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

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ISSN: 2056-9890

2-(4-Fluoro­phen­yl)-1-(3-meth­­oxy­phen­yl)-4,5-di­methyl-1H-imidazole

aDepartment of Physics, Seethalakshmi Ramaswami College (Autonomous), Tiruchirappalli 620 002, India, bDepartment of Physics, K. Ramakrishnan College of Engineering, Samayapuram, Tiruchirappalli 621 112, India, and cDepartment of Chemistry, S.K.P. Engineering College, Thiruvanamalai 606 611, India
*Correspondence e-mail: raghema2000@yahoo.co.in

(Received 26 November 2013; accepted 29 November 2013; online 4 December 2013)

In the title compound, C18H17FN2O, the imidazole ring makes dihedral angles of 68.81 (6) and 25.20 (8)° with the meth­oxy­phenyl and fluoro­phenyl rings, respectively. The dihedral angle between the meth­oxy­phenyl and fluoro­phenyl ring is 71.89 (6)°. In the crystal, mol­ecules are linked into inversion dimers with an R22(8) graph-set motif by pairs of weak C—H⋯F inter­actions.

Related literature

For related structures, see: Rizwana Begum et al. (2013[Rizwana Begum, S., Hema, R., Srinivasan, N. & Anitha, A. G. (2013). Acta Cryst. E69, o1154.]); Srinivasan et al. (2013[Srinivasan, N., Rizwana Begum, S. R. A., Hema, R., Sridhar, B. & Anitha, A. G. (2013). Acta Cryst. E69, o1599-o1600.]); Gayathri et al. (2010[Gayathri, P., Jayabharathi, J., Srinivasan, N., Thiruvalluvar, A. & Butcher, R. J. (2010). Acta Cryst. E66, o1703.]); Rosepriya et al. (2011[Rosepriya, S., Thiruvalluvar, A., Jayabharathi, J., Srinivasan, N., Butcher, R. J., Jasinski, J. P. & Golen, J. A. (2011). Acta Cryst. E67, o1065.]). For graph-set motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem.Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C18H17FN2O

  • Mr = 296.34

  • Triclinic, [P \overline 1]

  • a = 8.1196 (5) Å

  • b = 9.6014 (6) Å

  • c = 10.6116 (6) Å

  • α = 106.818 (3)°

  • β = 92.059 (3)°

  • γ = 96.114 (3)°

  • V = 785.45 (8) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 293 K

  • 0.30 × 0.30 × 0.25 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.974, Tmax = 0.979

  • 15949 measured reflections

  • 3597 independent reflections

  • 2477 reflections with I > 2σ(I)

  • Rint = 0.031

Refinement
  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.148

  • S = 1.03

  • 3597 reflections

  • 202 parameters

  • H-atom parameters constrained

  • Δρmax = 0.20 e Å−3

  • Δρmin = −0.22 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C15—H15⋯F2i 0.93 2.55 3.437 (2) 160
Symmetry code: (i) -x, -y, -z-1.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

In a continuation of structural studies of 4,5-dimethyl-1H-imidazole derivatives (Rizwana et al., 2013; Srinivasan et al., 2013; Gayathri et al., 2010; Rosepriya et al., 2011), we have taken up the title compound, (I), for crystallographic investigation.

In (I) (Fig. 1), C18H17FN2O, the imidazole ring is essentially planar and makes dihedral angles of 68.81 (6)° and 25.20 (8)° with the methoxyphenyl (C5-C10) and fluorophenyl rings (C13-C18) respectively. The dihedral angle between the methoxyphenyl and fluorophenyl ring is 71.89 (6)°. The C15—H15···F2 (-x,-y,-1 - z) interaction link pairs of molecules across centres of inversion to form dimers with ring motif R22(8) (Bernstein et al., (1995)) (Fig. 2).

Related literature top

For related structures, see: Rizwana Begum et al. (2013); Srinivasan et al. (2013); Gayathri et al. (2010); Rosepriya et al. (2011). For graph-set motifs, see: Bernstein et al. (1995).

Experimental top

To pure butane-2,3-dione (1.48 g, 15 mmol) in ethanol (10 ml), m-methoxy aniline (1.5 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: 1.94 g (48%).

Refinement top

All H atoms were placed in geometrically idealized positions (C—H = 0.93 Å) and constrained to ride on their parent atoms with Uiso(H) = 1.2Ueq(C) but the methyl H atoms were located in SHELX with an ideal geometry (C—H = 0.96 Å) , Uiso(H) = 1.5Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); 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-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented by circles of arbitrary radii.
[Figure 2] Fig. 2. Intermolecular C-H···F hydrogen bonding in (I).
2-(4-Fluorophenyl)-1-(3-methoxyphenyl)-4,5-dimethyl-1H-imidazole top
Crystal data top
C18H17FN2OZ = 2
Mr = 296.34F(000) = 312
Triclinic, P1Dx = 1.253 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.1196 (5) ÅCell parameters from 3597 reflections
b = 9.6014 (6) Åθ = 2.5–30.3°
c = 10.6116 (6) ŵ = 0.09 mm1
α = 106.818 (3)°T = 293 K
β = 92.059 (3)°Block, colourless
γ = 96.114 (3)°0.30 × 0.30 × 0.25 mm
V = 785.45 (8) Å3
Data collection top
Bruker Kappa APEXII CCD
diffractometer
3597 independent reflections
Radiation source: fine-focus sealed tube2477 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
ω and ϕ scanθmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
h = 1010
Tmin = 0.974, Tmax = 0.979k = 1212
15949 measured reflectionsl = 1313
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0689P)2 + 0.1414P]
where P = (Fo2 + 2Fc2)/3
3597 reflections(Δ/σ)max = 0.001
202 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.22 e Å3
Crystal data top
C18H17FN2Oγ = 96.114 (3)°
Mr = 296.34V = 785.45 (8) Å3
Triclinic, P1Z = 2
a = 8.1196 (5) ÅMo Kα radiation
b = 9.6014 (6) ŵ = 0.09 mm1
c = 10.6116 (6) ÅT = 293 K
α = 106.818 (3)°0.30 × 0.30 × 0.25 mm
β = 92.059 (3)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer
3597 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
2477 reflections with I > 2σ(I)
Tmin = 0.974, Tmax = 0.979Rint = 0.031
15949 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.148H-atom parameters constrained
S = 1.03Δρmax = 0.20 e Å3
3597 reflectionsΔρmin = 0.22 e Å3
202 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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
C10.2524 (2)0.71718 (19)0.06251 (16)0.0606 (4)
C20.2395 (3)0.8699 (2)0.0606 (2)0.0941 (7)
H2A0.27410.93660.14620.141*
H2B0.12650.87910.03780.141*
H2C0.30960.89270.00350.141*
C30.2938 (2)0.66931 (18)0.16587 (15)0.0574 (4)
C40.3379 (3)0.7478 (2)0.30717 (17)0.0771 (5)
H4A0.32210.84910.32410.116*
H4B0.45210.74070.32840.116*
H4C0.26830.70460.36050.116*
C50.29393 (19)0.41950 (17)0.19342 (14)0.0504 (4)
C60.1516 (2)0.33657 (19)0.20825 (17)0.0597 (4)
H60.05030.34310.16790.072*
C70.1631 (2)0.2430 (2)0.2848 (2)0.0709 (5)
H70.06830.18510.29520.085*
C80.3106 (3)0.2339 (2)0.34526 (19)0.0705 (5)
H80.31570.17070.39680.085*
C90.4529 (2)0.3186 (2)0.33012 (15)0.0609 (4)
C100.4455 (2)0.41192 (18)0.25281 (14)0.0551 (4)
H100.54080.46840.24100.066*
C110.7407 (3)0.3921 (3)0.3874 (2)0.0872 (6)
H11A0.76590.37540.29690.131*
H11B0.83080.36910.43580.131*
H11C0.72520.49310.42500.131*
C120.23901 (18)0.48287 (17)0.01663 (14)0.0504 (4)
C130.22060 (19)0.33656 (18)0.11246 (14)0.0526 (4)
C140.1224 (2)0.3145 (2)0.22791 (17)0.0648 (5)
H140.06510.38960.23860.078*
C150.1082 (3)0.1840 (2)0.32662 (19)0.0757 (5)
H150.04290.17050.40410.091*
C160.1914 (3)0.0748 (2)0.30879 (19)0.0712 (5)
C170.2885 (3)0.0901 (2)0.1976 (2)0.0758 (5)
H170.34390.01350.18800.091*
C180.3031 (2)0.2221 (2)0.09918 (17)0.0662 (5)
H180.36960.23440.02260.079*
N10.21906 (17)0.60175 (15)0.05036 (12)0.0574 (4)
N20.28515 (16)0.51797 (14)0.11500 (12)0.0509 (3)
O10.59387 (18)0.30194 (18)0.39395 (14)0.0866 (4)
F20.17789 (18)0.05430 (14)0.40697 (13)0.1043 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0682 (11)0.0603 (10)0.0551 (9)0.0035 (8)0.0008 (7)0.0217 (8)
C20.138 (2)0.0661 (12)0.0821 (14)0.0073 (12)0.0133 (13)0.0318 (11)
C30.0622 (10)0.0604 (10)0.0495 (8)0.0004 (7)0.0018 (7)0.0189 (7)
C40.1045 (15)0.0707 (12)0.0521 (10)0.0007 (10)0.0037 (9)0.0166 (9)
C50.0560 (9)0.0580 (9)0.0406 (7)0.0081 (7)0.0066 (6)0.0193 (7)
C60.0564 (9)0.0641 (10)0.0604 (9)0.0043 (7)0.0071 (7)0.0220 (8)
C70.0715 (12)0.0672 (11)0.0807 (12)0.0006 (9)0.0158 (9)0.0342 (10)
C80.0898 (14)0.0664 (11)0.0691 (11)0.0158 (10)0.0175 (10)0.0377 (9)
C90.0691 (11)0.0733 (11)0.0482 (8)0.0194 (9)0.0073 (7)0.0260 (8)
C100.0549 (9)0.0699 (10)0.0460 (8)0.0071 (7)0.0062 (6)0.0255 (7)
C110.0686 (13)0.1295 (19)0.0757 (13)0.0226 (12)0.0032 (10)0.0468 (13)
C120.0480 (8)0.0630 (9)0.0450 (8)0.0069 (7)0.0037 (6)0.0230 (7)
C130.0505 (8)0.0642 (10)0.0463 (8)0.0052 (7)0.0073 (6)0.0215 (7)
C140.0676 (11)0.0681 (11)0.0582 (10)0.0073 (8)0.0056 (8)0.0196 (8)
C150.0791 (13)0.0805 (13)0.0592 (11)0.0014 (10)0.0100 (9)0.0122 (10)
C160.0795 (13)0.0648 (11)0.0614 (11)0.0019 (9)0.0099 (9)0.0081 (9)
C170.0929 (14)0.0700 (12)0.0691 (12)0.0250 (10)0.0141 (10)0.0212 (10)
C180.0733 (11)0.0773 (12)0.0516 (9)0.0212 (9)0.0039 (8)0.0205 (9)
N10.0623 (8)0.0642 (8)0.0497 (7)0.0067 (6)0.0007 (6)0.0241 (7)
N20.0523 (7)0.0595 (8)0.0446 (6)0.0049 (6)0.0026 (5)0.0222 (6)
O10.0781 (9)0.1210 (12)0.0843 (9)0.0234 (8)0.0001 (7)0.0640 (9)
F20.1274 (11)0.0784 (8)0.0861 (9)0.0117 (7)0.0010 (7)0.0073 (7)
Geometric parameters (Å, º) top
C1—C31.351 (2)C9—C101.383 (2)
C1—N11.371 (2)C10—H100.9300
C1—C21.488 (3)C11—O11.413 (3)
C2—H2A0.9600C11—H11A0.9600
C2—H2B0.9600C11—H11B0.9600
C2—H2C0.9600C11—H11C0.9600
C3—N21.389 (2)C12—N11.3149 (19)
C3—C41.481 (2)C12—N21.3667 (18)
C4—H4A0.9600C12—C131.465 (2)
C4—H4B0.9600C13—C181.384 (2)
C4—H4C0.9600C13—C141.388 (2)
C5—C61.372 (2)C14—C151.372 (3)
C5—C101.381 (2)C14—H140.9300
C5—N21.4342 (18)C15—C161.360 (3)
C6—C71.382 (2)C15—H150.9300
C6—H60.9300C16—C171.357 (3)
C7—C81.361 (3)C16—F21.360 (2)
C7—H70.9300C17—C181.380 (3)
C8—C91.382 (3)C17—H170.9300
C8—H80.9300C18—H180.9300
C9—O11.357 (2)
C3—C1—N1110.58 (15)C5—C10—H10120.7
C3—C1—C2128.58 (17)C9—C10—H10120.7
N1—C1—C2120.83 (15)O1—C11—H11A109.5
C1—C2—H2A109.5O1—C11—H11B109.5
C1—C2—H2B109.5H11A—C11—H11B109.5
H2A—C2—H2B109.5O1—C11—H11C109.5
C1—C2—H2C109.5H11A—C11—H11C109.5
H2A—C2—H2C109.5H11B—C11—H11C109.5
H2B—C2—H2C109.5N1—C12—N2110.49 (14)
C1—C3—N2105.43 (14)N1—C12—C13122.62 (13)
C1—C3—C4131.90 (17)N2—C12—C13126.82 (13)
N2—C3—C4122.66 (14)C18—C13—C14117.93 (16)
C3—C4—H4A109.5C18—C13—C12124.26 (14)
C3—C4—H4B109.5C14—C13—C12117.67 (14)
H4A—C4—H4B109.5C15—C14—C13121.29 (17)
C3—C4—H4C109.5C15—C14—H14119.4
H4A—C4—H4C109.5C13—C14—H14119.4
H4B—C4—H4C109.5C16—C15—C14118.56 (17)
C6—C5—C10121.91 (14)C16—C15—H15120.7
C6—C5—N2119.19 (14)C14—C15—H15120.7
C10—C5—N2118.89 (14)C17—C16—C15122.62 (18)
C5—C6—C7118.12 (16)C17—C16—F2118.87 (18)
C5—C6—H6120.9C15—C16—F2118.51 (18)
C7—C6—H6120.9C16—C17—C18118.46 (18)
C8—C7—C6121.27 (17)C16—C17—H17120.8
C8—C7—H7119.4C18—C17—H17120.8
C6—C7—H7119.4C17—C18—C13121.13 (17)
C7—C8—C9120.05 (16)C17—C18—H18119.4
C7—C8—H8120.0C13—C18—H18119.4
C9—C8—H8120.0C12—N1—C1106.37 (13)
O1—C9—C8115.78 (15)C12—N2—C3107.12 (12)
O1—C9—C10124.26 (16)C12—N2—C5127.45 (13)
C8—C9—C10119.96 (16)C3—N2—C5124.53 (12)
C5—C10—C9118.68 (15)C9—O1—C11117.83 (14)
N1—C1—C3—N20.23 (19)C15—C16—C17—C180.1 (3)
C2—C1—C3—N2179.2 (2)F2—C16—C17—C18179.23 (17)
N1—C1—C3—C4179.06 (18)C16—C17—C18—C130.3 (3)
C2—C1—C3—C40.4 (4)C14—C13—C18—C170.1 (3)
C10—C5—C6—C70.3 (2)C12—C13—C18—C17175.54 (16)
N2—C5—C6—C7179.69 (15)N2—C12—N1—C10.27 (17)
C5—C6—C7—C80.7 (3)C13—C12—N1—C1177.54 (14)
C6—C7—C8—C90.4 (3)C3—C1—N1—C120.32 (19)
C7—C8—C9—O1179.92 (17)C2—C1—N1—C12179.21 (18)
C7—C8—C9—C100.4 (3)N1—C12—N2—C30.13 (17)
C6—C5—C10—C90.5 (2)C13—C12—N2—C3177.25 (14)
N2—C5—C10—C9178.94 (14)N1—C12—N2—C5169.55 (14)
O1—C9—C10—C5179.70 (15)C13—C12—N2—C513.3 (2)
C8—C9—C10—C50.8 (2)C1—C3—N2—C120.07 (17)
N1—C12—C13—C18151.38 (16)C4—C3—N2—C12179.02 (16)
N2—C12—C13—C1825.4 (2)C1—C3—N2—C5169.74 (15)
N1—C12—C13—C1424.2 (2)C4—C3—N2—C59.2 (2)
N2—C12—C13—C14158.97 (15)C6—C5—N2—C1262.4 (2)
C18—C13—C14—C150.5 (3)C10—C5—N2—C12118.14 (17)
C12—C13—C14—C15175.38 (16)C6—C5—N2—C3105.29 (18)
C13—C14—C15—C160.7 (3)C10—C5—N2—C374.2 (2)
C14—C15—C16—C170.3 (3)C8—C9—O1—C11176.56 (17)
C14—C15—C16—F2179.68 (17)C10—C9—O1—C113.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H15···F2i0.932.553.437 (2)160
Symmetry code: (i) x, y, z1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H15···F2i0.932.553.437 (2)159.6
Symmetry code: (i) x, y, z1.
 

Acknowledgements

SR thanks the University Grants Commission for financial support of this work (grant MRP-4335/12). The authors are thankful to the SAIF, IIT Madras, for the data collection.

References

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