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

Akkurt, M.; Yılmaz, Ü.; Küçükbay, H.; Büyükgüngör, O.

doi:10.1107/S1600536811013985

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1179

doi:10.1107/S1600536811013985

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

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

^aDepartment of Physics, Faculty of 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 18 March 2011; accepted 13 April 2011; online 22 April 2011)

The title molecule, C₂₅H₂₆N₂Se, has mirror symmetry, with the mirror plane passing through the atoms of the C=Se bond and the mid-points of the two C—C bonds of the benzene ring of the benzimidazole group. The dihedral angle between the benzimidazole ring system and the phenyl ring is 71.62 (14)°.

Related literature

For general background to benzimidazole derivatives, see: Aydın et al. (1998 ); Böhm & Herrmann (2000 ); Küçükbay et al. (1996 , 1997 ); Lappert et al. (2009 ); Wanzlick & Schikora (1960 ); Yıldırım et al. (2006 ); Yılmaz & Küçükbay (2009 ); Çetinkaya et al. (1994 , 1998 ). For related structures, see: Akkurt et al. (2004 ); Aydın et al. (1999 ); Yalçın et al. (2008 ).

Experimental

Crystal data

C₂₅H₂₆N₂Se
M_r = 433.44
Tetragonal, P 4₁ 2₁ 2
a = 10.5150 (3) Å
c = 19.8142 (8) Å
V = 2190.76 (13) Å³
Z = 4
Mo Kα radiation
μ = 1.73 mm⁻¹
T = 296 K
0.68 × 0.58 × 0.52 mm

Data collection

Stowe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.322, T_max = 0.408
16780 measured reflections
2531 independent reflections
2225 reflections with I > 2σ(I)
R_int = 0.055

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.066
S = 1.07
2531 reflections
128 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.24 e Å⁻³
Absolute structure: Flack (1983 ), 1003 Freidel pairs
Flack parameter: 0.004 (12)

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 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811013985/qm2004sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811013985/qm2004Isup2.hkl

checkCIF report

Comment top

Electron-rich olefins (EROs) have been attracted considerable attention in both organic and inorganic preparative literature due to their unique properties as reagent and reaction intermediates since their first report by Wanzlick in 1960 (Wanzlick & Schikora, 1960; Böhm & Herrmann, 2000).

Benzimidazolium salts are convenient precursors for EROs through reacting with a strong base such as NaH comparing with other methods such as reacting a secondary amine (N,N'-disubstituted-1,2-diaminobenzene) with an acetal, chloral or triethyl orthoformate. We have synthesized and isolated first time the ERO, bis(1,3-dimethybenzimidazolidine-2-ylidene) (Çetinkaya et al., 1994). We have also synthesized a number of EROs using different synthesis methods and used them to synthesize many organic or organometallic compounds (Küçükbay et al., 1996, Küçükbay et al., 1997, Çetinkaya et al., 1998; Aydın et al., 1998 Yıldırım et al., 2006; Yılmaz & Küçükbay, 2009). Their electron-richness confers on them a very high reactivity as strong nucleophiles, which assist in the preparation of numerous products by reaction, amongst others, with group 16 elements, transition metals, and many protic compounds (Lappert et al., 2009). It is known that the ultimate oxidation product of EROs with air is urea; sulfur, selenium and tellurium react similarly to give the corresponding analogues. The objective of the present study was to elucidate the crystal structure of the title compound which is new ERO derivative.

In the title molecule (I), Fig. 1, the Se═C bond length is 1.828 (2) Å, and this value is similar to those [1.829 (3) Å] found in 1-ethyl-3-(2-phenylethyl)benzimidazole-2-selone (Akkurt et al., 2004) and [1.825 (7) Å] found in 1,3-dimethylbenzimidazole-2-selone (Aydın et al., 1999), and is shorter than that [2.058 (4) Å] found for the Te═ C bond length in 1,3-bis(3-phenylpropyl)1H-benzimidazole- 2(3H)-tellurone (Yalçın et al., 2008).

The molecular structure is stabilized by a weak C—H···Se interaction (Table 1). The benzimidazole ring system (N1/C10/C11/C12/C13/N1a/C11a/C12a/C13a) of (I) is planar (r.m.s deviation of fitted atoms is 0.09 (3) Å). The dihedral angle between the phenyl ring (C1–C6) and the benzimidazole ring is 71.62 (14)°. The molecular packing in (I) is shown in Fig. 2.

Related literature top

For general background to benzimidazole derivatives, see: Aydın et al. (1998); Böhm & Herrmann (2000); Küçükbay et al. (1996, 1997); Lappert et al. (2009); Wanzlick & Schikora (1960); Yıldırım et al. (2006); Yılmaz & Küçükbay (2009); Çetinkaya et al. (1994, 1998). For related structures, see: Akkurt et al. (2004); Aydın et al. (1999); Yalçın et al. (2008).

Experimental top

A mixture of bis(1,3-di(3-phenylpropyl)benzimidazolidine-2-ylidene) (0.68 g, 0.96 mmol) and selenium (0.15 g, 1.90 mmol) in dry toluene (10 ml) was heated under reflux for 2 h. Then the mixture was filtered to remove unreacted selenium and all volatiles were removed in vacuo (0.02 m mH g). The crude product was crystallized from alcohol upon cooling to 243 K. Yield: 0.63 g, 76%; m.p.: 439–441 K; v_(CSe)= 1480 cm^-1. Anal. found: C 69.58, H 5.98, N 6.38%. Calculated for C₂₅H₂₆N₂Se: C 69.27, H 6.05, N 6.46%. ¹H-NMR (δ, CDCl₃): 7.26–7.06 (m, 14H, Ar—H), 4.47 (t, 4H, NCH₂CH₂CH₂C₆H₅, J = 7.8 Hz), 2.81 (t, 4H, NCH₂CH₂CH₂C₆H₅, J = 7.8 Hz), 2.23 (quint, 4H, NCH₂CH₂CH₂C₆H₅, J = 7.8 Hz). ¹³C-NMR (δ, CDCl₃): 165.7 (C=Se), 140.8, 132.9, 128.5, 128.4, 126.2, 123.2 and 109.5 (Ar-C), 46.1 (NCH₂CH₂CH₂C₆H₅), 33.0 (NCH₂CH₂CH₂C₆H₅), 29.3 (NCH₂CH₂CH₂C₆H₅).

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 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. View of the title molecule, showing the atom labelling scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level. (Symmetry code: (a) y, x, 1 - z).
	Fig. 2. The packing diagram of (I) viewing down the b axis. All hydrogen atoms have been omitted for clarity.

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

Crystal data top

C₂₅H₂₆N₂Se	D_x = 1.314 Mg m⁻³
M_r = 433.44	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P4₁2₁2	Cell parameters from 20954 reflections
Hall symbol: P 4abw 2nw	θ = 1.9–28.0°
a = 10.5150 (3) Å	µ = 1.73 mm⁻¹
c = 19.8142 (8) Å	T = 296 K
V = 2190.76 (13) Å³	Block, colourless
Z = 4	0.68 × 0.58 × 0.52 mm
F(000) = 896

Data collection top

Stowe IPDS 2 diffractometer	2531 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2225 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.055
Detector resolution: 6.67 pixels mm^-1	θ_max = 27.5°, θ_min = 2.2°
ω scans	h = −13→13
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −13→13
T_min = 0.322, T_max = 0.408	l = −25→25
16780 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)] = 0.032	H-atom parameters constrained
wR(F²) = 0.066	w = 1/[σ²(F_o²) + (0.0285P)² + 0.3345P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
2531 reflections	Δρ_max = 0.17 e Å⁻³
128 parameters	Δρ_min = −0.24 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1003 Freidel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.004 (12)

Crystal data top

C₂₅H₂₆N₂Se	Z = 4
M_r = 433.44	Mo Kα radiation
Tetragonal, P4₁2₁2	µ = 1.73 mm⁻¹
a = 10.5150 (3) Å	T = 296 K
c = 19.8142 (8) Å	0.68 × 0.58 × 0.52 mm
V = 2190.76 (13) Å³

Data collection top

Stowe IPDS 2 diffractometer	2531 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	2225 reflections with I > 2σ(I)
T_min = 0.322, T_max = 0.408	R_int = 0.055
16780 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	H-atom parameters constrained
wR(F²) = 0.066	Δρ_max = 0.17 e Å⁻³
S = 1.07	Δρ_min = −0.24 e Å⁻³
2531 reflections	Absolute structure: Flack (1983), 1003 Freidel pairs
128 parameters	Absolute structure parameter: 0.004 (12)
0 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
Se1	0.35581 (2)	0.35581 (2)	0.50000	0.0563 (1)
N1	0.20501 (16)	0.15139 (19)	0.55133 (8)	0.0486 (5)
C1	0.6763 (3)	0.0124 (4)	0.71439 (17)	0.0933 (12)
C2	0.7825 (3)	−0.0624 (5)	0.7188 (2)	0.116 (2)
C3	0.7813 (3)	−0.1823 (4)	0.69632 (19)	0.0997 (16)
C4	0.6739 (4)	−0.2301 (4)	0.6684 (2)	0.1013 (16)
C5	0.5668 (3)	−0.1541 (3)	0.66230 (17)	0.0868 (11)
C6	0.5656 (2)	−0.0317 (3)	0.68586 (12)	0.0593 (8)
C7	0.4485 (2)	0.0505 (3)	0.68283 (11)	0.0623 (9)
C8	0.3849 (2)	0.0578 (3)	0.61434 (11)	0.0587 (8)
C9	0.2714 (2)	0.1457 (3)	0.61606 (10)	0.0544 (7)
C10	0.2329 (2)	0.2329 (2)	0.50000	0.0474 (6)
C11	0.1061 (2)	0.0716 (2)	0.53275 (11)	0.0508 (7)
C12	0.0438 (3)	−0.0248 (3)	0.56674 (13)	0.0675 (9)
C13	−0.0536 (3)	−0.0863 (3)	0.53297 (16)	0.0813 (11)
H1	0.67910	0.09500	0.73110	0.1120*
H2	0.85650	−0.02940	0.73770	0.1390*
H3	0.85380	−0.23260	0.69990	0.1200*
H4	0.67210	−0.31380	0.65320	0.1220*
H5	0.49430	−0.18690	0.64180	0.1040*
H7A	0.47150	0.13590	0.69670	0.0750*
H7B	0.38720	0.01830	0.71520	0.0750*
H8A	0.44560	0.08840	0.58120	0.0700*
H8B	0.35770	−0.02650	0.60080	0.0700*
H9A	0.21270	0.11680	0.65050	0.0650*
H9B	0.29950	0.23050	0.62830	0.0650*
H12	0.06640	−0.04730	0.61050	0.0810*
H13	−0.09810	−0.15080	0.55470	0.0980*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Se1	0.0586 (1)	0.0586 (1)	0.0515 (2)	−0.0076 (2)	0.0010 (1)	−0.0010 (1)
N1	0.0503 (9)	0.0574 (10)	0.0382 (8)	0.0010 (9)	−0.0077 (7)	0.0101 (8)
C1	0.070 (2)	0.097 (2)	0.113 (2)	−0.0031 (16)	−0.0375 (17)	0.0133 (19)
C2	0.063 (2)	0.135 (4)	0.151 (4)	0.003 (2)	−0.040 (2)	0.024 (3)
C3	0.064 (2)	0.127 (3)	0.108 (3)	0.021 (2)	−0.0043 (18)	0.044 (2)
C4	0.086 (3)	0.088 (2)	0.130 (3)	0.0157 (19)	−0.001 (2)	0.018 (2)
C5	0.0574 (16)	0.087 (2)	0.116 (2)	−0.0015 (16)	−0.0133 (16)	0.005 (2)
C6	0.0501 (13)	0.0737 (17)	0.0540 (13)	−0.0025 (12)	−0.0056 (11)	0.0214 (12)
C7	0.0573 (14)	0.0798 (18)	0.0498 (12)	0.0021 (13)	−0.0118 (11)	0.0089 (12)
C8	0.0570 (15)	0.0762 (16)	0.0429 (11)	0.0077 (12)	−0.0055 (9)	0.0103 (10)
C9	0.0543 (12)	0.0730 (15)	0.0358 (9)	0.0014 (13)	−0.0081 (9)	0.0081 (12)
C10	0.0517 (10)	0.0517 (10)	0.0389 (13)	0.0066 (13)	−0.0040 (10)	0.0040 (10)
C11	0.0520 (14)	0.0536 (13)	0.0467 (11)	0.0019 (11)	−0.0064 (9)	0.0096 (10)
C12	0.0673 (16)	0.0664 (16)	0.0689 (15)	−0.0040 (12)	−0.0058 (13)	0.0236 (13)
C13	0.075 (2)	0.0690 (19)	0.100 (2)	−0.0168 (17)	−0.0071 (16)	0.0207 (16)

Geometric parameters (Å, º) top

Se1—C10	1.828 (2)	C12—C13	1.384 (4)
N1—C9	1.462 (3)	C13—C13ⁱ	1.394 (4)
N1—C10	1.362 (2)	C1—H1	0.9300
N1—C11	1.386 (3)	C2—H2	0.9300
C1—C2	1.369 (5)	C3—H3	0.9300
C1—C6	1.375 (4)	C4—H4	0.9300
C2—C3	1.337 (7)	C5—H5	0.9300
C3—C4	1.354 (5)	C7—H7A	0.9700
C4—C5	1.386 (5)	C7—H7B	0.9700
C5—C6	1.369 (4)	C8—H8A	0.9700
C6—C7	1.506 (4)	C8—H8B	0.9700
C7—C8	1.515 (3)	C9—H9A	0.9700
C8—C9	1.510 (4)	C9—H9B	0.9700
C11—C12	1.382 (4)	C12—H12	0.9300
C11—C11ⁱ	1.396 (3)	C13—H13	0.9300

C9—N1—C10	125.33 (18)	C2—C3—H3	120.00
C9—N1—C11	124.52 (19)	C4—C3—H3	120.00
C10—N1—C11	110.13 (16)	C3—C4—H4	120.00
C2—C1—C6	121.6 (4)	C5—C4—H4	120.00
C1—C2—C3	120.9 (3)	C4—C5—H5	119.00
C2—C3—C4	119.6 (3)	C6—C5—H5	119.00
C3—C4—C5	119.9 (4)	C6—C7—H7A	108.00
C4—C5—C6	121.3 (3)	C6—C7—H7B	108.00
C1—C6—C5	116.7 (3)	C8—C7—H7A	108.00
C1—C6—C7	121.0 (3)	C8—C7—H7B	108.00
C5—C6—C7	122.3 (2)	H7A—C7—H7B	108.00
C6—C7—C8	115.2 (2)	C7—C8—H8A	109.00
C7—C8—C9	111.1 (2)	C7—C8—H8B	109.00
N1—C9—C8	112.51 (19)	C9—C8—H8A	109.00
Se1—C10—N1	126.67 (11)	C9—C8—H8B	109.00
Se1—C10—N1ⁱ	126.67 (11)	H8A—C8—H8B	108.00
N1—C10—N1ⁱ	106.66 (17)	N1—C9—H9A	109.00
N1—C11—C12	132.1 (2)	N1—C9—H9B	109.00
N1—C11—C11ⁱ	106.54 (18)	C8—C9—H9A	109.00
C11ⁱ—C11—C12	121.4 (2)	C8—C9—H9B	109.00
C11—C12—C13	117.3 (2)	H9A—C9—H9B	108.00
C12—C13—C13ⁱ	121.4 (3)	C11—C12—H12	121.00
C2—C1—H1	119.00	C13—C12—H12	121.00
C6—C1—H1	119.00	C12—C13—H13	119.00
C1—C2—H2	120.00	C13ⁱ—C13—H13	119.00
C3—C2—H2	120.00

C11—N1—C10—Se1	−179.91 (16)	C3—C4—C5—C6	−2.0 (6)
C9—N1—C10—N1ⁱ	178.5 (2)	C4—C5—C6—C1	1.3 (5)
C11—N1—C10—N1ⁱ	0.1 (2)	C4—C5—C6—C7	−177.0 (3)
C9—N1—C11—C12	2.2 (4)	C1—C6—C7—C8	130.7 (3)
C10—N1—C11—C12	−179.4 (3)	C5—C6—C7—C8	−51.1 (4)
C9—N1—C11—C11ⁱ	−178.7 (2)	C6—C7—C8—C9	−178.1 (2)
C10—N1—C11—C11ⁱ	−0.2 (2)	C7—C8—C9—N1	−177.9 (2)
C9—N1—C10—Se1	−1.5 (3)	N1—C11—C12—C13	179.5 (3)
C10—N1—C9—C8	−88.2 (3)	C11ⁱ—C11—C12—C13	0.5 (4)
C11—N1—C9—C8	90.0 (3)	N1—C11—C11ⁱ—N1ⁱ	0.3 (2)
C6—C1—C2—C3	−1.1 (6)	N1—C11—C11ⁱ—C12ⁱ	179.6 (2)
C2—C1—C6—C5	0.2 (5)	C12—C11—C11ⁱ—N1ⁱ	179.6 (2)
C2—C1—C6—C7	178.5 (3)	C12—C11—C11ⁱ—C12ⁱ	−1.2 (4)
C1—C2—C3—C4	0.5 (6)	C11—C12—C13—C13ⁱ	0.9 (5)
C2—C3—C4—C5	1.0 (6)	C12—C13—C13ⁱ—C12ⁱ	−1.6 (5)

Symmetry code: (i) y, x, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···Se1	0.97	2.92	3.310 (3)	105

Experimental details

Crystal data
Chemical formula	C₂₅H₂₆N₂Se
M_r	433.44
Crystal system, space group	Tetragonal, P4₁2₁2
Temperature (K)	296
a, c (Å)	10.5150 (3), 19.8142 (8)
V (Å³)	2190.76 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.73
Crystal size (mm)	0.68 × 0.58 × 0.52

Data collection
Diffractometer	Stowe IPDS 2 diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.322, 0.408
No. of measured, independent and observed [I > 2σ(I)] reflections	16780, 2531, 2225
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.066, 1.07
No. of reflections	2531
No. of parameters	128
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.24
Absolute structure	Flack (1983), 1003 Freidel pairs
Absolute structure parameter	0.004 (12)

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

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund).

References

Akkurt, M., Öztürk, S., Küçükbay, H., Orhan, E. & Büyükgüngör, O. (2004). Acta Cryst. E60, o1263–o1265. Web of Science CSD CrossRef IUCr Journals Google Scholar
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