organic compounds
1-[4-(Prop-2-en-1-yloxy)benzyl]-2-[4-(prop-2-en-1-yloxy)phenyl]-1H-benzimidazole
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
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
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Refinement
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Data collection: CrysAlis PRO (Agilent, 2011); cell 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
10.1107/S160053681204559X/su2508sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053681204559X/su2508Isup2.hkl
Supporting information file. DOI: 10.1107/S160053681204559X/su2508Isup3.cml
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
(Lutfor et al., 2008).The H atoms were all located in a difference Fourier map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularize their geometry (C—H in the range 0.93–0.98 Å, N—H in the range 0.86–0.90 Å) and Uiso(H) in the range 1.2–1.5 times Ueq of the parent atom). In the final cycles of
they were refined as riding atoms.Data collection: CrysAlis PRO (Agilent, 2011); cell
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).Fig. 1. The molecular structure of the title molecule with the atom numbering. Displacement ellipsoids are drawn at the 50% probability level. |
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 |
C26H24N2O2 | V = 2010.78 (4) Å3 |
Mr = 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)° |
Agilent Technologies Gemini diffractometer | 3908 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | 3563 reflections with I > 2.0σ(I) |
Tmin = 0.80, Tmax = 0.95 | Rint = 0.029 |
38976 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.26 e Å−3 |
3891 reflections | Δρmin = −0.25 e Å−3 |
271 parameters |
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) |
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 |
Mr | 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) |
Tmin, Tmax | 0.80, 0.95 |
No. of measured, independent and observed [I > 2.0σ(I)] reflections | 38976, 3908, 3563 |
Rint | 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 |
Δρmax, Δρmin (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).
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).
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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].