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

The title mol-ecule, C(25)H(26)N(2)Se, 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 = 433.44

Tetragonal,

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[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.066

S = 1.07

2531 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −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 ▶).

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

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

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

C25H26N2Se	Dx = 1.314 Mg m−3
Mr = 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

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	Rint = 0.055
Detector resolution: 6.67 pixels mm-1	θmax = 27.5°, θmin = 2.2°
ω scans	h = −13→13
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −13→13
Tmin = 0.322, Tmax = 0.408	l = −25→25
16780 measured reflections

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(Fo2) + (0.0285P)2 + 0.3345P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2531 reflections	Δρmax = 0.17 e Å−3
128 parameters	Δρmin = −0.24 e Å−3
0 restraints	Absolute structure: Flack (1983), 1003 Freidel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.004 (12)

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	Uiso*/Ueq
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*

	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)

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)

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