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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1403.
Published online 2008 July 5. doi:  10.1107/S1600536808019879
PMCID: PMC2962036

5-(1H-1,2,3-Benzotriazol-1-ylmeth­yl)-3-phenyl-1,2,4-oxadiazole

Abstract

In the title mol­ecule, C15H11N5O, the 1,2,3-benzotriazole and 3-phenyl-1,2,4-oxadiazole units are individually essentially planar and the dihedral angle between them is 80.2 (2)°. In the crystal structure, mol­ecules are connected via weak inter­molecular C—H(...)N hydrogen bonds to form two-dimensional sheets.

Related literature

For related literature, see: Batista et al. (2000 [triangle]); Wardell et al. (2003 [triangle]); Srinivasan et al. (2007 [triangle]); Wang et al. (2004a [triangle],b [triangle],c [triangle], 2007 [triangle]); Romero (2001 [triangle]); Terashita et al. (2002 [triangle]); Zen et al. (1983 [triangle]).

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Object name is e-64-o1403-scheme1.jpg

Experimental

Crystal data

  • C15H11N5O
  • M r = 277.29
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1403-efi1.jpg
  • a = 4.7009 (13) Å
  • b = 11.100 (3) Å
  • c = 25.265 (7) Å
  • β = 95.234 (6)°
  • V = 1312.8 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 295 K
  • 0.18 × 0.14 × 0.12 mm

Data collection

  • Bruker SMART diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.983, T max = 0.989
  • 6803 measured reflections
  • 2322 independent reflections
  • 1324 reflections with I > 2σ(I)
  • R int = 0.053

Refinement

  • R[F 2 > 2σ(F 2)] = 0.050
  • wR(F 2) = 0.103
  • S = 1.02
  • 2322 reflections
  • 190 parameters
  • H-atom parameters constrained
  • Δρmax = 0.13 e Å−3
  • Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2003 [triangle]); cell refinement: SAINT (Bruker, 2003 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808019879/lh2650sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019879/lh2650Isup2.hkl

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

Acknowledgments

This work was supported by a grant from the Qinzhou University Foundation of Guangxi Zhuang Autonomous Region of the People’s Republic of China (grant No. 2007XJ15).

supplementary crystallographic information

Comment

Synthesis of 1,2,4-oxadiazole derivatives has attracted a great interest due to their pharmacological properties such as intrinsic analgesic (Zen et al., 1983; Terashita et al., 2002) and antipicornaviral (Romero, 2001) effects. Wang et al. (2004a,b,c;2007) have described the synthesis and crystal structures of a series of these types of compounds. Herein, we report the synthesis and crystal structure of the title compound, (I), containing both 1,2,4-oxadiazole and 1,2,3-benzotriazole organic functional groups. The molecular structure of (I) is shown in Fig. 1. The title molecule can be considered as two rings systems: the 3-phenyl-1,2,4-oxadiazol-5-yl (A) and benzotriazole (B). All atoms in A, B are individually essentially planar with dihedral angles of 4.4 (2) ° and 0.5 (2) ° between the rings in each, respectively. The dihedral angle between A and B is 80.2 (2) °. This conformation presents no nonbonded interactions (Batista et al.,2000). Molecules are connected via weak intermolecular C—H···N hydrogen bonds (Table. 1 and Fig. 2) to form two-dimensional sheets.

Experimental

Reagents and solvents used were of commercially available quality. 1,2,3-Benzotriazole (1 mmol) was dissolved in acetonitrile (80 ml) and potassium carbonate (15 mmol) was added followed by 3-phenyl-5-chloromethyl-1,2,4-oxadiazole (1 mmol). The resulting mixture was refluxed for 10 h. After cooling and filtering, the crude title compound was obtained and purified by recrystallization from ethyl acetate. Crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution of (I).

Refinement

H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93–0.97 Å and with Uiso(H) = 1.2 times Ueq(C).

Figures

Fig. 1.
The molecular structure with displacement ellipsoids at the 30% probability level.
Fig. 2.
Part of the crystal structure showing hydrogen bonds as dashed lines. H atoms, except for those involved in hydrogen bonds, are not included.

Crystal data

C15H11N5OF000 = 576
Mr = 277.29Dx = 1.403 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 760 reflections
a = 4.7009 (13) Åθ = 2.5–19.5º
b = 11.100 (3) ŵ = 0.09 mm1
c = 25.265 (7) ÅT = 295 K
β = 95.234 (6)ºBlock, colorless
V = 1312.8 (6) Å30.18 × 0.14 × 0.12 mm
Z = 4

Data collection

Bruker SMART diffractometer2322 independent reflections
Radiation source: fine-focus sealed tube1324 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.054
T = 295 Kθmax = 25.0º
[var phi] and ω scansθmin = 1.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −5→5
Tmin = 0.983, Tmax = 0.989k = −13→13
6803 measured reflectionsl = −20→29

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050H-atom parameters constrained
wR(F2) = 0.103  w = 1/[σ2(Fo2) + (0.036P)2 + 0.0112P] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
2322 reflectionsΔρmax = 0.13 e Å3
190 parametersΔρmin = −0.19 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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)

xyzUiso*/Ueq
O10.1731 (4)0.96111 (14)0.37087 (7)0.0620 (5)
N10.3748 (5)0.94501 (18)0.41561 (8)0.0626 (6)
N20.4253 (4)0.80085 (17)0.35428 (7)0.0477 (5)
N30.1502 (4)0.80219 (18)0.24592 (8)0.0488 (5)
N40.1194 (5)0.68098 (19)0.23986 (9)0.0626 (6)
N50.2711 (5)0.64667 (18)0.20147 (9)0.0644 (6)
C10.5148 (5)0.8490 (2)0.40357 (9)0.0443 (6)
C20.7410 (5)0.7967 (2)0.43988 (9)0.0445 (6)
C30.8252 (5)0.8510 (2)0.48824 (10)0.0587 (7)
H30.73930.92240.49760.070*
C41.0355 (6)0.7994 (3)0.52249 (10)0.0669 (8)
H41.09270.83690.55460.080*
C51.1613 (6)0.6933 (3)0.50957 (11)0.0675 (8)
H51.30190.65860.53300.081*
C61.0795 (6)0.6382 (2)0.46194 (11)0.0662 (8)
H61.16520.56630.45320.079*
C70.8703 (5)0.6893 (2)0.42703 (10)0.0550 (7)
H70.81570.65170.39480.066*
C80.2200 (5)0.8714 (2)0.33742 (9)0.0460 (6)
C90.0215 (5)0.8644 (2)0.28801 (9)0.0595 (7)
H9A−0.15120.82250.29560.071*
H9B−0.03130.94520.27630.071*
C100.3265 (5)0.8462 (2)0.21070 (9)0.0428 (6)
C110.4018 (5)0.7457 (2)0.18258 (9)0.0472 (6)
C120.5861 (5)0.7564 (2)0.14226 (10)0.0578 (7)
H120.63740.68980.12290.069*
C130.6871 (5)0.8689 (3)0.13269 (10)0.0630 (7)
H130.81250.87880.10660.076*
C140.6070 (5)0.9691 (2)0.16101 (10)0.0594 (7)
H140.67901.04420.15290.071*
C150.4258 (5)0.9607 (2)0.20035 (10)0.0515 (6)
H150.37241.02790.21900.062*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0714 (12)0.0570 (11)0.0567 (12)0.0150 (9)0.0015 (10)−0.0011 (10)
N10.0734 (15)0.0596 (14)0.0533 (15)0.0106 (12)−0.0026 (12)−0.0082 (12)
N20.0492 (12)0.0528 (12)0.0405 (13)0.0061 (10)0.0007 (10)0.0001 (11)
N30.0531 (12)0.0484 (13)0.0431 (13)0.0011 (10)−0.0055 (10)0.0021 (11)
N40.0712 (15)0.0494 (15)0.0642 (16)−0.0082 (11)−0.0104 (13)0.0118 (13)
N50.0798 (17)0.0458 (14)0.0649 (16)−0.0017 (12)−0.0070 (13)−0.0007 (13)
C10.0483 (14)0.0460 (15)0.0392 (16)−0.0039 (12)0.0066 (12)0.0000 (13)
C20.0461 (14)0.0511 (15)0.0370 (14)−0.0060 (12)0.0069 (12)−0.0030 (13)
C30.0609 (17)0.0646 (17)0.0502 (17)−0.0045 (14)0.0033 (14)−0.0087 (15)
C40.0683 (19)0.086 (2)0.0451 (17)−0.0147 (17)−0.0028 (15)−0.0076 (17)
C50.0631 (18)0.084 (2)0.0536 (19)−0.0015 (17)−0.0062 (15)0.0128 (18)
C60.0714 (19)0.0660 (18)0.0596 (19)0.0080 (15)−0.0031 (15)−0.0014 (16)
C70.0584 (16)0.0633 (17)0.0421 (15)−0.0026 (14)−0.0024 (13)−0.0053 (14)
C80.0496 (15)0.0492 (16)0.0401 (16)0.0014 (13)0.0087 (13)0.0022 (13)
C90.0555 (16)0.0702 (18)0.0519 (17)0.0105 (13)0.0005 (14)0.0054 (15)
C100.0470 (14)0.0412 (14)0.0375 (14)−0.0012 (12)−0.0113 (12)−0.0017 (13)
C110.0563 (15)0.0371 (14)0.0449 (15)0.0025 (13)−0.0138 (13)0.0014 (13)
C120.0666 (17)0.0570 (17)0.0479 (16)0.0153 (14)−0.0052 (14)−0.0071 (14)
C130.0647 (18)0.073 (2)0.0509 (18)0.0072 (15)0.0034 (14)0.0064 (16)
C140.0647 (17)0.0539 (17)0.0584 (18)−0.0072 (14)−0.0015 (15)0.0066 (15)
C150.0580 (16)0.0431 (15)0.0508 (17)−0.0012 (13)−0.0095 (13)−0.0049 (13)

Geometric parameters (Å, °)

O1—C81.338 (3)C5—H50.9300
O1—N11.419 (2)C6—C71.382 (3)
N1—C11.303 (3)C6—H60.9300
N2—C81.284 (3)C7—H70.9300
N2—C11.385 (3)C8—C91.491 (3)
N3—N41.360 (2)C9—H9A0.9700
N3—C101.361 (3)C9—H9B0.9700
N3—C91.446 (3)C10—C111.386 (3)
N4—N51.312 (3)C10—C151.387 (3)
N5—C111.366 (3)C11—C121.401 (3)
C1—C21.460 (3)C12—C131.365 (3)
C2—C31.387 (3)C12—H120.9300
C2—C71.390 (3)C13—C141.393 (3)
C3—C41.378 (3)C13—H130.9300
C3—H30.9300C14—C151.370 (3)
C4—C51.370 (3)C14—H140.9300
C4—H40.9300C15—H150.9300
C5—C61.373 (3)
C8—O1—N1105.82 (17)C2—C7—H7119.9
C1—N1—O1103.41 (18)N2—C8—O1114.0 (2)
C8—N2—C1102.7 (2)N2—C8—C9129.8 (2)
N4—N3—C10110.2 (2)O1—C8—C9116.2 (2)
N4—N3—C9120.5 (2)N3—C9—C8111.64 (19)
C10—N3—C9129.1 (2)N3—C9—H9A109.3
N5—N4—N3108.1 (2)C8—C9—H9A109.3
N4—N5—C11108.5 (2)N3—C9—H9B109.3
N1—C1—N2114.0 (2)C8—C9—H9B109.3
N1—C1—C2122.2 (2)H9A—C9—H9B108.0
N2—C1—C2123.8 (2)N3—C10—C11104.2 (2)
C3—C2—C7118.8 (2)N3—C10—C15133.4 (2)
C3—C2—C1120.9 (2)C11—C10—C15122.3 (2)
C7—C2—C1120.2 (2)N5—C11—C10108.9 (2)
C4—C3—C2120.2 (2)N5—C11—C12130.5 (2)
C4—C3—H3119.9C10—C11—C12120.5 (2)
C2—C3—H3119.9C13—C12—C11117.0 (2)
C5—C4—C3120.5 (2)C13—C12—H12121.5
C5—C4—H4119.7C11—C12—H12121.5
C3—C4—H4119.7C12—C13—C14121.6 (2)
C4—C5—C6119.9 (3)C12—C13—H13119.2
C4—C5—H5120.0C14—C13—H13119.2
C6—C5—H5120.0C15—C14—C13122.3 (2)
C5—C6—C7120.2 (3)C15—C14—H14118.9
C5—C6—H6119.9C13—C14—H14118.9
C7—C6—H6119.9C14—C15—C10116.2 (2)
C6—C7—C2120.3 (2)C14—C15—H15121.9
C6—C7—H7119.9C10—C15—H15121.9

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C9—H9B···N5i0.972.593.443 (3)147
C9—H9A···N2ii0.972.603.466 (3)149

Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) x−1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2650).

References

  • Batista, H., Carpenter, G. B. & Srivastava, R. M. (2000). J. Chem. Crystallogr.30, 131–134.
  • Bruker (2003). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Romero, J. R. (2001). Expert Opin. Investig. Drugs, 10, 369–379. [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Srinivasan, N., Nandhini, M. S., Ranjithkumar, R., Perumal, S. & Krishnakumar, R. V. (2007). Acta Cryst. E63, o3750.
  • Terashita, Z., Naruo, K. & Morimoto, S. (2002). PCT Int. Appl. WO 02060439.
  • Wang, H.-B., Chen, J.-H. & Wang, J.-T. (2004a). Acta Cryst. E60, o1478–o1480.
  • Wang, H.-B., Chen, J.-H. & Wang, J.-T. (2004b). Acta Cryst. E60, o1709–o1711.
  • Wang, H.-B., Chen, J.-H. & Wang, J.-T. (2004c). Acta Cryst. E60, o1917–o1918.
  • Wang, P., Wang, H., Kang, S., Li, H. & Wu, W. (2007). Acta Cryst. E63, o4180.
  • Wardell, S. M. S. V., Carvalho, C. E. M., Low, J. N. & Glidewell, C. (2003). Acta Cryst. E59, o1729–o1730.
  • Zen, S., Nishino, T., Harada, K., Nakamura, H. & Iitaka, Y. (1983). Chem. Pharm. Bull.31, 4181–4184.

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