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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): o2826.
Published online 2010 October 20. doi:  10.1107/S1600536810040535
PMCID: PMC3009043

4,5-Dimethyl-2-phenyl-1-(p-tol­yl)-1H-imidazole

Abstract

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.

Related literature

For related structures and applications of imidazole derivatives, see: Gayathri et al. (2010a [triangle],b [triangle],c [triangle],d [triangle]).

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Object name is e-66-o2826-scheme1.jpg

Experimental

Crystal data

  • C18H18N2
  • M r = 262.34
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2826-efi1.jpg
  • a = 9.6971 (3) Å
  • b = 7.5458 (2) Å
  • c = 19.8407 (7) Å
  • β = 96.604 (3)°
  • V = 1442.16 (8) Å3
  • Z = 4
  • Cu Kα radiation
  • μ = 0.55 mm−1
  • T = 123 K
  • 0.49 × 0.43 × 0.22 mm

Data collection

  • Oxford Diffraction Xcalibur Ruby Gemini diffractometer
  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 [triangle]) T min = 0.606, T max = 1.000
  • 5113 measured reflections
  • 2849 independent reflections
  • 2529 reflections with I > 2σ(I)
  • R int = 0.024

Refinement

  • R[F 2 > 2σ(F 2)] = 0.049
  • wR(F 2) = 0.138
  • S = 1.11
  • 2849 reflections
  • 184 parameters
  • H-atom parameters constrained
  • Δρmax = 0.28 e Å−3
  • Δρmin = −0.19 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 [triangle]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2002 (Burla et al., 2003 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810040535/rk2234sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040535/rk2234Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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.

supplementary crystallographic information

Comment

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.

Experimental

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%).

Refinement

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.

Figures

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.
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.

Crystal data

C18H18N2F(000) = 560
Mr = 262.34Dx = 1.208 Mg m3
Monoclinic, P21/nMelting point: 388 K
Hall symbol: -P 2ynCu Kα radiation, λ = 1.54184 Å
a = 9.6971 (3) ÅCell parameters from 3666 reflections
b = 7.5458 (2) Åθ = 4.6–74.1°
c = 19.8407 (7) ŵ = 0.55 mm1
β = 96.604 (3)°T = 123 K
V = 1442.16 (8) Å3Block, colourless
Z = 40.49 × 0.43 × 0.22 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer2849 independent reflections
Radiation source: Enhance (Cu) X-ray Source2529 reflections with I > 2σ(I)
graphiteRint = 0.024
Detector resolution: 10.5081 pixels mm-1θmax = 74.2°, θmin = 6.3°
ω scansh = −11→12
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)k = −8→9
Tmin = 0.606, Tmax = 1.000l = −24→23
5113 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138H-atom parameters constrained
S = 1.11w = 1/[σ2(Fo2) + (0.0624P)2 + 0.7809P] where P = (Fo2 + 2Fc2)/3
2849 reflections(Δ/σ)max = 0.001
184 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = −0.18 e Å3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
N10.96551 (13)0.70974 (17)0.05414 (6)0.0239 (4)
N31.08249 (13)0.78862 (17)−0.03075 (7)0.0248 (4)
C20.95773 (16)0.7589 (2)−0.01276 (7)0.0229 (4)
C41.17482 (16)0.7599 (2)0.02618 (8)0.0260 (5)
C51.10567 (16)0.7104 (2)0.07911 (8)0.0266 (5)
C110.85639 (16)0.6994 (2)0.09746 (7)0.0235 (4)
C120.83053 (17)0.5406 (2)0.12883 (8)0.0272 (5)
C130.73060 (17)0.5358 (2)0.17385 (8)0.0281 (5)
C140.65519 (16)0.6861 (2)0.18734 (8)0.0276 (5)
C150.68211 (17)0.8429 (2)0.15400 (8)0.0302 (5)
C160.78331 (16)0.8514 (2)0.10983 (8)0.0272 (5)
C170.54875 (18)0.6791 (3)0.23712 (9)0.0367 (6)
C210.83051 (16)0.7676 (2)−0.06104 (8)0.0241 (4)
C220.70724 (17)0.6803 (2)−0.05163 (8)0.0289 (5)
C230.59439 (18)0.6860 (3)−0.10129 (9)0.0337 (5)
C240.60157 (19)0.7807 (3)−0.16077 (9)0.0348 (5)
C250.72376 (19)0.8686 (2)−0.17049 (8)0.0334 (5)
C260.83700 (17)0.8621 (2)−0.12112 (8)0.0281 (5)
C411.32767 (17)0.7884 (3)0.02550 (9)0.0341 (5)
C511.15590 (18)0.6676 (3)0.15102 (8)0.0338 (5)
H120.880310.436520.119710.0327*
H130.713490.427490.195870.0338*
H150.630140.946230.161660.0362*
H160.802060.959960.088430.0326*
H17A0.481460.584940.223810.0550*
H17B0.500450.793130.237190.0550*
H17C0.595250.654600.282670.0550*
H220.700630.61651−0.010860.0346*
H230.511530.62463−0.094560.0404*
H240.523770.78531−0.194510.0417*
H250.729620.93342−0.211110.0401*
H260.920030.92255−0.128230.0338*
H41A1.347050.915760.024290.0512*
H41B1.357920.73153−0.014700.0512*
H41C1.377950.736560.066470.0512*
H51A1.255620.692090.159610.0507*
H51B1.139010.542010.159600.0507*
H51C1.106120.740570.181170.0507*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0248 (7)0.0269 (7)0.0204 (6)0.0011 (5)0.0039 (5)0.0000 (5)
N30.0272 (7)0.0242 (7)0.0238 (7)0.0009 (5)0.0064 (5)−0.0016 (5)
C20.0278 (8)0.0214 (7)0.0200 (7)0.0008 (6)0.0056 (6)−0.0013 (6)
C40.0262 (8)0.0248 (8)0.0273 (8)0.0020 (6)0.0047 (6)−0.0010 (6)
C50.0256 (8)0.0281 (8)0.0260 (8)0.0038 (6)0.0026 (6)−0.0012 (6)
C110.0230 (7)0.0294 (8)0.0185 (7)−0.0001 (6)0.0036 (6)−0.0012 (6)
C120.0309 (8)0.0264 (8)0.0246 (8)0.0023 (7)0.0044 (6)−0.0004 (6)
C130.0312 (8)0.0297 (9)0.0238 (8)−0.0032 (7)0.0045 (6)0.0025 (6)
C140.0231 (8)0.0374 (9)0.0224 (8)−0.0030 (6)0.0031 (6)−0.0030 (7)
C150.0294 (8)0.0312 (9)0.0307 (8)0.0054 (7)0.0063 (7)−0.0025 (7)
C160.0295 (8)0.0261 (8)0.0263 (8)0.0014 (6)0.0043 (6)0.0014 (6)
C170.0295 (9)0.0477 (11)0.0347 (9)−0.0034 (8)0.0114 (7)−0.0030 (8)
C210.0280 (8)0.0248 (8)0.0199 (7)0.0018 (6)0.0041 (6)−0.0043 (6)
C220.0314 (8)0.0328 (9)0.0233 (8)−0.0006 (7)0.0068 (6)−0.0024 (7)
C230.0278 (8)0.0420 (10)0.0315 (9)−0.0018 (7)0.0045 (7)−0.0085 (8)
C240.0324 (9)0.0422 (10)0.0280 (8)0.0063 (8)−0.0038 (7)−0.0077 (7)
C250.0417 (10)0.0367 (10)0.0216 (8)0.0039 (8)0.0026 (7)0.0000 (7)
C260.0321 (8)0.0296 (8)0.0234 (8)−0.0004 (7)0.0063 (6)−0.0025 (6)
C410.0263 (8)0.0398 (10)0.0369 (9)0.0004 (7)0.0061 (7)0.0006 (8)
C510.0320 (9)0.0442 (10)0.0245 (8)0.0041 (8)0.0007 (7)0.0020 (7)

Geometric parameters (Å, °)

N1—C21.3719 (18)C24—C251.391 (3)
N1—C51.392 (2)C25—C261.386 (2)
N1—C111.4400 (19)C12—H120.9500
N3—C21.319 (2)C13—H130.9500
N3—C41.375 (2)C15—H150.9500
C2—C211.474 (2)C16—H160.9500
C4—C51.362 (2)C17—H17A0.9800
C4—C411.499 (2)C17—H17B0.9800
C5—C511.489 (2)C17—H17C0.9800
C11—C121.386 (2)C22—H220.9500
C11—C161.385 (2)C23—H230.9500
C12—C131.392 (2)C24—H240.9500
C13—C141.392 (2)C25—H250.9500
C14—C151.395 (2)C26—H260.9500
C14—C171.509 (2)C41—H41A0.9800
C15—C161.390 (2)C41—H41B0.9800
C21—C221.396 (2)C41—H41C0.9800
C21—C261.397 (2)C51—H51A0.9800
C22—C231.386 (2)C51—H51B0.9800
C23—C241.388 (3)C51—H51C0.9800
N3···C12i3.324 (2)C21···H41Aii3.0800
N1···H222.8300C23···H41Bvi3.0400
N3···H262.5600C24···H17Av3.1000
N3···H12i2.5100C24···H15vii3.0500
N3···H16ii2.5400C41···H22i3.0800
C4···C22i3.530 (2)C41···H51A2.9200
C4···C26ii3.427 (2)C51···H41C2.9200
C5···C22i3.537 (2)C51···H25iv2.8500
C5···C26ii3.362 (2)H12···N3i2.5100
C11···C223.143 (2)H15···H17B2.3700
C12···N3i3.324 (2)H15···C24vii3.0500
C12···C513.278 (2)H16···C23.0500
C16···C213.530 (2)H16···N3ii2.5400
C16···C223.454 (2)H17A···H51Avi2.5400
C21···C163.530 (2)H17A···C24v3.1000
C22···C41i3.596 (3)H17B···H152.3700
C22···C4i3.530 (2)H22···N12.8300
C22···C113.143 (2)H22···C112.5600
C22···C163.454 (2)H22···C122.9700
C22···C5i3.537 (2)H22···C163.0100
C25···C51iii3.537 (2)H22···C41i3.0800
C26···C4ii3.427 (2)H23···H41Bvi2.4300
C26···C5ii3.362 (2)H23···C13v2.9300
C26···C51ii3.600 (3)H25···C51iii2.8500
C41···C22i3.596 (3)H26···N32.5600
C51···C123.278 (2)H26···C5ii2.9600
C51···C25iv3.537 (2)H41A···C21ii3.0800
C51···C26ii3.600 (3)H41B···C23viii3.0400
C2···H163.0500H41B···H23viii2.4300
C5···H26ii2.9600H41C···C512.9200
C11···H222.5600H41C···H51A2.3300
C11···H51C2.7900H51A···C17viii3.0700
C12···H51B2.9800H51A···C412.9200
C12···H222.9700H51A···H17Aviii2.5400
C13···H23v2.9300H51A···H41C2.3300
C16···H223.0100H51B···C122.9800
C17···H51Avi3.0700H51B···C21i3.0800
C21···H51Bi3.0800H51C···C112.7900
C2—N1—C5106.63 (12)C14—C13—H13119.00
C2—N1—C11129.03 (13)C14—C15—H15119.00
C5—N1—C11122.83 (12)C16—C15—H15119.00
C2—N3—C4106.36 (13)C11—C16—H16120.00
N1—C2—N3110.95 (13)C15—C16—H16120.00
N1—C2—C21126.14 (14)C14—C17—H17A109.00
N3—C2—C21122.80 (13)C14—C17—H17B109.00
N3—C4—C5110.17 (14)C14—C17—H17C109.00
N3—C4—C41121.39 (14)H17A—C17—H17B109.00
C5—C4—C41128.41 (15)H17A—C17—H17C109.00
N1—C5—C4105.89 (13)H17B—C17—H17C109.00
N1—C5—C51122.59 (14)C21—C22—H22120.00
C4—C5—C51131.50 (15)C23—C22—H22120.00
N1—C11—C12119.87 (14)C22—C23—H23120.00
N1—C11—C16119.14 (13)C24—C23—H23120.00
C12—C11—C16120.90 (14)C23—C24—H24120.00
C11—C12—C13119.07 (14)C25—C24—H24120.00
C12—C13—C14121.47 (14)C24—C25—H25120.00
C13—C14—C15117.96 (14)C26—C25—H25120.00
C13—C14—C17120.75 (15)C21—C26—H26120.00
C15—C14—C17121.29 (15)C25—C26—H26120.00
C14—C15—C16121.48 (14)C4—C41—H41A109.00
C11—C16—C15119.09 (14)C4—C41—H41B109.00
C2—C21—C22123.89 (14)C4—C41—H41C109.00
C2—C21—C26117.45 (14)H41A—C41—H41B109.00
C22—C21—C26118.58 (14)H41A—C41—H41C109.00
C21—C22—C23120.55 (15)H41B—C41—H41C109.00
C22—C23—C24120.50 (17)C5—C51—H51A109.00
C23—C24—C25119.36 (16)C5—C51—H51B109.00
C24—C25—C26120.24 (15)C5—C51—H51C109.00
C21—C26—C25120.77 (15)H51A—C51—H51B109.00
C11—C12—H12120.00H51A—C51—H51C109.00
C13—C12—H12120.00H51B—C51—H51C109.00
C12—C13—H13119.00
C5—N1—C2—N30.36 (17)N3—C4—C5—C51−178.79 (17)
C5—N1—C2—C21176.54 (14)C41—C4—C5—N1177.62 (16)
C11—N1—C2—N3166.40 (14)C41—C4—C5—C51−0.7 (3)
C11—N1—C2—C21−17.4 (2)N1—C11—C12—C13176.00 (14)
C2—N1—C5—C40.06 (16)C16—C11—C12—C13−0.7 (2)
C2—N1—C5—C51178.60 (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—C5111.5 (2)C11—C12—C13—C140.8 (2)
C2—N1—C11—C12122.48 (17)C12—C13—C14—C150.3 (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—C16103.27 (17)C17—C14—C15—C16177.82 (15)
C4—N3—C2—N1−0.62 (17)C14—C15—C16—C111.7 (2)
C4—N3—C2—C21−176.95 (14)C2—C21—C22—C23−176.04 (16)
C2—N3—C4—C50.66 (17)C26—C21—C22—C230.7 (2)
C2—N3—C4—C41−177.56 (15)C2—C21—C26—C25176.69 (14)
N1—C2—C21—C22−19.2 (2)C22—C21—C26—C25−0.3 (2)
N1—C2—C21—C26164.06 (15)C21—C22—C23—C24−0.9 (3)
N3—C2—C21—C22156.57 (15)C22—C23—C24—C250.7 (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—C210.0 (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.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C12—H12···N3i0.952.513.324 (2)144
C16—H16···N3ii0.952.543.465 (2)164

Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+2, −y+2, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2234).

References

  • 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. [PMC free article] [PubMed]
  • Gayathri, P., Jayabharathi, J., Srinivasan, N., Thiruvalluvar, A. & Butcher, R. J. (2010b). Acta Cryst. E66, o1703. [PMC free article] [PubMed]
  • Gayathri, P., Thiruvalluvar, A., Saravanan, K., Jayabharathi, J. & Butcher, R. J. (2010c). Acta Cryst. E66, o2219. [PMC free article] [PubMed]
  • Gayathri, P., Thiruvalluvar, A., Srinivasan, N., Jayabharathi, J. & Butcher, R. J. (2010d). Acta Cryst. E66, o2519. [PMC free article] [PubMed]
  • Oxford Diffraction (2010). CrysAlis PRO Oxford Diffraction Ltd, Yarnton, England.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

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