organic compounds
3-[1-(3-Hydroxybenzyl)-1H-benzimidazol-2-yl]phenol
aSchool of Chemical Science, Universiti Sains Malaysia, Minden, Penang, Malaysia, and bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: hkfun@usm.my
In the title molecule, C20H16N2O2, the benzimidazole mean plane forms dihedral angles of 56.55 (3) and 81.65 (4)° with the two benzene rings. In the intermolecular O—H⋯O and O—H⋯N hydrogen bonds link the molecules into layers parallel to the (101) plane. The crystal packing also exhibits weak intermolecular C—H⋯O and C—H⋯π interactions.
Related literature
For the biological activity of benzimidazole derivatives, see: Demirayak et al. (2002); Minoura et al. (2004); Pawar et al. (2004); Tomei et al. (2003). For related structures, see: Eltayeb et al. (2007a,b,c). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2005); cell SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).
Supporting information
10.1107/S1600536809018698/cv2563sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809018698/cv2563Isup2.hkl
To a solution of o-phenylenediamine (0.216 g, 2 mmol) in ethanol (30 ml) was added 3-hydroxybenzaldehyde (0.488 g, 4 mmol). The mixture was refluxed with stirring for half an hour. The resultant yellow solution was filtered. Crystals suitable for XRD were formed after several days of slow evaporation of solvent at room temperature.
H atoms were positioned geometrically [C—H = 0.93–0.97 Å] and refined using a riding model with Uiso(H) = 1.2Ueq(C). The O-bound H atoms were located on a Fourier map and were refined isotropically.
Data collection: APEX2 (Bruker, 2005); cell
SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids and the atom numbering scheme. |
C20H16N2O2 | F(000) = 664 |
Mr = 316.35 | Dx = 1.328 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 8327 reflections |
a = 10.5128 (2) Å | θ = 2.4–37.2° |
b = 12.1096 (2) Å | µ = 0.09 mm−1 |
c = 12.5235 (2) Å | T = 100 K |
β = 96.948 (1)° | Plate, colourless |
V = 1582.61 (5) Å3 | 0.55 × 0.34 × 0.15 mm |
Z = 4 |
Bruker SMART APEXII CCD area-detector diffractometer | 7426 independent reflections |
Radiation source: fine-focus sealed tube | 6004 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
ϕ and ω scans | θmax = 36.0°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −14→17 |
Tmin = 0.954, Tmax = 0.987 | k = −20→20 |
34106 measured reflections | l = −19→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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.136 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0723P)2 + 0.2344P] where P = (Fo2 + 2Fc2)/3 |
7426 reflections | (Δ/σ)max < 0.001 |
225 parameters | Δρmax = 0.51 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
C20H16N2O2 | V = 1582.61 (5) Å3 |
Mr = 316.35 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 10.5128 (2) Å | µ = 0.09 mm−1 |
b = 12.1096 (2) Å | T = 100 K |
c = 12.5235 (2) Å | 0.55 × 0.34 × 0.15 mm |
β = 96.948 (1)° |
Bruker SMART APEXII CCD area-detector diffractometer | 7426 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 6004 reflections with I > 2σ(I) |
Tmin = 0.954, Tmax = 0.987 | Rint = 0.040 |
34106 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.136 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.51 e Å−3 |
7426 reflections | Δρmin = −0.29 e Å−3 |
225 parameters |
Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K. |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.60369 (7) | 0.60548 (5) | 0.04595 (5) | 0.01932 (13) | |
O2 | 0.21201 (7) | 0.70928 (6) | 0.49193 (6) | 0.02850 (16) | |
N1 | 0.36876 (7) | 0.35014 (5) | 0.31082 (5) | 0.01366 (12) | |
N2 | 0.55084 (7) | 0.30903 (6) | 0.41524 (5) | 0.01468 (12) | |
C1 | 0.34113 (8) | 0.26119 (6) | 0.37376 (6) | 0.01385 (13) | |
C2 | 0.22644 (8) | 0.20556 (7) | 0.38301 (6) | 0.01625 (14) | |
H2A | 0.1502 | 0.2247 | 0.3415 | 0.019* | |
C3 | 0.23254 (9) | 0.12006 (7) | 0.45759 (7) | 0.01787 (15) | |
H3A | 0.1581 | 0.0820 | 0.4676 | 0.021* | |
C4 | 0.34872 (9) | 0.08978 (7) | 0.51829 (7) | 0.01903 (16) | |
H4A | 0.3497 | 0.0308 | 0.5659 | 0.023* | |
C5 | 0.46206 (9) | 0.14602 (7) | 0.50872 (7) | 0.01765 (15) | |
H5A | 0.5388 | 0.1255 | 0.5486 | 0.021* | |
C6 | 0.45615 (8) | 0.23468 (6) | 0.43671 (6) | 0.01408 (13) | |
C7 | 0.49493 (8) | 0.37658 (6) | 0.34028 (6) | 0.01328 (13) | |
C8 | 0.55758 (8) | 0.47449 (6) | 0.29966 (6) | 0.01346 (13) | |
C9 | 0.55681 (8) | 0.49315 (6) | 0.18938 (6) | 0.01442 (13) | |
H9A | 0.5214 | 0.4411 | 0.1398 | 0.017* | |
C10 | 0.60956 (8) | 0.59058 (6) | 0.15413 (6) | 0.01466 (14) | |
C11 | 0.66423 (8) | 0.66833 (7) | 0.22849 (6) | 0.01679 (15) | |
H11A | 0.6988 | 0.7333 | 0.2049 | 0.020* | |
C12 | 0.66666 (9) | 0.64783 (7) | 0.33810 (7) | 0.01769 (15) | |
H12A | 0.7041 | 0.6990 | 0.3876 | 0.021* | |
C13 | 0.61356 (8) | 0.55155 (7) | 0.37433 (6) | 0.01600 (14) | |
H13A | 0.6153 | 0.5385 | 0.4477 | 0.019* | |
C14 | 0.27189 (8) | 0.40916 (7) | 0.23858 (6) | 0.01493 (14) | |
H14A | 0.2199 | 0.3560 | 0.1948 | 0.018* | |
H14B | 0.3144 | 0.4556 | 0.1907 | 0.018* | |
C15 | 0.18581 (8) | 0.47993 (7) | 0.29866 (6) | 0.01546 (14) | |
C16 | 0.05416 (9) | 0.46392 (8) | 0.28541 (7) | 0.02214 (17) | |
H16A | 0.0182 | 0.4078 | 0.2409 | 0.027* | |
C17 | −0.02425 (10) | 0.53232 (10) | 0.33909 (9) | 0.0298 (2) | |
H17A | −0.1126 | 0.5226 | 0.3289 | 0.036* | |
C18 | 0.02893 (10) | 0.61473 (9) | 0.40753 (8) | 0.0276 (2) | |
H18A | −0.0235 | 0.6601 | 0.4432 | 0.033* | |
C19 | 0.16150 (9) | 0.62907 (8) | 0.42254 (7) | 0.02011 (16) | |
C20 | 0.23951 (8) | 0.56315 (7) | 0.36681 (6) | 0.01647 (14) | |
H20A | 0.3276 | 0.5746 | 0.3750 | 0.020* | |
H1O1 | 0.6430 (17) | 0.6716 (15) | 0.0307 (14) | 0.053 (5)* | |
H1O2 | 0.3026 (18) | 0.6952 (15) | 0.5216 (14) | 0.055 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0266 (3) | 0.0181 (3) | 0.0133 (2) | −0.0054 (2) | 0.0028 (2) | 0.00132 (19) |
O2 | 0.0206 (3) | 0.0285 (3) | 0.0336 (4) | 0.0103 (3) | −0.0083 (3) | −0.0167 (3) |
N1 | 0.0134 (3) | 0.0145 (3) | 0.0127 (3) | 0.0004 (2) | 0.0002 (2) | 0.0011 (2) |
N2 | 0.0139 (3) | 0.0155 (3) | 0.0144 (3) | 0.0006 (2) | 0.0007 (2) | 0.0009 (2) |
C1 | 0.0148 (3) | 0.0135 (3) | 0.0131 (3) | −0.0001 (2) | 0.0012 (3) | −0.0002 (2) |
C2 | 0.0151 (3) | 0.0170 (3) | 0.0162 (3) | −0.0022 (3) | 0.0003 (3) | −0.0013 (2) |
C3 | 0.0204 (4) | 0.0161 (3) | 0.0173 (3) | −0.0041 (3) | 0.0029 (3) | −0.0011 (2) |
C4 | 0.0242 (4) | 0.0149 (3) | 0.0181 (3) | −0.0023 (3) | 0.0027 (3) | 0.0015 (3) |
C5 | 0.0197 (4) | 0.0158 (3) | 0.0169 (3) | 0.0008 (3) | 0.0001 (3) | 0.0024 (2) |
C6 | 0.0147 (3) | 0.0136 (3) | 0.0137 (3) | 0.0002 (2) | 0.0008 (3) | −0.0003 (2) |
C7 | 0.0131 (3) | 0.0143 (3) | 0.0124 (3) | 0.0001 (2) | 0.0013 (2) | −0.0007 (2) |
C8 | 0.0122 (3) | 0.0142 (3) | 0.0140 (3) | 0.0001 (2) | 0.0018 (2) | −0.0003 (2) |
C9 | 0.0159 (3) | 0.0142 (3) | 0.0131 (3) | −0.0019 (2) | 0.0018 (3) | −0.0008 (2) |
C10 | 0.0154 (3) | 0.0151 (3) | 0.0138 (3) | −0.0006 (3) | 0.0026 (3) | −0.0001 (2) |
C11 | 0.0183 (4) | 0.0148 (3) | 0.0173 (3) | −0.0026 (3) | 0.0023 (3) | −0.0013 (2) |
C12 | 0.0186 (4) | 0.0180 (3) | 0.0165 (3) | −0.0035 (3) | 0.0021 (3) | −0.0036 (2) |
C13 | 0.0161 (4) | 0.0180 (3) | 0.0138 (3) | −0.0011 (3) | 0.0016 (3) | −0.0019 (2) |
C14 | 0.0145 (3) | 0.0177 (3) | 0.0120 (3) | 0.0020 (3) | −0.0010 (3) | 0.0002 (2) |
C15 | 0.0148 (3) | 0.0176 (3) | 0.0136 (3) | 0.0022 (3) | 0.0000 (3) | 0.0002 (2) |
C16 | 0.0145 (4) | 0.0283 (4) | 0.0229 (4) | 0.0005 (3) | −0.0007 (3) | −0.0069 (3) |
C17 | 0.0133 (4) | 0.0409 (6) | 0.0349 (5) | 0.0020 (4) | 0.0017 (4) | −0.0144 (4) |
C18 | 0.0162 (4) | 0.0369 (5) | 0.0292 (5) | 0.0071 (4) | 0.0002 (3) | −0.0126 (4) |
C19 | 0.0174 (4) | 0.0217 (4) | 0.0200 (4) | 0.0057 (3) | −0.0028 (3) | −0.0053 (3) |
C20 | 0.0137 (3) | 0.0178 (3) | 0.0172 (3) | 0.0026 (3) | −0.0006 (3) | −0.0017 (3) |
O1—C10 | 1.3607 (10) | C9—C10 | 1.3977 (11) |
O1—H1O1 | 0.931 (19) | C9—H9A | 0.9300 |
O2—C19 | 1.3671 (11) | C10—C11 | 1.3980 (11) |
O2—H1O2 | 0.994 (19) | C11—C12 | 1.3922 (11) |
N1—C7 | 1.3709 (10) | C11—H11A | 0.9300 |
N1—C1 | 1.3861 (10) | C12—C13 | 1.3922 (11) |
N1—C14 | 1.4641 (11) | C12—H12A | 0.9300 |
N2—C7 | 1.3275 (10) | C13—H13A | 0.9300 |
N2—C6 | 1.3923 (10) | C14—C15 | 1.5114 (11) |
C1—C2 | 1.3981 (11) | C14—H14A | 0.9700 |
C1—C6 | 1.3986 (12) | C14—H14B | 0.9700 |
C2—C3 | 1.3906 (11) | C15—C16 | 1.3874 (13) |
C2—H2A | 0.9300 | C15—C20 | 1.3951 (11) |
C3—C4 | 1.4070 (13) | C16—C17 | 1.3970 (13) |
C3—H3A | 0.9300 | C16—H16A | 0.9300 |
C4—C5 | 1.3901 (12) | C17—C18 | 1.3882 (14) |
C4—H4A | 0.9300 | C17—H17A | 0.9300 |
C5—C6 | 1.3987 (11) | C18—C19 | 1.3944 (14) |
C5—H5A | 0.9300 | C18—H18A | 0.9300 |
C7—C8 | 1.4763 (10) | C19—C20 | 1.3911 (11) |
C8—C9 | 1.3985 (10) | C20—H20A | 0.9300 |
C8—C13 | 1.3995 (11) | ||
C10—O1—H1O1 | 110.5 (11) | C9—C10—C11 | 120.33 (7) |
C19—O2—H1O2 | 113.3 (10) | C12—C11—C10 | 119.59 (7) |
C7—N1—C1 | 106.91 (6) | C12—C11—H11A | 120.2 |
C7—N1—C14 | 129.07 (7) | C10—C11—H11A | 120.2 |
C1—N1—C14 | 123.56 (7) | C11—C12—C13 | 120.69 (8) |
C7—N2—C6 | 105.62 (7) | C11—C12—H12A | 119.7 |
N1—C1—C2 | 131.58 (8) | C13—C12—H12A | 119.7 |
N1—C1—C6 | 105.82 (7) | C12—C13—C8 | 119.56 (7) |
C2—C1—C6 | 122.56 (7) | C12—C13—H13A | 120.2 |
C3—C2—C1 | 116.37 (8) | C8—C13—H13A | 120.2 |
C3—C2—H2A | 121.8 | N1—C14—C15 | 112.50 (6) |
C1—C2—H2A | 121.8 | N1—C14—H14A | 109.1 |
C2—C3—C4 | 121.56 (8) | C15—C14—H14A | 109.1 |
C2—C3—H3A | 119.2 | N1—C14—H14B | 109.1 |
C4—C3—H3A | 119.2 | C15—C14—H14B | 109.1 |
C5—C4—C3 | 121.52 (8) | H14A—C14—H14B | 107.8 |
C5—C4—H4A | 119.2 | C16—C15—C20 | 119.87 (7) |
C3—C4—H4A | 119.2 | C16—C15—C14 | 120.66 (7) |
C4—C5—C6 | 117.39 (8) | C20—C15—C14 | 119.46 (7) |
C4—C5—H5A | 121.3 | C15—C16—C17 | 119.85 (9) |
C6—C5—H5A | 121.3 | C15—C16—H16A | 120.1 |
N2—C6—C1 | 109.41 (7) | C17—C16—H16A | 120.1 |
N2—C6—C5 | 130.08 (8) | C18—C17—C16 | 120.42 (9) |
C1—C6—C5 | 120.50 (7) | C18—C17—H17A | 119.8 |
N2—C7—N1 | 112.19 (7) | C16—C17—H17A | 119.8 |
N2—C7—C8 | 124.10 (7) | C17—C18—C19 | 119.60 (8) |
N1—C7—C8 | 123.52 (7) | C17—C18—H18A | 120.2 |
C9—C8—C13 | 120.26 (7) | C19—C18—H18A | 120.2 |
C9—C8—C7 | 121.37 (7) | O2—C19—C20 | 121.29 (8) |
C13—C8—C7 | 118.31 (7) | O2—C19—C18 | 118.63 (8) |
C10—C9—C8 | 119.55 (7) | C20—C19—C18 | 120.08 (8) |
C10—C9—H9A | 120.2 | C19—C20—C15 | 120.13 (8) |
C8—C9—H9A | 120.2 | C19—C20—H20A | 119.9 |
O1—C10—C9 | 117.03 (7) | C15—C20—H20A | 119.9 |
O1—C10—C11 | 122.64 (7) | ||
C7—N1—C1—C2 | 175.17 (8) | N1—C7—C8—C13 | 121.97 (8) |
C14—N1—C1—C2 | 2.30 (12) | C13—C8—C9—C10 | −1.55 (12) |
C7—N1—C1—C6 | −2.40 (8) | C7—C8—C9—C10 | 175.65 (7) |
C14—N1—C1—C6 | −175.27 (6) | C8—C9—C10—O1 | −178.61 (7) |
N1—C1—C2—C3 | −178.27 (8) | C8—C9—C10—C11 | 0.81 (12) |
C6—C1—C2—C3 | −1.05 (11) | O1—C10—C11—C12 | 179.82 (8) |
C1—C2—C3—C4 | −1.54 (12) | C9—C10—C11—C12 | 0.44 (13) |
C2—C3—C4—C5 | 1.89 (13) | C10—C11—C12—C13 | −0.95 (13) |
C3—C4—C5—C6 | 0.40 (12) | C11—C12—C13—C8 | 0.22 (13) |
C7—N2—C6—C1 | −1.16 (8) | C9—C8—C13—C12 | 1.04 (12) |
C7—N2—C6—C5 | 180.00 (8) | C7—C8—C13—C12 | −176.24 (8) |
N1—C1—C6—N2 | 2.23 (8) | C7—N1—C14—C15 | −98.85 (9) |
C2—C1—C6—N2 | −175.61 (7) | C1—N1—C14—C15 | 72.35 (9) |
N1—C1—C6—C5 | −178.80 (7) | N1—C14—C15—C16 | −121.88 (9) |
C2—C1—C6—C5 | 3.37 (11) | N1—C14—C15—C20 | 59.08 (10) |
C4—C5—C6—N2 | 175.81 (8) | C20—C15—C16—C17 | 0.98 (14) |
C4—C5—C6—C1 | −2.93 (11) | C14—C15—C16—C17 | −178.05 (9) |
C6—N2—C7—N1 | −0.41 (8) | C15—C16—C17—C18 | −1.43 (17) |
C6—N2—C7—C8 | 174.77 (7) | C16—C17—C18—C19 | 0.02 (18) |
C1—N1—C7—N2 | 1.81 (8) | C17—C18—C19—O2 | −178.72 (10) |
C14—N1—C7—N2 | 174.16 (7) | C17—C18—C19—C20 | 1.83 (16) |
C1—N1—C7—C8 | −173.40 (7) | O2—C19—C20—C15 | 178.29 (8) |
C14—N1—C7—C8 | −1.05 (11) | C18—C19—C20—C15 | −2.28 (14) |
N2—C7—C8—C9 | 130.08 (8) | C16—C15—C20—C19 | 0.86 (13) |
N1—C7—C8—C9 | −55.28 (11) | C14—C15—C20—C19 | 179.91 (8) |
N2—C7—C8—C13 | −52.67 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O1···O2i | 0.931 (19) | 1.712 (19) | 2.6406 (9) | 175.4 (17) |
O2—H1O2···N2ii | 0.994 (19) | 1.646 (19) | 2.6297 (10) | 169.7 (16) |
C3—H3A···O1iii | 0.93 | 2.57 | 3.2987 (10) | 136 |
C9—H9A···O1iv | 0.93 | 2.59 | 3.4287 (10) | 150 |
C12—H12A···Cg1ii | 0.93 | 2.67 | 3.4521 (9) | 142 |
Symmetry codes: (i) x+1/2, −y+3/2, z−1/2; (ii) −x+1, −y+1, −z+1; (iii) x−1/2, −y+1/2, z+1/2; (iv) −x+1, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C20H16N2O2 |
Mr | 316.35 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 100 |
a, b, c (Å) | 10.5128 (2), 12.1096 (2), 12.5235 (2) |
β (°) | 96.948 (1) |
V (Å3) | 1582.61 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.55 × 0.34 × 0.15 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.954, 0.987 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 34106, 7426, 6004 |
Rint | 0.040 |
(sin θ/λ)max (Å−1) | 0.827 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.136, 1.05 |
No. of reflections | 7426 |
No. of parameters | 225 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.51, −0.29 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O1···O2i | 0.931 (19) | 1.712 (19) | 2.6406 (9) | 175.4 (17) |
O2—H1O2···N2ii | 0.994 (19) | 1.646 (19) | 2.6297 (10) | 169.7 (16) |
C3—H3A···O1iii | 0.93 | 2.57 | 3.2987 (10) | 136.1 |
C9—H9A···O1iv | 0.93 | 2.59 | 3.4287 (10) | 149.9 |
C12—H12A···Cg1ii | 0.93 | 2.67 | 3.4521 (9) | 142 |
Symmetry codes: (i) x+1/2, −y+3/2, z−1/2; (ii) −x+1, −y+1, −z+1; (iii) x−1/2, −y+1/2, z+1/2; (iv) −x+1, −y+1, −z. |
Acknowledgements
The authors thank the Malaysian Government, the Ministry of Science, Technology and Innovation (MOSTI) and Universiti Sains Malaysia for the E-Science Fund and RU research grants (Nos. PKIMIA/613308, PKIMIA/815002, and PKIMIA/811120). The International University of Africa (Sudan) is acknowledged for providing study leave to NEE. HKF and SRJ thank the Malaysian Government and Universiti Sains Malaysia for a Science Fund grant (No. 305/PFIZIK/613312). SRJ thanks Universiti Sains Malaysia for a post-doctoral research fellowship. HKF also thanks Universiti Sains Malaysia for a Research University Golden Goose grant (No. 1001/PFIZIK/811012).
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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 synthesis of benzimidazoles has received much attention owing to the varied biological activities such as antidiabetic (Minoura et al., 2004), antimicrobial, antifungal (Pawar et al., 2004), antiviral (Tomei et al., 2003), and anticancer (Demirayak et al., 2002) properties exhibited by a number of derivatives of these compounds. In continuation of our structural study of benzimidazole derivatives (Eltayeb et al. 2007a,b,c), we describe in this paper the crystal structure of the title compound (I).
In (I) (Fig. 1), the bond lengths and bond angles are normal (Allen et al., 1987). The benzimidazole unit is planar with the maximum deviation from planarity of 0.0403 (9) Å for atom C3. The dihedral angle formed by the benzimidazole unit with the two benzene rings (C8–C13 and C15–C20) are 56.55 (3)° and 81.65 (4)° respectively. The two benzene rings (C8–C13 and C15–C20) are inclined to each other forming a dihedral angle of 72.54 (4)°.
In the crystal, intermolecular O—H···O, O—H···N hydrogen bonds (Table 1) link the molecules into layers parallel to the (101) plane. The crystal packing exhibits also weak C—H···O and C—H···π interactions (Table 1).