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

Key, J.A.; Cairo, C.W.; Ferguson, M.J.

doi:10.1107/S1600536812041815

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Pages o3128-o3129

doi:10.1107/S1600536812041815

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

Jessie A. Key,^a Christopher W. Cairo ^a and Michael J. Ferguson ^b ^*

^aAlberta Glycomics Centre, Department of Chemistry, University of Alberta, Edmonton, AB T6G 2G2, Canada, and ^bX-ray Crystallography Laboratory, Department of Chemistry, University of Alberta, Edmonton, AB T6G 2G2, Canada
^*Correspondence e-mail: michael.ferguson@ualberta.ca

(Received 10 August 2012; accepted 5 October 2012; online 13 October 2012)

The title compound, C₁₄H₁₇N₅O, a 1,2,3-triazole derivative of benzoxadiazole (C₁₄H₁₇N₅O), was synthesized via Cu-catalysed azide–alkyne cycloaddition (CuAAC) from the corresponding n-octyne and 4-azidobenzoxadiazole. The benzoxadiazole 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 interactions 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_r = 271.33
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.036
wR(F²) = 0.099
S = 1.04
3120 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.22 e Å⁻³

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) -x+1, -y, -z+1; (ii) -x-1, -y+1, -z+1.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812041815/mw2081sup1.cif

Supporting information file. DOI: 10.1107/S1600536812041815/mw2081Isup2.cdx

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

Supporting information file. DOI: 10.1107/S1600536812041815/mw2081Isup4.cml

checkCIF report

Comment top

Fluorophores with properties responsive to their chemical environment, or which are reactive to the presence of specific functional groups, can be useful probes in chemistry and biology (Cairo et al., 2010; Lavis & Raines, 2008). We explored a series of analogs suitable for the Cu-catalyzed azide-alkyne cycloaddition (CuAAC) to identify substrates which were fluorogenic. Compounds with increased fluorescence upon conversion from either an azide or alkyne precursor to a triazole product would be of interest for detecting the presence of these functional groups in complex mixtures. The title compound, I, was found to be only weakly fluorescent, which is in contrast to the properties of the 4-azido-benzoxadiazole precursor, II. Thus, we designated compound I as a quenched fluorophore (Key & Cairo, 2011).

The benzoxadiazole and triazole rings of I are nearly eclipsed, as noted from the dihedral angle of 12.18 (5)° that was obtained from least-squares planes calculations. The hexyl side-chain adopted an essentially planar zigzag conformation [maximum deviation from the plane 0.0530 (8) Å]; the alkyl chain was twisted 20.89 (6)° with respect to the central triazole. There was an overall twist to the structure, with an angle of 32.86 (7)° between the benzoxadiazole group and the hexyl chain.

The packing of I in the solid state was stabilized by weak intermolecular C–H···N hydrogen bonds (H···N distances: 2.46-2.52 Å) and offset parallel stacking interactions (3.331-3.791 Å) of the triazole and benzoxadiazole rings (see Figures 3 and 4).

Related literature top

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 top

4-Azidobenzoxadiazole (30 mg, 0.19 mmol, 1 equiv) was dissolved in 1:1 water/methanol (5 mL), followed by addition of n-octyne (0.14 mL, 0.93 mmol, 5 equiv). Copper sulfate (6 mg, 0.037 mmol, 0.2 equiv) and ascorbic acid (10 mg, 0.056 mmol, 0.3 equiv) were then added to the mixture. The reaction was allowed to stir at room temperature for 6 h. The reaction was quenched with distilled water, and the crude product was extracted with chloroform, followed by water and brine washes. The organic layer was then dried over MgSO₄ and concentrated in vacuo. Purification was performed by column chromatography (EtOAc/hexanes). The product was obtained as white crystals (25 mg, 50%). m.p. 113.2–115.4 °C; ¹H NMR (400 MHz, CDCl₃): δ 8.19 (dd, 1H, ⁴J = 3.8 Hz, ⁴J = 1.84 Hz), 8.06 (m, 2H), 7.91 (s, 1H), 2.85 (t, 2H, ³J = 8.0 Hz), 1.77 (m, 2H), 1.31–1.47 (m, 6H),0.91 (m, 3H); ¹³C NMR (100 MHz, CDCl₃): δ150.5, 149.0, 148.4, 139.1, 126.8, 119.1, 118.9, 104.5, 31.8, 29.4, 29.1, 25.9, 22.8, 14.3; IR (microscope): ν = 3147, 3114, 3095, 3059, 2956, 2929, 2857, 1637, 1540 cm^-1; ES-HRMS calculated for C₁₄H₁₈N₅O [M+H]: 272.1506; observed: 272.1513. R_f = 0.51 (1:3 EtOAc/hexanes).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. : View of I. Non-hydrogen atoms are represented by Gaussian ellipsoids at the 50% probability level.
	Fig. 2. : Compounds used in this study.
	Fig. 3. : Packing of I, showing the offset stacking of the triazole and benzoxadiazole rings. C–H···N hydrogen bonds are indicated by dotted lines.
	Fig. 4. : Alternate view of the packing of I.

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

Crystal data top

C₁₄H₁₇N₅O	Z = 2
M_r = 271.33	F(000) = 288
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0495P)² + 0.1216P] where P = (F_o² + 2F_c²)/3
3120 reflections	(Δ/σ)_max = 0.002
181 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₄H₁₇N₅O	γ = 85.6240 (17)°
M_r = 271.33	V = 685.04 (17) Å³
Triclinic, P1	Z = 2
a = 5.3604 (8) Å	Mo Kα radiation
b = 7.8585 (11) Å	µ = 0.09 mm⁻¹
c = 16.357 (2) Å	T = 173 K
α = 87.4656 (17)°	1.02 × 0.35 × 0.03 mm
β = 86.2519 (16)°

Data collection top

Bruker APEXII CCD diffractometer	3120 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2568 reflections with I > 2σ(I)
T_min = 0.915, T_max = 0.997	R_int = 0.013
6114 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 1.04	Δρ_max = 0.20 e Å⁻³
3120 reflections	Δρ_min = −0.22 e Å⁻³
181 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y, −z+1; (ii) −x−1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₇N₅O
M_r	271.33
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	5.3604 (8), 7.8585 (11), 16.357 (2)
α, β, γ (°)	87.4656 (17), 86.2519 (16), 85.6240 (17)
V (Å³)	685.04 (17)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	1.02 × 0.35 × 0.03

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.915, 0.997
No. of measured, independent and observed [I > 2σ(I)] reflections	6114, 3120, 2568
R_int	0.013
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.099, 1.04
No. of reflections	3120
No. of parameters	181
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.22

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXD (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N2ⁱ	0.95	2.52	3.4674 (15)	177.0
C5—H5···N4ⁱⁱ	0.95	2.46	3.3445 (15)	154.2

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x−1, −y+1, −z+1.

Acknowledgements

This work was supported by the Natural Science and Engineering Research Council of Canada and the Alberta Glycomics Centre.

References

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