1-[4-(Prop-2-en-1-yl-oxy)benz-yl]-2-[4-(prop-2-en-1-yl-oxy)phen-yl]-1H-benzimidazole.

In the title compound, C26H24N2O2, the benzimidazole ring system is almost planar [maximum displacement = 0.025 (1) Å] and makes dihedral angles of 80.48 (5) and 41.57 (5)° with the benzene rings, which are inclined to one another by 65.33 (6)°. In the crystal, mol-ecules are linked via C-H⋯π and weak π-π inter-actions [centroid-centroid distance = 3.8070 (7) Å and inter-planar distance = 3.6160 (5) Å].

Related literature

For the activity of benzimidazole derivatives against viruses, see: Tamm & Sehgal (1978 ▶); Porcari et al. (1998 ▶); Migawa et al. (1998 ▶). For their other biological activity, see: Spasov et al. (1999 ▶); Nakano et al. (2000 ▶); Zhao et al. (2000 ▶); White et al. (2000 ▶); Xiangming et al. (2007 ▶). For related structures, see: Kia et al. (2009 ▶); Zhou et al. (2009 ▶). For synthetic details, see: Lutfor et al. (2008 ▶). For standard bond lengths, see Allen et al. (1987 ▶).

Experimental

Crystal data

C26H24N2O2

M = 396.49

Monoclinic,

a = 12.5455 (1) Å

b = 10.1989 (1) Å

c = 15.9340 (2) Å

β = 99.5027 (11)°

V = 2010.78 (4) Å3

Z = 4

Cu Kα radiation

μ = 0.66 mm−1

T = 100 K

0.35 × 0.23 × 0.08 mm

Data collection

Agilent Technologies Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.80, T max = 0.95

38976 measured reflections

3908 independent reflections

3563 reflections with I > 2.0σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.100

S = 0.99

3891 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: CRYSTALS.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681204559X/su2508sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681204559X/su2508Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681204559X/su2508Isup3.cml

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

C26H24N2O2	F(000) = 840
Mr = 396.49	Dx = 1.310 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2yn	Cell parameters from 17352 reflections
a = 12.5455 (1) Å	θ = 4–71°
b = 10.1989 (1) Å	µ = 0.66 mm−1
c = 15.9340 (2) Å	T = 100 K
β = 99.5027 (11)°	Block, pale brown
V = 2010.78 (4) Å3	0.35 × 0.23 × 0.08 mm
Z = 4

Agilent Technologies Gemini diffractometer	3908 independent reflections
Radiation source: sealed x-ray tube	3563 reflections with I > 2.0σ(I)
Graphite monochromator	Rint = 0.029
ω scans	θmax = 71.4°, θmin = 4.2°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	h = −15→15
Tmin = 0.80, Tmax = 0.95	k = −12→12
38976 measured reflections	l = −19→19

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038	H-atom parameters constrained
wR(F2) = 0.100	Method = Modified Sheldrick w = 1/[σ2(F2) + (0.06P)2 + 1.04P], where P = (max(Fo2,0) + 2Fc2)/3
S = 0.99	(Δ/σ)max = 0.002
3891 reflections	Δρmax = 0.26 e Å−3
271 parameters	Δρmin = −0.25 e Å−3
0 restraints

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 esds are taken into account in the estimation of distances, angles and torsion angles

	x	y	z	Uiso*/Ueq
O1	−0.10938 (7)	0.03132 (9)	0.75160 (6)	0.0210 (3)
O20	−0.08975 (7)	0.86587 (8)	0.53875 (6)	0.0204 (3)
N7	0.26914 (8)	0.41707 (10)	0.66850 (6)	0.0168 (3)
N9	0.32584 (8)	0.49128 (10)	0.55014 (7)	0.0187 (3)
C2	−0.02893 (10)	0.12293 (12)	0.75473 (8)	0.0183 (3)
C3	−0.01085 (10)	0.22357 (13)	0.81468 (8)	0.0207 (3)
C4	0.06903 (10)	0.31589 (13)	0.80889 (8)	0.0205 (3)
C5	0.13284 (9)	0.30980 (12)	0.74543 (7)	0.0174 (3)
C6	0.21706 (10)	0.41599 (12)	0.74388 (7)	0.0180 (3)
C8	0.25200 (10)	0.50155 (12)	0.59986 (8)	0.0169 (3)
C10	0.39729 (10)	0.39581 (12)	0.58841 (8)	0.0180 (3)
C11	0.36292 (9)	0.34893 (12)	0.66226 (8)	0.0174 (3)
C12	0.41964 (10)	0.25513 (12)	0.71540 (8)	0.0207 (3)
C13	0.51416 (10)	0.20871 (13)	0.69185 (9)	0.0233 (4)
C14	0.55011 (10)	0.25460 (13)	0.61838 (9)	0.0227 (4)
C15	0.49311 (10)	0.34782 (12)	0.56574 (8)	0.0208 (3)
C16	0.16006 (10)	0.59333 (12)	0.58484 (7)	0.0170 (3)
C17	0.17631 (10)	0.72115 (12)	0.55660 (7)	0.0181 (3)
C18	0.09167 (10)	0.80926 (12)	0.54134 (8)	0.0185 (3)
C19	−0.01170 (10)	0.77117 (12)	0.55381 (7)	0.0172 (3)
C21	−0.19187 (10)	0.83706 (13)	0.56480 (8)	0.0218 (4)
C22	−0.25815 (10)	0.95958 (13)	0.55465 (8)	0.0211 (3)
C23	−0.35254 (11)	0.96766 (14)	0.50457 (9)	0.0262 (4)
C24	−0.02971 (10)	0.64406 (12)	0.58006 (8)	0.0181 (3)
C25	0.05619 (10)	0.55642 (12)	0.59561 (7)	0.0180 (3)
C26	0.11566 (10)	0.20690 (12)	0.68709 (8)	0.0190 (3)
C27	0.03538 (10)	0.11448 (12)	0.69133 (8)	0.0196 (3)
C28	−0.18801 (10)	0.05439 (13)	0.80606 (8)	0.0212 (3)
C29	−0.27537 (10)	−0.04607 (13)	0.78754 (8)	0.0208 (3)
C30	−0.31212 (10)	−0.11109 (13)	0.84837 (9)	0.0229 (4)
H31	−0.05350	0.22920	0.86000	0.0269*
H41	0.08040	0.38680	0.84960	0.0251*
H61	0.27430	0.40430	0.79340	0.0235*
H62	0.18260	0.50240	0.74740	0.0230*
H121	0.39610	0.22590	0.76710	0.0255*
H131	0.55580	0.14310	0.72760	0.0285*
H141	0.61750	0.22060	0.60530	0.0280*
H151	0.51880	0.37840	0.51560	0.0261*
H171	0.24900	0.74770	0.54950	0.0226*
H181	0.10260	0.89680	0.52220	0.0235*
H211	−0.22950	0.76570	0.52890	0.0264*
H212	−0.17880	0.80930	0.62670	0.0282*
H221	−0.22850	1.03690	0.58740	0.0259*
H231	−0.38010	0.89420	0.46990	0.0337*
H232	−0.39470	1.04670	0.50120	0.0328*
H241	−0.10180	0.61580	0.58640	0.0238*
H251	0.04310	0.46810	0.61320	0.0223*
H261	0.15810	0.20230	0.64160	0.0234*
H271	0.02280	0.04320	0.65050	0.0239*
H281	−0.22060	0.14390	0.79440	0.0266*
H282	−0.15390	0.04870	0.86720	0.0255*
H291	−0.30710	−0.06000	0.72780	0.0250*
H301	−0.36980	−0.17230	0.83560	0.0284*
H302	−0.27840	−0.09670	0.90660	0.0289*

	U11	U22	U33	U12	U13	U23
O1	0.0197 (4)	0.0206 (4)	0.0237 (5)	−0.0026 (3)	0.0067 (4)	−0.0017 (4)
O20	0.0186 (4)	0.0183 (4)	0.0248 (5)	0.0026 (3)	0.0054 (3)	0.0036 (3)
N7	0.0171 (5)	0.0166 (5)	0.0167 (5)	0.0001 (4)	0.0027 (4)	0.0015 (4)
N9	0.0188 (5)	0.0188 (5)	0.0189 (5)	0.0005 (4)	0.0040 (4)	0.0009 (4)
C2	0.0165 (6)	0.0176 (6)	0.0202 (6)	0.0009 (5)	0.0010 (5)	0.0044 (5)
C3	0.0208 (6)	0.0250 (6)	0.0170 (6)	−0.0007 (5)	0.0048 (5)	0.0012 (5)
C4	0.0225 (6)	0.0224 (6)	0.0163 (6)	−0.0005 (5)	0.0020 (5)	−0.0018 (5)
C5	0.0167 (6)	0.0184 (6)	0.0164 (6)	0.0022 (5)	0.0010 (4)	0.0040 (5)
C6	0.0198 (6)	0.0193 (6)	0.0149 (6)	−0.0002 (5)	0.0029 (5)	0.0009 (5)
C8	0.0193 (6)	0.0153 (6)	0.0155 (6)	−0.0022 (5)	0.0010 (5)	−0.0004 (4)
C10	0.0190 (6)	0.0155 (6)	0.0190 (6)	−0.0020 (5)	0.0014 (5)	−0.0011 (5)
C11	0.0166 (6)	0.0158 (6)	0.0193 (6)	−0.0017 (5)	0.0012 (5)	−0.0020 (5)
C12	0.0217 (6)	0.0179 (6)	0.0211 (6)	−0.0014 (5)	−0.0002 (5)	0.0018 (5)
C13	0.0216 (6)	0.0182 (6)	0.0276 (7)	0.0019 (5)	−0.0032 (5)	0.0004 (5)
C14	0.0162 (6)	0.0211 (6)	0.0302 (7)	0.0003 (5)	0.0023 (5)	−0.0062 (5)
C15	0.0200 (6)	0.0194 (6)	0.0234 (6)	−0.0025 (5)	0.0051 (5)	−0.0034 (5)
C16	0.0201 (6)	0.0178 (6)	0.0126 (5)	0.0009 (5)	0.0012 (4)	−0.0012 (4)
C17	0.0190 (6)	0.0200 (6)	0.0155 (6)	−0.0011 (5)	0.0035 (4)	0.0000 (5)
C18	0.0229 (6)	0.0157 (6)	0.0170 (6)	−0.0006 (5)	0.0035 (5)	0.0015 (5)
C19	0.0194 (6)	0.0180 (6)	0.0137 (5)	0.0022 (5)	0.0011 (4)	−0.0012 (4)
C21	0.0176 (6)	0.0221 (6)	0.0262 (7)	0.0002 (5)	0.0049 (5)	0.0028 (5)
C22	0.0222 (6)	0.0210 (6)	0.0209 (6)	0.0004 (5)	0.0063 (5)	0.0009 (5)
C23	0.0242 (7)	0.0251 (7)	0.0285 (7)	0.0027 (5)	0.0019 (5)	−0.0005 (5)
C24	0.0171 (6)	0.0194 (6)	0.0173 (6)	−0.0013 (5)	0.0015 (4)	−0.0007 (5)
C25	0.0220 (6)	0.0154 (6)	0.0158 (6)	−0.0014 (5)	0.0008 (5)	−0.0005 (4)
C26	0.0187 (6)	0.0205 (6)	0.0185 (6)	0.0023 (5)	0.0051 (5)	0.0014 (5)
C27	0.0205 (6)	0.0179 (6)	0.0202 (6)	0.0019 (5)	0.0030 (5)	−0.0019 (5)
C28	0.0200 (6)	0.0223 (6)	0.0223 (6)	0.0003 (5)	0.0068 (5)	−0.0001 (5)
C29	0.0187 (6)	0.0228 (6)	0.0205 (6)	0.0015 (5)	0.0023 (5)	−0.0016 (5)
C30	0.0207 (6)	0.0230 (6)	0.0251 (7)	−0.0018 (5)	0.0040 (5)	−0.0030 (5)

O1—C2	1.3702 (15)	C24—C25	1.3905 (18)
O1—C28	1.4367 (16)	C26—C27	1.3892 (18)
O20—C19	1.3681 (15)	C28—C29	1.4937 (18)
O20—C21	1.4407 (16)	C29—C30	1.3188 (19)
N7—C6	1.4590 (15)	C3—H31	0.9700
N7—C8	1.3810 (16)	C4—H41	0.9700
N7—C11	1.3841 (15)	C6—H61	0.9800
N9—C8	1.3187 (16)	C6—H62	0.9900
N9—C10	1.3939 (16)	C12—H121	0.9700
C2—C3	1.3950 (18)	C13—H131	0.9700
C2—C27	1.3957 (18)	C14—H141	0.9700
C3—C4	1.3892 (18)	C15—H151	0.9600
C4—C5	1.3908 (17)	C17—H171	0.9800
C5—C6	1.5161 (17)	C18—H181	0.9600
C5—C26	1.3949 (17)	C21—H211	1.0000
C8—C16	1.4740 (18)	C21—H212	1.0100
C10—C11	1.4024 (18)	C22—H221	0.9800
C10—C15	1.3995 (18)	C23—H231	0.9600
C11—C12	1.3927 (17)	C23—H232	0.9600
C12—C13	1.3849 (18)	C24—H241	0.9700
C13—C14	1.4026 (19)	C25—H251	0.9700
C14—C15	1.3859 (18)	C26—H261	0.9700
C16—C17	1.4049 (17)	C27—H271	0.9700
C16—C25	1.3939 (18)	C28—H281	1.0000
C17—C18	1.3816 (18)	C28—H282	1.0000
C18—C19	1.3990 (18)	C29—H291	0.9800
C19—C24	1.3921 (17)	C30—H301	0.9500
C21—C22	1.4949 (19)	C30—H302	0.9700
C22—C23	1.3167 (19)
C2—O1—C28	116.19 (10)	C5—C4—H41	119.00
C19—O20—C21	116.76 (9)	N7—C6—H61	107.00
C6—N7—C8	128.63 (10)	N7—C6—H62	107.00
C6—N7—C11	123.84 (10)	C5—C6—H61	109.00
C8—N7—C11	106.23 (10)	C5—C6—H62	109.00
C8—N9—C10	104.92 (10)	H61—C6—H62	109.00
O1—C2—C3	124.21 (11)	C11—C12—H121	122.00
O1—C2—C27	116.22 (11)	C13—C12—H121	121.00
C3—C2—C27	119.54 (11)	C12—C13—H131	119.00
C2—C3—C4	119.39 (12)	C14—C13—H131	120.00
C3—C4—C5	121.74 (12)	C13—C14—H141	118.00
C4—C5—C6	117.79 (11)	C15—C14—H141	120.00
C4—C5—C26	118.29 (11)	C10—C15—H151	121.00
C6—C5—C26	123.92 (10)	C14—C15—H151	121.00
N7—C6—C5	115.27 (10)	C16—C17—H171	119.00
N7—C8—N9	113.16 (11)	C18—C17—H171	120.00
N7—C8—C16	122.69 (11)	C17—C18—H181	121.00
N9—C8—C16	124.15 (11)	C19—C18—H181	119.00
N9—C10—C11	109.92 (11)	O20—C21—H211	110.00
N9—C10—C15	130.48 (11)	O20—C21—H212	109.00
C11—C10—C15	119.57 (11)	C22—C21—H211	110.00
N7—C11—C10	105.77 (10)	C22—C21—H212	110.00
N7—C11—C12	131.02 (11)	H211—C21—H212	110.00
C10—C11—C12	123.18 (11)	C21—C22—H221	117.00
C11—C12—C13	116.39 (12)	C23—C22—H221	120.00
C12—C13—C14	121.32 (12)	C22—C23—H231	120.00
C13—C14—C15	121.95 (12)	C22—C23—H232	121.00
C10—C15—C14	117.59 (12)	H231—C23—H232	119.00
C8—C16—C17	119.36 (11)	C19—C24—H241	121.00
C8—C16—C25	122.07 (11)	C25—C24—H241	120.00
C17—C16—C25	118.56 (11)	C16—C25—H251	120.00
C16—C17—C18	120.79 (12)	C24—C25—H251	119.00
C17—C18—C19	119.86 (11)	C5—C26—H261	119.00
O20—C19—C18	115.62 (11)	C27—C26—H261	120.00
O20—C19—C24	124.28 (11)	C2—C27—H271	119.00
C18—C19—C24	120.10 (11)	C26—C27—H271	121.00
O20—C21—C22	107.67 (10)	O1—C28—H281	110.00
C21—C22—C23	123.12 (12)	O1—C28—H282	111.00
C19—C24—C25	119.52 (12)	C29—C28—H281	109.00
C16—C25—C24	121.15 (11)	C29—C28—H282	110.00
C5—C26—C27	120.77 (11)	H281—C28—H282	109.00
C2—C27—C26	120.24 (11)	C28—C29—H291	117.00
O1—C28—C29	108.84 (10)	C30—C29—H291	120.00
C28—C29—C30	122.26 (12)	C29—C30—H301	121.00
C2—C3—H31	120.00	C29—C30—H302	119.00
C4—C3—H31	120.00	H301—C30—H302	120.00
C3—C4—H41	119.00
C28—O1—C2—C3	9.44 (17)	C4—C5—C26—C27	1.28 (18)
C28—O1—C2—C27	−168.51 (11)	N9—C8—C16—C17	−40.64 (17)
C2—O1—C28—C29	173.88 (10)	N7—C8—C16—C25	−42.45 (17)
C21—O20—C19—C18	−169.69 (10)	N7—C8—C16—C17	139.28 (12)
C21—O20—C19—C24	10.16 (16)	N9—C8—C16—C25	137.63 (13)
C19—O20—C21—C22	171.61 (10)	N9—C10—C15—C14	177.71 (13)
C6—N7—C11—C10	−168.56 (11)	C11—C10—C15—C14	0.06 (19)
C8—N7—C11—C10	−0.61 (13)	C15—C10—C11—C12	−0.17 (19)
C6—N7—C11—C12	9.7 (2)	N9—C10—C11—N7	0.11 (14)
C8—N7—C11—C12	177.59 (13)	N9—C10—C11—C12	−178.27 (11)
C8—N7—C6—C5	104.28 (14)	C15—C10—C11—N7	178.21 (11)
C11—N7—C6—C5	−90.59 (14)	N7—C11—C12—C13	−177.85 (13)
C6—N7—C8—N9	168.14 (11)	C10—C11—C12—C13	0.08 (19)
C11—N7—C8—N9	0.97 (14)	C11—C12—C13—C14	0.11 (19)
C6—N7—C8—C16	−11.79 (19)	C12—C13—C14—C15	−0.2 (2)
C11—N7—C8—C16	−178.95 (11)	C13—C14—C15—C10	0.1 (2)
C10—N9—C8—N7	−0.88 (14)	C8—C16—C17—C18	179.53 (11)
C10—N9—C8—C16	179.04 (11)	C25—C16—C17—C18	1.20 (17)
C8—N9—C10—C11	0.46 (14)	C8—C16—C25—C24	−179.18 (11)
C8—N9—C10—C15	−177.37 (13)	C17—C16—C25—C24	−0.90 (17)
O1—C2—C3—C4	−176.16 (12)	C16—C17—C18—C19	−0.19 (18)
O1—C2—C27—C26	176.99 (11)	C17—C18—C19—O20	178.71 (11)
C27—C2—C3—C4	1.74 (19)	C17—C18—C19—C24	−1.16 (18)
C3—C2—C27—C26	−1.07 (19)	O20—C19—C24—C25	−178.39 (11)
C2—C3—C4—C5	−0.92 (19)	C18—C19—C24—C25	1.46 (18)
C3—C4—C5—C6	179.34 (11)	O20—C21—C22—C23	120.11 (14)
C3—C4—C5—C26	−0.59 (19)	C19—C24—C25—C16	−0.42 (18)
C4—C5—C6—N7	−170.42 (11)	C5—C26—C27—C2	−0.46 (19)
C6—C5—C26—C27	−178.65 (11)	O1—C28—C29—C30	133.16 (13)
C26—C5—C6—N7	9.50 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H121···Cg4i	0.97	2.62	3.5064 (13)	153
C23—H231···Cg3ii	0.96	2.73	3.6859 (15)	175
C30—H301···Cg2iii	0.95	2.72	3.6202 (14)	159

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C2–C5/C26/C27 ring; Cg3 is the centroid of the C10–C15 ring and Cg4 is the centroid of the C16–C19/C24/25 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H121⋯Cg4i	0.97	2.62	3.5064 (13)	153
C23—H231⋯Cg3ii	0.96	2.73	3.6859 (15)	175
C30—H301⋯Cg2iii	0.95	2.72	3.6202 (14)	159

Symmetry codes: (i) ; (ii) ; (iii) .