1,3-Bis(3-phenyl­prop­yl)-1H-benz­imidazole-2(3H)-tellurone

Yalçın, Ş.P.; Akkurt, M.; Yılmaz, Ü.; Küçükbay, H.; Büyükgüngör, O.

doi:10.1107/S1600536808004893

organic compounds

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ISSN: 2056-9890

Volume 64| Part 3| March 2008| Pages o621-o622

doi:10.1107/S1600536808004893

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1,3-Bis(3-phenylpropyl)-1H-benzimidazole-2(3H)-tellurone

Şerife Pınar Yalçın,^a Mehmet Akkurt,^a ^* Ülkü Yılmaz,^b Hasan Küçükbay ^b and Orhan Büyükgüngör ^c

^aDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey, ^bDepartment of Chemistry, Faculty of Arts and Sciences, Ínönü University, 44280 Malatya, Turkey, and ^cDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 16 January 2008; accepted 20 February 2008; online 22 February 2008)

The title compound, C₂₅H₂₆N₂Te, was synthesized from bis[1,3-bis(3-phenylpropyl)benzimidazolidin-2-ylidene] and Te in a toluene solution. The molecule possesses a twofold rotation axis passing through the Te atom and the center of the benzimidazole ring system. The benzimidazole ring system makes an angle of 67.9 (4)° with the phenyl rings.

Related literature

For related literature, see: Akkurt et al. (2004a ,b , 2005 ); Aydın et al. (1999 ); Chakravorty et al. (1985 ); Karaca et al. (2005 ); Lappert (1988 ); Lappert et al. (1980 ); Roeterdink et al. (1983 ); Türktekin et al. (2004 ); İngeç et al. (1999 ); Närhi et al. (2004 ); Sadekov et al. (1998 ); Singh et al. (2006 ).

Experimental

Crystal data

C₂₅H₂₆N₂Te
M_r = 482.08
Tetragonal, P 4₁ 2₁ 2
a = 10.6004 (2) Å
c = 20.4365 (6) Å
V = 2296.42 (9) Å³
Z = 4
Mo Kα radiation
μ = 1.31 mm⁻¹
T = 296 K
0.54 × 0.48 × 0.39 mm

Data collection

Stoe IPDSII diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.539, T_max = 0.630
28301 measured reflections
2264 independent reflections
2166 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.105
S = 1.09
2264 reflections
99 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.92 e Å⁻³
Δρ_min = −0.48 e Å⁻³
Absolute structure: Flack (1983 ), 889 Friedel pairs
Flack parameter: 0.01 (6)

Table 1
Selected bond lengths (Å)

Te1—C1	2.058 (4)

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808004893/ez2117sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808004893/ez2117Isup2.hkl

checkCIF report

Comment top

Electron-rich olefins are powerful reducing agents (Lappert, 1988). It is known that the ultimate oxidation products of electron-rich olefins with air are ureas; sulfur and selenium react similarly to form the corresponding analogues (Roeterdink et al., 1983; Lappert et al., 1980). The conversion of an electron-rich olefin into a tellurourea has a parallel in these known olefin reactions (Lappert et al., 1980). There are extensive studies of cyclic ureas containing imidazolidine groups, including their X-ray crystal structures. However, there is no example of an X-ray crystal structure study for the cyclic tellurourea containing a benzimidazole group. The objective of this study was to elucidate the first crystal structure of such a cyclic tellurourea and compare the results to the corresponding analogues contain sulfur (İngeç et al., 1999) and selenium (Aydın et al., 1999; Akkurt et al., 2004a).

The molecular structure of the title compound (I) is shown in Fig. 1. The molecule has a twofold screw axis through the midpoints of the C2—C2a and C4—C4a bonds and containing the atoms Te1 and C1 of the benzimidazole ring. The Te—C single bond length generally varies between 2.120 and 2.170 Å depending on the electron releasing effect of the ligand bonding to Te atom (Lappert et al., 1980; Sadekov et al., 1998; Närhi et al., 2004; Singh et al., 2006). In the title compound (I), the Te—C bond length [2.058 (4) Å] is short, which agrees with the results reported by Lappert et al. (1980). Tellurourea metal complexes may be described in terms of the resonance hybrids as shown in the scheme 2. For this reason, the Te?C bond may have partial double bond character.

All the geometric parameters of (I) are comparable with those in related compounds (Akkurt et al., 2004b; Akkurt et al., 2005; Türktekin et al., 2004, Karaca et al., 2005).

In the title molecule, the benzimidazole ring system (C1—C3/N1/C1a—C3a/N1a) is essentially planar, with maximum deviations of 0.007 (5) Å for C2 and -0.007 (5) Å for C2a. The symmetry-related phenyl rings (C8–C13 and C8a–C13a) are oriented at angles of 67.9 (4)° to the plane of the benzimidazole ring system.

Related literature top

For related literature, see: Akkurt et al. (2004a,b, 2005); Aydın et al. (1999); Chakravorty et al. (1985); Karaca et al. (2005); Lappert (1988); Lappert et al. (1980); Roeterdink et al. (1983); Türktekin et al. (2004); İngeç et al. (1999); Närhi et al. (2004); Sadekov et al. (1998); Singh et al. (2006).

Experimental top

A mixture of bis(1,3-di(3-phenylpropyl)benzimidazolidine-2-ylidene) (0.55 g; 0.78 mmol) and tellurium (0.22 g; 1.72 mmol) in toluene (10 ml) was heated under reflux for 2 h. The mixture was then filtered to remove unreacted tellurium and upon cooling the filtrate to 253 K, light yellow crystals of the title compound were obtained. (Yield: 0.54 g, 72%; m.p.: 390–391 K). ¹H-NMR (CDCl₃): δ 2.25 (q, 4H, CH₂), 2.83 (t, 4H, CH₂), 4.53 (t, 4H, N—CH₂), 7.14–7.24 (m, 14H, Ar—H). ¹³C-NMR (CDCl₃): δ 29.74, 32.99, 49.25, 110.26, 123.61, 126.20, 128.38, 128.50, 133.93, 140.73, 144.18. Analysis calculated for C₂₅H₂₆N₂Te: C 62.29, H 5.40, N 5.82%. Found: C 62.52, H 5.50, N 5.82%.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title compound (I) with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level. [Symmetry code: (a) -y + 1, -x + 1, -z + 3/2.]
	Fig. 2. The resonance hybrids of tellurourea metal complexes (Lappert et al., 1980).

1,3-Bis(3-phenylpropyl)-1H-benzimidazole-2(3H)-tellurone top

Crystal data top

C₂₅H₂₆N₂Te	D_x = 1.394 Mg m⁻³
M_r = 482.08	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P4₁2₁2	Cell parameters from 55040 reflections
Hall symbol: P 4abw 2nw	θ = 1.9–27.2°
a = 10.6004 (2) Å	µ = 1.31 mm⁻¹
c = 20.4365 (6) Å	T = 296 K
V = 2296.42 (9) Å³	Block, light yellow
Z = 4	0.54 × 0.48 × 0.39 mm
F(000) = 968

Data collection top

Stoe IPDSII diffractometer	2264 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2166 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.049
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.0°, θ_min = 2.2°
ω scans	h = −12→13
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −13→13
T_min = 0.539, T_max = 0.630	l = −25→25
28301 measured reflections

Refinement top

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)] = 0.037	H-atom parameters constrained
wR(F²) = 0.105	w = 1/[σ²(F_o²) + (0.0574P)² + 1.6917P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
2264 reflections	Δρ_max = 0.92 e Å⁻³
99 parameters	Δρ_min = −0.48 e Å⁻³
3 restraints	Absolute structure: Flack (1983), 889 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (6)

Crystal data top

C₂₅H₂₆N₂Te	Z = 4
M_r = 482.08	Mo Kα radiation
Tetragonal, P4₁2₁2	µ = 1.31 mm⁻¹
a = 10.6004 (2) Å	T = 296 K
c = 20.4365 (6) Å	0.54 × 0.48 × 0.39 mm
V = 2296.42 (9) Å³

Data collection top

Stoe IPDSII diffractometer	2264 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	2166 reflections with I > 2σ(I)
T_min = 0.539, T_max = 0.630	R_int = 0.049
28301 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.105	Δρ_max = 0.92 e Å⁻³
S = 1.09	Δρ_min = −0.48 e Å⁻³
2264 reflections	Absolute structure: Flack (1983), 889 Friedel pairs
99 parameters	Absolute structure parameter: 0.01 (6)
3 restraints

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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
Te1	0.13779 (3)	0.86221 (3)	0.75000	0.0633 (1)
N1	0.3555 (4)	0.6989 (4)	0.79960 (17)	0.0585 (11)
C1	0.2751 (4)	0.7249 (4)	0.75000	0.0550 (14)
C2	0.4349 (5)	0.6006 (5)	0.7811 (2)	0.0653 (17)
C3	0.5312 (6)	0.5400 (6)	0.8141 (3)	0.084 (2)
C4	0.5917 (7)	0.4441 (7)	0.7828 (4)	0.101 (3)
C5	0.3626 (6)	0.7656 (5)	0.8618 (2)	0.0630 (16)
C6	0.4521 (5)	0.8761 (5)	0.8597 (2)	0.0677 (16)
C7	0.4498 (6)	0.9471 (5)	0.9247 (3)	0.0723 (19)
C8	0.5329 (9)	1.0605 (7)	0.9284 (5)	0.1219 (15)
C9	0.4939 (9)	1.1694 (7)	0.9583 (5)	0.1219 (15)
C10	0.5698 (9)	1.2703 (7)	0.9670 (5)	0.1219 (15)
C11	0.6886 (9)	1.2679 (7)	0.9451 (5)	0.1219 (15)
C12	0.7332 (10)	1.1639 (7)	0.9160 (5)	0.1219 (15)
C13	0.6524 (9)	1.0587 (7)	0.9076 (5)	0.1219 (15)
H3	0.55390	0.56380	0.85620	0.1020*
H4	0.65670	0.40140	0.80390	0.1210*
H5A	0.38990	0.70730	0.89550	0.0750*
H5B	0.27910	0.79550	0.87340	0.0750*
H6A	0.42790	0.93270	0.82460	0.0810*
H6B	0.53690	0.84620	0.85100	0.0810*
H7A	0.36370	0.97330	0.93340	0.0870*
H7B	0.47420	0.88920	0.95920	0.0870*
H9	0.41130	1.17400	0.97330	0.1460*
H10	0.53940	1.34170	0.98830	0.1460*
H11	0.74010	1.33830	0.95000	0.1460*
H12	0.81630	1.16070	0.90150	0.1460*
H13	0.68330	0.98660	0.88720	0.1460*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Te1	0.0682 (2)	0.0682 (2)	0.0535 (2)	0.0114 (2)	0.0052 (2)	0.0052 (2)
N1	0.071 (2)	0.059 (2)	0.0454 (17)	−0.002 (2)	−0.0194 (17)	−0.0106 (15)
C1	0.061 (2)	0.061 (2)	0.043 (3)	−0.002 (2)	−0.004 (2)	−0.004 (2)
C2	0.073 (3)	0.061 (3)	0.062 (3)	0.003 (2)	−0.017 (2)	−0.017 (2)
C3	0.084 (4)	0.085 (4)	0.084 (3)	0.012 (3)	−0.039 (3)	−0.015 (3)
C4	0.082 (4)	0.085 (5)	0.136 (6)	0.024 (4)	−0.031 (4)	−0.020 (4)
C5	0.085 (3)	0.065 (3)	0.039 (2)	−0.001 (3)	−0.008 (2)	−0.0117 (18)
C6	0.085 (3)	0.064 (3)	0.054 (2)	−0.007 (3)	−0.014 (2)	−0.008 (2)
C7	0.091 (4)	0.062 (3)	0.064 (3)	0.005 (3)	−0.016 (3)	−0.021 (2)
C8	0.132 (3)	0.0736 (16)	0.160 (3)	−0.0065 (19)	−0.034 (3)	−0.0275 (19)
C9	0.132 (3)	0.0736 (16)	0.160 (3)	−0.0065 (19)	−0.034 (3)	−0.0275 (19)
C10	0.132 (3)	0.0736 (16)	0.160 (3)	−0.0065 (19)	−0.034 (3)	−0.0275 (19)
C11	0.132 (3)	0.0736 (16)	0.160 (3)	−0.0065 (19)	−0.034 (3)	−0.0275 (19)
C12	0.132 (3)	0.0736 (16)	0.160 (3)	−0.0065 (19)	−0.034 (3)	−0.0275 (19)
C13	0.132 (3)	0.0736 (16)	0.160 (3)	−0.0065 (19)	−0.034 (3)	−0.0275 (19)

Geometric parameters (Å, º) top

Te1—C1	2.058 (4)	C11—C12	1.339 (12)
N1—C1	1.353 (5)	C12—C13	1.417 (12)
N1—C2	1.392 (7)	C3—H3	0.9300
N1—C5	1.457 (6)	C4—H4	0.9300
C2—C3	1.382 (8)	C5—H5A	0.9700
C2—C2ⁱ	1.378 (6)	C5—H5B	0.9700
C3—C4	1.362 (10)	C6—H6A	0.9700
C4—C4ⁱ	1.444 (11)	C6—H6B	0.9700
C5—C6	1.508 (8)	C7—H7A	0.9700
C6—C7	1.527 (7)	C7—H7B	0.9700
C7—C8	1.492 (10)	C9—H9	0.9300
C8—C9	1.370 (12)	C10—H10	0.9300
C8—C13	1.336 (14)	C11—H11	0.9300
C9—C10	1.350 (12)	C12—H12	0.9300
C10—C11	1.337 (14)	C13—H13	0.9300

Te1···H5B	3.0200	H5A···H7B	2.4900
Te1···H3ⁱⁱ	3.1700	H5B···Te1	3.0200
Te1···H7Bⁱⁱ	3.2900	H5B···H7A	2.4200
Te1···H10ⁱⁱⁱ	3.3200	H6A···H7Bⁱⁱ	2.5900
Te1···H3^iv	3.1700	H6B···C13	2.8100
Te1···H7B^iv	3.2900	H6B···H13	2.2700
Te1···H10^v	3.3200	H7A···H5B	2.4200
Te1···H5Bⁱ	3.0200	H7A···H9	2.3300
C3···H5A	2.8600	H7A···C4^iv	3.0900
C4···H7A^vi	3.0900	H7A···H4^iv	2.5800
C5···H3	2.9500	H7B···H5A	2.4900
C6···H13	2.7700	H7B···Te1^vii	3.2900
C13···H6B	2.8100	H7B···H6A^vii	2.5900
H3···C5	2.9500	H7B···Te1^vi	3.2900
H3···H5A	2.4500	H9···H7A	2.3300
H3···Te1^vii	3.1700	H10···Te1^viii	3.3200
H3···Te1^vi	3.1700	H10···Te1^ix	3.3200
H4···H7A^vi	2.5800	H13···C6	2.7700
H5A···C3	2.8600	H13···H6B	2.2700
H5A···H3	2.4500

C1—N1—C2	109.3 (3)	N1—C5—H5A	109.00
C1—N1—C5	126.0 (4)	N1—C5—H5B	109.00
C2—N1—C5	124.7 (4)	C6—C5—H5A	109.00
Te1—C1—N1	126.1 (2)	C6—C5—H5B	109.00
Te1—C1—N1ⁱ	126.1 (2)	H5A—C5—H5B	108.00
N1—C1—N1ⁱ	107.8 (4)	C5—C6—H6A	110.00
N1—C2—C3	131.5 (4)	C5—C6—H6B	110.00
N1—C2—C2ⁱ	106.9 (4)	C7—C6—H6A	110.00
C2ⁱ—C2—C3	121.7 (5)	C7—C6—H6B	110.00
C2—C3—C4	117.8 (6)	H6A—C6—H6B	108.00
C3—C4—C4ⁱ	120.6 (7)	C6—C7—H7A	108.00
N1—C5—C6	112.6 (4)	C6—C7—H7B	108.00
C5—C6—C7	110.4 (4)	C8—C7—H7A	108.00
C6—C7—C8	115.6 (6)	C8—C7—H7B	108.00
C7—C8—C9	121.6 (8)	H7A—C7—H7B	107.00
C7—C8—C13	122.1 (7)	C8—C9—H9	118.00
C9—C8—C13	116.1 (8)	C10—C9—H9	118.00
C8—C9—C10	123.1 (9)	C9—C10—H10	120.00
C9—C10—C11	120.2 (8)	C11—C10—H10	120.00
C10—C11—C12	119.8 (8)	C10—C11—H11	120.00
C11—C12—C13	119.2 (9)	C12—C11—H11	120.00
C8—C13—C12	121.6 (8)	C11—C12—H12	120.00
C2—C3—H3	121.00	C13—C12—H12	120.00
C4—C3—H3	121.00	C8—C13—H13	119.00
C3—C4—H4	120.00	C12—C13—H13	119.00
C4ⁱ—C4—H4	120.00

C2—N1—C1—Te1	−179.6 (3)	C2ⁱ—C2—C3—C4	0.8 (9)
C5—N1—C1—Te1	−1.9 (7)	C2—C3—C4—C4ⁱ	0.3 (10)
C2—N1—C1—N1ⁱ	0.4 (5)	C3—C4—C4ⁱ—C3ⁱ	−0.8 (11)
C5—N1—C1—N1ⁱ	178.1 (4)	N1—C5—C6—C7	176.6 (4)
C1—N1—C2—C3	−179.6 (6)	C5—C6—C7—C8	−178.9 (6)
C5—N1—C2—C3	2.7 (9)	C6—C7—C8—C9	139.2 (8)
C1—N1—C2—C2ⁱ	−1.1 (5)	C6—C7—C8—C13	−46.2 (11)
C5—N1—C2—C2ⁱ	−178.8 (5)	C7—C8—C9—C10	174.7 (9)
C1—N1—C5—C6	−89.3 (6)	C13—C8—C9—C10	−0.1 (15)
C2—N1—C5—C6	88.1 (6)	C7—C8—C13—C12	−175.0 (9)
N1—C2—C3—C4	179.1 (6)	C9—C8—C13—C12	−0.2 (15)
N1—C2—C2ⁱ—C3ⁱ	180.0 (5)	C8—C9—C10—C11	1.1 (16)
C3—C2—C2ⁱ—N1ⁱ	180.0 (5)	C9—C10—C11—C12	−1.7 (15)
C3—C2—C2ⁱ—C3ⁱ	−1.3 (8)	C10—C11—C12—C13	1.4 (15)
N1—C2—C2ⁱ—N1ⁱ	1.3 (6)	C11—C12—C13—C8	−0.4 (15)

Symmetry codes: (i) −y+1, −x+1, −z+3/2; (ii) y−1/2, −x+3/2, z−1/4; (iii) y−3/2, −x+3/2, z−1/4; (iv) x−1/2, −y+3/2, −z+7/4; (v) x−1/2, −y+5/2, −z+7/4; (vi) x+1/2, −y+3/2, −z+7/4; (vii) −y+3/2, x+1/2, z+1/4; (viii) −y+3/2, x+3/2, z+1/4; (ix) x+1/2, −y+5/2, −z+7/4.

Experimental details

Crystal data
Chemical formula	C₂₅H₂₆N₂Te
M_r	482.08
Crystal system, space group	Tetragonal, P4₁2₁2
Temperature (K)	296
a, c (Å)	10.6004 (2), 20.4365 (6)
V (Å³)	2296.42 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.31
Crystal size (mm)	0.54 × 0.48 × 0.39

Data collection
Diffractometer	Stoe IPDSII diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.539, 0.630
No. of measured, independent and observed [I > 2σ(I)] reflections	28301, 2264, 2166
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.105, 1.09
No. of reflections	2264
No. of parameters	99
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.92, −0.48
Absolute structure	Flack (1983), 889 Friedel pairs
Absolute structure parameter	0.01 (6)

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top

Te1—C1

2.058 (4)

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDSII diffractometer (purchased under grant F.279 of the University Research Fund). ÜY and HK also thank the İnönü University Research Fund (BAPB-2006–41) for financial support of this study.

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