1,4-Bis(1H-benzimidazol-1-yl)but-2-ene

Dong, G.-Y.; Liu, T.-F.; Jiao, C.-H.; Deng, X.-C.; Shi, X.-G.

doi:10.1107/S1600536811024251

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1797

doi:10.1107/S1600536811024251

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1,4-Bis(1H-benzimidazol-1-yl)but-2-ene

Gui-Ying Dong,^a ^* Tong-Fei Liu,^a Cui-Huan Jiao,^a Xiao-Chen Deng ^b and Xiao-Ge Shi ^b

^aCollege of Chemical Engineering, Hebei United University, Tangshan 063009, People's Republic of China, and ^bQian'an College, Hebei United University, Tangshan 063009, People's Republic of China
^*Correspondence e-mail: tsdgying@126.com

(Received 6 June 2011; accepted 20 June 2011; online 25 June 2011)

In the pseudo-centrosymmetric molecule of the title compound, C₁₈H₁₆N₄, two benzimidazole fragments form the dihedral angles of 83.49 (7) and 79.37 (7)°, with the mean plane of the linking butene chain. No classical intermolecular interactions are observed. The porous crystal packing exhibits voids of 85 Å³.

Related literature

For applications of benzimidazole derivatives, see: Tidwell et al. (1993 ); Santra & Dogra (1999 ). For related structures, see: Su et al. (2003 ); Chen et al. (2007 ); Liu et al. (2011 ).

Experimental

Crystal data

C₁₈H₁₆N₄
M_r = 288.35
Monoclinic, P 2₁ /c
a = 12.564 (3) Å
b = 9.140 (2) Å
c = 18.131 (3) Å
β = 127.281 (12)°
V = 1656.7 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 295 K
0.20 × 0.18 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.956, T_max = 0.996
12226 measured reflections
2925 independent reflections
1639 reflections with I > 2σ(I)
R_int = 0.056

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.133
S = 1.01
2925 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); 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 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811024251/cv5116sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811024251/cv5116Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811024251/cv5116Isup3.cml

checkCIF report

Comment top

Bis-benzimidazole compounds have have been widely used due to their anti-viral activities (Tidwell et al., 1993), photochemical and photophysical properties (Santra & Dogra, 1999). They have found applications in supramolecular coordination chemistry to generate various coordination architectures (Su et al., 2003; Chen et al., 2007; Liu et al., 2011). Herewith we report the crystal structure of the title bis-benzimidazole compound (I).

In (I) (Fig. 1), the molecule adopts a trans conformation. Two benzimidazole fragments form the dihedral angles of 83.49 (7) and 79.37 (7) °, respectively, with the mean plane of linking them butene chain. The C11—C10—C9—C8 torsion angle is 176.5 (3)°. The average bond distances and angles for the benzimidazole ring are in agreement with those in related benzimidazole compounds (Chen et al., 2007; Liu et al.2011). In the absence of classical intermolecular interactions, the porous crystal packing exhibits voids of 85 Å³.

Related literature top

For applications of benzimidazole derivatives, see: Tidwell et al. (1993); Santra & Dogra (1999). For related structures, see: Su et al. (2003); Chen et al. (2007); Liu et al. (2011).

Experimental top

The title compound was prepared according to the literature (Liu et al., 2011). Single crystals were grown from an ethanol solution over a period of several days at room temperature.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of (I), showing displacement ellipsoids at the 30% probability level.

1,4-Bis(1H-benzimidazol-1-yl)but-2-ene top

Crystal data top

C₁₈H₁₆N₄	F(000) = 608
M_r = 288.35	D_x = 1.156 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4528 reflections
a = 12.564 (3) Å	θ = 3.5–20.3°
b = 9.140 (2) Å	µ = 0.07 mm⁻¹
c = 18.131 (3) Å	T = 295 K
β = 127.281 (12)°	Block, colourless
V = 1656.7 (6) Å³	0.20 × 0.18 × 0.17 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2925 independent reflections
Radiation source: fine–focus sealed tube	1639 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.056
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
T_min = 0.956, T_max = 0.996	k = −10→10
12226 measured reflections	l = −21→21

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.133	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0545P)²] where P = (F_o² + 2F_c²)/3
2925 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₁₈H₁₆N₄	V = 1656.7 (6) Å³
M_r = 288.35	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.564 (3) Å	µ = 0.07 mm⁻¹
b = 9.140 (2) Å	T = 295 K
c = 18.131 (3) Å	0.20 × 0.18 × 0.17 mm
β = 127.281 (12)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2925 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1639 reflections with I > 2σ(I)
T_min = 0.956, T_max = 0.996	R_int = 0.056
12226 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.133	H-atom parameters constrained
S = 1.01	Δρ_max = 0.19 e Å⁻³
2925 reflections	Δρ_min = −0.14 e Å⁻³
199 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
N1	0.93808 (17)	−0.12271 (19)	0.16716 (12)	0.0514 (5)
N2	1.0262 (2)	−0.1093 (2)	0.31752 (13)	0.0646 (6)
N3	0.55655 (17)	0.1198 (2)	−0.20779 (12)	0.0533 (5)
N4	0.4402 (2)	0.1102 (2)	−0.36219 (14)	0.0724 (6)
C1	1.0390 (2)	−0.0742 (2)	0.25325 (18)	0.0632 (7)
H1	1.1111	−0.0206	0.2655	0.076*
C2	0.9075 (2)	−0.1874 (2)	0.27030 (15)	0.0528 (6)
C3	0.8415 (3)	−0.2500 (3)	0.30264 (17)	0.0650 (7)
H3	0.8766	−0.2436	0.3648	0.078*
C4	0.7230 (3)	−0.3217 (3)	0.2396 (2)	0.0710 (7)
H4	0.6771	−0.3641	0.2595	0.085*
C5	0.6706 (2)	−0.3319 (3)	0.14720 (18)	0.0662 (7)
H5	0.5907	−0.3822	0.1068	0.079*
C6	0.7322 (2)	−0.2708 (2)	0.11317 (16)	0.0567 (6)
H6	0.6962	−0.2778	0.0509	0.068*
C7	0.8516 (2)	−0.1974 (2)	0.17686 (14)	0.0474 (6)
C8	0.9207 (2)	−0.0957 (2)	0.08116 (15)	0.0592 (6)
H8A	0.8973	−0.1865	0.0469	0.071*
H8B	1.0043	−0.0612	0.0955	0.071*
C9	0.8136 (2)	0.0152 (3)	0.02248 (17)	0.0590 (6)
H9	0.8277	0.1096	0.0460	0.071*
C10	0.7016 (2)	−0.0108 (2)	−0.05950 (17)	0.0600 (6)
H10	0.6902	−0.1037	−0.0843	0.072*
C11	0.5908 (2)	0.0964 (3)	−0.11649 (16)	0.0678 (7)
H11B	0.5122	0.0616	−0.1235	0.081*
H11A	0.6166	0.1892	−0.0839	0.081*
C12	0.4456 (2)	0.0739 (3)	−0.2902 (2)	0.0684 (7)
H12	0.3783	0.0207	−0.2953	0.082*
C13	0.5584 (2)	0.1877 (2)	−0.32404 (15)	0.0548 (6)
C14	0.6068 (3)	0.2551 (3)	−0.36690 (17)	0.0738 (8)
H14	0.5599	0.2508	−0.4308	0.089*
C15	0.7263 (3)	0.3282 (3)	−0.3115 (2)	0.0797 (8)
H15	0.7597	0.3761	−0.3388	0.096*
C16	0.7985 (2)	0.3327 (3)	−0.2160 (2)	0.0699 (7)
H16	0.8794	0.3827	−0.1807	0.084*
C17	0.7535 (2)	0.2653 (2)	−0.17234 (16)	0.0545 (6)
H17	0.8021	0.2673	−0.1082	0.065*
C18	0.6318 (2)	0.1941 (2)	−0.22858 (14)	0.0443 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0494 (11)	0.0484 (11)	0.0549 (12)	−0.0002 (9)	0.0308 (11)	0.0018 (9)
N2	0.0630 (13)	0.0578 (13)	0.0591 (13)	−0.0018 (11)	0.0297 (11)	−0.0044 (10)
N3	0.0467 (11)	0.0536 (12)	0.0573 (12)	0.0023 (10)	0.0303 (10)	0.0052 (10)
N4	0.0592 (14)	0.0724 (15)	0.0568 (13)	−0.0074 (12)	0.0201 (11)	−0.0030 (11)
C1	0.0531 (15)	0.0533 (16)	0.0684 (18)	−0.0049 (12)	0.0291 (15)	−0.0048 (13)
C2	0.0570 (15)	0.0439 (13)	0.0556 (15)	0.0049 (12)	0.0331 (13)	−0.0007 (11)
C3	0.084 (2)	0.0591 (16)	0.0631 (16)	0.0103 (14)	0.0507 (16)	0.0061 (12)
C4	0.0794 (19)	0.0583 (17)	0.094 (2)	0.0030 (15)	0.0625 (18)	0.0055 (15)
C5	0.0515 (15)	0.0570 (16)	0.084 (2)	−0.0026 (13)	0.0376 (15)	0.0007 (13)
C6	0.0537 (15)	0.0529 (15)	0.0532 (14)	0.0025 (12)	0.0269 (13)	0.0030 (11)
C7	0.0455 (13)	0.0417 (13)	0.0488 (14)	0.0046 (11)	0.0253 (12)	0.0022 (10)
C8	0.0641 (15)	0.0595 (15)	0.0607 (15)	0.0039 (13)	0.0413 (13)	0.0064 (12)
C9	0.0732 (16)	0.0531 (15)	0.0619 (16)	0.0067 (13)	0.0468 (15)	0.0067 (12)
C10	0.0753 (17)	0.0540 (15)	0.0641 (16)	0.0089 (14)	0.0492 (15)	0.0122 (12)
C11	0.0686 (17)	0.0706 (17)	0.0766 (18)	0.0148 (14)	0.0504 (15)	0.0169 (13)
C12	0.0478 (15)	0.0543 (16)	0.082 (2)	−0.0080 (12)	0.0285 (16)	0.0017 (14)
C13	0.0522 (15)	0.0512 (14)	0.0527 (14)	0.0033 (12)	0.0274 (13)	−0.0001 (11)
C14	0.083 (2)	0.082 (2)	0.0539 (16)	0.0163 (16)	0.0402 (16)	0.0155 (14)
C15	0.080 (2)	0.079 (2)	0.105 (2)	0.0119 (17)	0.0691 (19)	0.0235 (17)
C16	0.0555 (15)	0.0593 (17)	0.092 (2)	−0.0005 (13)	0.0430 (16)	0.0075 (14)
C17	0.0485 (14)	0.0457 (14)	0.0588 (15)	0.0036 (11)	0.0271 (13)	0.0026 (11)
C18	0.0420 (13)	0.0384 (12)	0.0490 (14)	0.0039 (11)	0.0258 (11)	0.0027 (10)

Geometric parameters (Å, º) top

N1—C1	1.358 (3)	C8—C9	1.495 (3)
N1—C7	1.382 (2)	C8—H8A	0.9700
N1—C8	1.458 (2)	C8—H8B	0.9700
N2—C1	1.309 (3)	C9—C10	1.308 (3)
N2—C2	1.387 (3)	C9—H9	0.9300
N3—C12	1.352 (3)	C10—C11	1.491 (3)
N3—C18	1.389 (2)	C10—H10	0.9300
N3—C11	1.452 (3)	C11—H11B	0.9700
N4—C12	1.308 (3)	C11—H11A	0.9700
N4—C13	1.393 (3)	C12—H12	0.9300
C1—H1	0.9300	C13—C18	1.384 (3)
C2—C7	1.389 (3)	C13—C14	1.387 (3)
C2—C3	1.395 (3)	C14—C15	1.372 (3)
C3—C4	1.375 (3)	C14—H14	0.9300
C3—H3	0.9300	C15—C16	1.387 (3)
C4—C5	1.383 (3)	C15—H15	0.9300
C4—H4	0.9300	C16—C17	1.365 (3)
C5—C6	1.368 (3)	C16—H16	0.9300
C5—H5	0.9300	C17—C18	1.383 (3)
C6—C7	1.391 (3)	C17—H17	0.9300
C6—H6	0.9300

C1—N1—C7	105.92 (18)	H8A—C8—H8B	108.0
C1—N1—C8	127.2 (2)	C10—C9—C8	124.8 (2)
C7—N1—C8	126.83 (18)	C10—C9—H9	117.6
C1—N2—C2	104.1 (2)	C8—C9—H9	117.6
C12—N3—C18	105.52 (19)	C9—C10—C11	125.3 (2)
C12—N3—C11	127.5 (2)	C9—C10—H10	117.3
C18—N3—C11	126.95 (19)	C11—C10—H10	117.3
C12—N4—C13	103.8 (2)	N3—C11—C10	113.18 (19)
N2—C1—N1	114.2 (2)	N3—C11—H11B	108.9
N2—C1—H1	122.9	C10—C11—H11B	108.9
N1—C1—H1	122.9	N3—C11—H11A	108.9
N2—C2—C7	110.3 (2)	C10—C11—H11A	108.9
N2—C2—C3	130.0 (2)	H11B—C11—H11A	107.8
C7—C2—C3	119.7 (2)	N4—C12—N3	114.8 (2)
C4—C3—C2	117.8 (2)	N4—C12—H12	122.6
C4—C3—H3	121.1	N3—C12—H12	122.6
C2—C3—H3	121.1	C18—C13—C14	119.7 (2)
C3—C4—C5	121.3 (2)	C18—C13—N4	110.2 (2)
C3—C4—H4	119.3	C14—C13—N4	130.1 (2)
C5—C4—H4	119.3	C15—C14—C13	117.6 (2)
C6—C5—C4	122.3 (2)	C15—C14—H14	121.2
C6—C5—H5	118.8	C13—C14—H14	121.2
C4—C5—H5	118.8	C14—C15—C16	121.7 (2)
C5—C6—C7	116.3 (2)	C14—C15—H15	119.1
C5—C6—H6	121.9	C16—C15—H15	119.1
C7—C6—H6	121.9	C17—C16—C15	121.6 (2)
N1—C7—C2	105.48 (19)	C17—C16—H16	119.2
N1—C7—C6	131.9 (2)	C15—C16—H16	119.2
C2—C7—C6	122.6 (2)	C16—C17—C18	116.5 (2)
N1—C8—C9	111.31 (18)	C16—C17—H17	121.8
N1—C8—H8A	109.4	C18—C17—H17	121.8
C9—C8—H8A	109.4	C17—C18—C13	122.9 (2)
N1—C8—H8B	109.4	C17—C18—N3	131.3 (2)
C9—C8—H8B	109.4	C13—C18—N3	105.72 (19)

C2—N2—C1—N1	0.1 (3)	C12—N3—C11—C10	108.2 (3)
C7—N1—C1—N2	−0.3 (2)	C18—N3—C11—C10	−71.6 (3)
C8—N1—C1—N2	176.94 (19)	C9—C10—C11—N3	123.4 (2)
C1—N2—C2—C7	0.2 (2)	C13—N4—C12—N3	−0.2 (3)
C1—N2—C2—C3	−178.6 (2)	C18—N3—C12—N4	−0.1 (3)
N2—C2—C3—C4	179.6 (2)	C11—N3—C12—N4	−179.9 (2)
C7—C2—C3—C4	0.8 (3)	C12—N4—C13—C18	0.4 (2)
C2—C3—C4—C5	0.2 (3)	C12—N4—C13—C14	−178.9 (2)
C3—C4—C5—C6	−0.7 (4)	C18—C13—C14—C15	−1.1 (3)
C4—C5—C6—C7	0.2 (3)	N4—C13—C14—C15	178.1 (2)
C1—N1—C7—C2	0.4 (2)	C13—C14—C15—C16	1.4 (4)
C8—N1—C7—C2	−176.86 (18)	C14—C15—C16—C17	−0.5 (4)
C1—N1—C7—C6	−179.6 (2)	C15—C16—C17—C18	−0.7 (3)
C8—N1—C7—C6	3.1 (3)	C16—C17—C18—C13	1.0 (3)
N2—C2—C7—N1	−0.4 (2)	C16—C17—C18—N3	−177.8 (2)
C3—C2—C7—N1	178.58 (19)	C14—C13—C18—C17	−0.1 (3)
N2—C2—C7—C6	179.66 (19)	N4—C13—C18—C17	−179.48 (19)
C3—C2—C7—C6	−1.3 (3)	C14—C13—C18—N3	178.9 (2)
C5—C6—C7—N1	−179.1 (2)	N4—C13—C18—N3	−0.4 (2)
C5—C6—C7—C2	0.8 (3)	C12—N3—C18—C17	179.2 (2)
C1—N1—C8—C9	−104.7 (2)	C11—N3—C18—C17	−0.9 (3)
C7—N1—C8—C9	72.0 (3)	C12—N3—C18—C13	0.3 (2)
N1—C8—C9—C10	−116.2 (2)	C11—N3—C18—C13	−179.85 (19)
C8—C9—C10—C11	176.37 (19)

Experimental details

Crystal data
Chemical formula	C₁₈H₁₆N₄
M_r	288.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	12.564 (3), 9.140 (2), 18.131 (3)
β (°)	127.281 (12)
V (Å³)	1656.7 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.20 × 0.18 × 0.17

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.956, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	12226, 2925, 1639
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.133, 1.01
No. of reflections	2925
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.14

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Acknowledgements

The authors thank Hebei United University for support of this work.

References

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