1-[4-(Prop-2-en-1-yl­oxy)benz­yl]-2-[4-(prop-2-en-1-yl­oxy)phen­yl]-1H-benzimidazole

Rahman, M.L.; Kwong, H.C.; Mohd. Yusoff, M.; Hegde, G.; Mohamed Tahir, M.I.

doi:10.1107/S160053681204559X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Pages o3311-o3312

doi:10.1107/S160053681204559X

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1-[4-(Prop-2-en-1-yloxy)benzyl]-2-[4-(prop-2-en-1-yloxy)phenyl]-1H-benzimidazole

Md. Lutfor Rahman,^a ^* Huey Chong Kwong,^b Mashitah Mohd. Yusoff,^a Gurumurthy Hegde ^a and Mohamed Ibrahim Mohamed Tahir ^b

^aUniversity Malaysia Pahang, Faculty of Industrial Sciences and Technology, 26300 Gambang, Kuantan, Pahang, Malaysia, and ^bDepartment Chemistry, Faculty Science, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia
^*Correspondence e-mail: lutfor73@gmail.com

(Received 1 October 2012; accepted 5 November 2012; online 10 November 2012)

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, molecules are linked via C—H⋯π and weak π–π interactions [centroid–centroid distance = 3.8070 (7) Å and interplanar 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_r = 396.49
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.038
wR(F²) = 0.100
S = 0.99
3891 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.25 e Å⁻³

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) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) -x, -y+1, -z+1; (iii) $[-x-{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681204559X/su2508sup1.cif

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

Supporting information file. DOI: 10.1107/S160053681204559X/su2508Isup3.cml

checkCIF report

Comment top

The importance of the benzimidazole nucleus is due to the fact that it is found in many biologically active compounds (Xiangming et al., 2007). Benzimidazole derivatives have been shown to have significant activity against several viruses such as, HIV (Porcari et al., 1998), herpes (Migawa et al., 1998), influenza (Tamm and Sehgal, 1978) and human cytomegalovirus (Porcari et al., 1998). Many benzimidazole containing compounds exhibited significant biological activities, such as novel anti-allergic agents (Nakano et al., 2000), factor Xa inhibitors (Zhao et al., 2000), poly (ADP-ribose) polymerase (PARP) inhibitors (White et al., 2000). Some substituted benzimidazole derivatives have been recently commercialized for applications in veterinarian medicine, and in diverse human therapeutic areas such as, the treatment of ulcers and as antihistamines (Spasov et al., 1999).

In the titled compound (Fig. 1) the bond lengths (Allen et al., 1987) and bond angles are normal. The benzimidazole ring system (N7/C8/N9/C10-C15) is almost planar, with a maximum displacement of 0.025 (1) Å for atom C8. The dihedral angle formed by the mean plane of the benzimidazole ring system and the two adjacent benzene rings (C2-C5/C26/C27 and C16-C19/C24/C25) are 80.48 (5)° and 41.57 (5)°, respectively. The benzene rings themselves are inclined to one another by 65.33 (6)°, rather than ca. 90° as observed elsewhere, for example in the related compounds, 4-[1-(4-Cyanobenzyl)-1H-benzimidazol-2-yl]benzonitrile (Kia et al., 2009) and 1-(4-tert-Butylbenzyl)-2-(4-tert-butylphenyl)-1H-benzimidazole (Zhou et al., 2009). The torsion angles of the allyloxy chains (O1-C28-C29-C30 and O20-C21-C22-C23) are 133.16 (13)° and 120.11 (14)°, respectively.

In the crystal, molecules are linked via C-H···π interactions (Table 1) and weak π-π interactions. The centroid to centroid distance, Cg1···Cg2ⁱ, is 3.8070 (7)Å with an interplanar distance of 3.6160 (5) Å [Cg1 and Cg2 are the centroids of the N7/C8/N9/C10/C11 and C2-C5/C26/C27 rings; symmetry code: (i) -x + 1/2, y + 1/2, -z + 3/2].

Related literature top

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 top

4-Hydroxybenzaldehyde (10.0 g, 83.25 mmol) was dissolved in dry acetone (150 mL). Then allyl bromide (12.097 g, 100 mmol), potassium carbonate (13.80 g, 100 mmol) and a catalytic amount of potassium iodide (20 mg) were added and the mixture was refluxed for 24 h under argon atmosphere. Afterwards, it was poured into ice-cold water and acidified with dilute hydrochloric acid (pH<5). The precipitate was filtered off and was crystallized from methanol/chloroform to yield the 4-(prop-2-en-1-yloxy)benzaldehyde. A solution of 4-(prop-2-en-1-yloxy)benzaldehyde (5.00 g, 30.82 mmol) in ethanol was added to a solution of o-phenylenediamine (1.66 g, 15.41 mmol) in ethanol. The mixture was refluxed with a few drops of acetic acid as catalyst for 12 h to yield the title compound as a slightly grey solid. The product was filtered off and recrystallized from absolute ethanol to give pale-brown block-like crystals of the title compound, suitable for X-ray diffraction analysis (Lutfor et al., 2008).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); 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 (Betteridge et al., 2003).

Figures top

Fig. 1. The molecular structure of the title molecule with the atom numbering. Displacement ellipsoids are drawn at the 50% probability level.

1-[4-(Prop-2-en-1-yloxy)benzyl]-2-[4-(prop-2-en-1-yloxy)phenyl]- 1H-benzimidazole top

Crystal data top

C₂₆H₂₄N₂O₂	F(000) = 840
M_r = 396.49	D_x = 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

Data collection top

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

Refinement top

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(F_o²,0) + 2F_c²)/3
S = 0.99	(Δ/σ)_max = 0.002
3891 reflections	Δρ_max = 0.26 e Å⁻³
271 parameters	Δρ_min = −0.25 e Å⁻³
0 restraints

Crystal data top

C₂₆H₂₄N₂O₂	V = 2010.78 (4) Å³
M_r = 396.49	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 12.5455 (1) Å	µ = 0.66 mm⁻¹
b = 10.1989 (1) Å	T = 100 K
c = 15.9340 (2) Å	0.35 × 0.23 × 0.08 mm
β = 99.5027 (11)°

Data collection top

Agilent Technologies Gemini diffractometer	3908 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	3563 reflections with I > 2.0σ(I)
T_min = 0.80, T_max = 0.95	R_int = 0.029
38976 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 0.99	Δρ_max = 0.26 e Å⁻³
3891 reflections	Δρ_min = −0.25 e Å⁻³
271 parameters

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1/2, y−1/2, −z+3/2; (ii) −x, −y+1, −z+1; (iii) −x−1/2, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₂₆H₂₄N₂O₂
M_r	396.49
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	12.5455 (1), 10.1989 (1), 15.9340 (2)
β (°)	99.5027 (11)
V (Å³)	2010.78 (4)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.66
Crystal size (mm)	0.35 × 0.23 × 0.08

Data collection
Diffractometer	Agilent Technologies Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.80, 0.95
No. of measured, independent and observed [I > 2.0σ(I)] reflections	38976, 3908, 3563
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.615

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.100, 0.99
No. of reflections	3891
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.25

Computer programs: CrysAlis PRO (Agilent, 2011), SIR92 (Altomare et al., 1994), CRYSTALS (Betteridge et al., 2003), Mercury (Macrae et al., 2008).

Hydrogen-bond geometry (Å, º) top

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) −x+1/2, y−1/2, −z+3/2; (ii) −x, −y+1, −z+1; (iii) −x−1/2, y−1/2, −z+3/2.

Acknowledgements

This research was supported by a UMP research grant (No. RDU100338).

References

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Volume 68| Part 12| December 2012| Pages o3311-o3312

doi:10.1107/S160053681204559X

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1-[4-(Prop-2-en-1-yl­­oxy)benz­yl]-2-[4-(prop-2-en-1-yl­­oxy)phen­yl]-1H-benzimidazole

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1-[4-(Prop-2-en-1-yloxy)benzyl]-2-[4-(prop-2-en-1-yloxy)phenyl]-1H-benzimidazole