Acta Cryst. (2010). E66, o2826 [ doi:10.1107/S1600536810040535 ]
In the title compound, C18H18N2, the imidazole ring is essentially planar [maximum deviation = 0.004 (1) Å] and makes dihedral angles of 68.91 (8) and 20.43 (9)° with the tolyl and phenyl rings, respectively. The dihedral angle between the latter rings is 73.62 (8)°. The crystal packing is stabilized by intermolecular C-H
N hydrogen bonds.
To pure butane-2,3-dione (1.48 g, 15 mmol) in ethanol (10 ml), p-toluidine (1.6 g, 15 mmol), ammonium acetate (1.15 g, 15 mmol) and benzaldehyde (1.5 g, 15 mmol) was added about 1 h by maintaining the temperature at 333 K. The reaction mixture was refluxed for 7 days and extracted with dichloromethane. The solid separated was purified by column chromatography using hexane: ethyl acetate as the eluent. Yield: 1.93 g (46%).
H atoms were positioned geometrically and allowed to ride on their parent atoms, with C–H = 0.95 - 0.98Å; Uiso(H) = kUeq(C), where k = 1.5 for methyl and 1.2 for all other H atoms.
Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).
![[Figure 1]](./rk2234fig1thm.gif)
| Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are shown as small spheres of arbitrary radius. |
![[Figure 2]](./rk2234fig2thm.gif)
| 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. |
| C18H18N2 | F(000) = 560 |
| Mr = 262.34 | Dx = 1.208 Mg m−3 |
| Monoclinic, P21/n | Melting point: 388 K |
| Hall symbol: -P 2yn | Cu Kα radiation, λ = 1.54184 Å |
| a = 9.6971 (3) Å | Cell parameters from 3666 reflections |
| b = 7.5458 (2) Å | θ = 4.6–74.1° |
| c = 19.8407 (7) Å | µ = 0.55 mm−1 |
| β = 96.604 (3)° | T = 123 K |
| V = 1442.16 (8) Å3 | Block, colourless |
| Z = 4 | 0.49 × 0.43 × 0.22 mm |
| Oxford Diffraction Xcalibur Ruby Gemini diffractometer | 2849 independent reflections |
| Radiation source: Enhance (Cu) X-ray Source | 2529 reflections with I > 2σ(I) |
| graphite | Rint = 0.024 |
| Detector resolution: 10.5081 pixels mm-1 | θmax = 74.2°, θmin = 6.3° |
| ω scans | h = −11→12 |
| Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) | k = −8→9 |
| Tmin = 0.606, Tmax = 1.000 | l = −24→23 |
| 5113 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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.138 | H-atom parameters constrained |
| S = 1.11 | w = 1/[σ2(Fo2) + (0.0624P)2 + 0.7809P] where P = (Fo2 + 2Fc2)/3 |
| 2849 reflections | (Δ/σ)max = 0.001 |
| 184 parameters | Δρmax = 0.28 e Å−3 |
| 0 restraints | Δρmin = −0.18 e Å−3 |
| C18H18N2 | V = 1442.16 (8) Å3 |
| Mr = 262.34 | Z = 4 |
| Monoclinic, P21/n | Cu Kα radiation |
| a = 9.6971 (3) Å | µ = 0.55 mm−1 |
| b = 7.5458 (2) Å | T = 123 K |
| c = 19.8407 (7) Å | 0.49 × 0.43 × 0.22 mm |
| β = 96.604 (3)° |
| Oxford Diffraction Xcalibur Ruby Gemini diffractometer | 2849 independent reflections |
| Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) | 2529 reflections with I > 2σ(I) |
| Tmin = 0.606, Tmax = 1.000 | Rint = 0.024 |
| 5113 measured reflections | θmax = 74.2° |
| R[F2 > 2σ(F2)] = 0.049 | H-atom parameters constrained |
| wR(F2) = 0.138 | Δρmax = 0.28 e Å−3 |
| S = 1.11 | Δρmin = −0.18 e Å−3 |
| 2849 reflections | Absolute structure: ? |
| 184 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 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 | 0.96551 (13) | 0.70974 (17) | 0.05414 (6) | 0.0239 (4) | |
| N3 | 1.08249 (13) | 0.78862 (17) | −0.03075 (7) | 0.0248 (4) | |
| C2 | 0.95773 (16) | 0.7589 (2) | −0.01276 (7) | 0.0229 (4) | |
| C4 | 1.17482 (16) | 0.7599 (2) | 0.02618 (8) | 0.0260 (5) | |
| C5 | 1.10567 (16) | 0.7104 (2) | 0.07911 (8) | 0.0266 (5) | |
| C11 | 0.85639 (16) | 0.6994 (2) | 0.09746 (7) | 0.0235 (4) | |
| C12 | 0.83053 (17) | 0.5406 (2) | 0.12883 (8) | 0.0272 (5) | |
| C13 | 0.73060 (17) | 0.5358 (2) | 0.17385 (8) | 0.0281 (5) | |
| C14 | 0.65519 (16) | 0.6861 (2) | 0.18734 (8) | 0.0276 (5) | |
| C15 | 0.68211 (17) | 0.8429 (2) | 0.15400 (8) | 0.0302 (5) | |
| C16 | 0.78331 (16) | 0.8514 (2) | 0.10983 (8) | 0.0272 (5) | |
| C17 | 0.54875 (18) | 0.6791 (3) | 0.23712 (9) | 0.0367 (6) | |
| C21 | 0.83051 (16) | 0.7676 (2) | −0.06104 (8) | 0.0241 (4) | |
| C22 | 0.70724 (17) | 0.6803 (2) | −0.05163 (8) | 0.0289 (5) | |
| C23 | 0.59439 (18) | 0.6860 (3) | −0.10129 (9) | 0.0337 (5) | |
| C24 | 0.60157 (19) | 0.7807 (3) | −0.16077 (9) | 0.0348 (5) | |
| C25 | 0.72376 (19) | 0.8686 (2) | −0.17049 (8) | 0.0334 (5) | |
| C26 | 0.83700 (17) | 0.8621 (2) | −0.12112 (8) | 0.0281 (5) | |
| C41 | 1.32767 (17) | 0.7884 (3) | 0.02550 (9) | 0.0341 (5) | |
| C51 | 1.15590 (18) | 0.6676 (3) | 0.15102 (8) | 0.0338 (5) | |
| H12 | 0.88031 | 0.43652 | 0.11971 | 0.0327* | |
| H13 | 0.71349 | 0.42749 | 0.19587 | 0.0338* | |
| H15 | 0.63014 | 0.94623 | 0.16166 | 0.0362* | |
| H16 | 0.80206 | 0.95996 | 0.08843 | 0.0326* | |
| H17A | 0.48146 | 0.58494 | 0.22381 | 0.0550* | |
| H17B | 0.50045 | 0.79313 | 0.23719 | 0.0550* | |
| H17C | 0.59525 | 0.65460 | 0.28267 | 0.0550* | |
| H22 | 0.70063 | 0.61651 | −0.01086 | 0.0346* | |
| H23 | 0.51153 | 0.62463 | −0.09456 | 0.0404* | |
| H24 | 0.52377 | 0.78531 | −0.19451 | 0.0417* | |
| H25 | 0.72962 | 0.93342 | −0.21111 | 0.0401* | |
| H26 | 0.92003 | 0.92255 | −0.12823 | 0.0338* | |
| H41A | 1.34705 | 0.91576 | 0.02429 | 0.0512* | |
| H41B | 1.35792 | 0.73153 | −0.01470 | 0.0512* | |
| H41C | 1.37795 | 0.73656 | 0.06647 | 0.0512* | |
| H51A | 1.25562 | 0.69209 | 0.15961 | 0.0507* | |
| H51B | 1.13901 | 0.54201 | 0.15960 | 0.0507* | |
| H51C | 1.10612 | 0.74057 | 0.18117 | 0.0507* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| N1 | 0.0248 (7) | 0.0269 (7) | 0.0204 (6) | 0.0011 (5) | 0.0039 (5) | 0.0000 (5) |
| N3 | 0.0272 (7) | 0.0242 (7) | 0.0238 (7) | 0.0009 (5) | 0.0064 (5) | −0.0016 (5) |
| C2 | 0.0278 (8) | 0.0214 (7) | 0.0200 (7) | 0.0008 (6) | 0.0056 (6) | −0.0013 (6) |
| C4 | 0.0262 (8) | 0.0248 (8) | 0.0273 (8) | 0.0020 (6) | 0.0047 (6) | −0.0010 (6) |
| C5 | 0.0256 (8) | 0.0281 (8) | 0.0260 (8) | 0.0038 (6) | 0.0026 (6) | −0.0012 (6) |
| C11 | 0.0230 (7) | 0.0294 (8) | 0.0185 (7) | −0.0001 (6) | 0.0036 (6) | −0.0012 (6) |
| C12 | 0.0309 (8) | 0.0264 (8) | 0.0246 (8) | 0.0023 (7) | 0.0044 (6) | −0.0004 (6) |
| C13 | 0.0312 (8) | 0.0297 (9) | 0.0238 (8) | −0.0032 (7) | 0.0045 (6) | 0.0025 (6) |
| C14 | 0.0231 (8) | 0.0374 (9) | 0.0224 (8) | −0.0030 (6) | 0.0031 (6) | −0.0030 (7) |
| C15 | 0.0294 (8) | 0.0312 (9) | 0.0307 (8) | 0.0054 (7) | 0.0063 (7) | −0.0025 (7) |
| C16 | 0.0295 (8) | 0.0261 (8) | 0.0263 (8) | 0.0014 (6) | 0.0043 (6) | 0.0014 (6) |
| C17 | 0.0295 (9) | 0.0477 (11) | 0.0347 (9) | −0.0034 (8) | 0.0114 (7) | −0.0030 (8) |
| C21 | 0.0280 (8) | 0.0248 (8) | 0.0199 (7) | 0.0018 (6) | 0.0041 (6) | −0.0043 (6) |
| C22 | 0.0314 (8) | 0.0328 (9) | 0.0233 (8) | −0.0006 (7) | 0.0068 (6) | −0.0024 (7) |
| C23 | 0.0278 (8) | 0.0420 (10) | 0.0315 (9) | −0.0018 (7) | 0.0045 (7) | −0.0085 (8) |
| C24 | 0.0324 (9) | 0.0422 (10) | 0.0280 (8) | 0.0063 (8) | −0.0038 (7) | −0.0077 (7) |
| C25 | 0.0417 (10) | 0.0367 (10) | 0.0216 (8) | 0.0039 (8) | 0.0026 (7) | 0.0000 (7) |
| C26 | 0.0321 (8) | 0.0296 (8) | 0.0234 (8) | −0.0004 (7) | 0.0063 (6) | −0.0025 (6) |
| C41 | 0.0263 (8) | 0.0398 (10) | 0.0369 (9) | 0.0004 (7) | 0.0061 (7) | 0.0006 (8) |
| C51 | 0.0320 (9) | 0.0442 (10) | 0.0245 (8) | 0.0041 (8) | 0.0007 (7) | 0.0020 (7) |
| N1—C2 | 1.3719 (18) | C24—C25 | 1.391 (3) |
| N1—C5 | 1.392 (2) | C25—C26 | 1.386 (2) |
| N1—C11 | 1.4400 (19) | C12—H12 | 0.9500 |
| N3—C2 | 1.319 (2) | C13—H13 | 0.9500 |
| N3—C4 | 1.375 (2) | C15—H15 | 0.9500 |
| C2—C21 | 1.474 (2) | C16—H16 | 0.9500 |
| C4—C5 | 1.362 (2) | C17—H17A | 0.9800 |
| C4—C41 | 1.499 (2) | C17—H17B | 0.9800 |
| C5—C51 | 1.489 (2) | C17—H17C | 0.9800 |
| C11—C12 | 1.386 (2) | C22—H22 | 0.9500 |
| C11—C16 | 1.385 (2) | C23—H23 | 0.9500 |
| C12—C13 | 1.392 (2) | C24—H24 | 0.9500 |
| C13—C14 | 1.392 (2) | C25—H25 | 0.9500 |
| C14—C15 | 1.395 (2) | C26—H26 | 0.9500 |
| C14—C17 | 1.509 (2) | C41—H41A | 0.9800 |
| C15—C16 | 1.390 (2) | C41—H41B | 0.9800 |
| C21—C22 | 1.396 (2) | C41—H41C | 0.9800 |
| C21—C26 | 1.397 (2) | C51—H51A | 0.9800 |
| C22—C23 | 1.386 (2) | C51—H51B | 0.9800 |
| C23—C24 | 1.388 (3) | C51—H51C | 0.9800 |
| N3···C12i | 3.324 (2) | C21···H41Aii | 3.0800 |
| N1···H22 | 2.8300 | C23···H41Bvi | 3.0400 |
| N3···H26 | 2.5600 | C24···H17Av | 3.1000 |
| N3···H12i | 2.5100 | C24···H15vii | 3.0500 |
| N3···H16ii | 2.5400 | C41···H22i | 3.0800 |
| C4···C22i | 3.530 (2) | C41···H51A | 2.9200 |
| C4···C26ii | 3.427 (2) | C51···H41C | 2.9200 |
| C5···C22i | 3.537 (2) | C51···H25iv | 2.8500 |
| C5···C26ii | 3.362 (2) | H12···N3i | 2.5100 |
| C11···C22 | 3.143 (2) | H15···H17B | 2.3700 |
| C12···N3i | 3.324 (2) | H15···C24vii | 3.0500 |
| C12···C51 | 3.278 (2) | H16···C2 | 3.0500 |
| C16···C21 | 3.530 (2) | H16···N3ii | 2.5400 |
| C16···C22 | 3.454 (2) | H17A···H51Avi | 2.5400 |
| C21···C16 | 3.530 (2) | H17A···C24v | 3.1000 |
| C22···C41i | 3.596 (3) | H17B···H15 | 2.3700 |
| C22···C4i | 3.530 (2) | H22···N1 | 2.8300 |
| C22···C11 | 3.143 (2) | H22···C11 | 2.5600 |
| C22···C16 | 3.454 (2) | H22···C12 | 2.9700 |
| C22···C5i | 3.537 (2) | H22···C16 | 3.0100 |
| C25···C51iii | 3.537 (2) | H22···C41i | 3.0800 |
| C26···C4ii | 3.427 (2) | H23···H41Bvi | 2.4300 |
| C26···C5ii | 3.362 (2) | H23···C13v | 2.9300 |
| C26···C51ii | 3.600 (3) | H25···C51iii | 2.8500 |
| C41···C22i | 3.596 (3) | H26···N3 | 2.5600 |
| C51···C12 | 3.278 (2) | H26···C5ii | 2.9600 |
| C51···C25iv | 3.537 (2) | H41A···C21ii | 3.0800 |
| C51···C26ii | 3.600 (3) | H41B···C23viii | 3.0400 |
| C2···H16 | 3.0500 | H41B···H23viii | 2.4300 |
| C5···H26ii | 2.9600 | H41C···C51 | 2.9200 |
| C11···H22 | 2.5600 | H41C···H51A | 2.3300 |
| C11···H51C | 2.7900 | H51A···C17viii | 3.0700 |
| C12···H51B | 2.9800 | H51A···C41 | 2.9200 |
| C12···H22 | 2.9700 | H51A···H17Aviii | 2.5400 |
| C13···H23v | 2.9300 | H51A···H41C | 2.3300 |
| C16···H22 | 3.0100 | H51B···C12 | 2.9800 |
| C17···H51Avi | 3.0700 | H51B···C21i | 3.0800 |
| C21···H51Bi | 3.0800 | H51C···C11 | 2.7900 |
| C2—N1—C5 | 106.63 (12) | C14—C13—H13 | 119.00 |
| C2—N1—C11 | 129.03 (13) | C14—C15—H15 | 119.00 |
| C5—N1—C11 | 122.83 (12) | C16—C15—H15 | 119.00 |
| C2—N3—C4 | 106.36 (13) | C11—C16—H16 | 120.00 |
| N1—C2—N3 | 110.95 (13) | C15—C16—H16 | 120.00 |
| N1—C2—C21 | 126.14 (14) | C14—C17—H17A | 109.00 |
| N3—C2—C21 | 122.80 (13) | C14—C17—H17B | 109.00 |
| N3—C4—C5 | 110.17 (14) | C14—C17—H17C | 109.00 |
| N3—C4—C41 | 121.39 (14) | H17A—C17—H17B | 109.00 |
| C5—C4—C41 | 128.41 (15) | H17A—C17—H17C | 109.00 |
| N1—C5—C4 | 105.89 (13) | H17B—C17—H17C | 109.00 |
| N1—C5—C51 | 122.59 (14) | C21—C22—H22 | 120.00 |
| C4—C5—C51 | 131.50 (15) | C23—C22—H22 | 120.00 |
| N1—C11—C12 | 119.87 (14) | C22—C23—H23 | 120.00 |
| N1—C11—C16 | 119.14 (13) | C24—C23—H23 | 120.00 |
| C12—C11—C16 | 120.90 (14) | C23—C24—H24 | 120.00 |
| C11—C12—C13 | 119.07 (14) | C25—C24—H24 | 120.00 |
| C12—C13—C14 | 121.47 (14) | C24—C25—H25 | 120.00 |
| C13—C14—C15 | 117.96 (14) | C26—C25—H25 | 120.00 |
| C13—C14—C17 | 120.75 (15) | C21—C26—H26 | 120.00 |
| C15—C14—C17 | 121.29 (15) | C25—C26—H26 | 120.00 |
| C14—C15—C16 | 121.48 (14) | C4—C41—H41A | 109.00 |
| C11—C16—C15 | 119.09 (14) | C4—C41—H41B | 109.00 |
| C2—C21—C22 | 123.89 (14) | C4—C41—H41C | 109.00 |
| C2—C21—C26 | 117.45 (14) | H41A—C41—H41B | 109.00 |
| C22—C21—C26 | 118.58 (14) | H41A—C41—H41C | 109.00 |
| C21—C22—C23 | 120.55 (15) | H41B—C41—H41C | 109.00 |
| C22—C23—C24 | 120.50 (17) | C5—C51—H51A | 109.00 |
| C23—C24—C25 | 119.36 (16) | C5—C51—H51B | 109.00 |
| C24—C25—C26 | 120.24 (15) | C5—C51—H51C | 109.00 |
| C21—C26—C25 | 120.77 (15) | H51A—C51—H51B | 109.00 |
| C11—C12—H12 | 120.00 | H51A—C51—H51C | 109.00 |
| C13—C12—H12 | 120.00 | H51B—C51—H51C | 109.00 |
| C12—C13—H13 | 119.00 | ||
| C5—N1—C2—N3 | 0.36 (17) | N3—C4—C5—C51 | −178.79 (17) |
| C5—N1—C2—C21 | 176.54 (14) | C41—C4—C5—N1 | 177.62 (16) |
| C11—N1—C2—N3 | 166.40 (14) | C41—C4—C5—C51 | −0.7 (3) |
| C11—N1—C2—C21 | −17.4 (2) | N1—C11—C12—C13 | 176.00 (14) |
| C2—N1—C5—C4 | 0.06 (16) | C16—C11—C12—C13 | −0.7 (2) |
| C2—N1—C5—C51 | 178.60 (16) | N1—C11—C16—C15 | −177.22 (14) |
| C11—N1—C5—C4 | −167.05 (13) | C12—C11—C16—C15 | −0.5 (2) |
| C11—N1—C5—C51 | 11.5 (2) | C11—C12—C13—C14 | 0.8 (2) |
| C2—N1—C11—C12 | 122.48 (17) | C12—C13—C14—C15 | 0.3 (2) |
| C2—N1—C11—C16 | −60.8 (2) | C12—C13—C14—C17 | −179.07 (15) |
| C5—N1—C11—C12 | −73.49 (19) | C13—C14—C15—C16 | −1.6 (2) |
| C5—N1—C11—C16 | 103.27 (17) | C17—C14—C15—C16 | 177.82 (15) |
| C4—N3—C2—N1 | −0.62 (17) | C14—C15—C16—C11 | 1.7 (2) |
| C4—N3—C2—C21 | −176.95 (14) | C2—C21—C22—C23 | −176.04 (16) |
| C2—N3—C4—C5 | 0.66 (17) | C26—C21—C22—C23 | 0.7 (2) |
| C2—N3—C4—C41 | −177.56 (15) | C2—C21—C26—C25 | 176.69 (14) |
| N1—C2—C21—C22 | −19.2 (2) | C22—C21—C26—C25 | −0.3 (2) |
| N1—C2—C21—C26 | 164.06 (15) | C21—C22—C23—C24 | −0.9 (3) |
| N3—C2—C21—C22 | 156.57 (15) | C22—C23—C24—C25 | 0.7 (3) |
| N3—C2—C21—C26 | −20.2 (2) | C23—C24—C25—C26 | −0.2 (3) |
| N3—C4—C5—N1 | −0.43 (17) | C24—C25—C26—C21 | 0.0 (2) |
| Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+2, −y+2, −z; (iii) x−1/2, −y+3/2, z−1/2; (iv) x+1/2, −y+3/2, z+1/2; (v) −x+1, −y+1, −z; (vi) x−1, y, z; (vii) −x+1, −y+2, −z; (viii) x+1, y, z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C12—H12···N3i | 0.95 | 2.51 | 3.324 (2) | 144 |
| C16—H16···N3ii | 0.95 | 2.54 | 3.465 (2) | 164 |
| Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+2, −y+2, −z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C12—H12···N3i | 0.95 | 2.51 | 3.324 (2) | 144 |
| C16—H16···N3ii | 0.95 | 2.54 | 3.465 (2) | 164 |
| Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+2, −y+2, −z. |
JJ is thankful tothe Department of Science and Technology [No. SR/S1/IC-07/2007], University Grants commission (F. No. 36-21/2008 (SR)) for providing funding for this research work. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.
Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Gayathri, P., Jayabharathi, J., Saravanan, K., Thiruvalluvar, A. & Butcher, R. J. (2010a). Acta Cryst. E66, o1791.
Gayathri, P., Jayabharathi, J., Srinivasan, N., Thiruvalluvar, A. & Butcher, R. J. (2010b). Acta Cryst. E66, o1703.
Gayathri, P., Thiruvalluvar, A., Saravanan, K., Jayabharathi, J. & Butcher, R. J. (2010c). Acta Cryst. E66, o2219.
Gayathri, P., Thiruvalluvar, A., Srinivasan, N., Jayabharathi, J. & Butcher, R. J. (2010d). Acta Cryst. E66, o2519.
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Spek, A. L. (2009). Acta Cryst. D65, 148–155.
As part of our research (Gayathri et al., (2010a, b, c & d)), we have synthesized the title compound, I and report its crystal structure here.
In I (Fig. 1), C18H18N2, the imidazole ring is essentially planar with maximum deviation = 0.004 (1)Å for N3. The imidazole ring makes dihedral angles of 68.91 (8)° and 20.43 (9)° with the benzene (C11-C16) and phenyl (C21-C26) rings respectively. The dihedral angle between the benzene and phenyl rings is 73.62 (8)°. The crystal packing is stabilized by C12–H12···N3i and C16–H16···N3ii intermolecular non-classical hydrogen bonds (Table 1, Fig. 2). Symmetry codes: (i) -x+2, -y+1, -z; (ii) -x+2, -y+2, -z.