organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890
Volume 67| Part 5| May 2011| Page o1065

1-(3,5-Di­methyl­phenyl)-2-(4-fluoro­phenyl)-4,5-di­methyl-1H-imidazole

aPG 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 Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
*Correspondence e-mail: thiruvalluvar.a@gmail.com

(Received 26 March 2011; accepted 31 March 2011; online 7 April 2011)

In the title compound, C19H19FN2, the imidazole ring is essentially planar [maximum deviation of 0.0015 (9) Å] and makes dihedral angles of 77.61 (9) and 26.93 (10)° with the benzene rings attached to nitro­gen and carbon, respectively. The dihedral angle between the two benzene rings is 78.84 (8)°. A C—H⋯π inter­action is found in the crystal structure.

Related literature

For related structures and applications of imidazole derivatives, see: Gayathri et al. (2010[Gayathri, P., Thiruvalluvar, A., Srinivasan, N., Jayabharathi, J. & Butcher, R. J. (2010). Acta Cryst. E66, o2776.]); Rosepriya et al. (2011[Rosepriya, S., Thiruvalluvar, A., Jayabharathi, J., Venkatesh Perumal, M., Butcher, R. J., Jasinski, J. P. & Golen, J. A. (2011). Acta Cryst. E67, o989.]).

[Scheme 1]

Experimental

Crystal data
  • C19H19FN2

  • Mr = 294.36

  • Triclinic, [P \overline 1]

  • a = 8.4226 (10) Å

  • b = 9.5572 (10) Å

  • c = 11.0351 (11) Å

  • α = 105.423 (9)°

  • β = 105.677 (9)°

  • γ = 95.781 (9)°

  • V = 810.07 (17) Å3

  • Z = 2

  • Cu Kα radiation

  • μ = 0.63 mm−1

  • T = 170 K

  • 0.25 × 0.20 × 0.15 mm

Data collection
  • Oxford Diffraction Xcalibur Eos Gemini diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.858, Tmax = 0.911

  • 5121 measured reflections

  • 3054 independent reflections

  • 2771 reflections with I > 2σ(I)

  • Rint = 0.011

Refinement
  • R[F2 > 2σ(F2)] = 0.052

  • wR(F2) = 0.159

  • S = 1.07

  • 3054 reflections

  • 203 parameters

  • H-atom parameters constrained

  • Δρmax = 0.31 e Å−3

  • Δρmin = −0.23 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C21–C26 ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C12—H12⋯Cg3i 0.95 2.86 3.7969 (19) 169
Symmetry code: (i) -x, -y, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Rosepriya et al. (2011) have reported the crystal structure of 1,2-Diphenyl-1H-imidazo[4,5-f][1,10]phenanthroline. As part of our research (Gayathri et al., (2010)), we have synthesized the title compound (I) and report its crystal structure here. Since our group doing the research in organic light emitting devices, we are interested to use the title compound as ligand for synthesizing Ir(III) complexes.

In the title compound (Fig. 1), C19H19FN2, the imidazole ring is essentially planar [maximum deviation of 0.0015 (9) Å for C4]. The imidazole ring makes dihedral angles of 77.61 (9) and 26.93 (10)° with the benzene rings attached to N1 and C2, respectively. The dihedral angle between the two benzene rings is 78.84 (8)°. A C12—H12···π interaction involving (C21—C26) ring is found in the crystal structure (Table 1).

Related literature top

For related structures and applications of imidazole derivatives, see: Gayathri et al. (2010); Rosepriya et al. (2011).

Experimental top

To pure butane-2,3-dione (1.48 g, 15 mmol) in ethanol (10 ml), 3,5-xylidine (1.8 g, 15 mmol), ammonium acetate (1.15 g, 15 mmol) and 4-fluorobenzaldehyde (1.7 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: 2.1 g (48%). Crystals suitable for X-ray diffraction studies were grown by slow solvent evaporation of a solution of the compound in dichloromethane.

Refinement top

H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.95 - 0.98 Å; Uiso(H) = kUeq(C), where k = 1.5 for methyl and 1.2 for all other H atoms.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis RED (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); 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).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids drawn at the 30% probability level. H atoms are shown as small spheres of arbitrary radius.
1-(3,5-Dimethylphenyl)-2-(4-fluorophenyl)-4,5-dimethyl-1H-imidazole top
Crystal data top
C19H19FN2Z = 2
Mr = 294.36F(000) = 312
Triclinic, P1Dx = 1.207 Mg m3
Hall symbol: -P 1Melting point: 377 K
a = 8.4226 (10) ÅCu Kα radiation, λ = 1.54178 Å
b = 9.5572 (10) ÅCell parameters from 3721 reflections
c = 11.0351 (11) Åθ = 5.6–71.2°
α = 105.423 (9)°µ = 0.63 mm1
β = 105.677 (9)°T = 170 K
γ = 95.781 (9)°Block, colourless
V = 810.07 (17) Å30.25 × 0.20 × 0.15 mm
Data collection top
Oxford Diffraction Xcalibur Eos Gemini
diffractometer
3054 independent reflections
Radiation source: Enhance (Cu) X-ray Source2771 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.011
Detector resolution: 16.1500 pixels mm-1θmax = 71.3°, θmin = 5.6°
ω scansh = 910
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2010)
k = 1111
Tmin = 0.858, Tmax = 0.911l = 1310
5121 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0944P)2 + 0.144P]
where P = (Fo2 + 2Fc2)/3
3054 reflections(Δ/σ)max = 0.001
203 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.23 e Å3
Crystal data top
C19H19FN2γ = 95.781 (9)°
Mr = 294.36V = 810.07 (17) Å3
Triclinic, P1Z = 2
a = 8.4226 (10) ÅCu Kα radiation
b = 9.5572 (10) ŵ = 0.63 mm1
c = 11.0351 (11) ÅT = 170 K
α = 105.423 (9)°0.25 × 0.20 × 0.15 mm
β = 105.677 (9)°
Data collection top
Oxford Diffraction Xcalibur Eos Gemini
diffractometer
3054 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2010)
2771 reflections with I > 2σ(I)
Tmin = 0.858, Tmax = 0.911Rint = 0.011
5121 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0520 restraints
wR(F2) = 0.159H-atom parameters constrained
S = 1.07Δρmax = 0.31 e Å3
3054 reflectionsΔρmin = 0.23 e Å3
203 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
F40.29950 (19)0.53513 (14)0.86850 (14)0.0964 (5)
N10.19985 (15)0.06005 (14)0.37504 (12)0.0449 (4)
N30.32289 (16)0.11576 (15)0.55605 (13)0.0520 (4)
C20.27033 (18)0.00885 (17)0.50979 (14)0.0453 (4)
C40.2859 (2)0.23874 (19)0.44868 (16)0.0532 (5)
C50.20944 (19)0.20827 (17)0.33550 (15)0.0488 (5)
C110.14226 (18)0.02522 (16)0.28741 (14)0.0435 (4)
C120.02859 (18)0.01651 (18)0.23336 (15)0.0480 (5)
C130.08585 (19)0.10368 (18)0.15377 (15)0.0494 (5)
C140.0323 (2)0.19566 (17)0.12941 (14)0.0515 (5)
C150.2035 (2)0.20141 (16)0.17950 (15)0.0487 (5)
C160.25852 (18)0.11506 (16)0.26059 (14)0.0464 (4)
C170.2713 (2)0.0990 (2)0.0987 (2)0.0692 (7)
C180.3276 (3)0.2979 (2)0.1464 (2)0.0698 (7)
C210.28022 (18)0.14031 (17)0.59540 (15)0.0472 (5)
C220.1660 (2)0.2313 (2)0.56533 (17)0.0566 (5)
C230.1740 (3)0.3655 (2)0.6562 (2)0.0654 (6)
C240.2952 (3)0.4060 (2)0.77740 (19)0.0660 (6)
C250.4109 (2)0.3201 (2)0.81121 (19)0.0655 (6)
C260.4030 (2)0.1881 (2)0.71957 (16)0.0558 (5)
C410.3314 (3)0.3824 (2)0.4636 (2)0.0787 (8)
C510.1442 (2)0.3012 (2)0.19482 (17)0.0623 (6)
H120.106450.048730.250550.0575*
H140.005530.256860.076530.0618*
H160.375140.118000.297120.0556*
H17A0.293020.131470.019610.1037*
H17B0.309480.164600.165260.1037*
H17C0.331970.002290.075260.1037*
H18A0.346080.242830.064310.1046*
H18B0.434130.327420.218390.1046*
H18C0.283390.386100.134900.1046*
H220.081760.200910.481630.0679*
H230.097290.428250.635100.0784*
H250.493980.351140.895520.0785*
H260.482610.127770.740920.0670*
H41A0.450090.381000.470680.1181*
H41B0.262020.463860.386330.1181*
H41C0.311770.396290.543600.1181*
H51A0.148870.404670.189250.0934*
H51B0.213020.268450.145150.0934*
H51C0.027750.291690.157280.0934*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F40.1034 (10)0.0696 (8)0.0947 (9)0.0084 (7)0.0297 (8)0.0060 (7)
N10.0417 (6)0.0541 (7)0.0451 (7)0.0131 (5)0.0125 (5)0.0248 (5)
N30.0508 (7)0.0622 (8)0.0497 (7)0.0169 (6)0.0121 (6)0.0291 (6)
C20.0399 (7)0.0568 (9)0.0451 (7)0.0108 (6)0.0128 (6)0.0250 (6)
C40.0533 (9)0.0573 (9)0.0561 (9)0.0180 (7)0.0150 (7)0.0279 (7)
C50.0466 (8)0.0547 (9)0.0516 (8)0.0152 (6)0.0156 (6)0.0243 (7)
C110.0430 (7)0.0527 (8)0.0410 (7)0.0148 (6)0.0131 (6)0.0222 (6)
C120.0418 (8)0.0586 (9)0.0494 (8)0.0121 (6)0.0143 (6)0.0250 (7)
C130.0469 (8)0.0581 (9)0.0445 (8)0.0182 (7)0.0102 (6)0.0187 (7)
C140.0634 (10)0.0533 (9)0.0448 (8)0.0218 (7)0.0150 (7)0.0243 (7)
C150.0567 (9)0.0479 (8)0.0496 (8)0.0139 (6)0.0223 (7)0.0206 (6)
C160.0418 (7)0.0533 (8)0.0490 (8)0.0134 (6)0.0155 (6)0.0207 (6)
C170.0519 (10)0.0793 (12)0.0756 (12)0.0238 (9)0.0056 (8)0.0327 (10)
C180.0764 (12)0.0665 (11)0.0864 (13)0.0152 (9)0.0385 (11)0.0419 (10)
C210.0437 (7)0.0569 (9)0.0481 (8)0.0075 (6)0.0178 (6)0.0248 (7)
C220.0565 (9)0.0630 (10)0.0535 (9)0.0151 (7)0.0163 (7)0.0224 (8)
C230.0670 (11)0.0609 (10)0.0762 (12)0.0192 (8)0.0287 (9)0.0248 (9)
C240.0680 (11)0.0561 (10)0.0684 (11)0.0007 (8)0.0275 (9)0.0082 (8)
C250.0548 (10)0.0716 (11)0.0589 (10)0.0022 (8)0.0124 (8)0.0123 (8)
C260.0460 (8)0.0654 (10)0.0559 (9)0.0054 (7)0.0132 (7)0.0227 (8)
C410.1018 (16)0.0660 (12)0.0736 (12)0.0332 (11)0.0157 (11)0.0351 (10)
C510.0685 (11)0.0640 (10)0.0532 (9)0.0186 (8)0.0135 (8)0.0192 (8)
Geometric parameters (Å, º) top
F4—C241.359 (2)C24—C251.375 (3)
N1—C21.3713 (19)C25—C261.374 (3)
N1—C51.385 (2)C12—H120.9500
N1—C111.442 (2)C14—H140.9500
N3—C21.322 (2)C16—H160.9500
N3—C41.367 (2)C17—H17A0.9800
C2—C211.466 (2)C17—H17B0.9800
C4—C51.362 (2)C17—H17C0.9800
C4—C411.500 (3)C18—H18A0.9800
C5—C511.486 (2)C18—H18B0.9800
C11—C121.385 (2)C18—H18C0.9800
C11—C161.381 (2)C22—H220.9500
C12—C131.393 (2)C23—H230.9500
C13—C141.389 (2)C25—H250.9500
C13—C171.507 (2)C26—H260.9500
C14—C151.387 (2)C41—H41A0.9800
C15—C161.394 (2)C41—H41B0.9800
C15—C181.506 (3)C41—H41C0.9800
C21—C221.393 (2)C51—H51A0.9800
C21—C261.401 (2)C51—H51B0.9800
C22—C231.385 (3)C51—H51C0.9800
C23—C241.374 (3)
C2—N1—C5107.12 (13)C13—C14—H14119.00
C2—N1—C11127.30 (14)C15—C14—H14119.00
C5—N1—C11125.28 (12)C11—C16—H16120.00
C2—N3—C4106.09 (13)C15—C16—H16120.00
N1—C2—N3110.65 (14)C13—C17—H17A109.00
N1—C2—C21126.33 (14)C13—C17—H17B109.00
N3—C2—C21122.95 (13)C13—C17—H17C109.00
N3—C4—C5110.80 (16)H17A—C17—H17B110.00
N3—C4—C41121.02 (15)H17A—C17—H17C109.00
C5—C4—C41128.18 (16)H17B—C17—H17C110.00
N1—C5—C4105.35 (14)C15—C18—H18A109.00
N1—C5—C51122.36 (14)C15—C18—H18B109.00
C4—C5—C51132.29 (16)C15—C18—H18C109.00
N1—C11—C12119.20 (14)H18A—C18—H18B109.00
N1—C11—C16119.31 (14)H18A—C18—H18C109.00
C12—C11—C16121.49 (15)H18B—C18—H18C110.00
C11—C12—C13119.80 (15)C21—C22—H22120.00
C12—C13—C14118.19 (15)C23—C22—H22120.00
C12—C13—C17120.13 (16)C22—C23—H23121.00
C14—C13—C17121.67 (16)C24—C23—H23121.00
C13—C14—C15122.39 (15)C24—C25—H25121.00
C14—C15—C16118.59 (15)C26—C25—H25121.00
C14—C15—C18120.88 (16)C21—C26—H26119.00
C16—C15—C18120.54 (16)C25—C26—H26119.00
C11—C16—C15119.50 (15)C4—C41—H41A109.00
C2—C21—C22123.84 (14)C4—C41—H41B109.00
C2—C21—C26117.57 (15)C4—C41—H41C109.00
C22—C21—C26118.34 (16)H41A—C41—H41B109.00
C21—C22—C23120.67 (17)H41A—C41—H41C109.00
C22—C23—C24118.6 (2)H41B—C41—H41C109.00
F4—C24—C23118.8 (2)C5—C51—H51A109.00
F4—C24—C25118.53 (18)C5—C51—H51B109.00
C23—C24—C25122.71 (19)C5—C51—H51C109.00
C24—C25—C26118.09 (17)H51A—C51—H51B109.00
C21—C26—C25121.54 (17)H51A—C51—H51C109.00
C11—C12—H12120.00H51B—C51—H51C109.00
C13—C12—H12120.00
C5—N1—C2—N30.02 (19)C41—C4—C5—C511.4 (3)
C5—N1—C2—C21176.74 (15)N1—C11—C12—C13176.87 (14)
C11—N1—C2—N3173.88 (14)C16—C11—C12—C132.3 (2)
C11—N1—C2—C219.4 (3)N1—C11—C16—C15177.86 (14)
C2—N1—C5—C40.20 (18)C12—C11—C16—C151.3 (2)
C2—N1—C5—C51179.77 (15)C11—C12—C13—C141.1 (2)
C11—N1—C5—C4173.87 (15)C11—C12—C13—C17177.75 (15)
C11—N1—C5—C516.2 (2)C12—C13—C14—C151.1 (2)
C2—N1—C11—C12105.84 (19)C17—C13—C14—C15179.93 (15)
C2—N1—C11—C1673.4 (2)C13—C14—C15—C162.1 (2)
C5—N1—C11—C1281.3 (2)C13—C14—C15—C18177.47 (16)
C5—N1—C11—C1699.51 (18)C14—C15—C16—C110.9 (2)
C4—N3—C2—N10.16 (18)C18—C15—C16—C11178.71 (15)
C4—N3—C2—C21177.05 (15)C2—C21—C22—C23174.03 (18)
C2—N3—C4—C50.3 (2)C26—C21—C22—C230.0 (3)
C2—N3—C4—C41178.74 (17)C2—C21—C26—C25173.55 (16)
N1—C2—C21—C2227.5 (3)C22—C21—C26—C250.9 (3)
N1—C2—C21—C26158.45 (16)C21—C22—C23—C241.0 (3)
N3—C2—C21—C22148.95 (17)C22—C23—C24—F4177.64 (19)
N3—C2—C21—C2625.2 (2)C22—C23—C24—C251.3 (3)
N3—C4—C5—N10.30 (19)F4—C24—C25—C26178.47 (18)
N3—C4—C5—C51179.66 (17)C23—C24—C25—C260.5 (3)
C41—C4—C5—N1178.63 (19)C24—C25—C26—C210.7 (3)
Hydrogen-bond geometry (Å, º) top
Cg3 is the centroid of the C21–C26 ring.
D—H···AD—HH···AD···AD—H···A
C12—H12···Cg3i0.952.863.7969 (19)169
Symmetry code: (i) x, y, z+1.

Experimental details

Crystal data
Chemical formulaC19H19FN2
Mr294.36
Crystal system, space groupTriclinic, P1
Temperature (K)170
a, b, c (Å)8.4226 (10), 9.5572 (10), 11.0351 (11)
α, β, γ (°)105.423 (9), 105.677 (9), 95.781 (9)
V3)810.07 (17)
Z2
Radiation typeCu Kα
µ (mm1)0.63
Crystal size (mm)0.25 × 0.20 × 0.15
Data collection
DiffractometerOxford Diffraction Xcalibur Eos Gemini
diffractometer
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2010)
Tmin, Tmax0.858, 0.911
No. of measured, independent and
observed [I > 2σ(I)] reflections
5121, 3054, 2771
Rint0.011
(sin θ/λ)max1)0.614
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.159, 1.07
No. of reflections3054
No. of parameters203
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.31, 0.23

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), CrysAlis RED (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg3 is the centroid of the C21–C26 ring.
D—H···AD—HH···AD···AD—H···A
C12—H12···Cg3i0.952.863.7969 (19)169
Symmetry code: (i) x, y, z+1.
 

Acknowledgements

JPJ acknowledges the NSF–MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

References

First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
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Volume 67| Part 5| May 2011| Page o1065
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