organic compounds
1,2-Diphenyl-1H-benzimidazole
aPostgraduate Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamilnadu, India, bDepartment of Chemistry, Annamalai University, Annamalai Nagar 608 002, Tamilnadu, India, cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, and dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey
*Correspondence e-mail: thiruvalluvar.a@gmail.com
In the title molecule, C19H14N2, the benzimidazole unit is close to being planar [maximum deviation = 0.0102 (6) Å] and forms dihedral angles of 55.80 (2) and 40.67 (3)° with the adjacent phenyl rings; the dihedral angle between the phenyl rings is 62.37 (3)°. In the crystal, one C—H⋯N hydrogen bond and three weak C—H⋯π interactions involving the fused benzene ring and the imidazole ring are observed, leading to a three-dimensional architecture.
Related literature
For the use of benzoimidazoles and phenanthroimidazoles as light-emitting devices and dye-sensitized solar cells, see: Fang et al. (2007); Ge et al. (2008); Lai et al. (2008); Shin et al. (2007); Tsai et al. (2007). For a closely related see: Jayamoorthy et al. (2012).
Experimental
Crystal data
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Refinement
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Data collection: CrysAlis PRO (Agilent, 2012); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: PLATON.
Supporting information
10.1107/S1600536812044960/hg5265sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812044960/hg5265Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812044960/hg5265Isup3.cdx
Supporting information file. DOI: 10.1107/S1600536812044960/hg5265Isup4.cml
The pure N-phenyl-o-phenylenediamine (3.128 g, 17 mmol) in ethanol (10 ml), benzaldehyde (1.72 ml, 17 mmol) and ammonium acetate (3 g) was added about 1 h by maintaining the temperature at 353 K. The reaction mixture was refluxed for appropriate time and the completion of reaction was monitored by TLC, finally the reaction extracted with dichloromethane. The solid separated was purified by
using petroleum ether: ethyl acetate as the Yield: 2.49 g (50%). The title compound was dissolved in acetonitrile and allowed to slow evaporation for two days to obtain crystals suitable for X-ray diffraction studies.The H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.93 Å. Uiso(H) = 1.2Ueq(C).
Data collection: CrysAlis PRO (Agilent, 2012); cell
CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius. | |
Fig. 2. The packing of the title compound, viewed down the a axis. Dashed lines indicate hydrogen bonds. H atoms not involved in hydrogen bonding have been omitted. |
C19H14N2 | F(000) = 1136 |
Mr = 270.32 | Dx = 1.261 Mg m−3 |
Monoclinic, C2/c | Melting point: 380 K |
Hall symbol: -C 2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 10.1878 (3) Å | Cell parameters from 6755 reflections |
b = 16.6399 (4) Å | θ = 3.4–37.7° |
c = 17.4959 (5) Å | µ = 0.08 mm−1 |
β = 106.205 (3)° | T = 123 K |
V = 2848.13 (14) Å3 | Block, colourless |
Z = 8 | 0.60 × 0.40 × 0.35 mm |
Agilent Xcalibur Ruby Gemini diffractometer | 7296 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 5803 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
Detector resolution: 10.5081 pixels mm-1 | θmax = 37.8°, θmin = 3.5° |
ω scans | h = −17→16 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | k = −27→27 |
Tmin = 0.957, Tmax = 0.974 | l = −29→29 |
25253 measured reflections |
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.063P)2 + 1.1529P] where P = (Fo2 + 2Fc2)/3 |
7296 reflections | (Δ/σ)max = 0.001 |
190 parameters | Δρmax = 0.52 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
C19H14N2 | V = 2848.13 (14) Å3 |
Mr = 270.32 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 10.1878 (3) Å | µ = 0.08 mm−1 |
b = 16.6399 (4) Å | T = 123 K |
c = 17.4959 (5) Å | 0.60 × 0.40 × 0.35 mm |
β = 106.205 (3)° |
Agilent Xcalibur Ruby Gemini diffractometer | 7296 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | 5803 reflections with I > 2σ(I) |
Tmin = 0.957, Tmax = 0.974 | Rint = 0.028 |
25253 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.52 e Å−3 |
7296 reflections | Δρmin = −0.25 e Å−3 |
190 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 e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
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 > 2σ(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 | ||
N1 | −0.02193 (7) | 0.41603 (4) | 0.11513 (4) | 0.0171 (2) | |
N3 | −0.10490 (7) | 0.53588 (4) | 0.13995 (4) | 0.0203 (2) | |
C2 | 0.00172 (8) | 0.49743 (5) | 0.12929 (4) | 0.0175 (2) | |
C4 | −0.33775 (9) | 0.48436 (6) | 0.13998 (5) | 0.0236 (2) | |
C5 | −0.41655 (9) | 0.41533 (6) | 0.13157 (6) | 0.0246 (2) | |
C6 | −0.36456 (9) | 0.34053 (6) | 0.11689 (5) | 0.0230 (2) | |
C7 | −0.23322 (9) | 0.33246 (5) | 0.10945 (5) | 0.0204 (2) | |
C8 | −0.15513 (8) | 0.40216 (5) | 0.11787 (4) | 0.0175 (2) | |
C9 | −0.20463 (8) | 0.47749 (5) | 0.13339 (5) | 0.0189 (2) | |
C11 | 0.07472 (8) | 0.35411 (5) | 0.11440 (4) | 0.0170 (2) | |
C12 | 0.04519 (9) | 0.29794 (5) | 0.05292 (5) | 0.0219 (2) | |
C13 | 0.13562 (10) | 0.23476 (5) | 0.05505 (6) | 0.0249 (2) | |
C14 | 0.25548 (10) | 0.22842 (5) | 0.11667 (6) | 0.0249 (2) | |
C15 | 0.28460 (9) | 0.28592 (6) | 0.17671 (5) | 0.0244 (2) | |
C16 | 0.19401 (9) | 0.34852 (5) | 0.17652 (5) | 0.0207 (2) | |
C21 | 0.13044 (8) | 0.53770 (5) | 0.12998 (5) | 0.0180 (2) | |
C22 | 0.20146 (9) | 0.51883 (5) | 0.07441 (5) | 0.0206 (2) | |
C23 | 0.32060 (9) | 0.56028 (6) | 0.07548 (5) | 0.0235 (2) | |
C24 | 0.36977 (9) | 0.61969 (6) | 0.13203 (6) | 0.0253 (2) | |
C25 | 0.29922 (10) | 0.63848 (5) | 0.18729 (6) | 0.0254 (2) | |
C26 | 0.17964 (9) | 0.59817 (5) | 0.18609 (5) | 0.0217 (2) | |
H4 | −0.37244 | 0.53382 | 0.14972 | 0.0283* | |
H5 | −0.50543 | 0.41859 | 0.13571 | 0.0296* | |
H6 | −0.41968 | 0.29520 | 0.11203 | 0.0275* | |
H7 | −0.19908 | 0.28296 | 0.09934 | 0.0245* | |
H12 | −0.03397 | 0.30262 | 0.01096 | 0.0262* | |
H13 | 0.11560 | 0.19638 | 0.01481 | 0.0299* | |
H14 | 0.31565 | 0.18613 | 0.11775 | 0.0299* | |
H15 | 0.36562 | 0.28249 | 0.21748 | 0.0293* | |
H16 | 0.21306 | 0.38614 | 0.21746 | 0.0248* | |
H22 | 0.16910 | 0.47870 | 0.03688 | 0.0248* | |
H23 | 0.36739 | 0.54820 | 0.03826 | 0.0281* | |
H24 | 0.44992 | 0.64692 | 0.13297 | 0.0303* | |
H25 | 0.33243 | 0.67821 | 0.22513 | 0.0305* | |
H26 | 0.13210 | 0.61136 | 0.22266 | 0.0260* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0164 (3) | 0.0143 (3) | 0.0209 (3) | 0.0033 (2) | 0.0056 (2) | −0.0001 (2) |
N3 | 0.0191 (3) | 0.0166 (3) | 0.0259 (3) | 0.0036 (2) | 0.0075 (2) | −0.0006 (2) |
C2 | 0.0188 (3) | 0.0147 (3) | 0.0193 (3) | 0.0029 (2) | 0.0057 (2) | 0.0005 (2) |
C4 | 0.0185 (3) | 0.0227 (4) | 0.0298 (4) | 0.0047 (3) | 0.0073 (3) | −0.0014 (3) |
C5 | 0.0175 (3) | 0.0274 (4) | 0.0289 (4) | 0.0022 (3) | 0.0063 (3) | 0.0002 (3) |
C6 | 0.0199 (3) | 0.0235 (4) | 0.0242 (3) | −0.0013 (3) | 0.0041 (3) | 0.0005 (3) |
C7 | 0.0207 (3) | 0.0175 (3) | 0.0224 (3) | 0.0011 (3) | 0.0049 (3) | −0.0001 (3) |
C8 | 0.0168 (3) | 0.0169 (3) | 0.0185 (3) | 0.0031 (2) | 0.0043 (2) | 0.0006 (2) |
C9 | 0.0177 (3) | 0.0171 (3) | 0.0220 (3) | 0.0035 (2) | 0.0055 (2) | −0.0002 (2) |
C11 | 0.0183 (3) | 0.0143 (3) | 0.0194 (3) | 0.0039 (2) | 0.0069 (2) | 0.0012 (2) |
C12 | 0.0214 (3) | 0.0205 (3) | 0.0236 (3) | 0.0028 (3) | 0.0062 (3) | −0.0045 (3) |
C13 | 0.0275 (4) | 0.0197 (4) | 0.0304 (4) | 0.0034 (3) | 0.0130 (3) | −0.0051 (3) |
C14 | 0.0271 (4) | 0.0198 (3) | 0.0319 (4) | 0.0088 (3) | 0.0148 (3) | 0.0038 (3) |
C15 | 0.0227 (4) | 0.0248 (4) | 0.0256 (4) | 0.0095 (3) | 0.0064 (3) | 0.0054 (3) |
C16 | 0.0222 (3) | 0.0197 (3) | 0.0196 (3) | 0.0058 (3) | 0.0049 (3) | 0.0012 (3) |
C21 | 0.0190 (3) | 0.0157 (3) | 0.0200 (3) | 0.0033 (2) | 0.0066 (2) | 0.0029 (2) |
C22 | 0.0212 (3) | 0.0214 (3) | 0.0199 (3) | 0.0043 (3) | 0.0068 (3) | 0.0020 (3) |
C23 | 0.0226 (4) | 0.0250 (4) | 0.0253 (4) | 0.0058 (3) | 0.0107 (3) | 0.0063 (3) |
C24 | 0.0225 (4) | 0.0217 (4) | 0.0335 (4) | 0.0009 (3) | 0.0109 (3) | 0.0060 (3) |
C25 | 0.0275 (4) | 0.0181 (3) | 0.0322 (4) | −0.0028 (3) | 0.0109 (3) | −0.0008 (3) |
C26 | 0.0253 (4) | 0.0166 (3) | 0.0255 (3) | −0.0001 (3) | 0.0109 (3) | −0.0007 (3) |
N1—C2 | 1.3859 (11) | C21—C26 | 1.3974 (12) |
N1—C8 | 1.3905 (11) | C22—C23 | 1.3916 (13) |
N1—C11 | 1.4277 (11) | C23—C24 | 1.3894 (14) |
N3—C2 | 1.3180 (11) | C24—C25 | 1.3918 (14) |
N3—C9 | 1.3872 (11) | C25—C26 | 1.3857 (14) |
C2—C21 | 1.4697 (12) | C4—H4 | 0.9300 |
C4—C5 | 1.3855 (14) | C5—H5 | 0.9300 |
C4—C9 | 1.3975 (13) | C6—H6 | 0.9300 |
C5—C6 | 1.4042 (14) | C7—H7 | 0.9300 |
C6—C7 | 1.3866 (13) | C12—H12 | 0.9300 |
C7—C8 | 1.3908 (12) | C13—H13 | 0.9300 |
C8—C9 | 1.4056 (12) | C14—H14 | 0.9300 |
C11—C12 | 1.3930 (11) | C15—H15 | 0.9300 |
C11—C16 | 1.3891 (12) | C16—H16 | 0.9300 |
C12—C13 | 1.3915 (13) | C22—H22 | 0.9300 |
C13—C14 | 1.3892 (15) | C23—H23 | 0.9300 |
C14—C15 | 1.3903 (13) | C24—H24 | 0.9300 |
C15—C16 | 1.3911 (13) | C25—H25 | 0.9300 |
C21—C22 | 1.4000 (12) | C26—H26 | 0.9300 |
C2—N1—C8 | 106.18 (7) | C24—C25—C26 | 120.20 (9) |
C2—N1—C11 | 128.39 (7) | C21—C26—C25 | 120.04 (8) |
C8—N1—C11 | 124.24 (7) | C5—C4—H4 | 121.00 |
C2—N3—C9 | 105.18 (7) | C9—C4—H4 | 121.00 |
N1—C2—N3 | 113.00 (7) | C4—C5—H5 | 119.00 |
N1—C2—C21 | 123.87 (7) | C6—C5—H5 | 119.00 |
N3—C2—C21 | 123.11 (7) | C5—C6—H6 | 119.00 |
C5—C4—C9 | 118.06 (9) | C7—C6—H6 | 119.00 |
C4—C5—C6 | 121.16 (9) | C6—C7—H7 | 122.00 |
C5—C6—C7 | 121.75 (9) | C8—C7—H7 | 122.00 |
C6—C7—C8 | 116.60 (8) | C11—C12—H12 | 120.00 |
N1—C8—C7 | 132.04 (8) | C13—C12—H12 | 120.00 |
N1—C8—C9 | 105.36 (7) | C12—C13—H13 | 120.00 |
C7—C8—C9 | 122.59 (8) | C14—C13—H13 | 120.00 |
N3—C9—C4 | 129.88 (8) | C13—C14—H14 | 120.00 |
N3—C9—C8 | 110.28 (7) | C15—C14—H14 | 120.00 |
C4—C9—C8 | 119.85 (8) | C14—C15—H15 | 120.00 |
N1—C11—C12 | 119.36 (7) | C16—C15—H15 | 120.00 |
N1—C11—C16 | 119.76 (7) | C11—C16—H16 | 120.00 |
C12—C11—C16 | 120.83 (8) | C15—C16—H16 | 120.00 |
C11—C12—C13 | 119.18 (8) | C21—C22—H22 | 120.00 |
C12—C13—C14 | 120.68 (8) | C23—C22—H22 | 120.00 |
C13—C14—C15 | 119.35 (9) | C22—C23—H23 | 120.00 |
C14—C15—C16 | 120.80 (8) | C24—C23—H23 | 120.00 |
C11—C16—C15 | 119.14 (8) | C23—C24—H24 | 120.00 |
C2—C21—C22 | 121.66 (7) | C25—C24—H24 | 120.00 |
C2—C21—C26 | 118.58 (8) | C24—C25—H25 | 120.00 |
C22—C21—C26 | 119.72 (8) | C26—C25—H25 | 120.00 |
C21—C22—C23 | 119.83 (8) | C21—C26—H26 | 120.00 |
C22—C23—C24 | 120.13 (8) | C25—C26—H26 | 120.00 |
C23—C24—C25 | 120.07 (9) | ||
C8—N1—C2—N3 | −0.56 (8) | C5—C6—C7—C8 | 0.47 (13) |
C8—N1—C2—C21 | −178.75 (7) | C6—C7—C8—N1 | 179.10 (8) |
C11—N1—C2—N3 | −168.36 (7) | C6—C7—C8—C9 | 0.20 (12) |
C11—N1—C2—C21 | 13.45 (12) | N1—C8—C9—N3 | 0.02 (8) |
C2—N1—C8—C7 | −178.75 (8) | N1—C8—C9—C4 | −179.91 (7) |
C2—N1—C8—C9 | 0.30 (8) | C7—C8—C9—N3 | 179.18 (7) |
C11—N1—C8—C7 | −10.30 (13) | C7—C8—C9—C4 | −0.76 (12) |
C11—N1—C8—C9 | 168.74 (7) | N1—C11—C12—C13 | −175.99 (8) |
C2—N1—C11—C12 | −134.48 (8) | C16—C11—C12—C13 | 1.25 (13) |
C2—N1—C11—C16 | 48.25 (11) | N1—C11—C16—C15 | 177.36 (8) |
C8—N1—C11—C12 | 59.73 (10) | C12—C11—C16—C15 | 0.14 (13) |
C8—N1—C11—C16 | −117.54 (9) | C11—C12—C13—C14 | −1.38 (14) |
C9—N3—C2—N1 | 0.56 (9) | C12—C13—C14—C15 | 0.13 (15) |
C9—N3—C2—C21 | 178.77 (7) | C13—C14—C15—C16 | 1.29 (14) |
C2—N3—C9—C4 | 179.58 (9) | C14—C15—C16—C11 | −1.42 (14) |
C2—N3—C9—C8 | −0.35 (9) | C2—C21—C22—C23 | 177.85 (8) |
N1—C2—C21—C22 | 40.41 (12) | C26—C21—C22—C23 | 0.10 (12) |
N1—C2—C21—C26 | −141.81 (8) | C2—C21—C26—C25 | −178.67 (8) |
N3—C2—C21—C22 | −137.60 (8) | C22—C21—C26—C25 | −0.85 (13) |
N3—C2—C21—C26 | 40.18 (11) | C21—C22—C23—C24 | 0.64 (14) |
C9—C4—C5—C6 | 0.03 (14) | C22—C23—C24—C25 | −0.65 (14) |
C5—C4—C9—N3 | −179.31 (9) | C23—C24—C25—C26 | −0.11 (14) |
C5—C4—C9—C8 | 0.62 (12) | C24—C25—C26—C21 | 0.86 (14) |
C4—C5—C6—C7 | −0.60 (14) |
Cg2 is the centroid of the C4–C9 fused benzene ring and Cg1 is the centroid of the N1/C2/N3/C9/C8 imidazole ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···N3i | 0.93 | 2.62 | 3.4829 (11) | 154 |
C16—H16···Cg2ii | 0.93 | 2.68 | 3.4843 (9) | 146 |
C22—H22···Cg1iii | 0.93 | 2.91 | 3.3966 (9) | 114 |
C23—H23···Cg2iii | 0.93 | 2.83 | 3.4609 (9) | 126 |
Symmetry codes: (i) x+1/2, y−1/2, z; (ii) −x, y, −z+1/2; (iii) −x, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C19H14N2 |
Mr | 270.32 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 123 |
a, b, c (Å) | 10.1878 (3), 16.6399 (4), 17.4959 (5) |
β (°) | 106.205 (3) |
V (Å3) | 2848.13 (14) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.60 × 0.40 × 0.35 |
Data collection | |
Diffractometer | Agilent Xcalibur Ruby Gemini diffractometer |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2012) |
Tmin, Tmax | 0.957, 0.974 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 25253, 7296, 5803 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.862 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.137, 1.06 |
No. of reflections | 7296 |
No. of parameters | 190 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.52, −0.25 |
Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009), PLATON (Spek, 2009).
Cg2 is the centroid of the C4–C9 fused benzene ring and Cg1 is the centroid of the N1/C2/N3/C9/C8 imidazole ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···N3i | 0.93 | 2.62 | 3.4829 (11) | 154 |
C16—H16···Cg2ii | 0.93 | 2.68 | 3.4843 (9) | 146 |
C22—H22···Cg1iii | 0.93 | 2.91 | 3.3966 (9) | 114 |
C23—H23···Cg2iii | 0.93 | 2.83 | 3.4609 (9) | 126 |
Symmetry codes: (i) x+1/2, y−1/2, z; (ii) −x, y, −z+1/2; (iii) −x, −y+1, −z. |
Acknowledgements
KJ thanks the DST (No. SR/S1/IC-73/2010) for a fellowship. JJ thanks the DST (No. SR/S1/IC-73/2010), the UGC [F. No. 36–21/2008 (SR)] and the DRDO (NRB-213/MAT/10–11) for providing funds for this research study. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.
References
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Fused imidazole derivatives such as benzoimidazoles and phenanthroimidazoles [Fang et al., (2007), Ge et al., (2008), Lai et al., (2008)] have been used in the fabrication of light-emitting devices, employing them as electron-transporting layer and as sensitizers in dye-sensitized solar cells [Shin et al., (2007), Tsai et al., (2007)] due to their wide optical absorption, bright luminescence and bipolar transport characteristics. Since our research group is working in organic light emitting devices, we are interested to use the title compound as ligand for synthesizing Ir(III) complexes. Jayamoorthy et al., (2012) have reported a closely related crystal structure of 2-(4-Fluorophenyl)-1-phenyl-1H-benzimidazole.
In the title molecule, C19H14N2 (Fig. 1), the benzimidazole unit is almost planar [maximum deviation = 0.0102 (6) Å for C2]. The dihedral angles between the planes of the benzimidazole and the phenyl ring at N1 and the phenyl at C2 are 55.80 (2) and 40.67 (3)°, respectively. The dihedral angle between the planes of the adjacent phenyl rings is 62.37 (3)°. Intermolecular C14—H14···N3 hydrogen bond and weak C16—H16···π interaction involving the fused benzene ring, C22—H22···π interaction involving the imidazole ring and C23—H23···π interaction involving the fused benzene ring are found in the crystal structure (Fig. 2, Table 1).