)
C2—C3—C4—C5	0.75 (15)	C9—C10—C11—C12	175.60 (10)
C7—N3—C4—C3	−12.56 (16)	C10—C11—C12—C13	−179.91 (10)
N4—N3—C4—C3	167.88 (9)	C11—C12—C13—C14	178.54 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N2i	0.95	2.52	3.4674 (15)	177
C5—H5···N4ii	0.95	2.46	3.3445 (15)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯N2i	0.95	2.52	3.4674 (15)	177
C5—H5⋯N4ii	0.95	2.46	3.3445 (15)	154

Symmetry codes: (i) ; (ii) .