organic compounds
2-(4-Fluorophenyl)-1-phenyl-1H-benzimidazole
aDepartment of Chemistry, Annamalai University, Annamalai Nagar 608 002, Tamilnadu, India, bPG Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamilnadu, India, and cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
*Correspondence e-mail: thiruvalluvar.a@gmail.com
In the title molecule, C19H13FN2, the benzimidazole unit is close to planar [maximum deviation = 0.0342 (9) Å] and forms dihedral angles of 58.94 (3) and 51.43 (3)° with the phenyl and fluorobenzene rings, respectively; the dihedral angle between the phenyl and fluorobenzene rings is 60.17 (6)°. In the crystal, three C—H⋯F hydrogen bonds and two weak C—H⋯π interactions involving the fused benzene ring lead to a three-dimensional architecture.
Related literature
For linear and non-linear optical properties of benzimidazole compounds, see: Cross et al. (1995); Bu et al. (1996); Dirk et al. (1990). For a related structure, see: Rosepriya et al. (2011).
Experimental
Crystal data
|
Refinement
|
Data collection: CrysAlis PRO (Agilent, 2012); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2004 (Burla et al., 2005); 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/S1600536812035155/tk5141sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812035155/tk5141Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812035155/tk5141Isup3.cdx
Supporting information file. DOI: 10.1107/S1600536812035155/tk5141Isup4.cml
To N-phenyl-o-phenylenediamine (3.128 g, 17 mmol) in ethanol (10 ml) was added 4-fluorobenzaldehyde (1.9 ml, 17 mmol) and ammonium acetate (3 g) over about 1 h while maintaining the temperature at 353 K. The reaction mixture was refluxed until the completion of reaction, as monitored by TLC. The reaction mixture was extracted with dichloromethane. The solid that separated out was purified by
using petroleum ether: ethyl acetate as the Yield: 2.47 g (50%). The title compound was dissolved in acetonitrile and allowed to slowly evaporate 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 and 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: SIR2004 (Burla et al., 2005); 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).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. The packing of the title compound, viewed down the b axis. Dashed lines indicate hydrogen bonds. H atoms not involved in hydrogen bonding have been omitted. |
C19H13FN2 | F(000) = 600 |
Mr = 288.31 | Dx = 1.308 Mg m−3 |
Monoclinic, P21/n | Melting point: 369 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 8.7527 (4) Å | Cell parameters from 3202 reflections |
b = 10.1342 (4) Å | θ = 3.1–37.6° |
c = 17.0211 (6) Å | µ = 0.09 mm−1 |
β = 104.187 (4)° | T = 123 K |
V = 1463.75 (11) Å3 | Plate, colourless |
Z = 4 | 0.47 × 0.42 × 0.15 mm |
Agilent Xcalibur Ruby Gemini diffractometer | 7347 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 5352 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
Detector resolution: 10.5081 pixels mm-1 | θmax = 37.7°, θmin = 3.1° |
ω scans | h = −12→15 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | k = −12→17 |
Tmin = 0.961, Tmax = 1.000 | l = −28→24 |
13721 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)] = 0.063 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.160 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0685P)2 + 0.2726P] where P = (Fo2 + 2Fc2)/3 |
7347 reflections | (Δ/σ)max = 0.001 |
199 parameters | Δρmax = 0.52 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
C19H13FN2 | V = 1463.75 (11) Å3 |
Mr = 288.31 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.7527 (4) Å | µ = 0.09 mm−1 |
b = 10.1342 (4) Å | T = 123 K |
c = 17.0211 (6) Å | 0.47 × 0.42 × 0.15 mm |
β = 104.187 (4)° |
Agilent Xcalibur Ruby Gemini diffractometer | 7347 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | 5352 reflections with I > 2σ(I) |
Tmin = 0.961, Tmax = 1.000 | Rint = 0.031 |
13721 measured reflections |
R[F2 > 2σ(F2)] = 0.063 | 0 restraints |
wR(F2) = 0.160 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.52 e Å−3 |
7347 reflections | Δρmin = −0.22 e Å−3 |
199 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 | ||
F4 | 0.45822 (10) | −0.05502 (7) | 0.23042 (4) | 0.0296 (2) | |
N1 | 0.25329 (11) | 0.44506 (9) | −0.01000 (5) | 0.0181 (2) | |
N3 | 0.32447 (11) | 0.53932 (9) | 0.11392 (5) | 0.0204 (2) | |
C2 | 0.30699 (12) | 0.42744 (10) | 0.07314 (6) | 0.0181 (2) | |
C4 | 0.27719 (14) | 0.77382 (11) | 0.06432 (7) | 0.0224 (3) | |
C5 | 0.22041 (14) | 0.84918 (11) | −0.00490 (7) | 0.0241 (3) | |
C6 | 0.16727 (14) | 0.79006 (11) | −0.08140 (7) | 0.0242 (3) | |
C7 | 0.17379 (14) | 0.65470 (11) | −0.09192 (6) | 0.0227 (3) | |
C8 | 0.23331 (12) | 0.57999 (10) | −0.02222 (6) | 0.0184 (2) | |
C9 | 0.28005 (12) | 0.63684 (10) | 0.05527 (6) | 0.0192 (2) | |
C11 | 0.21724 (12) | 0.34608 (10) | −0.07164 (6) | 0.0181 (2) | |
C12 | 0.29236 (14) | 0.34944 (12) | −0.13497 (6) | 0.0250 (3) | |
C13 | 0.25650 (17) | 0.25270 (14) | −0.19472 (7) | 0.0326 (4) | |
C14 | 0.14865 (18) | 0.15428 (13) | −0.19126 (7) | 0.0342 (4) | |
C15 | 0.07463 (16) | 0.15197 (12) | −0.12781 (8) | 0.0296 (3) | |
C16 | 0.10831 (13) | 0.24826 (11) | −0.06771 (6) | 0.0222 (3) | |
C21 | 0.34251 (12) | 0.29683 (10) | 0.11128 (6) | 0.0184 (2) | |
C22 | 0.43985 (13) | 0.20730 (11) | 0.08453 (6) | 0.0207 (3) | |
C23 | 0.47933 (13) | 0.08832 (11) | 0.12460 (6) | 0.0226 (3) | |
C24 | 0.41834 (13) | 0.06137 (11) | 0.19050 (6) | 0.0216 (3) | |
C25 | 0.31950 (14) | 0.14570 (11) | 0.21819 (6) | 0.0240 (3) | |
C26 | 0.28287 (14) | 0.26534 (11) | 0.17816 (6) | 0.0224 (3) | |
H4 | 0.31207 | 0.81317 | 0.11491 | 0.0269* | |
H5 | 0.21753 | 0.94056 | −0.00049 | 0.0289* | |
H6 | 0.12661 | 0.84318 | −0.12621 | 0.0290* | |
H7 | 0.14030 | 0.61573 | −0.14271 | 0.0273* | |
H12 | 0.36522 | 0.41522 | −0.13727 | 0.0299* | |
H13 | 0.30549 | 0.25419 | −0.23741 | 0.0391* | |
H14 | 0.12581 | 0.08983 | −0.23133 | 0.0410* | |
H15 | 0.00225 | 0.08581 | −0.12547 | 0.0355* | |
H16 | 0.05837 | 0.24707 | −0.02538 | 0.0266* | |
H22 | 0.47838 | 0.22748 | 0.03966 | 0.0248* | |
H23 | 0.54500 | 0.02834 | 0.10762 | 0.0271* | |
H25 | 0.27886 | 0.12332 | 0.26204 | 0.0288* | |
H26 | 0.21808 | 0.32514 | 0.19596 | 0.0269* |
U11 | U22 | U33 | U12 | U13 | U23 | |
F4 | 0.0397 (4) | 0.0227 (3) | 0.0241 (3) | 0.0008 (3) | 0.0033 (3) | 0.0082 (3) |
N1 | 0.0235 (4) | 0.0161 (3) | 0.0140 (3) | −0.0019 (3) | 0.0035 (3) | −0.0001 (3) |
N3 | 0.0259 (4) | 0.0195 (4) | 0.0158 (3) | −0.0011 (3) | 0.0051 (3) | −0.0005 (3) |
C2 | 0.0208 (4) | 0.0193 (4) | 0.0144 (3) | −0.0009 (3) | 0.0047 (3) | 0.0010 (3) |
C4 | 0.0266 (5) | 0.0188 (4) | 0.0221 (4) | −0.0028 (4) | 0.0065 (4) | −0.0029 (4) |
C5 | 0.0275 (5) | 0.0183 (4) | 0.0280 (5) | −0.0008 (4) | 0.0096 (4) | 0.0009 (4) |
C6 | 0.0279 (5) | 0.0209 (5) | 0.0235 (4) | 0.0007 (4) | 0.0059 (4) | 0.0055 (4) |
C7 | 0.0279 (5) | 0.0217 (5) | 0.0174 (4) | −0.0007 (4) | 0.0032 (3) | 0.0028 (3) |
C8 | 0.0214 (4) | 0.0170 (4) | 0.0167 (4) | −0.0021 (3) | 0.0045 (3) | 0.0002 (3) |
C9 | 0.0214 (4) | 0.0197 (4) | 0.0167 (4) | −0.0021 (3) | 0.0048 (3) | −0.0003 (3) |
C11 | 0.0203 (4) | 0.0186 (4) | 0.0148 (3) | 0.0007 (3) | 0.0030 (3) | −0.0010 (3) |
C12 | 0.0285 (5) | 0.0289 (5) | 0.0192 (4) | 0.0028 (4) | 0.0091 (4) | 0.0010 (4) |
C13 | 0.0437 (7) | 0.0362 (7) | 0.0192 (4) | 0.0128 (6) | 0.0102 (5) | −0.0029 (4) |
C14 | 0.0464 (8) | 0.0263 (6) | 0.0244 (5) | 0.0114 (5) | −0.0017 (5) | −0.0089 (4) |
C15 | 0.0329 (6) | 0.0203 (5) | 0.0307 (5) | 0.0001 (4) | −0.0017 (4) | −0.0051 (4) |
C16 | 0.0236 (5) | 0.0207 (4) | 0.0211 (4) | −0.0011 (4) | 0.0034 (3) | −0.0015 (4) |
C21 | 0.0211 (4) | 0.0194 (4) | 0.0144 (3) | −0.0013 (3) | 0.0039 (3) | 0.0009 (3) |
C22 | 0.0230 (4) | 0.0222 (5) | 0.0180 (4) | 0.0003 (4) | 0.0073 (3) | 0.0027 (3) |
C23 | 0.0244 (5) | 0.0219 (5) | 0.0218 (4) | 0.0019 (4) | 0.0062 (4) | 0.0024 (4) |
C24 | 0.0266 (5) | 0.0189 (4) | 0.0170 (4) | −0.0022 (4) | 0.0010 (3) | 0.0042 (3) |
C25 | 0.0322 (5) | 0.0244 (5) | 0.0167 (4) | −0.0023 (4) | 0.0086 (4) | 0.0027 (4) |
C26 | 0.0278 (5) | 0.0233 (5) | 0.0178 (4) | 0.0009 (4) | 0.0090 (4) | 0.0008 (3) |
F4—C24 | 1.3633 (13) | C21—C22 | 1.3952 (15) |
N1—C2 | 1.3890 (13) | C21—C26 | 1.4005 (15) |
N1—C8 | 1.3877 (14) | C22—C23 | 1.3867 (15) |
N1—C11 | 1.4298 (13) | C23—C24 | 1.3825 (15) |
N3—C2 | 1.3186 (13) | C24—C25 | 1.3787 (16) |
N3—C9 | 1.3908 (13) | C25—C26 | 1.3893 (15) |
C2—C21 | 1.4735 (14) | C4—H4 | 0.9300 |
C4—C5 | 1.3897 (16) | C5—H5 | 0.9300 |
C4—C9 | 1.3976 (15) | C6—H6 | 0.9300 |
C5—C6 | 1.4050 (16) | C7—H7 | 0.9300 |
C6—C7 | 1.3864 (16) | C12—H12 | 0.9300 |
C7—C8 | 1.3961 (14) | C13—H13 | 0.9300 |
C8—C9 | 1.4052 (14) | C14—H14 | 0.9300 |
C11—C12 | 1.3939 (15) | C15—H15 | 0.9300 |
C11—C16 | 1.3883 (15) | C16—H16 | 0.9300 |
C12—C13 | 1.3919 (17) | C22—H22 | 0.9300 |
C13—C14 | 1.384 (2) | C23—H23 | 0.9300 |
C14—C15 | 1.3891 (19) | C25—H25 | 0.9300 |
C15—C16 | 1.3920 (17) | C26—H26 | 0.9300 |
C2—N1—C8 | 106.15 (8) | F4—C24—C25 | 118.13 (9) |
C2—N1—C11 | 128.03 (9) | C23—C24—C25 | 123.67 (10) |
C8—N1—C11 | 125.75 (8) | C24—C25—C26 | 117.52 (10) |
C2—N3—C9 | 104.91 (8) | C21—C26—C25 | 120.69 (10) |
N1—C2—N3 | 113.10 (9) | C5—C4—H4 | 121.00 |
N1—C2—C21 | 123.13 (9) | C9—C4—H4 | 121.00 |
N3—C2—C21 | 123.76 (9) | C4—C5—H5 | 119.00 |
C5—C4—C9 | 117.69 (10) | C6—C5—H5 | 119.00 |
C4—C5—C6 | 121.32 (10) | C5—C6—H6 | 119.00 |
C5—C6—C7 | 121.80 (10) | C7—C6—H6 | 119.00 |
C6—C7—C8 | 116.45 (10) | C6—C7—H7 | 122.00 |
N1—C8—C7 | 131.97 (9) | C8—C7—H7 | 122.00 |
N1—C8—C9 | 105.45 (8) | C11—C12—H12 | 121.00 |
C7—C8—C9 | 122.51 (9) | C13—C12—H12 | 121.00 |
N3—C9—C4 | 129.50 (9) | C12—C13—H13 | 120.00 |
N3—C9—C8 | 110.38 (9) | C14—C13—H13 | 120.00 |
C4—C9—C8 | 120.12 (9) | C13—C14—H14 | 120.00 |
N1—C11—C12 | 119.29 (10) | C15—C14—H14 | 120.00 |
N1—C11—C16 | 119.75 (9) | C14—C15—H15 | 120.00 |
C12—C11—C16 | 120.96 (10) | C16—C15—H15 | 120.00 |
C11—C12—C13 | 118.90 (11) | C11—C16—H16 | 120.00 |
C12—C13—C14 | 120.69 (12) | C15—C16—H16 | 120.00 |
C13—C14—C15 | 119.87 (12) | C21—C22—H22 | 120.00 |
C14—C15—C16 | 120.29 (12) | C23—C22—H22 | 120.00 |
C11—C16—C15 | 119.30 (10) | C22—C23—H23 | 121.00 |
C2—C21—C22 | 121.34 (9) | C24—C23—H23 | 121.00 |
C2—C21—C26 | 118.84 (9) | C24—C25—H25 | 121.00 |
C22—C21—C26 | 119.75 (10) | C26—C25—H25 | 121.00 |
C21—C22—C23 | 120.23 (10) | C21—C26—H26 | 120.00 |
C22—C23—C24 | 118.14 (10) | C25—C26—H26 | 120.00 |
F4—C24—C23 | 118.21 (10) | ||
C8—N1—C2—N3 | −0.88 (13) | C6—C7—C8—N1 | 178.40 (12) |
C8—N1—C2—C21 | 179.88 (10) | C6—C7—C8—C9 | 1.94 (17) |
C11—N1—C2—N3 | −178.02 (10) | N1—C8—C9—N3 | −1.25 (12) |
C11—N1—C2—C21 | 2.74 (17) | N1—C8—C9—C4 | 178.72 (10) |
C2—N1—C8—C7 | −175.66 (12) | C7—C8—C9—N3 | 176.02 (10) |
C2—N1—C8—C9 | 1.24 (12) | C7—C8—C9—C4 | −4.00 (17) |
C11—N1—C8—C7 | 1.56 (19) | N1—C11—C12—C13 | −179.97 (12) |
C11—N1—C8—C9 | 178.46 (10) | C16—C11—C12—C13 | 0.00 (17) |
C2—N1—C11—C12 | −123.95 (12) | N1—C11—C16—C15 | −179.68 (10) |
C2—N1—C11—C16 | 56.07 (16) | C12—C11—C16—C15 | 0.33 (17) |
C8—N1—C11—C12 | 59.44 (15) | C11—C12—C13—C14 | −0.32 (19) |
C8—N1—C11—C16 | −120.54 (12) | C12—C13—C14—C15 | 0.3 (2) |
C9—N3—C2—N1 | 0.11 (13) | C13—C14—C15—C16 | 0.1 (2) |
C9—N3—C2—C21 | 179.34 (10) | C14—C15—C16—C11 | −0.36 (18) |
C2—N3—C9—C4 | −179.25 (12) | C2—C21—C22—C23 | 176.01 (10) |
C2—N3—C9—C8 | 0.72 (12) | C26—C21—C22—C23 | −0.90 (16) |
N1—C2—C21—C22 | 50.81 (15) | C2—C21—C26—C25 | −177.04 (10) |
N1—C2—C21—C26 | −132.26 (11) | C22—C21—C26—C25 | −0.06 (17) |
N3—C2—C21—C22 | −128.35 (12) | C21—C22—C23—C24 | 0.67 (16) |
N3—C2—C21—C26 | 48.58 (16) | C22—C23—C24—F4 | −179.40 (10) |
C9—C4—C5—C6 | 0.15 (18) | C22—C23—C24—C25 | 0.53 (17) |
C5—C4—C9—N3 | −177.21 (11) | F4—C24—C25—C26 | 178.48 (10) |
C5—C4—C9—C8 | 2.83 (17) | C23—C24—C25—C26 | −1.45 (17) |
C4—C5—C6—C7 | −2.2 (2) | C24—C25—C26—C21 | 1.18 (17) |
C5—C6—C7—C8 | 1.13 (18) |
Cg2 is the centroid of the fused benzene ring (C4–C9). |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···F4i | 0.93 | 2.46 | 3.3640 (14) | 164 |
C7—H7···F4ii | 0.93 | 2.43 | 3.3058 (13) | 157 |
C26—H26···F4iii | 0.93 | 2.52 | 3.4348 (14) | 166 |
C16—H16···Cg2iv | 0.93 | 2.75 | 3.5443 (12) | 144 |
C22—H22···Cg2v | 0.93 | 2.80 | 3.5245 (13) | 136 |
Symmetry codes: (i) x, y+1, z; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x+1/2, y+1/2, −z+1/2; (iv) −x, −y+1, −z; (v) −x+1, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C19H13FN2 |
Mr | 288.31 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 123 |
a, b, c (Å) | 8.7527 (4), 10.1342 (4), 17.0211 (6) |
β (°) | 104.187 (4) |
V (Å3) | 1463.75 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.47 × 0.42 × 0.15 |
Data collection | |
Diffractometer | Agilent Xcalibur Ruby Gemini diffractometer |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2012) |
Tmin, Tmax | 0.961, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13721, 7347, 5352 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.859 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.063, 0.160, 1.04 |
No. of reflections | 7347 |
No. of parameters | 199 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.52, −0.22 |
Computer programs: CrysAlis PRO (Agilent, 2012), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009), PLATON (Spek, 2009).
Cg2 is the centroid of the fused benzene ring (C4–C9). |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···F4i | 0.93 | 2.46 | 3.3640 (14) | 164 |
C7—H7···F4ii | 0.93 | 2.43 | 3.3058 (13) | 157 |
C26—H26···F4iii | 0.93 | 2.52 | 3.4348 (14) | 166 |
C16—H16···Cg2iv | 0.93 | 2.75 | 3.5443 (12) | 144 |
C22—H22···Cg2v | 0.93 | 2.80 | 3.5245 (13) | 136 |
Symmetry codes: (i) x, y+1, z; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x+1/2, y+1/2, −z+1/2; (iv) −x, −y+1, −z; (v) −x+1, −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), and the UGC [F. No. 36–21/2008 (SR)] and the DRDO (NRB-213/MAT/10–11) for providing funds to this research study. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.
References
Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Bu, X. R., Li, H., Derveer, D. V. & Mintz, E. A. (1996). Tetrahedron Lett. 37, 7331–7334. CSD CrossRef CAS Web of Science Google Scholar
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Cross, E. M., White, K. M., Moshrefzadeh, R. S. & Francis, C. V. (1995). Macromolecules, 28, 2526–2532. CrossRef CAS Web of Science Google Scholar
Dirk, C. W., Katz, H. E., Schilling, M. L. & King, L. A. (1990). Chem. Mater. 2, 700–705. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Rosepriya, S., Thiruvalluvar, A., Jayamoorthy, K., Jayabharathi, J. & Linden, A. (2011). Acta Cryst. E67, o3519. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
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.
Benzimidazole based chromophores have received increasing attention due to their distinctive linear, non-linear optical properties and also due to their excellent thermal stability in guest-host systems (Cross et al., 1995). The imidazole ring can be easily tailored to accommodate functional groups, which allows the covalent incorporation of the NLO chromophores into polyamides leading to NLO side chain polymers (Bu et al., 1996). Most π-conjugated systems play a major role in determining second-order NLO response (Dirk et al., 1990). Since our group is doing research in organic light emitting devices (OLEDs), we are interested in using the title compound as a ligand in the preparation of Ir(III) complexes and in studying the photophysical properties of these complexes. Rosepriya et al. (2011) have reported a related crystal structure, namely 1-(4-Methylbenzyl)-2-(4-methylphenyl)-1H-benzimidazole.
In the title molecule, C19H13FN2 (Fig. 1), the benzimidazole unit is almost planar [maximum deviation = 0.0342 (9) Å for C6]. The dihedral angles between the planes of the benzimidazole and the phenyl and the fluorobenzene groups are 58.94 (3) and 51.43 (3)°, respectively. The dihedral angle between the planes of the phenyl and the fluorobenzene rings is 60.17 (6)°. Intermolecular C4—H4···F4, C7—H7···F4 and C26—H26···F4 hydrogen bonds and weak C16—H16···π and C22—H22···π interactions involving the fused benzene ring are found in the crystal structure (Fig. 2, Table 1).