Literature DB >> 21201955

1,3-Bis(3-phenyl-prop-yl)-1H-benz-imidazole-2(3H)-tellurone.

Serife Pınar Yalçın, Mehmet Akkurt, Ulkü Yılmaz, Hasan Küçükbay, Orhan Büyükgüngör.

Abstract

The title compound, C(25)H(26)N(2)Te, was synthesized from bis-[1,3-bis-(3-phenyl-prop-yl)benzimidazolidin-2-yl-idene] 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.

Entities: Chemical Disease Gene

Year: 2008 PMID： 21201955 PMCID： PMC2960818 DOI： 10.1107/S1600536808004893

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

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 = 482.08 Tetragonal, 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[F 2 > 2σ(F 2)] = 0.037 wR(F 2) = 0.105 S = 1.09 2264 reflections 99 parameters 3 restraints H-atom parameters constrained Δρmax = 0.92 e Å−3 Δρmin = −0.48 e Å−3 Absolute structure: Flack (1983 ▶), 889 Friedel pairs Flack parameter: 0.01 (6) 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 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808004893/ez2117sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808004893/ez2117Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₂₅H₂₆N₂Te	Z = 4
M_r = 482.08	F₀₀₀ = 968
Tetragonal, P4₁2₁2	D_x = 1.394 Mg m⁻³
Hall symbol: P 4abw 2nw	Mo Kα radiation λ = 0.71073 Å
a = 10.6004 (2) Å	Cell parameters from 55040 reflections
b = 10.6004 (2) Å	θ = 1.9–27.2º
c = 20.4365 (6) Å	µ = 1.31 mm⁻¹
α = 90º	T = 296 K
β = 90º	Block, light yellow
γ = 90º	0.54 × 0.48 × 0.39 mm
V = 2296.42 (9) Å³

Stoe IPDSII diffractometer	2264 independent reflections
Monochromator: plane graphite	2166 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm^-1	R_int = 0.049
T = 296 K	θ_max = 26.0º
ω scans	θ_min = 2.2º
Absorption correction: integration(X-RED32; Stoe & Cie, 2002)	h = −12→13
T_min = 0.539, T_max = 0.630	k = −13→13
28301 measured reflections	l = −25→25

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.037	w = 1/[σ²(F_o²) + (0.0574P)² + 1.6917P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.105	(Δ/σ)_max < 0.001
S = 1.09	Δρ_max = 0.92 e Å⁻³
2264 reflections	Δρ_min = −0.48 e Å⁻³
99 parameters	Extinction correction: none
3 restraints	Absolute structure: Flack (1983), 889 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.01 (6)
Secondary atom site location: difference Fourier map

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.

	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*

	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)

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)

Table 1

Selected bond lengths (Å)

Te1—C1

2.058 (4)

1 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

1 in total

1. 1,3-Bis(3-phenyl-prop-yl)-1H-1,3-benzimidazole-2(3H)-selone.

Authors: Mehmet Akkurt; Ulkü Yılmaz; Hasan Küçükbay; Orhan Büyükgüngör
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2011-04-22

1 in total