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

In the title compound, C(15)H(11)N(5)O, which was prepared as part of a study to identify fluoro-genic substrates for the Cu-catalysed azide-alkyne cyclo-addition (CuAAC) reaction, the benzoxa-diazole unit and the triazole ring are much more closely coplanar [dihedral angle = 10.92 (7)°] than either is to the benzyl group [dihedral angles = 69.13 (3)° and 78.20 (4)°, respectively]. The crystal structure features two different sets of weak inter-molecular C-H⋯N inter-actions between adjacent benzoxadiazole and triazole rings, forming a chain that propagates in the [-110] direction parallel to the ab plane.

Related literature

For the synthesis of the title compound, see: Key & Cairo (2011 ▶). For computational studies of the absorption and fluorescence of the title compound, see: Brown et al. (2012 ▶). For structures with 4-aryl substituted 1-benzyl-1,2,3-triazole rings, see: Key et al. (2008) ▶; Li et al. (2011 ▶); Raghavendra & Lam (2004 ▶); Sarmiento-Sánchez et al. (2011) ▶. For two related benzoxadiazole structures, see: Key, Cairo & Ferguson (2012 ▶); Key, Cairo & McDonald (2012 ▶). For the synthesis of analogous triazole-substituted coumarin structures, see: Key et al. (2009 ▶). For information on reactive chromophores, see: Cairo et al. (2010 ▶). For recent work on small mol­ecule fluoro­phores, see: Lavis & Raines (2008 ▶).

Experimental

Crystal data

C15H11N5O

M = 277.29

Triclinic,

a = 5.7526 (4) Å

b = 9.9261 (6) Å

c = 11.7012 (8) Å

α = 90.3799 (7)°

β = 99.2517 (7)°

γ = 103.2900 (7)°

V = 641.14 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 173 K

0.50 × 0.29 × 0.23 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: numerical (SADABS; Sheldrick, 2008 ▶) T min = 0.953, T max = 0.978

5667 measured reflections

2879 independent reflections

2489 reflections with I > 2σ(I)

R int = 0.012

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.096

S = 1.06

2879 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.17 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: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812041827/mw2083sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812041827/mw2083Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812041827/mw2083Isup3.cml

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

C15H11N5O	Z = 2
Mr = 277.29	F(000) = 288
Triclinic, P1	Dx = 1.436 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.7526 (4) Å	Cell parameters from 4623 reflections
b = 9.9261 (6) Å	θ = 2.7–27.3°
c = 11.7012 (8) Å	µ = 0.10 mm−1
α = 90.3799 (7)°	T = 173 K
β = 99.2517 (7)°	Fragment, colourless
γ = 103.2900 (7)°	0.50 × 0.29 × 0.23 mm
V = 641.14 (7) Å3

Bruker APEXII CCD diffractometer	2879 independent reflections
Radiation source: fine-focus sealed tube	2489 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.012
Detector resolution: 8.26 pixels mm-1	θmax = 27.3°, θmin = 1.8°
ω scans	h = −7→7
Absorption correction: numerical (SADABS; Sheldrick, 2008)	k = −12→12
Tmin = 0.953, Tmax = 0.978	l = −15→15
5667 measured reflections

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)] = 0.035	H-atom parameters constrained
wR(F2) = 0.096	w = 1/[σ2(Fo2) + (0.0444P)2 + 0.1305P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2879 reflections	Δρmax = 0.23 e Å−3
191 parameters	Δρmin = −0.17 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraints	Extinction coefficient: 0.027 (4)
Primary atom site location: structure-invariant direct methods

Geometry. All standard uncertainties (s.u.'s) (except the s.u. in the dihedral angle between two least-squares planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving least-squares 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	0.37047 (18)	0.60313 (9)	−0.24598 (8)	0.0488 (3)
N1	0.5182 (2)	0.51386 (12)	−0.25718 (9)	0.0454 (3)
N2	0.2225 (2)	0.56215 (11)	−0.16419 (9)	0.0426 (3)
N3	0.3192 (2)	0.05933 (11)	0.11897 (9)	0.0397 (3)
N4	0.2143 (2)	−0.00352 (11)	0.20195 (9)	0.0405 (3)
N5	0.02778 (17)	0.05338 (10)	0.21296 (8)	0.0326 (2)
C1	0.4623 (2)	0.41788 (12)	−0.18298 (10)	0.0351 (3)
C2	0.2785 (2)	0.44754 (12)	−0.12510 (10)	0.0337 (3)
C3	0.1868 (2)	0.36165 (12)	−0.03855 (10)	0.0324 (2)
H3	0.0650	0.3818	0.0002	0.039*
C4	0.28041 (19)	0.24890 (11)	−0.01314 (9)	0.0298 (2)
C5	0.4649 (2)	0.21869 (12)	−0.07346 (10)	0.0340 (3)
H5	0.5248	0.1388	−0.0539	0.041*
C6	0.5554 (2)	0.29873 (13)	−0.15607 (10)	0.0370 (3)
H6	0.6760	0.2766	−0.1946	0.044*
C7	0.2003 (2)	0.15745 (11)	0.07735 (9)	0.0303 (2)
C8	0.0138 (2)	0.15328 (12)	0.13786 (10)	0.0332 (3)
H8	−0.1008	0.2093	0.1285	0.040*
C9	−0.1176 (2)	0.01211 (12)	0.30362 (10)	0.0354 (3)
H9A	−0.0691	−0.0676	0.3429	0.042*
H9B	−0.2903	−0.0184	0.2678	0.042*
C10	−0.0894 (2)	0.12825 (11)	0.39256 (9)	0.0305 (2)
C11	0.1235 (2)	0.22895 (13)	0.42168 (11)	0.0382 (3)
H11	0.2570	0.2280	0.3835	0.046*
C12	0.1428 (2)	0.33104 (13)	0.50619 (11)	0.0432 (3)
H12	0.2891	0.4004	0.5251	0.052*
C13	−0.0481 (2)	0.33292 (13)	0.56299 (10)	0.0416 (3)
H13	−0.0332	0.4023	0.6218	0.050*
C14	−0.2610 (2)	0.23349 (15)	0.53388 (11)	0.0442 (3)
H14	−0.3934	0.2341	0.5729	0.053*
C15	−0.2825 (2)	0.13267 (13)	0.44798 (10)	0.0381 (3)
H15	−0.4314	0.0659	0.4269	0.046*

	U11	U22	U33	U12	U13	U23
O	0.0609 (6)	0.0388 (5)	0.0460 (5)	0.0100 (4)	0.0090 (4)	0.0048 (4)
N1	0.0503 (6)	0.0426 (6)	0.0405 (6)	0.0057 (5)	0.0074 (5)	−0.0029 (5)
N2	0.0504 (6)	0.0356 (6)	0.0421 (6)	0.0119 (5)	0.0060 (5)	0.0023 (4)
N3	0.0464 (6)	0.0395 (6)	0.0409 (6)	0.0237 (5)	0.0101 (4)	0.0023 (4)
N4	0.0477 (6)	0.0387 (6)	0.0426 (6)	0.0241 (5)	0.0091 (5)	0.0027 (4)
N5	0.0361 (5)	0.0305 (5)	0.0329 (5)	0.0136 (4)	0.0029 (4)	−0.0026 (4)
C1	0.0359 (6)	0.0367 (6)	0.0293 (5)	0.0039 (5)	0.0025 (4)	−0.0075 (5)
C2	0.0347 (6)	0.0319 (6)	0.0328 (6)	0.0089 (5)	−0.0008 (4)	−0.0063 (4)
C3	0.0314 (5)	0.0339 (6)	0.0333 (6)	0.0118 (5)	0.0034 (4)	−0.0050 (4)
C4	0.0289 (5)	0.0309 (5)	0.0288 (5)	0.0089 (4)	−0.0004 (4)	−0.0076 (4)
C5	0.0348 (6)	0.0356 (6)	0.0336 (6)	0.0149 (5)	0.0018 (4)	−0.0085 (5)
C6	0.0343 (6)	0.0433 (7)	0.0345 (6)	0.0115 (5)	0.0061 (5)	−0.0089 (5)
C7	0.0317 (5)	0.0291 (5)	0.0308 (5)	0.0125 (4)	−0.0002 (4)	−0.0064 (4)
C8	0.0344 (6)	0.0332 (6)	0.0344 (6)	0.0149 (5)	0.0028 (4)	−0.0002 (4)
C9	0.0383 (6)	0.0302 (6)	0.0370 (6)	0.0069 (5)	0.0060 (5)	0.0000 (5)
C10	0.0337 (6)	0.0285 (5)	0.0294 (5)	0.0085 (4)	0.0037 (4)	0.0040 (4)
C11	0.0336 (6)	0.0388 (6)	0.0413 (6)	0.0049 (5)	0.0090 (5)	−0.0032 (5)
C12	0.0430 (7)	0.0369 (7)	0.0440 (7)	−0.0006 (5)	0.0055 (5)	−0.0050 (5)
C13	0.0538 (8)	0.0392 (7)	0.0333 (6)	0.0160 (6)	0.0042 (5)	−0.0033 (5)
C14	0.0415 (7)	0.0581 (8)	0.0365 (6)	0.0159 (6)	0.0111 (5)	−0.0012 (6)
C15	0.0336 (6)	0.0431 (7)	0.0353 (6)	0.0036 (5)	0.0065 (5)	0.0012 (5)

O—N1	1.3804 (15)	C6—H6	0.9500
O—N2	1.3833 (14)	C7—C8	1.3706 (16)
N1—C1	1.3133 (16)	C8—H8	0.9500
N2—C2	1.3173 (15)	C9—C10	1.5107 (15)
N3—N4	1.3112 (14)	C9—H9A	0.9900
N3—C7	1.3633 (14)	C9—H9B	0.9900
N4—N5	1.3452 (13)	C10—C15	1.3821 (16)
N5—C8	1.3370 (14)	C10—C11	1.3833 (16)
N5—C9	1.4582 (15)	C11—C12	1.3845 (17)
C1—C6	1.4237 (17)	C11—H11	0.9500
C1—C2	1.4260 (16)	C12—C13	1.3756 (18)
C2—C3	1.4168 (16)	C12—H12	0.9500
C3—C4	1.3642 (16)	C13—C14	1.3766 (19)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.4486 (15)	C14—C15	1.3844 (18)
C4—C7	1.4609 (16)	C14—H14	0.9500
C5—C6	1.3485 (17)	C15—H15	0.9500
C5—H5	0.9500
N1—O—N2	112.34 (9)	C8—C7—C4	130.21 (10)
C1—N1—O	104.58 (10)	N5—C8—C7	105.21 (10)
C2—N2—O	104.48 (10)	N5—C8—H8	127.4
N4—N3—C7	108.93 (9)	C7—C8—H8	127.4
N3—N4—N5	107.19 (9)	N5—C9—C10	112.41 (9)
C8—N5—N4	110.86 (10)	N5—C9—H9A	109.1
C8—N5—C9	128.06 (10)	C10—C9—H9A	109.1
N4—N5—C9	120.90 (9)	N5—C9—H9B	109.1
N1—C1—C6	130.24 (11)	C10—C9—H9B	109.1
N1—C1—C2	109.44 (11)	H9A—C9—H9B	107.9
C6—C1—C2	120.32 (11)	C15—C10—C11	118.90 (11)
N2—C2—C3	129.42 (11)	C15—C10—C9	118.67 (10)
N2—C2—C1	109.17 (11)	C11—C10—C9	122.42 (10)
C3—C2—C1	121.40 (10)	C10—C11—C12	120.27 (11)
C4—C3—C2	117.34 (10)	C10—C11—H11	119.9
C4—C3—H3	121.3	C12—C11—H11	119.9
C2—C3—H3	121.3	C13—C12—C11	120.54 (12)
C3—C4—C5	120.84 (11)	C13—C12—H12	119.7
C3—C4—C7	120.67 (10)	C11—C12—H12	119.7
C5—C4—C7	118.48 (10)	C12—C13—C14	119.45 (11)
C6—C5—C4	123.01 (11)	C12—C13—H13	120.3
C6—C5—H5	118.5	C14—C13—H13	120.3
C4—C5—H5	118.5	C13—C14—C15	120.20 (12)
C5—C6—C1	117.08 (10)	C13—C14—H14	119.9
C5—C6—H6	121.5	C15—C14—H14	119.9
C1—C6—H6	121.5	C10—C15—C14	120.61 (11)
N3—C7—C8	107.80 (10)	C10—C15—H15	119.7
N3—C7—C4	121.94 (10)	C14—C15—H15	119.7
N2—O—N1—C1	0.09 (13)	N4—N3—C7—C8	−0.26 (13)
N1—O—N2—C2	−0.13 (13)	N4—N3—C7—C4	177.60 (10)
C7—N3—N4—N5	0.44 (13)	C3—C4—C7—N3	−168.10 (11)
N3—N4—N5—C8	−0.47 (13)	C5—C4—C7—N3	10.64 (16)
N3—N4—N5—C9	−176.07 (10)	C3—C4—C7—C8	9.23 (18)
O—N1—C1—C6	−179.98 (11)	C5—C4—C7—C8	−172.03 (11)
O—N1—C1—C2	−0.02 (12)	N4—N5—C8—C7	0.31 (13)
O—N2—C2—C3	178.79 (11)	C9—N5—C8—C7	175.51 (10)
O—N2—C2—C1	0.11 (12)	N3—C7—C8—N5	−0.03 (12)
N1—C1—C2—N2	−0.06 (13)	C4—C7—C8—N5	−177.65 (11)
C6—C1—C2—N2	179.90 (10)	C8—N5—C9—C10	−61.08 (15)
N1—C1—C2—C3	−178.86 (10)	N4—N5—C9—C10	113.69 (11)
C6—C1—C2—C3	1.10 (16)	N5—C9—C10—C15	149.78 (10)
N2—C2—C3—C4	−178.88 (11)	N5—C9—C10—C11	−31.20 (15)
C1—C2—C3—C4	−0.34 (16)	C15—C10—C11—C12	0.90 (18)
C2—C3—C4—C5	−0.45 (16)	C9—C10—C11—C12	−178.12 (11)
C2—C3—C4—C7	178.26 (9)	C10—C11—C12—C13	0.7 (2)
C3—C4—C5—C6	0.53 (17)	C11—C12—C13—C14	−1.0 (2)
C7—C4—C5—C6	−178.21 (10)	C12—C13—C14—C15	−0.1 (2)
C4—C5—C6—C1	0.22 (16)	C11—C10—C15—C14	−2.06 (18)
N1—C1—C6—C5	178.95 (12)	C9—C10—C15—C14	177.00 (11)
C2—C1—C6—C5	−1.00 (16)	C13—C14—C15—C10	1.69 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···N3i	0.95	2.50	3.3483 (15)	148
C8—H8···N2ii	0.95	2.57	3.4367 (15)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯N3i	0.95	2.50	3.3483 (15)	148
C8—H8⋯N2ii	0.95	2.57	3.4367 (15)	151

Symmetry codes: (i) ; (ii) .