1-[1-(2,1,3-Benzoxadiazol-5-ylmeth-yl)-1H-1,2,3-triazol-4-yl]hexan-1-one.

The title compound, C(15)H(17)N(5)O(2), was synthesized as part of a series of benzoxadiazole analogs which were examined for fluorescent properties by Cu-catalysed azide-alkyne cyclo-addition (CuAAC) of a 4-azido-methyl-benzoxadiazole substrate. The structure shows a nearly coplanar orientation of the hexa-none keto group and the 1,2,3-triazole ring [dihedral angle = 4.3 (3)°], while the benzoxadiazole and triazole groups are much more severely inclined [dihedral angle = 70.87 (4)°]. In the crystal, weak C-H⋯N inter-actions connect translationally-related triazole rings, while another set of C-H⋯N inter-actions is formed between inversion-related benzoxadiazole units, forming a three-dimensional network. The crystal studied was a non-merohedral twin with refined value of the twin fraction of 0.2289 (16).

Related literature

For the synthesis of similar benzoxadiazole compounds, see: Key & Cairo (2011 ▶); Li et al. (2010 ▶). For two related benzoxadiazole-triazole structures, see: Key, Cairo & Ferguson (2012 ▶); Key, Cairo & McDonald (2012 ▶). For structures of 1-(ar­yl)methyl-1,2,3-triazole compounds with 4-carbonyl substituents [RC(O) or ROC(O)], see: Harju et al. (2003 ▶); Huang et al. (2010 ▶); Dong & Cheng (2011 ▶); Jia & Lu (2011 ▶); Menendez et al. (2012 ▶).

Experimental

Crystal data

C15H17N5O2

M = 299.34

Monoclinic,

a = 16.5752 (16) Å

b = 5.5429 (5) Å

c = 16.2452 (16) Å

β = 91.3612 (13)°

V = 1492.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 173 K

0.74 × 0.14 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (TWINABS; Bruker, 2008 ▶) T min = 0.935, T max = 0.995

45733 measured reflections

3079 independent reflections

2413 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.091

S = 1.03

3079 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.19 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, New_Global_Publ_Block. DOI: 10.1107/S1600536812041839/mw2084sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812041839/mw2084Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812041839/mw2084Isup3.cml

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

C15H17N5O2	F(000) = 632
Mr = 299.34	Dx = 1.333 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5974 reflections
a = 16.5752 (16) Å	θ = 2.5–24.3°
b = 5.5429 (5) Å	µ = 0.09 mm−1
c = 16.2452 (16) Å	T = 173 K
β = 91.3612 (13)°	Rod, colourless
V = 1492.1 (2) Å3	0.74 × 0.14 × 0.06 mm
Z = 4

Bruker APEXII CCD diffractometer	3079 independent reflections
Radiation source: fine-focus sealed tube	2413 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.051
Detector resolution: 8.26 pixels mm-1	θmax = 26.5°, θmin = 1.2°
ω scans	h = −20→20
Absorption correction: multi-scan (TWINABS; Bruker, 2008)	k = −6→6
Tmin = 0.935, Tmax = 0.995	l = −20→20
45733 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)] = 0.040	H-atom parameters constrained
wR(F2) = 0.091	w = 1/[σ2(Fo2) + (0.0331P)2 + 0.4646P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3079 reflections	Δρmax = 0.19 e Å−3
201 parameters	Δρmin = −0.17 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: 0.0114 (15)

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
O1	−0.07380 (7)	0.1919 (2)	0.16041 (7)	0.0409 (3)
O2	0.51268 (8)	0.0088 (2)	0.11538 (10)	0.0593 (4)
N1	−0.03444 (8)	−0.0165 (3)	0.18558 (9)	0.0382 (4)
N2	−0.03404 (8)	0.3110 (3)	0.09850 (9)	0.0363 (3)
N3	0.29027 (7)	0.1559 (2)	0.00229 (8)	0.0272 (3)
N4	0.29675 (8)	0.3994 (2)	0.00904 (9)	0.0317 (3)
N5	0.36597 (7)	0.4428 (2)	0.04758 (9)	0.0309 (3)
C1	0.02958 (9)	−0.0270 (3)	0.13892 (9)	0.0287 (4)
C2	0.02964 (8)	0.1752 (3)	0.08476 (9)	0.0272 (3)
C3	0.09143 (9)	0.2061 (3)	0.02610 (9)	0.0278 (3)
H3	0.0918	0.3406	−0.0101	0.033*
C4	0.14968 (9)	0.0339 (3)	0.02451 (9)	0.0256 (3)
C5	0.14964 (9)	−0.1700 (3)	0.07982 (10)	0.0289 (3)
H5	0.1919	−0.2850	0.0766	0.035*
C6	0.09180 (9)	−0.2039 (3)	0.13617 (10)	0.0311 (4)
H6	0.0927	−0.3392	0.1721	0.037*
C7	0.21712 (9)	0.0526 (3)	−0.03636 (10)	0.0314 (4)
H7A	0.2294	−0.1098	−0.0580	0.038*
H7B	0.1994	0.1553	−0.0833	0.038*
C8	0.35461 (9)	0.0453 (3)	0.03618 (10)	0.0293 (4)
H8	0.3646	−0.1233	0.0395	0.035*
C9	0.40295 (9)	0.2287 (3)	0.06506 (10)	0.0288 (4)
C10	0.48268 (9)	0.2074 (3)	0.10742 (10)	0.0330 (4)
C11	0.52284 (9)	0.4320 (3)	0.13876 (11)	0.0331 (4)
H11A	0.4886	0.5057	0.1811	0.040*
H11B	0.5268	0.5484	0.0928	0.040*
C12	0.60693 (9)	0.3892 (3)	0.17585 (11)	0.0349 (4)
H12A	0.6029	0.2767	0.2229	0.042*
H12B	0.6409	0.3117	0.1341	0.042*
C13	0.64772 (9)	0.6203 (3)	0.20530 (10)	0.0320 (4)
H13A	0.6496	0.7355	0.1588	0.038*
H13B	0.6149	0.6941	0.2488	0.038*
C14	0.73289 (10)	0.5801 (3)	0.23904 (12)	0.0422 (4)
H14A	0.7665	0.5154	0.1946	0.051*
H14B	0.7315	0.4576	0.2833	0.051*
C15	0.77195 (11)	0.8090 (4)	0.27312 (11)	0.0450 (5)
H15A	0.8265	0.7723	0.2939	0.054*
H15B	0.7397	0.8722	0.3180	0.054*
H15C	0.7748	0.9300	0.2293	0.054*

	U11	U22	U33	U12	U13	U23
O1	0.0309 (6)	0.0481 (8)	0.0440 (7)	0.0059 (6)	0.0048 (5)	−0.0042 (6)
O2	0.0466 (8)	0.0264 (7)	0.1034 (13)	0.0055 (6)	−0.0278 (8)	−0.0033 (7)
N1	0.0341 (7)	0.0428 (9)	0.0379 (8)	0.0016 (7)	0.0028 (6)	−0.0012 (7)
N2	0.0316 (7)	0.0373 (8)	0.0400 (8)	0.0036 (6)	−0.0019 (6)	−0.0019 (7)
N3	0.0270 (6)	0.0249 (7)	0.0297 (7)	−0.0020 (5)	0.0035 (5)	−0.0010 (6)
N4	0.0301 (7)	0.0256 (7)	0.0395 (8)	−0.0010 (6)	0.0011 (6)	0.0004 (6)
N5	0.0277 (7)	0.0242 (7)	0.0409 (8)	−0.0001 (5)	0.0004 (6)	0.0006 (6)
C1	0.0264 (8)	0.0317 (9)	0.0279 (8)	−0.0042 (7)	−0.0016 (6)	−0.0018 (7)
C2	0.0244 (7)	0.0258 (8)	0.0310 (8)	−0.0003 (6)	−0.0061 (6)	−0.0037 (7)
C3	0.0304 (8)	0.0248 (8)	0.0281 (8)	−0.0035 (7)	−0.0041 (6)	0.0008 (7)
C4	0.0254 (7)	0.0259 (8)	0.0254 (8)	−0.0039 (6)	−0.0045 (6)	−0.0033 (6)
C5	0.0281 (8)	0.0250 (8)	0.0334 (8)	0.0024 (6)	−0.0024 (6)	−0.0016 (7)
C6	0.0354 (8)	0.0256 (8)	0.0323 (9)	−0.0004 (7)	−0.0019 (7)	0.0037 (7)
C7	0.0311 (8)	0.0339 (9)	0.0292 (9)	−0.0043 (7)	−0.0012 (6)	−0.0042 (7)
C8	0.0288 (8)	0.0235 (8)	0.0359 (9)	0.0006 (6)	0.0040 (6)	0.0007 (7)
C9	0.0277 (8)	0.0228 (8)	0.0359 (9)	0.0004 (6)	0.0036 (6)	−0.0001 (7)
C10	0.0290 (8)	0.0258 (9)	0.0442 (10)	0.0011 (7)	−0.0009 (7)	0.0014 (8)
C11	0.0287 (8)	0.0285 (9)	0.0422 (10)	−0.0003 (7)	−0.0007 (7)	−0.0011 (7)
C12	0.0323 (8)	0.0312 (9)	0.0410 (10)	−0.0020 (7)	−0.0037 (7)	0.0050 (8)
C13	0.0295 (8)	0.0344 (9)	0.0321 (9)	−0.0017 (7)	−0.0005 (7)	0.0001 (7)
C14	0.0370 (9)	0.0402 (11)	0.0488 (11)	−0.0043 (8)	−0.0115 (8)	0.0055 (9)
C15	0.0410 (10)	0.0518 (12)	0.0418 (11)	−0.0113 (9)	−0.0077 (8)	0.0025 (9)

O1—N2	1.3831 (18)	C7—H7B	0.9900
O1—N1	1.3835 (18)	C8—C9	1.370 (2)
O2—C10	1.214 (2)	C8—H8	0.9500
N1—C1	1.320 (2)	C9—C10	1.480 (2)
N2—C2	1.320 (2)	C10—C11	1.495 (2)
N3—C8	1.3376 (19)	C11—C12	1.524 (2)
N3—N4	1.3581 (18)	C11—H11A	0.9900
N3—C7	1.4682 (19)	C11—H11B	0.9900
N4—N5	1.3160 (17)	C12—C13	1.520 (2)
N5—C9	1.3627 (19)	C12—H12A	0.9900
C1—C2	1.425 (2)	C12—H12B	0.9900
C1—C6	1.425 (2)	C13—C14	1.519 (2)
C2—C3	1.426 (2)	C13—H13A	0.9900
C3—C4	1.358 (2)	C13—H13B	0.9900
C3—H3	0.9500	C14—C15	1.523 (2)
C4—C5	1.444 (2)	C14—H14A	0.9900
C4—C7	1.513 (2)	C14—H14B	0.9900
C5—C6	1.354 (2)	C15—H15A	0.9800
C5—H5	0.9500	C15—H15B	0.9800
C6—H6	0.9500	C15—H15C	0.9800
C7—H7A	0.9900
N2—O1—N1	112.57 (11)	N5—C9—C10	123.94 (14)
C1—N1—O1	104.30 (13)	C8—C9—C10	127.49 (14)
C2—N2—O1	104.33 (13)	O2—C10—C9	118.73 (15)
C8—N3—N4	111.20 (12)	O2—C10—C11	122.74 (14)
C8—N3—C7	129.75 (13)	C9—C10—C11	118.53 (14)
N4—N3—C7	119.02 (13)	C10—C11—C12	113.64 (14)
N5—N4—N3	106.65 (12)	C10—C11—H11A	108.8
N4—N5—C9	108.83 (12)	C12—C11—H11A	108.8
N1—C1—C2	109.40 (14)	C10—C11—H11B	108.8
N1—C1—C6	129.85 (15)	C12—C11—H11B	108.8
C2—C1—C6	120.73 (14)	H11A—C11—H11B	107.7
N2—C2—C1	109.39 (14)	C13—C12—C11	112.92 (14)
N2—C2—C3	129.38 (15)	C13—C12—H12A	109.0
C1—C2—C3	121.22 (14)	C11—C12—H12A	109.0
C4—C3—C2	116.78 (14)	C13—C12—H12B	109.0
C4—C3—H3	121.6	C11—C12—H12B	109.0
C2—C3—H3	121.6	H12A—C12—H12B	107.8
C3—C4—C5	121.82 (14)	C14—C13—C12	113.13 (14)
C3—C4—C7	120.05 (14)	C14—C13—H13A	109.0
C5—C4—C7	118.13 (14)	C12—C13—H13A	109.0
C6—C5—C4	122.70 (15)	C14—C13—H13B	109.0
C6—C5—H5	118.6	C12—C13—H13B	109.0
C4—C5—H5	118.6	H13A—C13—H13B	107.8
C5—C6—C1	116.74 (15)	C13—C14—C15	113.11 (15)
C5—C6—H6	121.6	C13—C14—H14A	109.0
C1—C6—H6	121.6	C15—C14—H14A	109.0
N3—C7—C4	111.25 (12)	C13—C14—H14B	109.0
N3—C7—H7A	109.4	C15—C14—H14B	109.0
C4—C7—H7A	109.4	H14A—C14—H14B	107.8
N3—C7—H7B	109.4	C14—C15—H15A	109.5
C4—C7—H7B	109.4	C14—C15—H15B	109.5
H7A—C7—H7B	108.0	H15A—C15—H15B	109.5
N3—C8—C9	104.76 (14)	C14—C15—H15C	109.5
N3—C8—H8	127.6	H15A—C15—H15C	109.5
C9—C8—H8	127.6	H15B—C15—H15C	109.5
N5—C9—C8	108.57 (13)
N2—O1—N1—C1	−0.28 (17)	C2—C1—C6—C5	−0.3 (2)
N1—O1—N2—C2	0.55 (16)	C8—N3—C7—C4	94.95 (19)
C8—N3—N4—N5	0.04 (18)	N4—N3—C7—C4	−82.78 (18)
C7—N3—N4—N5	178.17 (12)	C3—C4—C7—N3	98.31 (16)
N3—N4—N5—C9	0.00 (17)	C5—C4—C7—N3	−81.66 (17)
O1—N1—C1—C2	−0.09 (16)	N4—N3—C8—C9	−0.05 (17)
O1—N1—C1—C6	−178.92 (15)	C7—N3—C8—C9	−177.93 (14)
O1—N2—C2—C1	−0.58 (16)	N4—N5—C9—C8	−0.03 (18)
O1—N2—C2—C3	178.43 (14)	N4—N5—C9—C10	179.26 (15)
N1—C1—C2—N2	0.45 (18)	N3—C8—C9—N5	0.05 (17)
C6—C1—C2—N2	179.40 (14)	N3—C8—C9—C10	−179.21 (15)
N1—C1—C2—C3	−178.66 (14)	N5—C9—C10—O2	−175.34 (17)
C6—C1—C2—C3	0.3 (2)	C8—C9—C10—O2	3.8 (3)
N2—C2—C3—C4	−178.81 (15)	N5—C9—C10—C11	4.8 (2)
C1—C2—C3—C4	0.1 (2)	C8—C9—C10—C11	−176.09 (16)
C2—C3—C4—C5	−0.4 (2)	O2—C10—C11—C12	4.1 (3)
C2—C3—C4—C7	179.59 (13)	C9—C10—C11—C12	−176.03 (15)
C3—C4—C5—C6	0.4 (2)	C10—C11—C12—C13	178.46 (14)
C7—C4—C5—C6	−179.61 (14)	C11—C12—C13—C14	−177.59 (15)
C4—C5—C6—C1	0.0 (2)	C12—C13—C14—C15	−176.65 (15)
N1—C1—C6—C5	178.39 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N2i	0.95	2.58	3.475 (2)	158
C8—H8···N5ii	0.95	2.41	3.350 (2)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯N2i	0.95	2.58	3.475 (2)	158
C8—H8⋯N5ii	0.95	2.41	3.350 (2)	171

Symmetry codes: (i) ; (ii) .