(E)-1,2-Bis(1-propyl-5,6-dimethyl-1H-benzimidazol-2-yl)ethene.

In the title compound, C(26)H(32)N(4), the essentially planar (r.m.s. deviations of 0.0053 and 0.0242 Å) benzimidazole fragments are trans with respect to a central ethene fragment, and are canted in opposite directions by 2.78 (6) and 5.87 (6)° with respect to the ethene plane, giving the mol-ecule a propeller conformation. The terminal ethyl fragments of the pendant n-propyl groups protrude to either side of the benzimidazole planes. Overall, the mol-ecule exhibits a pseudo-center of symmetry at the mid-point of the ethene fragment. Both π-π stacking and typical C-H⋯π inter-actions are notably absent, as are inter-molecular hydrogen bonds. When viewed along the a axis, the structure appears as criss-crossed layers of mol-ecules with the planar fragments separated along the c-cell direction by the protruding ethyl groups.

Related literature

For applications of bis­(imidazoles), bis­(benzimidazoles) and their complexes with metal ions, see: Knapp et al. (1990 ▶); Stibrany et al. (2002 ▶, 2003 ▶, 2004 ▶); Stibrany & Potenza (2008 ▶). The title compound was prepared from rac-1,2-bis­(1H-5,6-dimethyl­benzimidazol-2-yl)-1-hydroxy­ethane (Taffs et al., 1961 ▶). Alkyl­ation was effected according to a reported method (Stibrany et al., 2004 ▶). For related structures see: Stibrany et al. (2005 ▶); Stibrany & Potenza (2006a ▶,b ▶, 2009 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C26H32N4

M = 400.56

Monoclinic,

a = 12.7822 (15) Å

b = 10.4802 (12) Å

c = 16.5944 (19) Å

β = 100.284 (2)°

V = 2187.3 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 100 K

0.32 × 0.28 × 0.11 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Blessing, 1995 ▶) T min = 0.795, T max = 1.00

20415 measured reflections

4324 independent reflections

3596 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.151

S = 1.00

4324 reflections

277 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT-Plus (Bruker, 2000 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶) and ORTEP-32 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810003405/jh2128sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810003405/jh2128Isup2.hkl

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

C26H32N4	F(000) = 864
Mr = 400.56	Dx = 1.216 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 953 reflections
a = 12.7822 (15) Å	θ = 2.3–25.6°
b = 10.4802 (12) Å	µ = 0.07 mm−1
c = 16.5944 (19) Å	T = 100 K
β = 100.284 (2)°	Plate, yellow
V = 2187.3 (4) Å3	0.32 × 0.28 × 0.11 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	4324 independent reflections
Radiation source: fine-focus sealed tube	3596 reflections with I > 2σ(I)
graphite	Rint = 0.041
φ and ω scans	θmax = 26.1°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Blessing, 1995)	h = −15→15
Tmin = 0.795, Tmax = 1.00	k = −12→12
20415 measured reflections	l = −20→20

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.090P)2 + 1.071P] where P = (Fo2 + 2Fc2)/3
4324 reflections	(Δ/σ)max < 0.001
277 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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.

	x	y	z	Uiso*/Ueq
N23	−0.03575 (12)	0.86314 (15)	0.21188 (9)	0.0185 (4)
N13	0.04680 (12)	0.38211 (15)	0.29290 (9)	0.0184 (4)
C13	0.12082 (14)	0.28848 (18)	0.32073 (10)	0.0162 (4)
N11	0.20831 (12)	0.47168 (14)	0.32962 (9)	0.0164 (3)
N21	−0.19800 (12)	0.77194 (14)	0.18947 (9)	0.0164 (3)
C16	0.29931 (14)	0.13963 (18)	0.38184 (11)	0.0179 (4)
C24	−0.10049 (14)	1.08026 (18)	0.15724 (11)	0.0188 (4)
H24	−0.0327	1.1202	0.1677	0.023*
C11	0.22163 (14)	0.34258 (17)	0.34411 (10)	0.0154 (4)
C21	−0.21246 (14)	0.89625 (18)	0.16303 (10)	0.0168 (4)
C26	−0.29142 (15)	1.08870 (18)	0.10388 (11)	0.0187 (4)
C17	0.31163 (14)	0.27017 (18)	0.37496 (11)	0.0182 (4)
H17	0.3792	0.3093	0.3907	0.022*
C23	−0.11131 (14)	0.95179 (18)	0.17796 (10)	0.0170 (4)
C15	0.19728 (14)	0.08225 (18)	0.35742 (10)	0.0175 (4)
C14	0.10936 (14)	0.15596 (18)	0.32759 (11)	0.0179 (4)
H14	0.0416	0.1172	0.3118	0.021*
C25	−0.18941 (15)	1.14824 (18)	0.12140 (11)	0.0191 (4)
C12	0.10150 (14)	0.49004 (17)	0.29953 (11)	0.0164 (4)
C22	−0.09024 (14)	0.75650 (18)	0.21683 (11)	0.0167 (4)
C27	−0.30311 (14)	0.96279 (18)	0.12593 (11)	0.0180 (4)
H27	−0.3709	0.9227	0.1161	0.022*
C2	−0.04547 (15)	0.63331 (18)	0.24519 (11)	0.0186 (4)
H2	−0.0918	0.5619	0.2418	0.022*
C1	0.05794 (14)	0.61551 (18)	0.27588 (11)	0.0178 (4)
H1	0.1042	0.6872	0.2824	0.021*
C19	0.39431 (15)	0.05820 (19)	0.41661 (12)	0.0221 (4)
H19A	0.4580	0.1119	0.4284	0.033*
H19B	0.4045	−0.0075	0.3767	0.033*
H19C	0.3821	0.0174	0.4673	0.033*
C18	0.18662 (16)	−0.06113 (18)	0.36216 (12)	0.0228 (4)
H18A	0.1118	−0.0852	0.3457	0.034*
H18B	0.2125	−0.0895	0.4185	0.034*
H18C	0.2288	−0.1016	0.3254	0.034*
C28	−0.17841 (16)	1.28882 (19)	0.10451 (13)	0.0251 (5)
H28A	−0.1030	1.3123	0.1150	0.038*
H28B	−0.2161	1.3385	0.1404	0.038*
H28C	−0.2090	1.3068	0.0472	0.038*
C29	−0.38687 (16)	1.1613 (2)	0.06029 (12)	0.0250 (5)
H29A	−0.4496	1.1060	0.0533	0.037*
H29B	−0.3741	1.1888	0.0065	0.037*
H29C	−0.3989	1.2362	0.0928	0.037*
C6	−0.28135 (14)	0.67505 (18)	0.17675 (11)	0.0175 (4)
H6A	−0.3499	0.7144	0.1829	0.021*
H6B	−0.2645	0.6078	0.2190	0.021*
C3	0.29247 (14)	0.56624 (17)	0.35368 (11)	0.0167 (4)
H3A	0.2768	0.6433	0.3192	0.020*
H3B	0.3611	0.5308	0.3443	0.020*
C4	0.30192 (15)	0.60307 (19)	0.44332 (11)	0.0210 (4)
H4A	0.2370	0.6497	0.4509	0.025*
H4B	0.3067	0.5246	0.4770	0.025*
C5	0.39858 (16)	0.6861 (2)	0.47298 (12)	0.0248 (4)
H5A	0.4634	0.6375	0.4703	0.037*
H5B	0.3986	0.7124	0.5297	0.037*
H5C	0.3961	0.7618	0.4381	0.037*
C7	−0.29199 (15)	0.61516 (19)	0.09218 (12)	0.0222 (4)
H7A	−0.3002	0.6833	0.0502	0.027*
H7B	−0.2265	0.5669	0.0884	0.027*
C8	−0.38697 (17)	0.5262 (2)	0.07528 (14)	0.0312 (5)
H8A	−0.3838	0.4657	0.1207	0.047*
H8B	−0.3858	0.4793	0.0244	0.047*
H8C	−0.4527	0.5761	0.0699	0.047*

	U11	U22	U33	U12	U13	U23
N23	0.0164 (8)	0.0184 (8)	0.0205 (8)	0.0018 (6)	0.0026 (6)	0.0001 (6)
N13	0.0171 (8)	0.0177 (8)	0.0194 (8)	0.0012 (6)	0.0008 (6)	0.0012 (6)
C13	0.0158 (9)	0.0196 (10)	0.0134 (8)	0.0000 (7)	0.0030 (7)	−0.0004 (7)
N11	0.0164 (8)	0.0155 (8)	0.0169 (7)	−0.0006 (6)	0.0017 (6)	−0.0001 (6)
N21	0.0160 (8)	0.0153 (8)	0.0179 (7)	0.0006 (6)	0.0028 (6)	0.0006 (6)
C16	0.0191 (9)	0.0193 (10)	0.0150 (8)	0.0041 (7)	0.0023 (7)	0.0000 (7)
C24	0.0178 (9)	0.0186 (10)	0.0207 (9)	−0.0016 (7)	0.0053 (7)	−0.0018 (7)
C11	0.0188 (9)	0.0137 (9)	0.0138 (8)	−0.0003 (7)	0.0035 (7)	−0.0004 (7)
C21	0.0200 (9)	0.0172 (9)	0.0131 (8)	0.0006 (7)	0.0027 (7)	−0.0020 (7)
C26	0.0204 (10)	0.0193 (10)	0.0163 (9)	0.0032 (8)	0.0032 (7)	−0.0013 (7)
C17	0.0153 (9)	0.0203 (10)	0.0184 (9)	−0.0006 (7)	0.0012 (7)	−0.0006 (7)
C23	0.0175 (9)	0.0195 (10)	0.0144 (8)	0.0020 (7)	0.0038 (7)	−0.0012 (7)
C15	0.0226 (10)	0.0161 (9)	0.0137 (8)	−0.0021 (7)	0.0028 (7)	0.0005 (7)
C14	0.0171 (9)	0.0190 (10)	0.0173 (9)	−0.0043 (7)	0.0025 (7)	−0.0022 (7)
C25	0.0247 (10)	0.0178 (10)	0.0160 (9)	0.0014 (8)	0.0070 (7)	0.0002 (7)
C12	0.0160 (9)	0.0184 (9)	0.0144 (8)	−0.0002 (7)	0.0015 (7)	−0.0003 (7)
C22	0.0169 (9)	0.0181 (9)	0.0149 (8)	0.0013 (7)	0.0025 (7)	−0.0014 (7)
C27	0.0173 (9)	0.0203 (10)	0.0160 (9)	−0.0011 (7)	0.0016 (7)	−0.0022 (7)
C2	0.0196 (10)	0.0186 (10)	0.0183 (9)	−0.0011 (7)	0.0056 (7)	−0.0003 (7)
C1	0.0200 (10)	0.0158 (9)	0.0179 (9)	0.0002 (7)	0.0041 (7)	−0.0003 (7)
C19	0.0214 (10)	0.0190 (10)	0.0244 (10)	0.0032 (8)	0.0004 (8)	0.0024 (8)
C18	0.0263 (10)	0.0168 (10)	0.0242 (10)	−0.0014 (8)	0.0014 (8)	0.0001 (8)
C28	0.0267 (11)	0.0204 (11)	0.0284 (10)	0.0008 (8)	0.0056 (8)	0.0039 (8)
C29	0.0247 (11)	0.0237 (11)	0.0252 (10)	0.0037 (8)	0.0010 (8)	0.0033 (8)
C6	0.0154 (9)	0.0172 (9)	0.0198 (9)	−0.0013 (7)	0.0029 (7)	0.0016 (7)
C3	0.0144 (9)	0.0140 (9)	0.0216 (9)	−0.0023 (7)	0.0030 (7)	0.0014 (7)
C4	0.0226 (10)	0.0190 (10)	0.0221 (10)	−0.0033 (8)	0.0056 (8)	−0.0007 (8)
C5	0.0255 (10)	0.0245 (11)	0.0236 (10)	−0.0039 (9)	0.0022 (8)	−0.0044 (8)
C7	0.0245 (10)	0.0189 (10)	0.0226 (10)	0.0014 (8)	0.0028 (8)	−0.0011 (8)
C8	0.0253 (11)	0.0297 (12)	0.0370 (12)	0.0001 (9)	0.0013 (9)	−0.0121 (10)

N23—C22	1.327 (2)	C2—H2	0.9500
N23—C23	1.385 (2)	C1—H1	0.9500
N13—C12	1.324 (2)	C19—H19A	0.9800
N13—C13	1.384 (2)	C19—H19B	0.9800
C13—C11	1.398 (2)	C19—H19C	0.9800
C13—C14	1.403 (3)	C18—H18A	0.9800
N11—C11	1.379 (2)	C18—H18B	0.9800
N11—C12	1.381 (2)	C18—H18C	0.9800
N11—C3	1.465 (2)	C28—H28A	0.9800
N21—C21	1.377 (2)	C28—H28B	0.9800
N21—C22	1.381 (2)	C28—H28C	0.9800
N21—C6	1.460 (2)	C29—H29A	0.9800
C16—C17	1.384 (3)	C29—H29B	0.9800
C16—C15	1.428 (3)	C29—H29C	0.9800
C16—C19	1.512 (3)	C6—C7	1.521 (3)
C24—C25	1.383 (3)	C6—H6A	0.9900
C24—C23	1.403 (3)	C6—H6B	0.9900
C24—H24	0.9500	C3—C4	1.521 (3)
C11—C17	1.397 (3)	C3—H3A	0.9900
C21—C27	1.397 (3)	C3—H3B	0.9900
C21—C23	1.399 (3)	C4—C5	1.519 (3)
C26—C27	1.385 (3)	C4—H4A	0.9900
C26—C25	1.428 (3)	C4—H4B	0.9900
C26—C29	1.508 (3)	C5—H5A	0.9800
C17—H17	0.9500	C5—H5B	0.9800
C15—C14	1.381 (3)	C5—H5C	0.9800
C15—C18	1.512 (3)	C7—C8	1.517 (3)
C14—H14	0.9500	C7—H7A	0.9900
C25—C28	1.511 (3)	C7—H7B	0.9900
C12—C1	1.454 (3)	C8—H8A	0.9800
C22—C2	1.456 (3)	C8—H8B	0.9800
C27—H27	0.9500	C8—H8C	0.9800
C2—C1	1.342 (3)
C22—N23—C23	104.73 (15)	H19A—C19—H19B	109.5
C12—N13—C13	104.98 (15)	C16—C19—H19C	109.5
N13—C13—C11	110.28 (16)	H19A—C19—H19C	109.5
N13—C13—C14	130.83 (17)	H19B—C19—H19C	109.5
C11—C13—C14	118.90 (17)	C15—C18—H18A	109.5
C11—N11—C12	106.44 (15)	C15—C18—H18B	109.5
C11—N11—C3	123.67 (15)	H18A—C18—H18B	109.5
C12—N11—C3	129.41 (15)	C15—C18—H18C	109.5
C21—N21—C22	106.56 (15)	H18A—C18—H18C	109.5
C21—N21—C6	124.01 (15)	H18B—C18—H18C	109.5
C22—N21—C6	128.73 (15)	C25—C28—H28A	109.5
C17—C16—C15	120.30 (17)	C25—C28—H28B	109.5
C17—C16—C19	119.60 (17)	H28A—C28—H28B	109.5
C15—C16—C19	120.09 (17)	C25—C28—H28C	109.5
C25—C24—C23	119.38 (17)	H28A—C28—H28C	109.5
C25—C24—H24	120.3	H28B—C28—H28C	109.5
C23—C24—H24	120.3	C26—C29—H29A	109.5
N11—C11—C17	131.66 (17)	C26—C29—H29B	109.5
N11—C11—C13	105.69 (16)	H29A—C29—H29B	109.5
C17—C11—C13	122.65 (17)	C26—C29—H29C	109.5
N21—C21—C27	131.78 (17)	H29A—C29—H29C	109.5
N21—C21—C23	105.66 (15)	H29B—C29—H29C	109.5
C27—C21—C23	122.53 (17)	N21—C6—C7	111.30 (15)
C27—C26—C25	120.02 (17)	N21—C6—H6A	109.4
C27—C26—C29	119.42 (17)	C7—C6—H6A	109.4
C25—C26—C29	120.55 (17)	N21—C6—H6B	109.4
C16—C17—C11	117.96 (17)	C7—C6—H6B	109.4
C16—C17—H17	121.0	H6A—C6—H6B	108.0
C11—C17—H17	121.0	N11—C3—C4	111.38 (14)
N23—C23—C21	110.38 (16)	N11—C3—H3A	109.4
N23—C23—C24	130.64 (17)	C4—C3—H3A	109.4
C21—C23—C24	118.97 (17)	N11—C3—H3B	109.4
C14—C15—C16	120.66 (17)	C4—C3—H3B	109.4
C14—C15—C18	119.97 (17)	H3A—C3—H3B	108.0
C16—C15—C18	119.34 (17)	C5—C4—C3	112.34 (16)
C15—C14—C13	119.53 (17)	C5—C4—H4A	109.1
C15—C14—H14	120.2	C3—C4—H4A	109.1
C13—C14—H14	120.2	C5—C4—H4B	109.1
C24—C25—C26	120.87 (17)	C3—C4—H4B	109.1
C24—C25—C28	119.06 (17)	H4A—C4—H4B	107.9
C26—C25—C28	120.01 (17)	C4—C5—H5A	109.5
N13—C12—N11	112.60 (16)	C4—C5—H5B	109.5
N13—C12—C1	125.38 (16)	H5A—C5—H5B	109.5
N11—C12—C1	121.99 (16)	C4—C5—H5C	109.5
N23—C22—N21	112.63 (16)	H5A—C5—H5C	109.5
N23—C22—C2	125.90 (16)	H5B—C5—H5C	109.5
N21—C22—C2	121.45 (16)	C8—C7—C6	111.16 (16)
C26—C27—C21	118.16 (17)	C8—C7—H7A	109.4
C26—C27—H27	120.9	C6—C7—H7A	109.4
C21—C27—H27	120.9	C8—C7—H7B	109.4
C1—C2—C22	123.34 (18)	C6—C7—H7B	109.4
C1—C2—H2	118.3	H7A—C7—H7B	108.0
C22—C2—H2	118.3	C7—C8—H8A	109.5
C2—C1—C12	122.13 (18)	C7—C8—H8B	109.5
C2—C1—H1	118.9	H8A—C8—H8B	109.5
C12—C1—H1	118.9	C7—C8—H8C	109.5
C16—C19—H19A	109.5	H8A—C8—H8C	109.5
C16—C19—H19B	109.5	H8B—C8—H8C	109.5
C12—N13—C13—C11	−0.16 (19)	C23—C24—C25—C26	−1.2 (3)
C12—N13—C13—C14	−179.65 (18)	C23—C24—C25—C28	175.89 (17)
C12—N11—C11—C17	−179.41 (18)	C27—C26—C25—C24	2.7 (3)
C3—N11—C11—C17	−6.7 (3)	C29—C26—C25—C24	−176.39 (17)
C12—N11—C11—C13	0.71 (18)	C27—C26—C25—C28	−174.33 (17)
C3—N11—C11—C13	173.39 (15)	C29—C26—C25—C28	6.6 (3)
N13—C13—C11—N11	−0.36 (19)	C13—N13—C12—N11	0.6 (2)
C14—C13—C11—N11	179.20 (15)	C13—N13—C12—C1	178.64 (17)
N13—C13—C11—C17	179.75 (16)	C11—N11—C12—N13	−0.9 (2)
C14—C13—C11—C17	−0.7 (3)	C3—N11—C12—N13	−172.99 (16)
C22—N21—C21—C27	176.43 (18)	C11—N11—C12—C1	−178.96 (16)
C6—N21—C21—C27	5.3 (3)	C3—N11—C12—C1	8.9 (3)
C22—N21—C21—C23	−1.54 (18)	C23—N23—C22—N21	−1.3 (2)
C6—N21—C21—C23	−172.65 (15)	C23—N23—C22—C2	176.97 (16)
C15—C16—C17—C11	0.4 (3)	C21—N21—C22—N23	1.9 (2)
C19—C16—C17—C11	−178.72 (16)	C6—N21—C22—N23	172.42 (16)
N11—C11—C17—C16	−179.49 (18)	C21—N21—C22—C2	−176.52 (16)
C13—C11—C17—C16	0.4 (3)	C6—N21—C22—C2	−6.0 (3)
C22—N23—C23—C21	0.30 (19)	C25—C26—C27—C21	−1.9 (3)
C22—N23—C23—C24	−178.94 (18)	C29—C26—C27—C21	177.25 (16)
N21—C21—C23—N23	0.80 (19)	N21—C21—C27—C26	−178.11 (18)
C27—C21—C23—N23	−177.40 (15)	C23—C21—C27—C26	−0.4 (3)
N21—C21—C23—C24	−179.86 (15)	N23—C22—C2—C1	5.1 (3)
C27—C21—C23—C24	1.9 (3)	N21—C22—C2—C1	−176.72 (17)
C25—C24—C23—N23	178.11 (17)	C22—C2—C1—C12	−176.52 (16)
C25—C24—C23—C21	−1.1 (3)	N13—C12—C1—C2	0.9 (3)
C17—C16—C15—C14	−0.8 (3)	N11—C12—C1—C2	178.73 (16)
C19—C16—C15—C14	178.29 (16)	C21—N21—C6—C7	83.2 (2)
C17—C16—C15—C18	177.44 (17)	C22—N21—C6—C7	−85.9 (2)
C19—C16—C15—C18	−3.5 (2)	C11—N11—C3—C4	−81.9 (2)
C16—C15—C14—C13	0.5 (3)	C12—N11—C3—C4	89.0 (2)
C18—C15—C14—C13	−177.76 (16)	N11—C3—C4—C5	171.72 (15)
N13—C13—C14—C15	179.71 (17)	N21—C6—C7—C8	−173.22 (16)
C11—C13—C14—C15	0.3 (2)