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

Xu, S.-Q.; Li, J.-M.

doi:10.1107/S1600536808019879

organic compounds

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Volume 64| Part 8| August 2008| Page o1403

doi:10.1107/S1600536808019879

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

Shu-Qing Xu ^a and Jia-Ming Li ^a ^*

^aLaboratory of Beibu Gulf Marine Protection and Exploitation, Department of Chemistry and Biology, Qinzhou University, Qinzhou, Guangxi 535000, People's Republic of China
^*Correspondence e-mail: ljmmarise@163.com

(Received 21 June 2008; accepted 30 June 2008; online 5 July 2008)

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 ); Wardell et al. (2003 ); Srinivasan et al. (2007 ); Wang et al. (2004a ,b ,c , 2007 ); Romero (2001 ); Terashita et al. (2002 ); Zen et al. (1983 ).

Experimental

Crystal data

C₁₅H₁₁N₅O
M_r = 277.29
Monoclinic, P 2₁ /c
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 ) 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[F² > 2σ(F²)] = 0.050
wR(F²) = 0.103
S = 1.02
2322 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9B⋯N5ⁱ	0.97	2.59	3.443 (3)	147
C9—H9A⋯N2ⁱⁱ	0.97	2.60	3.466 (3)	149
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x-1, y, z.

Data collection: SMART (Bruker, 2003 ); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (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 global, I. DOI: 10.1107/S1600536808019879/lh2650sup1.cif

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

checkCIF report

Comment top

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.

Related literature top

For related literature, see: Batista et al. (2000); Wardell et al. (2003); Srinivasan et al. (2007); Wang et al. (2004a,b,c, 2007).

For related literature, see: Romero (2001); Terashita et al. (2002); Zen et al. (1983).

Experimental top

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).

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (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. 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.

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

Crystal data top

C₁₅H₁₁N₅O	F(000) = 576
M_r = 277.29	D_x = 1.403 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 760 reflections
a = 4.7009 (13) Å	θ = 2.5–19.5°
b = 11.100 (3) Å	µ = 0.09 mm⁻¹
c = 25.265 (7) Å	T = 295 K
β = 95.234 (6)°	Block, colorless
V = 1312.8 (6) Å³	0.18 × 0.14 × 0.12 mm
Z = 4

Data collection top

Bruker SMART diffractometer	2322 independent reflections
Radiation source: fine-focus sealed tube	1324 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.054
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→5
T_min = 0.983, T_max = 0.989	k = −13→13
6803 measured reflections	l = −20→29

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.103	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.036P)² + 0.0112P] where P = (F_o² + 2F_c²)/3
2322 reflections	(Δ/σ)_max < 0.001
190 parameters	Δρ_max = 0.13 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₅H₁₁N₅O	V = 1312.8 (6) Å³
M_r = 277.29	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 4.7009 (13) Å	µ = 0.09 mm⁻¹
b = 11.100 (3) Å	T = 295 K
c = 25.265 (7) Å	0.18 × 0.14 × 0.12 mm
β = 95.234 (6)°

Data collection top

Bruker SMART diffractometer	2322 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1324 reflections with I > 2σ(I)
T_min = 0.983, T_max = 0.989	R_int = 0.054
6803 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.02	Δρ_max = 0.13 e Å⁻³
2322 reflections	Δρ_min = −0.19 e Å⁻³
190 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
O1	0.1731 (4)	0.96111 (14)	0.37087 (7)	0.0620 (5)
N1	0.3748 (5)	0.94501 (18)	0.41561 (8)	0.0626 (6)
N2	0.4253 (4)	0.80085 (17)	0.35428 (7)	0.0477 (5)
N3	0.1502 (4)	0.80219 (18)	0.24592 (8)	0.0488 (5)
N4	0.1194 (5)	0.68098 (19)	0.23986 (9)	0.0626 (6)
N5	0.2711 (5)	0.64667 (18)	0.20147 (9)	0.0644 (6)
C1	0.5148 (5)	0.8490 (2)	0.40357 (9)	0.0443 (6)
C2	0.7410 (5)	0.7967 (2)	0.43988 (9)	0.0445 (6)
C3	0.8252 (5)	0.8510 (2)	0.48824 (10)	0.0587 (7)
H3	0.7393	0.9224	0.4976	0.070*
C4	1.0355 (6)	0.7994 (3)	0.52249 (10)	0.0669 (8)
H4	1.0927	0.8369	0.5546	0.080*
C5	1.1613 (6)	0.6933 (3)	0.50957 (11)	0.0675 (8)
H5	1.3019	0.6586	0.5330	0.081*
C6	1.0795 (6)	0.6382 (2)	0.46194 (11)	0.0662 (8)
H6	1.1652	0.5663	0.4532	0.079*
C7	0.8703 (5)	0.6893 (2)	0.42703 (10)	0.0550 (7)
H7	0.8157	0.6517	0.3948	0.066*
C8	0.2200 (5)	0.8714 (2)	0.33742 (9)	0.0460 (6)
C9	0.0215 (5)	0.8644 (2)	0.28801 (9)	0.0595 (7)
H9A	−0.1512	0.8225	0.2956	0.071*
H9B	−0.0313	0.9452	0.2763	0.071*
C10	0.3265 (5)	0.8462 (2)	0.21070 (9)	0.0428 (6)
C11	0.4018 (5)	0.7457 (2)	0.18258 (9)	0.0472 (6)
C12	0.5861 (5)	0.7564 (2)	0.14226 (10)	0.0578 (7)
H12	0.6374	0.6898	0.1229	0.069*
C13	0.6871 (5)	0.8689 (3)	0.13269 (10)	0.0630 (7)
H13	0.8125	0.8788	0.1066	0.076*
C14	0.6070 (5)	0.9691 (2)	0.16101 (10)	0.0594 (7)
H14	0.6790	1.0442	0.1529	0.071*
C15	0.4258 (5)	0.9607 (2)	0.20035 (10)	0.0515 (6)
H15	0.3724	1.0279	0.2190	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0714 (12)	0.0570 (11)	0.0567 (12)	0.0150 (9)	0.0015 (10)	−0.0011 (10)
N1	0.0734 (15)	0.0596 (14)	0.0533 (15)	0.0106 (12)	−0.0026 (12)	−0.0082 (12)
N2	0.0492 (12)	0.0528 (12)	0.0405 (13)	0.0061 (10)	0.0007 (10)	0.0001 (11)
N3	0.0531 (12)	0.0484 (13)	0.0431 (13)	0.0011 (10)	−0.0055 (10)	0.0021 (11)
N4	0.0712 (15)	0.0494 (15)	0.0642 (16)	−0.0082 (11)	−0.0104 (13)	0.0118 (13)
N5	0.0798 (17)	0.0458 (14)	0.0649 (16)	−0.0017 (12)	−0.0070 (13)	−0.0007 (13)
C1	0.0483 (14)	0.0460 (15)	0.0392 (16)	−0.0039 (12)	0.0066 (12)	0.0000 (13)
C2	0.0461 (14)	0.0511 (15)	0.0370 (14)	−0.0060 (12)	0.0069 (12)	−0.0030 (13)
C3	0.0609 (17)	0.0646 (17)	0.0502 (17)	−0.0045 (14)	0.0033 (14)	−0.0087 (15)
C4	0.0683 (19)	0.086 (2)	0.0451 (17)	−0.0147 (17)	−0.0028 (15)	−0.0076 (17)
C5	0.0631 (18)	0.084 (2)	0.0536 (19)	−0.0015 (17)	−0.0062 (15)	0.0128 (18)
C6	0.0714 (19)	0.0660 (18)	0.0596 (19)	0.0080 (15)	−0.0031 (15)	−0.0014 (16)
C7	0.0584 (16)	0.0633 (17)	0.0421 (15)	−0.0026 (14)	−0.0024 (13)	−0.0053 (14)
C8	0.0496 (15)	0.0492 (16)	0.0401 (16)	0.0014 (13)	0.0087 (13)	0.0022 (13)
C9	0.0555 (16)	0.0702 (18)	0.0519 (17)	0.0105 (13)	0.0005 (14)	0.0054 (15)
C10	0.0470 (14)	0.0412 (14)	0.0375 (14)	−0.0012 (12)	−0.0113 (12)	−0.0017 (13)
C11	0.0563 (15)	0.0371 (14)	0.0449 (15)	0.0025 (13)	−0.0138 (13)	0.0014 (13)
C12	0.0666 (17)	0.0570 (17)	0.0479 (16)	0.0153 (14)	−0.0052 (14)	−0.0071 (14)
C13	0.0647 (18)	0.073 (2)	0.0509 (18)	0.0072 (15)	0.0034 (14)	0.0064 (16)
C14	0.0647 (17)	0.0539 (17)	0.0584 (18)	−0.0072 (14)	−0.0015 (15)	0.0066 (15)
C15	0.0580 (16)	0.0431 (15)	0.0508 (17)	−0.0012 (13)	−0.0095 (13)	−0.0049 (13)

Geometric parameters (Å, º) top

O1—C8	1.338 (3)	C5—H5	0.9300
O1—N1	1.419 (2)	C6—C7	1.382 (3)
N1—C1	1.303 (3)	C6—H6	0.9300
N2—C8	1.284 (3)	C7—H7	0.9300
N2—C1	1.385 (3)	C8—C9	1.491 (3)
N3—N4	1.360 (2)	C9—H9A	0.9700
N3—C10	1.361 (3)	C9—H9B	0.9700
N3—C9	1.446 (3)	C10—C11	1.386 (3)
N4—N5	1.312 (3)	C10—C15	1.387 (3)
N5—C11	1.366 (3)	C11—C12	1.401 (3)
C1—C2	1.460 (3)	C12—C13	1.365 (3)
C2—C3	1.387 (3)	C12—H12	0.9300
C2—C7	1.390 (3)	C13—C14	1.393 (3)
C3—C4	1.378 (3)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.370 (3)
C4—C5	1.370 (3)	C14—H14	0.9300
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.373 (3)

C8—O1—N1	105.82 (17)	C2—C7—H7	119.9
C1—N1—O1	103.41 (18)	N2—C8—O1	114.0 (2)
C8—N2—C1	102.7 (2)	N2—C8—C9	129.8 (2)
N4—N3—C10	110.2 (2)	O1—C8—C9	116.2 (2)
N4—N3—C9	120.5 (2)	N3—C9—C8	111.64 (19)
C10—N3—C9	129.1 (2)	N3—C9—H9A	109.3
N5—N4—N3	108.1 (2)	C8—C9—H9A	109.3
N4—N5—C11	108.5 (2)	N3—C9—H9B	109.3
N1—C1—N2	114.0 (2)	C8—C9—H9B	109.3
N1—C1—C2	122.2 (2)	H9A—C9—H9B	108.0
N2—C1—C2	123.8 (2)	N3—C10—C11	104.2 (2)
C3—C2—C7	118.8 (2)	N3—C10—C15	133.4 (2)
C3—C2—C1	120.9 (2)	C11—C10—C15	122.3 (2)
C7—C2—C1	120.2 (2)	N5—C11—C10	108.9 (2)
C4—C3—C2	120.2 (2)	N5—C11—C12	130.5 (2)
C4—C3—H3	119.9	C10—C11—C12	120.5 (2)
C2—C3—H3	119.9	C13—C12—C11	117.0 (2)
C5—C4—C3	120.5 (2)	C13—C12—H12	121.5
C5—C4—H4	119.7	C11—C12—H12	121.5
C3—C4—H4	119.7	C12—C13—C14	121.6 (2)
C4—C5—C6	119.9 (3)	C12—C13—H13	119.2
C4—C5—H5	120.0	C14—C13—H13	119.2
C6—C5—H5	120.0	C15—C14—C13	122.3 (2)
C5—C6—C7	120.2 (3)	C15—C14—H14	118.9
C5—C6—H6	119.9	C13—C14—H14	118.9
C7—C6—H6	119.9	C14—C15—C10	116.2 (2)
C6—C7—C2	120.3 (2)	C14—C15—H15	121.9
C6—C7—H7	119.9	C10—C15—H15	121.9

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···N5ⁱ	0.97	2.59	3.443 (3)	147
C9—H9A···N2ⁱⁱ	0.97	2.60	3.466 (3)	149

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₁N₅O
M_r	277.29
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	4.7009 (13), 11.100 (3), 25.265 (7)
β (°)	95.234 (6)
V (Å³)	1312.8 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.18 × 0.14 × 0.12

Data collection
Diffractometer	Bruker SMART diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.983, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	6803, 2322, 1324
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.103, 1.02
No. of reflections	2322
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.19

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (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
C9—H9B···N5ⁱ	0.97	2.59	3.443 (3)	146.9
C9—H9A···N2ⁱⁱ	0.97	2.60	3.466 (3)	148.8

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

Acknowledgements

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).

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